caprylates profile

A group of esters derived from caprylic acid (octanoic acid). They are commonly used as emulsifiers, stabilizers, and anti-microbial agents in cosmetics, food, and pharmaceuticals. Caprylates are generally considered safe for topical use and are often used in products for sensitive skin. They are produced through the esterification of caprylic acid with various alcohols, such as glycerol, propylene glycol, and sorbitol. The specific properties of caprylates vary depending on the alcohol used in their synthesis. Caprylates have been studied for their potential antimicrobial activity against bacteria, fungi, and yeast. They are also known to have moisturizing and emollient properties. Due to their safety and versatility, caprylates are widely used in various industries, including cosmetics, pharmaceuticals, and food. Their potential benefits for skin health and their antimicrobial properties make them a subject of ongoing research and development.'

Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	119389
CHEBI ID	25646
MeSH ID	M0003307

Synonym
1-heptanecarboxylate
octanoic acid, ion(1-)
CHEBI:25646
n-octylate
74-81-7
caprylate
caprilate
ch3-[ch2]6-coo(-)
n-octoate
n-octanoate
n-caprylate
octanoate
octanoate (n-c8:0)
n-octic acid
capryloate
octanoate, 1
bdbm23432
A805133
caprylates
WWZKQHOCKIZLMA-UHFFFAOYSA-M
STL483483
3NQ9
DTXSID70995277
Q27109891

Excerpt	Reference	Relevance
"The influence of mixtures of taurocholate (TC), oleic acid (OA), caprylic acid (CA), and monolein (MO) on the toxic effects of deoxycholate (DC) in rat jejunum have been investigated using both a closed loop and perfusion technique."	( Influence of mixtures of taurocholate, fatty acids, and monolein on the toxic effects of deoxycholate in rat jejunum in vivo. Guiraldes, E; Harries, JT; Lamabadusuriya, SP, 1975)	0.25
" Ammonium perfluorononanoate was classified as moderately toxic by the acute inhalation route."	( Acute inhalation toxicity of ammonium perfluorononanoate. Chromey, NC; Kennedy, GL; Kinney, LA, 1989)	0.28
" In an earlier study the male rats were more susceptible to the toxic effects of perfluorooctanoic acid (PFO) than females."	( Elimination and toxicity of perfluorooctanoic acid during subchronic administration in the Wistar rat. Hanhijärvi, H; Kojo, A; Kosma, VM; Ylinen, M, 1987)	0.27
" The compound was found to be moderately toxic following single 4-hr exposures, with an LC50 of 980 mg/m3."	( Inhalation toxicity of ammonium perfluorooctanoate. Barnes, JR; Brittelli, MR; Chen, HC; Hall, GT; Kennedy, GL, 1986)	0.27
" The dermal LD50 was 4300 mg/kg for rabbits, 7000 mg/kg for male rats, and greater than 7500 mg/kg for female rats."	( Dermal toxicity of ammonium perfluorooctanoate. Kennedy, GL, 1985)	0.27
" NDFDA has unusually high toxic potency for a perfluorinated hydrocarbon, and some of the toxic effects caused by this acid are remarkably similar to those seen with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)."	( The acute toxicity of perfluorooctanoic and perfluorodecanoic acids in male rats and effects on tissue fatty acids. Andersen, ME; Olson, CT, 1983)	0.27
" MO at 50 cm pressure and Ch at both 40 and 50 cm pressure were significantly more toxic than saline."	( Toxic effects of intrahepatic reflux of monooctanoin in a canine model. Gadacz, TR; Sharp, KW, 1984)	0.27
" Toxic effects on the conceptus were noted only in the groups given the highest level of APFO by each route."	( The embryo-fetal toxicity and teratogenic potential of ammonium perfluorooctanoate (APFO) in the rat. Burgess, BA; Kerns, WD; Staples, RE, 1984)	0.27
" The rat oral LD50 was 540 mg/kg; no deaths resulted from a one hour rat inhalation exposure at a nominal concentration of 18."	( Animal toxicity studies with ammonium perfluorooctanoate. Griffith, FD; Long, JE, 1980)	0.26
"Monooctanoin, a cholesterol gallstone solvent, has been gaining wide acceptance as an effective safe agent for dissolving retained common bile duct stones when infused into the biliary tract."	( Systemic side effects from the intrabiliary infusion of monooctanoin for the dissolution of gallstones. Hoofnagle, JH; Jones, EA; Minuk, GY, 1982)	0.26
" The ability to identify this type of alteration via 2DE, in association with specific toxic effects by chemically related compounds, may provide new and additional markers for chemical-induced tissue damage."	( Induction of enoyl-CoA hydratase by LD50 exposure to perfluorocarboxylic acids detected by two-dimensional electrophoresis. Jarnot, BM; Parker, DN; Witzmann, FA, 1994)	0.29
" Adverse events were generally mild and occurred with similar frequency in each group."	( IGIV-C, a novel intravenous immunoglobulin: evaluation of safety, efficacy, mechanisms of action, and impact on quality of life. Abshire, TC; Angiolillo, A; Brenner, B; Bussel, JB; Eldor, A; Gillis, S; Kelleher, J; Kelton, JG; Kulkarni, R; Varon, D, 2004)	0.32
" The incidence of early adverse reactions (all mild) was similar for both antivenoms (15% and 24%; P>0."	( Efficacy and safety of two whole IgG polyvalent antivenoms, refined by caprylic acid fractionation with or without beta-propiolactone, in the treatment of Bothrops asper bites in Colombia. Alzate, C; Arrieta, AB; Arroyo, Y; Ayala, S; Barona, J; Conrado, LL; Córdoba, E; Díaz, A; Fabra, PE; Fernández, D; Fernández, J; Gutiérrez, JM; León, G; López, M; Meza, JJ; Mosquera, D; Núñez, V; Ospina, CE; Otero, R; Paniagua, CA; Quintana, JC; Ramírez, E; Ramírez, P; Rodríguez, V; Rojas, G; Silva, JF; Theakston, RD; Toro, MF; Warrell, DA, 2006)	0.33
" A total of 92 subjects were enrolled with no dose-related pattern of serious adverse events (AEs)."	( Safety and tolerability of arundic acid in acute ischemic stroke. Albers, GW; Funakoshi, Y; Gorman, M; Grotta, JC; Ishibashi, H; Kasner, SE; Pettigrew, LC; Sherman, DG, 2006)	0.33
"Intravenous immunoglobulin (IGIV) therapy is generally considered to be a safe and effective treatment for idiopathic thrombocytopenic purpura (ITP)."	( Safety and tolerability of a novel chromatography-based intravenous immunoglobulin when administered at a high infusion rate in patients with immune thrombocytopenic purpura. Bussel, JB; Hanna, K, 2007)	0.34
" In mice, PFOA is developmentally toxic producing mortality, delayed eye opening, growth deficits, and altered pubertal maturation."	( Perfluorooctanoic acid induced developmental toxicity in the mouse is dependent on expression of peroxisome proliferator activated receptor-alpha. Abbott, BD; Das, KP; Helfant, L; Lau, C; Lindstrom, AB; Nakayama, S; Schmid, JE; Strynar, MJ; Wolf, CJ; Zehr, RD, 2007)	0.34
" In conclusion, our results demonstrate that PFOA causes a toxic effect on the liver but not to the kidney."	( Perfluorooctanoic acid-induced hepatic toxicity following 21-day oral exposure in mice. Bae, HI; Kim, SH; Shin, HI; Son, HY; Yang, JH, 2008)	0.35
" In recent years, there are increasing distribution of PFOS/PFOA in environmental systems, and accumulation and toxic effects of PFOS/PFOA in living organisms."	( [Researching progresses in environmental pollution behavior, toxic effects and mechanisms of PFOS/PFOA]. Hu, XG; Zhou, QX, 2007)	0.34
" PFOS was more toxic than PFOA for all species tested in this study."	( Toxicity of perfluorooctane sulfonate and perfluorooctanoic acid to plants and aquatic invertebrates. Li, MH, 2009)	0.35
"In general, the rank order of adverse effects was PFOSA > PFOS > PFBS approximately PFOA."	( Developmental neurotoxicity of perfluorinated chemicals modeled in vitro. MacKillop, EA; Melnick, RL; Seidler, FJ; Slotkin, TA; Thayer, KA, 2008)	0.35
" In general, PFOS is approximately 10 times more toxic than PFOA in these organisms."	( Toxicity of perfluorooctane sulfonic acid and perfluorooctanoic acid on freshwater macroinvertebrates (Daphnia magna and Moina macrocopa) and fish (Oryzias latipes). Ahn, B; Choi, K; Ji, K; Jo, H; Kim, Y; Oh, S, 2008)	0.35
" Concerns about possible toxic effects of these chemicals date back to seventies, but only in 2000 the Environmental Protection Agency (EPA) stated PFOA and PFOS withdrawal to avoid environmental pollution."	( [Characteristics, use and toxicity of fluorochemicals: review of the literature]. Esabon, G; Ferrari, M; Ghittori, S; Imbriani, M; Maestri, L; Negri, S; Zadra, P, )	0.13
" The paper focuses on the distribution, bioaccumulation and toxic effects of PFOS and PFOA in the water."	( Contamination, bioaccumulation and toxic effects of perfluorinated chemicals (PFCs) in the water environment: a review paper. Pramanik, BK; Suja, F; Zain, SM, 2009)	0.35
" We investigated the toxicological interactions of the most toxic surfactant, docusate sodium, with two chlorinated compounds, triclosan and 2,4,6-trichlorophenol (TCP), in their binary and ternary mixtures using the method of the combination index based on the median-effect equation."	( Ecotoxicological assessment of surfactants in the aquatic environment: combined toxicity of docusate sodium with chlorinated pollutants. Boltes, K; Fernández-Piñas, F; Leganés, F; Petre, A; Rodea-Palomares, I; Rosal, R, 2010)	0.36
" The toxicity of PFOS and PFOA has been studied extensively in rodents with several adverse effects mainly a hepatocarcinogenic potential."	( Impacts of two perfluorinated compounds (PFOS and PFOA) on human hepatoma cells: cytotoxicity but no genotoxicity? Deblonde, T; Diguio, N; Florentin, A; Hartemann, P; Hautemaniere, A, 2011)	0.37
"51) in the incidence of early adverse reactions to antivenom administration (28."	( Comparative study of the efficacy and safety of two polyvalent, caprylic acid fractionated [IgG and F(ab')2] antivenoms, in Bothrops asper bites in Colombia. Angulo, Y; Arrieta, AB; Arroyo, Y; Barona, J; Betancur, D; Conrado, NL; Córdoba, EA; Díaz, A; Estrada, S; Fabra, P; Fernández, D; Fernández, J; Gómez, JP; Gutiérrez, JM; Herrera, M; León, G; Mosquera, DC; Ortiz, R; Otero-Patiño, R; Perea, M; Pereañez, A; Pupo, L; Quintana, JC; Ramírez, CE; Ramírez, P; Rivero, A; Segura, A; Suárez, AM; Vargas, LJ, 2012)	0.38
" We developed a novel partial life-cycle assay that incorporates exposures to brooding adult female mussels and used this method in combination with acute toxicity tests to assess adverse effects of perfluoroctanesulfonic acid (PFOS) and perfluoroctanoic acid (PFOA) on freshwater mussels."	( Partial life-cycle and acute toxicity of perfluoroalkyl acids to freshwater mussels. Barnhart, MC; Bringolf, RB; Cope, WG; Hazelton, PD; Mosher, S; Pandolfo, TJ; Strynar, MJ, 2012)	0.38
" The disturbance of cholesterol biosynthesis could have adverse impact on fatty acid metabolism, consequently induce the decrease of carnitine and increase of acylcarnitines in treated groups."	( [Hepatotoxicity of perfluorooctanoic acid in human hepatocytes using metabonomics]. Peng, S; Shen, H; Yan, L; Zhang, J, 2012)	0.38
"It is well established that exposure of mice to perfluorooctanoate (PFOA) or perfluorooctane sulfonate (PFOS) exerts adverse effects on the thymus and spleen."	( High-dose dietary exposure of mice to perfluorooctanoate or perfluorooctane sulfonate exerts toxic effects on myeloid and B-lymphoid cells in the bone marrow and these effects are partially dependent on reduced food consumption. Abedi-Valugerdi, M; DePierre, JW; Nelson, BD; Qazi, MR, 2012)	0.38
" In addition to commonly recognized chain length and functional group effects, several structural factors are also involved in the toxic actions of PFCs, including hydrophobicity and molecular size, and so on."	( Environmental toxicity of PFCs: an enhanced integrated biomarker assessment and structure-activity analysis. Chang, VW; Gin, KY; Liu, C, 2013)	0.39
" The toxic effects on Xenopus embryos were evaluated using different methods."	( In vivo evaluation and comparison of developmental toxicity and teratogenicity of perfluoroalkyl compounds using Xenopus embryos. Bae, JS; Chae, S; Choo, YS; Ji, Y; Jun, C; Kim, M; Kim, SH; Kwon, TK; Lee, HS; Park, MJ; Park, MS; Ryoo, J; Son, J; Yoon, D; Yoon, H, 2013)	0.39
" Considering liver is the primary toxic target organ for these two groups of chemicals, it is interesting to evaluate the possible joint effects of them on liver."	( Enhanced cytotoxicity of pentachlorophenol by perfluorooctane sulfonate or perfluorooctanoic acid in HepG2 cells. Shan, G; Ye, M; Zhu, B; Zhu, L, 2013)	0.39
" In the present study, the acute toxic effect of PFOA in the absence and presence of either chromium (III) or tetra butyl ammonium (TBA) towards Pseudomonas putida in the aquatic environment was investigated by microcalorimetry."	( Toxicity of perfluorooctanoic acid to Pseudomonas putida in the aquatic environment. Cai, M; Chen, H; Liu, H; Wang, F; Yao, J, 2013)	0.39
" Animal studies indicated that PFOA caused a wide array of toxic effects including liver and brain dysfunction, carcinogenicity and reproductive and developmental toxicity."	( Mechanistic approach for the toxic effects of perfluorooctanoic acid on isolated rat liver and brain mitochondria. Hashemzaei, M; Hosseini, MJ; Mashayekhi, V; Shahraki, J; Tabrizian, K; Tehrani, KH, 2015)	0.42
"Due to the fact that PFOA had toxic effects on the mitochondria isolated, it could be suggested that mitochondrial toxicity could be a plausible mechanism for the toxic effects of this fluorochemical on liver and brain function."	( Mechanistic approach for the toxic effects of perfluorooctanoic acid on isolated rat liver and brain mitochondria. Hashemzaei, M; Hosseini, MJ; Mashayekhi, V; Shahraki, J; Tabrizian, K; Tehrani, KH, 2015)	0.42
" However, data on their possible combined toxic effects on aquatic organisms are still lacking."	( Evaluation of single and joint toxicity of perfluorooctane sulfonate, perfluorooctanoic acid, and copper to Carassius auratus using oxidative stress biomarkers. Feng, M; He, Q; Meng, L; Sun, P; Wang, Z; Zhang, X, 2015)	0.42
" C10 is more toxic at lower concentrations than C8."	( New insights into the toxicity mechanism of octanoic and decanoic acids on Saccharomyces cerevisiae. Borrull, A; Cordero-Otero, R; López-Martínez, G; Poblet, M; Rozès, N, 2015)	0.42
" In this study, we compare the sensitivity of three avian species to the toxic effects of perfluorooctane sulfonate (PFOS) and perfluorooctanoate (PFOA)."	( Developmental toxicity of PFOS and PFOA in great cormorant (Phalacrocorax carbo sinensis), herring gull (Larus argentatus) and chicken (Gallus gallus domesticus). Berger, U; Engwall, M; Nordén, M, 2016)	0.43
" In the present study, safe and effective ionic liquids for transdermal absorption were obtained as salts generated by a neutralization reaction between highly biocompatible aliphatic carboxylic acids (octanoic acid or isostearic acid) and aliphatic amines (diisopropanolamine or triisopropanolamine) (Medrx Co."	( The molecular assembly of the ionic liquid/aliphatic carboxylic acid/aliphatic amine as effective and safety transdermal permeation enhancers. Kubota, K; Shibata, A; Yamaguchi, T, 2016)	0.43
" This study clearly demonstrates that soil contamination of PFOA can lead to adverse effects on soil health."	( Toxicity of perfluorooctanoic acid towards earthworm and enzymatic activities in soil. He, W; Megharaj, M; Naidu, R, 2016)	0.43
" Due to the hazardous effects of many of these chemicals, manufacturers are developing next generation potential less toxic alternatives."	( Acute mixture toxicity of halogenated chemicals and their next generation counterparts on zebrafish embryos. Abdel-Moneim, A; Godfrey, A; Sepúlveda, MS, 2017)	0.46
" The results of acute toxicity testing using a filter paper contact test and a natural field soil test showed that PFOA and PFOS exhibited acute toxicity in earthworms, and the toxic effect of PFOS was greater than that of PFOA."	( Effects of perfluorooctanoic acid and perfluorooctane sulfonate on acute toxicity, superoxide dismutase, and cellulase activity in the earthworm Eisenia fetida. Li, J; Liu, H; Yuan, Z; Zhang, J; Zhao, L, 2017)	0.46
" Compared with PFOA and PFOS, 6:2 Cl-PFESA, HFPO trimer acid (HFPO-TA), HFPO tetramer acid (HFPO-TeA), and 6:2 FTSA showed greater toxic effects on cell viabilities."	( Cytotoxicity of novel fluorinated alternatives to long-chain perfluoroalkyl substances to human liver cell line and their binding capacity to human liver fatty acid binding protein. Cui, R; Dai, J; Guo, Y; Sheng, N; Wang, J, 2018)	0.48
" The models help us to gain a better understanding of the toxic mechanism of PFASs, and provide a tool to evaluate adverse effects for the whole group of compounds with one mathematical equation."	( Immunotoxicity in green mussels under perfluoroalkyl substance (PFAS) exposure: Reversible response and response model development. Gin, KY; Liu, C, 2018)	0.48
"Perfluorooctanoic acid (PFOA) is widely distributed in various environmental media and is toxic to organisms."	( Role of the Nrf2-ARE pathway in perfluorooctanoic acid (PFOA)-induced hepatotoxicity in Rana nigromaculata. Chen, B; Ding, Y; Du, Q; Gao, N; He, J; Jia, X; Jiang, J; Li, N; Liu, W; Liu, Z; Lu, X; Tang, J; Wu, Y; Zhang, H; Zhu, W, 2018)	0.48
"High-throughput screening (HTS) of liver toxicants can bridge the gap in understanding adverse effects of chemicals on humans."	( High-throughput toxicity testing of chemicals and mixtures in organotypic multi-cellular cultures of primary human hepatic cells. Ehrich, MF; Orbach, SM; Rajagopalan, P, 2018)	0.48
" It has been shown that some PFAS lead to adverse health effects in the male reproductive system."	( Genotoxicity assessment of perfluoroalkyl substances on human sperm. Çetin, Ö; Emerce, E, 2018)	0.48
" However, data on their possible joint toxic effects on microorganisms are still lacking."	( Evaluation of Single and Joint Toxicity of Perfluorinated Carboxylic Acids and Copper to Metal-Resistant Cai, Y; Chen, H; Li, H; Wang, F; Yang, S, 2019)	0.51
"This study investigated the adverse effects of perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) on mouse primary hepatocytes by conducting cell viability, apoptosis, intracellular oxidative stress level, superoxide dismutase (SOD), catalase (CAT) activity and glutathione level assays."	( PFOA and PFOS interact with superoxide dismutase and induce cytotoxicity in mouse primary hepatocytes: A combined cellular and molecular methods. Liu, R; Niu, Q; Wan, J; Xu, M, 2019)	0.51
" PFOS was the most toxic and PFHxA the least cytotoxic."	( In vitro and in silico modeling of perfluoroalkyl substances mixture toxicity in an amphibian fibroblast cell line. Guffey, S; Hoover, G; Kar, S; Leszczynski, J; Sepúlveda, MS, 2019)	0.51
" IGIV-C showed good tolerability with no serious adverse events."	( A Phase 3 Multicenter, Prospective, Open-Label Efficacy and Safety Study of Immune Globulin (Human) 10% Caprylate/Chromatography Purified in Patients with Myasthenia Gravis Exacerbations. Ayguasanosa, J; Balasa, R; Bril, V; Camprubi, S; Chen, J; De Bleecker, JL; Garcia, B; Griffin, R; Heckmann, JM; Henriquez, W; Karelis, G; Lagrange, E; Mondou, E; Nicolle, M; Stuchevskaya, T; Van Damme, P; Vilciu, C; Villa, A, 2019)	0.51
" We present an up-to-date review on low-accumulating crop varieties for PFOA and PFOS in reference to toxic metals and other organic pollutants, including the variety identification, physiological-biochemical mechanisms, molecular uptake mechanisms, and molecular docking, to call for attention and research efforts to decrease human intakes of PFOA and PFOS via crop consumption."	( Food Safety Concerns: Crop Breeding as a Potential Strategy To Address Issues Associated with the Recently Lowered Reference Doses for Perfluorooctanoic Acid and Perfluorooctane Sulfonate. Cai, QY; Feng, NX; Li, H; Li, QX; Li, YW; Mo, CH; Xiang, L; Yu, PF; Zhao, HM, 2020)	0.56
"Poly- and perfluoroalkyl substances (PFASs) are becoming common pollutants in natural environment, while the toxic effects and defense mechanisms in agricultural plants are poorly understood."	( Phytotoxicity induced by perfluorooctanoic acid and perfluorooctane sulfonate via metabolomics. Guo, Y; Li, J; Li, P; Li, Z; Liu, B; Oyang, X; Tian, X; Xi, J; Xiao, Z; Xie, X; Yang, H, 2020)	0.56
" These results demonstrate that dermal exposure to PFOA is immunotoxic and raise concern about potential adverse effects from dermal exposure."	( Immunotoxicity and allergenic potential induced by topical application of perfluorooctanoic acid (PFOA) in a murine model. Anderson, SE; Baur, R; Lukomska, E; Shane, HL; Weatherly, L, 2020)	0.56
" However, it remains to characterize the binding of PFOA with serum albumin and to address the role of this interaction in related toxic effects."	( Fetal bovine serum attenuating perfluorooctanoic acid-inducing toxicity to multiple human cell lines via albumin binding. Chen, B; Luan, T; Zhang, H; Zhang, R, 2020)	0.56
" Taken together, these results demonstrate the potential adverse impact of PFOS and PFOA exposure on spermatogenesis and provide valuable data for PFC risk assessment."	( Male reproductive toxicity involved in spermatogenesis induced by perfluorooctane sulfonate and perfluorooctanoic acid in Caenorhabditis elegans. Bu, Y; Jian, Z; Liu, R; Pu, Y; Wang, D; Yin, J; Yin, L; Yu, X; Zhu, G, 2021)	0.62
" PFAAs cross the blood-brain-barrier and have been observed to induce adverse neurobehavioural effects in humans and animals as well as adverse effects in neuronal in vitro studies."	( Perfluoroalkyl acids potentiate glutamate excitotoxicity in rat cerebellar granule neurons. Berntsen, HF; Bjørklund, CG; Haug, TM; Moldes-Anaya, A; Paulsen, RE; Ragazzi, L; Ropstad, E; Strandabø, RAU; Tasker, RA; Verhaegen, S, 2020)	0.56
"Per- and poly-fluoroalkyl-substances (PFASs) are synthetic compounds that raised concern due to their potential adverse effects on human health."	( The new generation PFAS C6O4 does not produce adverse effects on thyroid cells in vitro. Chiovato, L; Coperchini, F; Croce, L; Gangemi, D; Imbriani, M; Magri, F; Pignatti, P; Ricci, G; Rotondi, M, 2021)	0.62
"The present in vitro study constitutes the first evaluation of the potential adverse effects of the new emerging PFAS C6O4 in cultured rat and human thyroid cells, suggesting its safety for thyroid cells in vitro."	( The new generation PFAS C6O4 does not produce adverse effects on thyroid cells in vitro. Chiovato, L; Coperchini, F; Croce, L; Gangemi, D; Imbriani, M; Magri, F; Pignatti, P; Ricci, G; Rotondi, M, 2021)	0.62
"Perfluorooctanoic acid (PFOA) and its substitute GenX are toxic chemicals that are widespread in the aquatic environment."	( Toxic effects and mechanisms of PFOA and its substitute GenX on the photosynthesis of Chlorella pyrenoidosa. Fan, Z; Gao, X; Huang, J; Li, Y; Liu, X; Yang, M; Zhang, L; Zheng, X, 2021)	0.62
"Perfluorooctanoic acid is a synthetic perfluoroalkyl-persistent in the environment and toxic to humans."	( N-acetyl cysteine co-treatment abates perfluorooctanoic acid-induced reproductive toxicity in male rats. Akomolafe, AP; Imosemi, IO; Odunola, OA; Owumi, SE; Oyelere, AK, 2021)	0.62
"To simulate the real cell status and morphology in the living systems is substantial for using cell models to address the detrimental effects of toxic contaminants."	( Metabolomics analysis of the 3D L-02 cell cultures revealing the key role of metabolism of amino acids in ameliorating hepatotoxicity of perfluorooctanoic acid. Chen, B; Lu, W; Luan, T; Tu, L; Yao, Y; Yu, T; Zhang, R, 2022)	0.72
" PFOA and PFOS have toxic effects on the immune system of the body."	( Immunotoxicity mechanisms of perfluorinated compounds PFOA and PFOS. Bin, L; Huang, W; Lai, KP; Li, R; Liang, L; Liu, Y; Pan, Y, 2022)	0.72
" However, data on their possible combined toxic effects on terrestrial organisms are still lacking."	( Evaluation of single and joint toxicity of perfluorooctanoic acid and arsenite to earthworm (Eisenia fetida): A multi-biomarker approach. Li, C; Liu, L; Meng, L; Qi, F; Shi, Y; Wang, Z; Zhang, Z, 2022)	0.72
" Identification of the target cell population provides clear information of the toxic endpoint of PFOA, which sheds new light on the risk assessment of PFOA on aquatic organisms."	( Toxicity of perfluorooctanoic acid on zebrafish early embryonic development determined by single-cell RNA sequencing. Chen, L; Cheng, W; Gu, C; Jia, M; Ren, HQ; Wu, B; Yu, J, 2022)	0.72
" Our results will provide new insights into evaluating adverse effects of PFOA and monitoring marine ecosystem."	( Immunotoxicity of Perfluorooctanoic Acid to the Marine Bivalve Species Ruditapes philippinarum. Gong, X; Jiang, Y; Li, F; Li, Z; Liu, Z; Qu, M; Tan, Z; Yao, L; Yu, Y, 2022)	0.72
" The adverse effects of individual MPs or PFCs on aquatic organisms have been extensively reported; however, the combined toxicity of MPs and PFCs remains unknown."	( Combined toxicity of polystyrene microplastics and ammonium perfluorooctanoate to Daphnia magna: Mediation of intestinal blockage. Chen, CC; Jiang, Y; Ma, J; Pan, K; Qian, W; Shi, Y; Tao, Y; Zeng, J; Zhou, S; Zhu, X; Zhu, Y, 2022)	0.72
" With over 9000 compounds belonging to this chemical class, there is increasing concern regarding human exposure to these compounds due to their persistent, bioaccumulative, and toxic nature."	( Health-related toxicity of emerging per- and polyfluoroalkyl substances: Comparison to legacy PFOS and PFOA. Ford, J; Jane L Espartero, L; Juhasz, A; Owens, G; Prow, T; Yamada, M, 2022)	0.72
" Collectively, these results showed how iron particles and PFOA could result in enhanced toxicity effects in drinking water: (i) PFOA could increase the toxicity of iron particles by reducing particle size and inducing higher generation of ·OH; (ii) iron particles could induce the transformation of PFOA into more toxic PFOS through digestion."	( Enhanced toxicity effects of iron particles together with PFOA in drinking water. Liu, S; Ma, J; Qin, X; Shi, B; Zhuang, Y, 2022)	0.72
" Altogether, it appears that PFOS and 6:2 Cl-PFESA are more toxic than PFOA."	( Assessing the hepatotoxicity of PFOA, PFOS, and 6:2 Cl-PFESA in black-spotted frogs (Rana nigromaculata) and elucidating potential association with gut microbiota. Chen, J; Lin, H; Liu, F; Liu, Z; Shen, L; Wu, H; Yang, H; Zhang, H; Zhang, X; Zhong, Y, 2022)	0.72
" In this study, the toxic effects of different concentrations of PFOA on zebrafish liver cells were systematically assessed by recording cell survival, ultrastructural observations, and transcriptome analyses."	( Toxic effects and transcriptional responses in zebrafish liver cells following perfluorooctanoic acid exposure. Chen, SS; Cheng, L; Liu, X; Rao, QX; Song, W; Song, WG; Wang, XL; Wu, DL; Yao, CX; Zhang, QC; Zhou, JX, 2022)	0.72
" The current data shows that the HFPO-DA and HFPO-TA might not be safe alternatives to PFOA."	( Comparison of developmental toxicity induced by PFOA, HFPO-DA, and HFPO-TA in zebrafish embryos. Chen, X; Jiang, S; Lu, G; Wang, B; Wang, Y, 2023)	0.91
" IBRv2 analysis indicated that PFOA and PFOS had a similar effect on these immune indicators, but PFOS was more toxic than PFOA."	( Perfluorooctanoic acid and perfluorooctanesulfonic acid induce immunotoxicity through the NF-κB pathway in black-spotted frog (Rana nigromaculata). Feng, Y; Han, Y; Lin, H; Liu, Z; Shen, X; Shi, C; Zhang, H; Zheng, Y; Zhong, Y; Zhu, R, 2023)	0.91
"The ocean is an important sink for perfluorinated alkyl acids (PFAAs), but the toxic mechanisms of PFAAs to marine organisms have not been clearly studied."	( Bioaccumulation and toxicity of perfluorooctanoic acid and perfluorooctane sulfonate in marine algae Chlorella sp. Cao, W; Jiang, W; Li, M; Mao, W; Wang, X; Xu, F; Xue, X, 2023)	0.91
" Accumulated evidence implies that GenX exposure might exert adverse health effects, although the underlying mechanisms have not been fully revealed."	( Gestational GenX and PFOA exposures induce hepatotoxicity, metabolic pathway, and microbiome shifts in weanling mice. Chen, YK; Lai, MQ; Wang, Q; Xie, XL; Xu, LL; Zhang, QY; Zhong, MT, 2024)	1.44

Excerpt	Reference	Relevance
" On the other hand, the peak concentration and duration of exposure to valproic acid and ethylhexanoic acid were very similar despite a more severe teratologic outcome following valproic acid, which indicated higher intrinsic activity of this latter agent."	( Pharmacokinetic determinants of embryotoxicity in rats associated with organic acids. Collins, MD; Nau, H; Scott, WJ, 1994)	0.29
" Pharmacokinetic parameters were determined after the third infusion of each product."	( Pharmacokinetics and tolerability of a new intravenous immunoglobulin preparation, IGIV-C, 10% (Gamunex, 10%). Ballow, M; Berger, M; Bonilla, FA; Buckley, RH; Cunningham-Rundles, CH; Fireman, P; Kaliner, M; Lathia, C; Ochs, HD; Skoda-Smith, S; Sweetser, MT; Taki, H, 2003)	0.32
"The pharmacokinetic profiles observed in these trials indicate that IGIV-C, 10% may replace, and be administered in a manner similar to, IGIV-SD, 10%."	( Pharmacokinetics and tolerability of a new intravenous immunoglobulin preparation, IGIV-C, 10% (Gamunex, 10%). Ballow, M; Berger, M; Bonilla, FA; Buckley, RH; Cunningham-Rundles, CH; Fireman, P; Kaliner, M; Lathia, C; Ochs, HD; Skoda-Smith, S; Sweetser, MT; Taki, H, 2003)	0.32
" Serum PFOA followed first-order elimination kinetics after the last dose, with a half-life of approximately 20 days."	( Pharmacokinetics of perfluorooctanoate in cynomolgus monkeys. Butenhoff, JL; Gorman, GS; Hansen, KJ; Hinderliter, PM; Jung, R; Kennedy, GL; Lieder, PH; Noker, PE; Thomford, PJ, 2004)	0.32
" We tried to build a one-compartment pharmacokinetic model using the reported half-lives in human."	( Renal clearance of perfluorooctane sulfonate and perfluorooctanoate in humans and their species-specific excretion. Harada, K; Inoue, K; Koizumi, A; Morikawa, A; Saito, N; Yoshinaga, T, 2005)	0.33
" The mean terminal half-life was approximately 2 to 3 hours."	( Pharmacokinetics of arundic acid, an astrocyte modulating agent, in acute ischemic stroke. Funakoshi, Y; Hiramatsu, M; Ishibashi, H; Pettigrew, LC, 2007)	0.34
"The present investigation determined the molecular structure and the pharmacokinetic and pharmacodynamic profiles of oral unfractionated heparin containing oral absorption enhancer sodium N-[8-(2-hydroxybenzoyl) amino]caprylate, salcaprozate sodium (SNAC) and assessed the safety and tolerability of the orally dosed heparin solid dosage form versus other routes."	( Pharmacokinetics and pharmacodynamics of oral heparin solid dosage form in healthy human subjects. Aljada, A; Castelli, MC; Chaturvedi, S; Chi, L; Friedman, K; Goldberg, MM; Linhardt, RJ; Mousa, SA; Takieddin, M; Zhang, F; Zhang, H, 2007)	0.34
" Compared with oral administration, maximum plasma concentration (Cmax) was significantly lower, and time to reach Cmax (Tmax) delayed with all formulated tenoxicam TDS."	( Pharmacokinetics of formulated tenoxicam transdermal delivery systems. Chun, I; Gwak, H; Kang, E; Kim, T, 2008)	0.35
" Development of BB2r-targeted agents, based on the bombesin (BBN) peptide, has largely involved the use of the bifunctional chelate approach in which the linking group serves several key roles including pharmacokinetic modification."	( Evaluation of the pharmacokinetic effects of various linking group using the 111In-DOTA-X-BBN(7-14)NH2 structural paradigm in a prostate cancer model. Figueroa, SD; Garrison, JC; Hoffman, TJ; Naz, F; Rold, TL; Sieckman, GL; Sublett, SV; Volkert, WA, 2008)	0.35
"Selecting the appropriate pharmacokinetic (PK) model given the available data is investigated for perfluorooctanoic acid (PFOA), which has been widely analyzed with an empirical, one-compartment model."	( Comparing models for perfluorooctanoic acid pharmacokinetics using Bayesian analysis. Barton, HA; Setzer, RW; Wambaugh, JF, 2008)	0.35
" The pharmacokinetic parameters were calculated using the MULTI computer program."	( Enhanced transdermal absorption and pharmacokinetic evaluation of pranoprofen-ethylene-vinyl acetate matrix containing penetration enhancer in rats. Cho, CW; Choi, JS; Shin, SC; Yang, KH, 2009)	0.35
"To investigate the possible use of a (13)C-uracil breath test for gastric emptying by evaluating the pharmacokinetic properties of (13)C-uracil in a breath test in rats, in comparison with (13)C-acetate and (13)C-octanoate, traditional (13)C-probes for gastric emptying."	( Desirable pharmacokinetic properties of (13)C-uracil as a breath test probe of gastric emptying in comparison with (13)C-acetate and (13)C-octanoate in rats. Hirao, Y; Inada, M; Kashimoto, M; Kunizaki, J; Sato, H; Sugiyama, E; Tobita, K; Yoshida, T, 2009)	0.35
"This study showed that (13)C-uracil has desirable pharmacokinetic properties as an in vivo probe of gastric emptying."	( Desirable pharmacokinetic properties of (13)C-uracil as a breath test probe of gastric emptying in comparison with (13)C-acetate and (13)C-octanoate in rats. Hirao, Y; Inada, M; Kashimoto, M; Kunizaki, J; Sato, H; Sugiyama, E; Tobita, K; Yoshida, T, 2009)	0.35
" Here we describe the application of a simple one compartment pharmacokinetic model to estimate total intakes of PFOA and PFOS for the general population of urban areas on the east coast of Australia."	( Use of simple pharmacokinetic modeling to characterize exposure of Australians to perfluorooctanoic acid and perfluorooctane sulfonic acid. Calafat, AM; Kato, K; Lorber, M; Mueller, JF; Thompson, J; Toms, LL, 2010)	0.36
" We modeled the half-life in former residents who lived in two water districts with high exposure levels using a two-segment log-linear spline."	( Accumulation and clearance of perfluorooctanoic acid (PFOA) in current and former residents of an exposed community. Bartell, SM; Seals, R; Steenland, K, 2011)	0.37
" Half-life was estimated in two water districts comprising a total of 1,573 individuals."	( Accumulation and clearance of perfluorooctanoic acid (PFOA) in current and former residents of an exposed community. Bartell, SM; Seals, R; Steenland, K, 2011)	0.37
" Limited pharmacokinetic data is available in humans; however, human data exists for two communities with drinking water contaminated by PFAAs."	( Evaluation and prediction of pharmacokinetics of PFOA and PFOS in the monkey and human using a PBPK model. Andersen, ME; Campbell, JL; Clewell, HJ; Loccisano, AE, 2011)	0.37
" The other model is a simple one-compartment, first-order pharmacokinetic (PK) model."	( Simple intake and pharmacokinetic modeling to characterize exposure of Americans to perfluoroctanoic acid, PFOA. Egeghy, PP; Lorber, M, 2011)	0.37
" Limited PK data for PFAAs is available for humans; however, toxicological and pharmacokinetic data exist for rats, which can be useful for cross-species extrapolation."	( Comparison and evaluation of pharmacokinetics of PFOA and PFOS in the adult rat using a physiologically based pharmacokinetic model. Andersen, ME; Butenhoff, JL; Campbell, JL; Clewell, HJ; Loccisano, AE, 2012)	0.38
" The half-life of OA was 87."	( An open-label, single-dose, crossover study of the pharmacokinetics and metabolism of two oral formulations of 1-octanol in patients with essential tremor. Bowen, D; Buchwald, P; Dong, C; Grimes, GJ; Hallett, M; Haubenberger, D; Ippolito, D; Kalowitz, D; Nahab, FB; Potti, G; Starling, J; Toro, C; Wittevrongel, L, 2011)	0.37
" The pharmacokinetic properties of vitamin B12 were characterized by noncompartmental analysis."	( Pharmacokinetics of oral cyanocobalamin formulated with sodium N-[8-(2-hydroxybenzoyl)amino]caprylate (SNAC): an open-label, randomized, single-dose, parallel-group study in healthy male subjects. Castelli, MC; Friedman, K; Riley, MG; Wong, DF, 2011)	0.37
"5 and 5 mg PTH134 (containing 200 mg 5-CNAC) demonstrated Cmax and AUC0-last values closest to those of sc teriparatide 20 μg (Forsteo®)."	( The single dose pharmacokinetic profile of a novel oral human parathyroid hormone formulation in healthy postmenopausal women. Arnold, M; Azria, M; Hämmerle, SP; Harfst, E; John, MR; Kiese, B; Launonen, A; Loeffler, R; Mindeholm, L, 2012)	0.38
"The biodistribution data suggest that (EH)3 is able to improve the pharmacokinetic properties of peptidic radiopharmaceuticals, leading to reduced uptake in organs such as the liver, an important site of metastatic disease."	( Pharmacokinetic properties of peptidic radiopharmaceuticals: reduced uptake of (EH)3-conjugates in important organs. Bauder-Wüst, U; Eder, M; Eisenhut, M; Haberkorn, U; Löhr, T; Mier, W; Reber, M; Schäfer, M, 2013)	0.39
"We used a physiologically based pharmacokinetic (PBPK) model of pregnancy to assess how much of the PFAS-birth weight association observed in epidemiologic studies might be attributable to GFR."	( Associations of Perfluoroalkyl Substances (PFAS) with Lower Birth Weight: An Evaluation of Potential Confounding by Glomerular Filtration Rate Using a Physiologically Based Pharmacokinetic Model (PBPK). Andersen, ME; Chen, MH; Clewell, HJ; Hsieh, WS; Kishi, R; Loccisano, AE; Longnecker, MP; Maisonet, M; Marcus, M; McDougall, R; Miyashita, C; Morken, NH; Verner, MA; Wu, H; Yoon, M, 2015)	0.42
"We developed a Monte Carlo (MC) physiologically-based pharmacokinetic (PBPK) model of PFAS to simulate plasma PFAS levels in a hypothetical female population aged 2 to 20years old."	( Can the observed association between serum perfluoroalkyl substances and delayed menarche be explained on the basis of puberty-related changes in physiology and pharmacokinetics? Andersen, ME; Clewell, HJ; Longnecker, MP; Luo, M; Verner, MA; Wu, H; Xue, J; Yoon, M, 2015)	0.42
" In this study, we aimed to (i) develop a two-generation pharmacokinetic model of prenatal and postnatal exposure to perfluorooctanoic acid (PFOA), perfluorooctanesulfonate (PFOS), and perfluorohexanesulfonate (PFHxS); and to (ii) evaluate it against measured children's levels in two studies."	( A Simple Pharmacokinetic Model of Prenatal and Postnatal Exposure to Perfluoroalkyl Substances (PFASs). Fromme, H; Granum, B; Jensen, ET; Longnecker, MP; Ngueta, G; Nygaard, UC; Verner, MA; Völkel, W, 2016)	0.43
"The aim of this study was to confirm and investigate the gender differences in pharmacokinetic (PK) characteristics and tissue distribution of 3 perfluoroalkyl and polyfluoroalkyl substances (PFASs) consisted of perfluorooctanoic acid (PFOA), perfluorooctanesulfonic acid (PFOS), and perfluorohexane sulfonic acid (PFHxS) in both male and female rats."	( Gender differences in pharmacokinetics and tissue distribution of 3 perfluoroalkyl and polyfluoroalkyl substances in rats. Cho, HY; Heo, SH; Hwang, IG; Kim, SJ; Lee, DS; Lee, YB, 2016)	0.43
"Manufacturing of perfluorooctanoic acid (PFOA), a synthetic chemical with a long half-life in humans, peaked between 1970 and 2002, and has since diminished."	( Physiologically based pharmacokinetic modeling of human exposure to perfluorooctanoic acid suggests historical non drinking-water exposures are important for predicting current serum concentrations. Fisher, J; Worley, RR; Yang, X, 2017)	0.46
"Physiologically based pharmacokinetic (PBPK) modeling is a powerful in silico tool that can be used to simulate the toxicokinetics and tissue distribution of xenobiotic substances, such as perfluorooctanoic acid (PFOA), in organisms."	( A Permeability-Limited Physiologically Based Pharmacokinetic (PBPK) Model for Perfluorooctanoic acid (PFOA) in Male Rats. Cheng, W; Ng, CA, 2017)	0.46
" In this study, we reconstruct the past human exposure trends in two different regions, USA and Australia, by inferring the historical intake from cross-sectional biomonitoring data of PFOS, PFOA and PFHxS using a population-based pharmacokinetic model."	( Historical human exposure to perfluoroalkyl acids in the United States and Australia reconstructed from biomonitoring data using population-based pharmacokinetic modelling. Cousins, IT; Gomis, MI; MacLeod, M; Mueller, JF; Vestergren, R, 2017)	0.46
"Physiologically based pharmacokinetic (PBPK) models are considered useful tools to describe the absorption, distribution, metabolism and excretion of xenobiotics."	( Evaluating parameter availability for physiologically based pharmacokinetic (PBPK) modeling of perfluorooctanoic acid (PFOA) in zebrafish. Khazaee, M; Ng, CA, 2018)	0.48
" The pharmacokinetic parameters upon oral administration were calculated using the GastroPlus software."	( Improved Oral Pharmacokinetics of Pentoxifylline with Palm Oil and Capmul® MCM Containing Self-Nano-Emulsifying Drug Delivery System. Ghate, VM; Kinra, M; Lewis, SA; Shailendrakumar, AM, 2020)	0.56
" Recent data suggest that sodium N-[8-(2-hydroxybenzoyl) amino] caprylate (SNAC) is an effective permeability enhancer, yet the pharmacokinetic (PK) and systemic effects of SNAC are poorly understood, specifically its oral bioavailability and systemic effects on distribution, which could influence the safety of certain drugs."	( Evaluating the Pharmacokinetics and Systemic Effects of a Permeability Enhancer Sodium N-[8-(2-hydroxybenzoyl)amino] Caprylate in Rats. Chen, JZ; Chiang, PC; Deshmukh, G; Durk, MR; Li, R; Liu, J; Nagapudi, K; Plise, EG; Valle, N, 2020)	0.56
" We evaluated this by linking a model of thyroid disease status over the lifetime to a physiologically based pharmacokinetic model of PFOA and PFOS."	( Pharmacokinetic bias analysis of an association between clinical thyroid disease and two perfluoroalkyl substances. Allen, BC; Clewell, HJ; Dzierlenga, MW; Longnecker, MP, 2020)	0.56
"Physiologically based pharmacokinetic (PBPK) modeling is a powerful technique to inform risk assessment of xenobiotic substances such as perfluorooctanoic acid (PFOA)."	( Bayesian Refinement of the Permeability-Limited Physiologically Based Pharmacokinetic Model for Perfluorooctanoic Acid in Male Rats. Cheng, W; Ng, CA, 2021)	0.62
"These three Phase I trials showed that N-AbA and excipient SNAC had excellent linear pharmacokinetic characteristics."	( Open-Label, Phase I, Pharmacokinetic Studies in Healthy Chinese Subjects to Evaluate the Bioequivalence and Food Effect of a Novel Formulation of Abiraterone Acetate Tablets. Feng, Z; Huang, J; Huang, Y; Kuang, Y; Li, J; Liu, Y; Pei, Q; Yang, G; Yang, S; Ye, L, 2022)	0.72

Excerpt	Reference	Relevance
"The antilisterial activity of monocaprylin (MC) and its combination with acetic acid (AA) on frankfurters was investigated."	( Inactivation of Listeria monocytogenes on frankfurters by monocaprylin alone or in combination with acetic acid. Amalaradjou, MA; Annamalai, T; Dzurec, D; Faustman, C; Garcia, M; Hoagland, T; Lee, S; Nair, MK; Surendranath, S; Venkitanarayanan, K, 2007)	0.34
" Moreover, more information can be provided on the evaluation of toxicity of phorate using metabonomics combined with clinical chemistry."	( Metabonomics evaluation of urine from rats administered with phorate under long-term and low-level exposure by ultra-performance liquid chromatography-mass spectrometry. Guo, L; Hou, Y; Sun, C; Sun, X; Xu, W; Zeng, Y; Zhao, X, 2014)	0.4
" The results show that PFOA can be greatly combined with MnOx formed in-situ through a Mn(II) oxidation process by free chlorine."	( Enhanced perfluorooctanoic acid (PFOA) accumulation by combination with in-situ formed Mn oxides under drinking water conditions. Chen, R; Shi, B; Yu, Y; Zhuang, Y, 2021)	0.62

Excerpt	Reference	Relevance
" When the absorption rate was plotted against the perfusate concentration, a linear relationship was found between these two parameters in the ileum and colon."	( Vitamin K2 colonic and ileal in vivo absorption: bile, fatty acids, and pH effects on transport. Hollander, D; Rim, E; Ruble, PE, 1977)	0.26
" Increasing the bile salt concentration to 20 mM or the addition of long chain fatty acids, monoolein, or lecithin all resulted in significant (P less than 0-05) decrease in the absorption rate of the vitamin."	( Factors affecting the absorption of vitamin K-1 in vitro. Hollander, D; Rim, E, 1976)	0.26
" The good bioavailability and the long duration of action of some of these compounds was demonstrated using ex vivo measurement of the TxRA activity upon oral administration to guinea pigs."	( Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 4. 8-[[(4-Chlorophenyl)sulfonyl]amino]-4-(3-(3-pyridinyl) propyl)octanoic acid and analogs. Bhagwat, SS; Boswell, C; Cohen, DS; Contardo, N; Dotson, R; Furness, P; Gude, C; Lee, W; Mathis, J; Zoganas, H, 1992)	0.28
" After rectal administration in the absence of absorption-promoter, the bioavailability of acyclovir was 37%."	( The effect of fatty acids on the rectal absorption of acyclovir in rats. Itoh, S; Kobayashi, M; Komatsu, T; Sawanoi, M; Suzuki, S; Tanabe, K; Yamazaki, M, 1990)	0.28
" However, GM absorption was marked when 90 mg of solid SA or CA was added (the bioavailability of GM was 58% with SA, and 59% with CA)."	( Rectal absorption enhancement of gentamicin in rabbits from hollow type suppositories by sodium salicylate or sodium caprylate. Matsumoto, M; Matsumoto, Y; Murakami, C; Murakoshi, R; Tojima, T; Watanabe, Y, 1989)	0.28
" This study demonstrates that MO can be used in the two types of hollow suppositories as an effective enhancing agent of rectal absorption of poorly absorbed drugs such as GM."	( Enhancing effect of glyceryl-1-monooctanoate on the rectal absorption of gentamicin from hollow-type suppositories in rabbits. Hori, N; Ku, YS; Matsumoto, M; Matsumoto, Y; Naritomi, S; Watanabe, Y, 1989)	0.28
" These actions of caprylate on membranes are considered one possible mechanism by which it promotes the absorption of water-soluble and poorly absorbed drugs."	( Fluorescence study of the membrane-perturbing action of sodium caprylate as related to promotion of drug absorption. Awazu, S; Hayashi, M; Horie, T; Kajii, H, 1988)	0.27
" In the in vivo evaluation using abdominal rat skin, the ethanol/panasate 800 (40/60)-7% (w/w) ethylcellulose gel produced a good feature as a sustained-release preparation, with a relatively high bioavailability (BA) of theophylline, and dose dependency was observed."	( Transdermal delivery of theophylline using an ethanol/panasate 800-ethylcellulose gel preparation. Goto, S; Kim, NS; Kitagawa, K; Lee, CK; Uchida, T, 1995)	0.29
" This indicates that the enantiomers have pharmacologic profile and bioavailability similar to that of the corresponding racemic compound."	( Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 5. Synthesis and evaluation of enantiomers of 8-[[(4-chlorophenyl)sulfonyl]amino]-4-(3-pyridinylalkyl)octanoic acid. Bhagwat, SS; Cohen, DS; Dotson, R; Furness, P; Gude, C; Lee, W; Mathis, J, 1993)	0.29
" The absorption enhancing activity of w/o microemulsions incorporating these lipids was evaluated in the rat using Calcein (MW = 623) a water-soluble and poorly absorbed marker molecule."	( Water-in-oil microemulsions containing medium-chain fatty acids/salts: formulation and intestinal absorption enhancement evaluation. Constantinides, PP; Ellens, H; Owen, AB; Smith, PL; Sturgis, S; Welzel, G; Yiv, SH, 1996)	0.29
" However, SNAC itself was well absorbed across Caco-2 and its mechanism of permeation was determined."	( Heparin absorption across the intestine: effects of sodium N-[8-(2-hydroxybenzoyl)amino]caprylate in rat in situ intestinal instillations and in Caco-2 monolayers. Agarwal, R; Brayden, D; Creed, E; Leipold, H; Leone-Bay, A; O'Connell, A, 1997)	0.3
" The development of oral heparin therapy, based on combining heparin with the carrier molecule Sodium N-(8[2-hydroxybenzoyl]amino) caprylate (SNAC) to enhance its intestinal absorption and bioavailability for the prophylaxis and treatment of DVT has been demonstrated to be effective in animal models."	( Development of oral heparin therapy for prophylaxis and treatment of deep venous thrombosis. Money, SR; York, JW, 2001)	0.31
"The oral bioavailability of heparin is negligible."	( Pathway of oral absorption of heparin with sodium N-[8-(2-hydroxybenzoyl)amino] caprylate. Dinh, S; Gomez-Orellana, I; Malkov, D; Wang, HZ, 2002)	0.31
"To study the relationship between cellular membrane fluidity and relative bioavailability (Fr) of protein and peptide drugs combined with absorption enhancers after pulmonary administration in rats."	( [Study on pulmonary delivery of peptide drugs in rats: effects of absorption enhancers on cellular membrane fluidity]. Wang, ZY; Zhang, Q, 2003)	0.32
"Tacrolimus is characterized by a highly variable oral bioavailability and narrow therapeutic window."	( The rate of gastric emptying determines the timing but not the extent of oral tacrolimus absorption: simultaneous measurement of drug exposure and gastric emptying by carbon-14-octanoic acid breath test in stable renal allograft recipients. Claes, K; Evenepoel, P; Kuypers, DR; Maes, B; Vanrenterghem, Y, 2004)	0.32
"The present study revealed that the self-nanoemulsified drug delivery system of all-trans-retinol acetate increased its dissolution rate and has the potential to enhance its bioavailability without interaction or incompatibility between the ingredients."	( Preparation and in vitro characterization of self-nanoemulsified drug delivery system (SNEDDS) of all-trans-retinol acetate. Al-Saidan, S; Khan, MA; Samy, AM; Taha, EI, 2004)	0.32
"It is important to characterize drug-albumin binding during drug discovery and lead optimization as strong binding may reduce bioavailability and/or increase the drug's in vivo half-life."	( Epitope mapping and competitive binding of HSA drug site II ligands by NMR diffusion measurements. Larive, CK; Lucas, LH; Price, KE, 2004)	0.32
"Oral administration of sodium N-[8-(2-hydroxybenzoyl)amino]caprylate (SNAC) has been reported to increase the bioavailability of various macromolecules."	( Investigation of the enhancing mechanism of sodium N-[8-(2-hydroxybenzoyl)amino]caprylate effect on the intestinal permeability of polar molecules utilizing a voltage clamp method. Hess, S; Hoffman, A; Rotshild, V, 2005)	0.33
" Oral bioavailability of 38a was 16% in marmosets."	( Novel 2,7-dialkyl-substituted 5(S)-amino-4(S)-hydroxy-8-phenyl-octanecarboxamide transition state peptidomimetics are potent and orally active inhibitors of human renin. Baum, HP; Cohen, NC; Cumin, F; Forgiarini, P; Fuhrer, W; Göschke, R; Gruetter, MG; Maibaum, J; Rahuel, J; Rasetti, V; Rigollier, P; Schilling, W; Schnell, CR; Stutz, S; Wagner, T; Wood, JM, 2007)	0.34
" The pharmacokinetics and bioavailability of quinupramine from an EVA matrix were examined to determine the level of percutaneous absorption in rats."	( Development and biopharmaceutical evaluation of quinupramine-EVA matrix containing penetration enhancer for the enhanced transdermal absorption in rats. Cho, CW; Kim, J; Kim, SJ; Kim, WJ; Shin, SC, 2007)	0.34
" The vehicle-dependent bioavailability of FLA suggests a need for the judicious selection of vehicles in evaluating oral toxicity studies for risk assessment purposes."	( Vehicle-dependent disposition kinetics of fluoranthene in Fisher-344 rats. Harris, DL; Hood, DB; Ramesh, A, 2008)	0.35
" The pharmacokinetics and bioavailability of pranoprofen, an anti-inflammatory drug, were examined to determine the feasibility of an enhanced transdermal delivery system for pranoprofen from an EVA matrix containing caprylic acid as the enhancer in rats."	( Enhanced transdermal absorption and pharmacokinetic evaluation of pranoprofen-ethylene-vinyl acetate matrix containing penetration enhancer in rats. Cho, CW; Choi, JS; Shin, SC; Yang, KH, 2009)	0.35
"All the (13)C-probes employed were well absorbed from the intestine after intraduodenal administration."	( Desirable pharmacokinetic properties of (13)C-uracil as a breath test probe of gastric emptying in comparison with (13)C-acetate and (13)C-octanoate in rats. Hirao, Y; Inada, M; Kashimoto, M; Kunizaki, J; Sato, H; Sugiyama, E; Tobita, K; Yoshida, T, 2009)	0.35
" Such binding plays a crucial role in determining the ADME (absorption, distribution, metabolism, and excretion) and bioavailability of the pollutants."	( Combined fluorescence and electrochemical investigation on the binding interaction between organic acid and human serum albumin. Chen, YM; Guo, LH, 2009)	0.35
"A self-microemulsifying drug delivery system (SMEDDS) has been developed to enhance diffusion rate and oral bioavailability of valsartan."	( Preparation and bioavailability assessment of SMEDDS containing valsartan. Dixit, AR; Patel, SG; Rajput, SJ, 2010)	0.36
" An increase of 63% in the relative bioavailability compared with the commercial suspension was obtained with ABZ-SMEDDS as measured by albendazole sulfoxide (ABZSO) plasma levels."	( Development and oral bioavailability assessment of a supersaturated self-microemulsifying drug delivery system (SMEDDS) of albendazole. Mukherjee, T; Plakogiannis, FM, 2010)	0.36
" Vitamin B12 absolute bioavailability estimates were calculated between the oral (A, B, and C) and IV (D) treatments using non-baseline-adjusted vitamin B12 concentrations as well as baseline-adjusted vitamin B12 concentrations, with or without body weight adjustments."	( Pharmacokinetics of oral cyanocobalamin formulated with sodium N-[8-(2-hydroxybenzoyl)amino]caprylate (SNAC): an open-label, randomized, single-dose, parallel-group study in healthy male subjects. Castelli, MC; Friedman, K; Riley, MG; Wong, DF, 2011)	0.37
" The oral cyanocobalamin formulation containing SNAC had greater mean absolute bioavailability than the commercial oral formulation (5."	( Pharmacokinetics of oral cyanocobalamin formulated with sodium N-[8-(2-hydroxybenzoyl)amino]caprylate (SNAC): an open-label, randomized, single-dose, parallel-group study in healthy male subjects. Castelli, MC; Friedman, K; Riley, MG; Wong, DF, 2011)	0.37
"An oral formulation of 5-mg cyanocobalamin containing 100-mg SNAC, an absorption enhancer, provided significantly improved bioavailability and a significant decrease in T(max) for B12 in a small study of normal healthy subjects compared with a commercially available 5-mg cyanocobalamin oral formulation."	( Pharmacokinetics of oral cyanocobalamin formulated with sodium N-[8-(2-hydroxybenzoyl)amino]caprylate (SNAC): an open-label, randomized, single-dose, parallel-group study in healthy male subjects. Castelli, MC; Friedman, K; Riley, MG; Wong, DF, 2011)	0.37
" Oral bioavailability of the tablets was examined in fasted beagle dogs."	( Novel gastroretentive sustained-release tablet of tacrolimus based on self-microemulsifying mixture: in vitro evaluation and in vivo bioavailability test. Gan, Y; Wang, YP; Zhang, XX, 2011)	0.37
" Compared with the commercially available capsules of tacrolimus, the relative bioavailability of the SME gastroretentive sustained-release tablets was 553."	( Novel gastroretentive sustained-release tablet of tacrolimus based on self-microemulsifying mixture: in vitro evaluation and in vivo bioavailability test. Gan, Y; Wang, YP; Zhang, XX, 2011)	0.37
"SME gastroretentive sustained-release tablets can enhance the oral bioavailability of tacrolimus with poor solubility and a narrow absorption window."	( Novel gastroretentive sustained-release tablet of tacrolimus based on self-microemulsifying mixture: in vitro evaluation and in vivo bioavailability test. Gan, Y; Wang, YP; Zhang, XX, 2011)	0.37
"Carvedilol, a widely prescribed cardiovascular drug for hypertension and congestive heart failure, exhibits low and variable bioavailability owing to poor absorption and extensive hepatic first-pass metabolism."	( Development of optimized self-nano-emulsifying drug delivery systems (SNEDDS) of carvedilol with enhanced bioavailability potential. Bandyopadhyay, S; Kapil, R; Katare, OO; Khurana, L; Singh, B, 2011)	0.37
" In four cohorts of 28, 21, 19 and 29 healthy volunteers, the impact of the carrier molecule sodium N-[8-(2-hydroxybenzoyl) amino] caprylate (SNAC, CAS number: 203787-91-1) on the bioavailability of IBN was investigated."	( Phase I clinical study to select a novel oral formulation for ibandronate containing the excipient sodium N-[8-(2-hydroxybenzoyl) amino] caprylate (SNAC). Ahmed, H; Bittner, B; Chokshi, H; Fotaki, N; Infeld, M; Jordan, P; Ma, H; McIntyre, C; Phuapradit, W; Portron, A; Schmidt, J; Shah, N; Tang, K; Tian, H, 2012)	0.38
"To improve the solubility, permeability and oral bioavailability of cefpodoxime proxetil, β-lactam antibiotic."	( Self-nanoemulsifying drug delivery system of cefpodoxime proxetil containing tocopherol polyethylene glycol succinate. Bajaj, A; Khole, I; Munjapara, G; Rao, MR, 2013)	0.39
"SNEDDS formulations led to improved oral bioavailability due to enhanced solubilization of selected drug."	( Self-nanoemulsifying drug delivery system of cefpodoxime proxetil containing tocopherol polyethylene glycol succinate. Bajaj, A; Khole, I; Munjapara, G; Rao, MR, 2013)	0.39
"A solid form of self-microemulsifying drug delivery system (Solid SMEDDS) was developed by spray-drying with dextran as the inert solid carrier, to improve the oral bioavailability of a poorly water-soluble drug, fenofibrate."	( Enhancement of oral bioavailability of fenofibrate by solid self-microemulsifying drug delivery systems. Choi, HG; Hiep, TT; Kim, GG; Kim, JO; Lee, DW; Marasini, N; Poudel, BK; Yang, KY; Yong, CS, 2013)	0.39
"This study is the first to demonstrate in canines the ability of silica-lipid hybrid (SLH) microparticles to enhance the bioavailability and efficacy of a poorly water-soluble drug after oral administration."	( Silica-lipid hybrid (SLH) formulations enhance the oral bioavailability and efficacy of celecoxib: An in vivo evaluation. Boyd, BJ; Edwards, GA; Ngo, D; Nguyen, TH; Porter, CJ; Prestidge, CA; Santos, L; Tan, A, 2013)	0.39
"2-fold improved oral bioavailability of leuprolide oleate SMEDDS compared to a leuprolide acetate control solution."	( In vivo evaluation of an oral self-microemulsifying drug delivery system (SMEDDS) for leuprorelin. Bernkop-Schnürch, A; Hauptstein, S; Hintzen, F; Laffleur, F; Müller, C; Perera, G, 2014)	0.4
" In general, this research provides important information about the factors influencing the bioaccessibility of emulsified vitamin E, which could be used to design more effective emulsion-based delivery systems for increasing the oral bioavailability of this important bioactive component."	( Enhancing vitamin E bioaccessibility: factors impacting solubilization and hydrolysis of α-tocopherol acetate encapsulated in emulsion-based delivery systems. Decker, EA; McClements, DJ; Xiao, H; Yang, Y, 2015)	0.42
" The solubility and bioavailability of poorly soluble drugs can be enhanced by self-nanoemulsifying systems."	( The preparation and evaluation of self-nanoemulsifying systems containing Swietenia oil and an examination of its anti-inflammatory effects. Aziz, R; Eid, AM; El-Enshasy, HA; Elmarzugi, NA, 2014)	0.4
"The bioavailability of perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) in seven biosolids-amended soils without any additionally spiking to earthworms (Eisenia fetida) was studied."	( Bioavailability of perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) in biosolids-amended soils to earthworms (Eisenia fetida). Hu, X; Li, L; Liu, Y; Shan, XQ; Wen, B; Zhang, H; Zhang, S, 2015)	0.42
"Food is a major source of human exposure to perfluorooctanoic acid (PFOA), however, PFOA bioavailability in food has not been studied."	( In vivo bioavailability and in vitro bioaccessibility of perfluorooctanoic acid (PFOA) in food matrices: correlation analysis and method development. Cui, XY; Juhasz, AL; Li, C; Li, K; Ma, LQ; Yu, NY, 2015)	0.42
" By optimizing the mixed oil formulation, the absolute amount of surfactant in drug-loaded microemulsions was reduced but increased drug oral bioavailability in rats was maintained."	( Optimized mixed oils remarkably reduce the amount of surfactants in microemulsions without affecting oral bioavailability of ibuprofen by simultaneously enlarging microemulsion areas and enhancing drug solubility. Chen, Y; Hu, H; Huang, H; Liu, D; Mai, J; Song, J; Tuo, J; Wu, C; Xie, Y; You, X, 2015)	0.42
"The current study was aimed to investigate the potential of solid self-nanoemulsifying drug delivery system (S-SNEDDS) composed of Capmul MCM C8 (oil), Tween 80 (surfactant) and Transcutol P (co-surfactant) in improving the dissolution and oral bioavailability of darunavir."	( Solid self-nanoemulsifying drug delivery system (S-SNEDDS) of darunavir for improved dissolution and oral bioavailability: In vitro and in vivo evaluation. Bandari, S; Dhurke, R; Eedara, BB; Inugala, S; Jukanti, R; Kandadi, P; Sunkavalli, S, 2015)	0.42
" This study suggests that the effects of DOM on PFAS bioconcentration depend not only on the concentration but also on the molecule weight of DOM, which should be considered in the bioavailability assessment of PFASs."	( Bioconcentration of perfluoroalkyl substances by Chironomus plumosus larvae in water with different types of dissolved organic matters. Chen, X; Li, H; Li, Y; Wang, H; Wen, W; Xia, X; Zhu, B, 2016)	0.43
" Thus, WT soil being sandy in nature with low clay content showed higher PFOA bioavailability and hence showed higher toxicity."	( Toxicity of perfluorooctanoic acid towards earthworm and enzymatic activities in soil. He, W; Megharaj, M; Naidu, R, 2016)	0.43
" These findings suggested important evidence that the co-existence of PFASs and Cd reduced the bioavailability of PFASs while enhanced the bioavailability of Cd in soil, which increased the associated environmental risk for Cd but decreased for PFASs."	( Interaction effects on uptake and toxicity of perfluoroalkyl substances and cadmium in wheat (Triticum aestivum L.) and rapeseed (Brassica campestris L.) from co-contaminated soil. Fan, Z; Liu, L; Sun, L; Xing, Y; Zhao, S; Zhou, T, 2017)	0.46
" However, NAC suffers from drawbacks such as poor oral bioavailability and suboptimal blood-brain-barrier (BBB) permeability limiting its clinical success."	( Pediatric oral formulation of dendrimer-N-acetyl-l-cysteine conjugates for the treatment of neuroinflammation. Ghandehari, H; Kambhampati, SP; Kannan, RM; Mishra, MK; Mohammadpour, R; Sayre, C; Yellepeddi, VK, 2018)	0.48
" The aim of the presented study was to improve the bioavailability of a dermal administered tetrapeptide GEKG (amino acid sequence in one-letter notation)."	( Dermal peptide delivery using enhancer molecules and colloidal carrier systems. Part III: Tetrapeptide GEKG. Mentel, M; Mrestani, Y; Neubert, RHH; Sommer, E; Tuchscherer, B; Wohlrab, J, 2018)	0.48
" The performed cytotoxicity, cell apoptosis and pharmacokinetic experiments showed an enhanced bioavailability of BUF after encapsulation."	( In situ phase transition of microemulsions for parenteral injection yielding lyotropic liquid crystalline carriers of the antitumor drug bufalin. Angelova, A; Drechsler, M; Garamus, VM; Gong, Y; Li, N; Li, Y; Liu, J; Zou, A, 2019)	0.51
" The soil concentrations were influenced by multiple physicochemical properties of the soil, which suggests differences in bioavailability and sorption/desorption capacities between different soil types."	( Influence of soil physicochemical properties on the depth profiles of perfluoroalkylated acids (PFAAs) in soil along a distance gradient from a fluorochemical plant and associations with soil microbial parameters. Bervoets, L; Eens, M; Groffen, T; Prinsen, E; Rijnders, J; Verbrigghe, N; Verbruggen, E, 2019)	0.51
" Rh_2 possessed variety of activities,but bioavailability of oral administration Rh_2 was extremely low due to poor absorption."	( [Synthesis and anti-tumor activity of ginsenoside Rh_2 caprylic acid monoester]. Liu, FG; Zhang, WY; Zheng, YN, 2019)	0.51
"Abiraterone acetate (AbA) is a poorly water-soluble drug with an oral bioavailability of <10% and a significant pharmaceutical food effect."	( Supersaturated-Silica Lipid Hybrids Improve in Vitro Solubilization of Abiraterone Acetate. Joyce, P; Prestidge, CA; Schultz, HB; Thomas, N, 2020)	0.56
"SLH and super-SLH improve in vitro solubilization of AbA, remove the food effect and demonstrate potential to improve oral bioavailability in vivo."	( Supersaturated-Silica Lipid Hybrids Improve in Vitro Solubilization of Abiraterone Acetate. Joyce, P; Prestidge, CA; Schultz, HB; Thomas, N, 2020)	0.56
" The present study aimed to formulate, characterize, and improve the oral bioavailability of PTX using SNEDDS."	( Improved Oral Pharmacokinetics of Pentoxifylline with Palm Oil and Capmul® MCM Containing Self-Nano-Emulsifying Drug Delivery System. Ghate, VM; Kinra, M; Lewis, SA; Shailendrakumar, AM, 2020)	0.56
" Recent data suggest that sodium N-[8-(2-hydroxybenzoyl) amino] caprylate (SNAC) is an effective permeability enhancer, yet the pharmacokinetic (PK) and systemic effects of SNAC are poorly understood, specifically its oral bioavailability and systemic effects on distribution, which could influence the safety of certain drugs."	( Evaluating the Pharmacokinetics and Systemic Effects of a Permeability Enhancer Sodium N-[8-(2-hydroxybenzoyl)amino] Caprylate in Rats. Chen, JZ; Chiang, PC; Deshmukh, G; Durk, MR; Li, R; Liu, J; Nagapudi, K; Plise, EG; Valle, N, 2020)	0.56
"Silica-lipid hybrid (SLH) microparticles are a solidified lipid-based drug delivery system under investigation for their aptitude to enhance the oral bioavailability of poorly water-soluble drugs."	( Enhancing the oral bioavailability of simvastatin with silica-lipid hybrid particles: The effect of supersaturation and silica geometry. Meola, TR; Peressin, KF; Prestidge, CA; Schultz, HB, 2020)	0.56
"Transient permeability enhancers (PEs), such as caprylate, caprate, and salcaprozate sodium (SNAC), improve the bioavailability of poorly permeable macromolecular drugs."	( Influence of Bile Composition on Membrane Incorporation of Transient Permeability Enhancers. Bergström, CAS; Höök, F; Hossain, S; Jõemetsa, S; Joyce, P; Larsson, P; Parrow, A, 2020)	0.56
" In this study, the uptake of 14C-PFOA from soil by alfalfa and 14C-PFOA bioavailability from consumption of this alfalfa was evaluated in Sprague-Dawley rats."	( Perfluorooctanoic Acid Uptake by Alfalfa (Medicago sativa) and Bioavailability in Sprague-Dawley Rats. Hakk, H; Lupton, SJ, 2021)	0.62
" In this study, the uptake of 14C-PFOA from soil by alfalfa and 14C-PFOA bioavailability from consumption of this alfalfa was evaluated in Sprague-Dawley rats."	( Perfluorooctanoic Acid Uptake by Alfalfa (Medicago sativa) and Bioavailability in Sprague-Dawley Rats. Hakk, H; Lupton, SJ, 2021)	0.62
"The objective of this study was to develop a novel acetaminophen and tramadol hydrochloride-loaded soft capsule (ATSC) with enhanced bioavailability of tramadol."	( Acetaminophen and tramadol hydrochloride-loaded soft gelatin capsule: preparation, dissolution and pharmacokinetics in beagle dogs. Cho, JH; Choi, HG, 2021)	0.62
" However, oral administration of biological drugs exhibits low oral bioavailability (BA) due to enzymatic degradation and low intestinal absorption."	( In Silico-Based Experiments on Mechanistic Interactions between Several Intestinal Permeation Enhancers with a Lipid Bilayer Model. Hossain, S; Kneiszl, R; Larsson, P, 2022)	0.72
" Extensive analysis in other self-cultivated food items on a larger spatial scale is highly recommended, taking into account potential factors that may affect PFAS bioavailability to garden produce."	( Home-produced eggs: An important human exposure pathway of perfluoroalkylated substances (PFAS). Bervoets, L; Coertjens, D; Eens, M; Gebbink, WA; Groffen, T; Hofman, J; Lasters, R, 2022)	0.72

Excerpt	Relevance	Reference
" The hourly 14CO2 production was measured for 12 h for estimating the oxidation rate of dosed triacylglycerols."	( Limits of medium-chain and long-chain triacylglycerol utilization by neonatal piglets. Chiang, SH; Clarke, SD; Cornelius, SG; Pettigrew, JE, 1990)	0.28
" The dose-response curve for NH4Cl was affected by simultaneous subcoma doses of VP and OA but not by PB."	( Valproic acid induction of coma in rats: synergism with NH4+ and pentobarbital. Lyftogt, C; Zieve, L, 1989)	0.28
" To circumvent the effects of LCFAO inhibition, diabetic mice were dosed with TDGA and given a diet containing 9% octanoic acid."	( Prevention of the metabolic effects of 2-tetradecylglycidate by octanoic acid in the genetically diabetic mouse (db/db). Bahl, JJ; Bressler, R; Lee, SM, 1985)	0.27
" The catecholamine analogue dose-response curves were shifted to the right."	( Impaired metabolic response to nerve stimulation in brown adipose tissue of hypothyroid rats. Giacobino, JP; Girardier, L; Seydoux, J, 1982)	0.26
"3 mg, single dosage per mouse) and 2-bromoethanol in 2 dosages (1."	( [Carcinogenic activity of ethylene oxide and its reaction products 2-chlorethanol, 2-bromoethanol, ethylene glycol and diethylene glycol. II. Testing of 2-chlorethanol and 2-bromoethanol for carcinogenic activity]. Dunkelberg, H, 1983)	0.27
" When various smaller dosage combinations of NH+4, methanethiol, and octanoic acid were injected simultaneously, coma occurred at lower brain and blood concentrations of ammonia and methanethiol."	( Brain methanethiol and ammonia concentrations in experimental hepatic coma and coma induced by injections of various combinations of these substances. Doizaki, WM; Lyftogt, C; Zieve, L, 1984)	0.27
" The effects of cholestyramine rapidly disappeared when it was withdrawn from the diet, while the effects of gemfibrozil persisted after dosage was stopped."	( Some comparative effects of gemfibrozil, clofibrate, bezafibrate, cholestyramine and compactin on sterol metabolism in rats. Maxwell, RE; Nawrocki, JW; Uhlendorf, PD, 1983)	0.27
" Rats from each group were killed at 2, 4, 8, and 16 days after dosing for fatty acid analysis."	( The acute toxicity of perfluorooctanoic and perfluorodecanoic acids in male rats and effects on tissue fatty acids. Andersen, ME; Olson, CT, 1983)	0.27
" Dose-response curves were developed which showed that one-half the animals became deeply comatose with 540 mumol of intraperitoneal phenol and 100% with 600 mumol."	( Encephalopathic effect of phenol in rats. Brunner, G; Lyftogt, C; Windus-Podehl, G; Zieve, L, 1983)	0.27
"Two experiments were conducted to investigate the causes of the failure of orally dosed medium-chain triglycerides (MCT) in improving the survival of neonatal pigs."	( Causes of reduced survival of neonatal pigs by medium-chain triglycerides: blood metabolite and behavioral activity approaches. Chiang, SH; Lee, HF; Lin, CL, 1995)	0.29
"05) with increasing MCT dosage through 9 mL of NE and 6 mL of emulsified MCT."	( Utilization of medium-chain triglycerides by neonatal pigs: effects of emulsification and dose delivered. Lin, X; Odle, J; Wieland, TM, 1993)	0.29
" Five groups of approximately 20 pregnant female rats received TCAN in CO at 15, 35, 55, and 75 mg/kg/d, and in Tricap at 15 mg/kg/d (10 ml/kg dosing volume)."	( Developmental effects of trichloroacetonitrile administered in corn oil to pregnant Long-Evans rats. Christ, SA; Read, EJ; Smith, MK; Stober, JA, 1996)	0.29
" The dose-response for palmitate was similar for the increase in TG and inhibition of glucose-induced insulin secretion."	( Inhibitory effects of fatty acids on glucose-regulated B-cell function: association with increased islet triglyceride stores and altered effect of fatty acid oxidation on glucose metabolism. Grill, VE; Ling, ZC; Zhou, YP, 1996)	0.29
"Increases in activated partial thromboplastin time (aPTT), anti-factors IIa and Xa, and tissue factor pathway inhibitor (TFPI) concentrations were detected when normal volunteers were dosed with 10."	( Oral delivery of anticoagulant doses of heparin. A randomized, double-blind, controlled study in humans. Agarwal, RK; Baughman, RA; Catella-Lawson, F; FitzGerald, GA; Kapoor, SC; Kisicki, J, 1998)	0.3
" Anti-Xa levels were elevated at 15 minutes after dosing in the OHEP/SNAC group and remained significantly elevated at 4 hours (P<0."	( Orally administered unfractionated heparin with carrier agent is therapeutic for deep venous thrombosis. Baughman, RA; Gonze, MD; Leone-Bay, A; Money, SR; Salartash, K; Sternbergh, WC, 2000)	0.31
" Unfortunately, PTH is only effective when dosed by injection because it has no oral bioavailability."	( Oral delivery of biologically active parathyroid hormone. Baughman, RA; Carozza, M; Chou, J; Hunt, AH; Leone-Bay, A; McDonough, J; Paton, D; Sarubbi, D; Sato, M, 2001)	0.31
"SV2 cells; kinetics and dose-response studies established that maximal MCAD gene stimulation was reached 4 h after addition of 50 microM oleate (C18:1) in the culture medium."	( Effects of fatty acids on mitochondrial beta-oxidation enzyme gene expression in renal cell lines. Bastin, J; Djouadi, F; Ouali, F, 2002)	0.31
" One 30/20 mg/kg/day monkey developed the signs of toxicity noted above and a possible dosing injury, and this monkey was sacrificed in extremis on Day 29."	( Toxicity of ammonium perfluorooctanoate in male cynomolgus monkeys after oral dosing for 6 months. Butenhoff, J; Costa, G; Elcombe, C; Farrar, D; Hansen, K; Iwai, H; Jung, R; Kennedy, G; Lieder, P; Olsen, G; Thomford, P, 2002)	0.31
" Male and female Sprague-Dawley rats were dosed orally with 0, 1, 3, 10, or 30 mg/kg APFO."	( The reproductive toxicology of ammonium perfluorooctanoate (APFO) in the rat. Butenhoff, JL; Frame, SR; Kennedy, GL; O'Connor, JC; York, RG, 2004)	0.32
"The pharmacokinetics of perfluorooctanoate (PFOA) in cynomolgus monkeys were studied in a six-month oral capsule dosing study of ammonium perfluorooctanoate (APFO) and in a single-dose iv study."	( Pharmacokinetics of perfluorooctanoate in cynomolgus monkeys. Butenhoff, JL; Gorman, GS; Hansen, KJ; Hinderliter, PM; Jung, R; Kennedy, GL; Lieder, PH; Noker, PE; Thomford, PJ, 2004)	0.32
" Time-mated female rats were dosed by oral gavage once daily at concentrations of 3, 10, or 30 mg/kg/day of the ammonium salt of PFOA (APFO) starting on gestation (G) day 4 and continuing until sacrifice."	( Perfluorooctanoate: Placental and lactational transport pharmacokinetics in rats. Butenhoff, JL; Gannon, SA; Hinderliter, PM; Kennedy, GL; Mylchreest, E, 2005)	0.33
" Exogenous ghrelin increased food intake in both genotypes with a bell-shaped dose-response curve that was shifted to the left in ghrelin(-/-) mice."	( Energy homeostasis and gastric emptying in ghrelin knockout mice. Buyse, J; Coulie, B; Cryns, K; De Smet, B; Depoortere, I; Moechars, D; Moreaux, B; Peeters, TL; Swennen, Q; Tack, J, 2006)	0.33
" Mean body weights were about 20% lower in rats and mice dosed with 30 mg/kg of linear/branched or linear APFO compared to controls, and 3-5% lower in animals dosed with 30 mg/kg of branched APFO."	( Comparative responses of rats and mice exposed to linear/branched, linear, or branched ammonium perfluorooctanoate (APFO). Everds, NE; Finlay, C; Frame, SR; Gillies, PJ; Kennedy, GL; Loveless, SE; O'Connor, JC; Powley, CR, 2006)	0.33
" These results demonstrate that the pharmacokinetic properties of inhaled PFOA in male and female rats are similar to those observed in male and female rats following oral dosing with PFOA."	( Perfluorooctanoic acid: relationship between repeated inhalation exposures and plasma PFOA concentration in the rat. DeLorme, MP; Hinderliter, PM; Kennedy, GL, 2006)	0.33
" Objectives were to simultaneously determine plasma LD elimination, gastric emptying, and clinical response after a single intake of the same LD dosage as LD/CD--or as (LD/CD/EN) formulation on 2 consecutive days."	( Impact of gastric emptying on levodopa pharmacokinetics in Parkinson disease patients. Bremen, D; Erdmann, C; Goetze, O; Muhlack, S; Müller, T; Schmidt, WE; Woitalla, D, )	0.13
" None of the dosage regimens of either antivenom used guaranteed resolution of venom-induced coagulopathy within 6 h, nor did they prevent recurrences."	( Efficacy and safety of two whole IgG polyvalent antivenoms, refined by caprylic acid fractionation with or without beta-propiolactone, in the treatment of Bothrops asper bites in Colombia. Alzate, C; Arrieta, AB; Arroyo, Y; Ayala, S; Barona, J; Conrado, LL; Córdoba, E; Díaz, A; Fabra, PE; Fernández, D; Fernández, J; Gutiérrez, JM; León, G; López, M; Meza, JJ; Mosquera, D; Núñez, V; Ospina, CE; Otero, R; Paniagua, CA; Quintana, JC; Ramírez, E; Ramírez, P; Rodríguez, V; Rojas, G; Silva, JF; Theakston, RD; Toro, MF; Warrell, DA, 2006)	0.33
" Plasma samples collected 24h after dosing from 3- to 5-week-old rats indicated a slightly but significantly higher male plasma concentration at 30 and 32 days of age as compared to 23 days of age for the 30mg/kg dose group only."	( Age effect on perfluorooctanoate (PFOA) plasma concentration in post-weaning rats following oral gavage with ammonium perfluorooctanoate (APFO). Butenhoff, JL; Han, X; Hinderliter, PM; Kennedy, GL, 2006)	0.33
" Pregnant CD-1 mice were dosed on gestation days (GD) 1-17 with 0, 3, or 5 mg PFOA/kg body weight, and pups were fostered at birth to give seven treatment groups: unexposed controls, pups exposed in utero (3U and 5U), lactationally (3L and 5L), or in utero + lactationally (3U + L and 5U + L)."	( Developmental toxicity of perfluorooctanoic acid in the CD-1 mouse after cross-foster and restricted gestational exposures. Abbott, BD; Bryant, XA; Calafat, AM; Das, KP; Fenton, SE; Kuklenyik, Z; Lau, CS; Schmid, JE; Thibodeaux, J; White, SS; Wolf, CJ, 2007)	0.34
" To determine whether effects were linked to gestational time of exposure or to subsequent lactational changes, timed-pregnant CD-1 mice were orally dosed with 5 mg PFOA/kg on gestation days (GD) 1-17, 8-17, 12-17, or vehicle on GD 1-17."	( Gestational PFOA exposure of mice is associated with altered mammary gland development in dams and female offspring. Calafat, AM; Fenton, SE; Helfant, L; Kuklenyik, Z; Lindstrom, AB; Strynar, MJ; Thibodeaux, JR; Villanueva, L; White, SS; Wood, C; Zehr, RD, 2007)	0.34
" A dosage of 10."	( Expression of S100 protein and protective effect of arundic acid on the rat brain in chronic cerebral hypoperfusion. Kitaguchi, H; Nakaji, K; Ohtani, R; Takahashi, R; Tomimoto, H; Wakita, H, 2007)	0.34
" In the liver, 52% and 27% of PFOA dosed was recovered 2 h after an intravenous injection at the low and the high doses, respectively."	( Tissue distribution and hepatic subcellular distribution of perfluorooctanoic acid at low dose are different from those at high dose in rats. Hibino, Y; Kawashima, Y; Kudo, N; Mitsumoto, A; Sakai, A; Tsuda, T, 2007)	0.34
" Thirty timed-pregnant CD-1 mice were orally dosed from gestation days 1-17 with either 0, 1, 3, 5, or 10mg/(kgday) PFOA in water."	( Gene expression profiling in the lung and liver of PFOA-exposed mouse fetuses. Lau, C; Rosen, MB; Schmid, JE; Thibodeaux, JR; Wood, CR; Zehr, RD, 2007)	0.34
" We evaluated pairs of rat studies of PFOS, PFOA, and PFBS performed with the same design for which dose-response curves could be modeled for the concordant endpoints, but we were unable to identify a scaling system that gave values consistently within an order of magnitude for the same compounds."	( Combining perfluoroalkane acid exposure levels for risk assessment. Iannucci, A; Scialli, AR; Turim, J, 2007)	0.34
"Recent studies have reported developmental toxicity among rodents dosed with perfluorooctane sulfonate (PFOS) and perfluorooctanoate (PFOA)."	( Cord serum concentrations of perfluorooctane sulfonate (PFOS) and perfluorooctanoate (PFOA) in relation to weight and size at birth. Apelberg, BJ; Calafat, AM; Goldman, LR; Halden, RU; Herbstman, JB; Needham, LL; Witter, FR, 2007)	0.34
"The present investigation determined the molecular structure and the pharmacokinetic and pharmacodynamic profiles of oral unfractionated heparin containing oral absorption enhancer sodium N-[8-(2-hydroxybenzoyl) amino]caprylate, salcaprozate sodium (SNAC) and assessed the safety and tolerability of the orally dosed heparin solid dosage form versus other routes."	( Pharmacokinetics and pharmacodynamics of oral heparin solid dosage form in healthy human subjects. Aljada, A; Castelli, MC; Chaturvedi, S; Chi, L; Friedman, K; Goldberg, MM; Linhardt, RJ; Mousa, SA; Takieddin, M; Zhang, F; Zhang, H, 2007)	0.34
" Tretinoin-loaded nanocapsules improved tretinoin photostability, independently on the type of oily phase used in this study, and represent a potential system to be incorporated in topical or systemic dosage forms containing tretinoin."	( Tretinoin-loaded nanocapsules: Preparation, physicochemical characterization, and photostability study. Beck, RC; Guterres, SS; Ourique, AF; Pohlmann, AR, 2008)	0.35
" In summary, our findings reiterate that absorption characteristics of FLA were governed by the dose as well as the dosing vehicle."	( Vehicle-dependent disposition kinetics of fluoranthene in Fisher-344 rats. Harris, DL; Hood, DB; Ramesh, A, 2008)	0.35
" To study the mechanism associated with PFOA toxicity, wild-type and PPARalpha-null mice were orally dosed for 7 days with PFOA (1 or 3 mg/kg) or the PPARalpha agonist Wy14,643 (50 mg/kg)."	( Gene profiling in the livers of wild-type and PPARalpha-null mice exposed to perfluorooctanoic acid. Abbott, BD; Blair, ET; Corton, JC; Das, KP; Lau, C; Rosen, MB; Schmid, JE; Wolf, DC; Wood, CR; Zehr, RD, 2008)	0.35
"The aim of this study was to evaluate PFOA effects on humoral and cellular immunity using standard assays for assessing immune function, and to derive dose-response data."	( Perfluorooctanoic acid-induced immunomodulation in adult C57BL/6J or C57BL/6N female mice. Copeland, CB; Dewitt, JC; Luebke, RW; Strynar, MJ, 2008)	0.35
" With pentadecafluorooctanoic acid, increasing dosage up to 10 mg/kg body wt brought about progressive increase in expression of affected genes."	( Comparative hepatic gene expression profiling of rats treated with 1H,1H,2H,2H-heptadecafluorodecan-1-ol or with pentadecafluorooctanoic acid. Berger, U; Fonnum, F; Haug, KH; Landin, MA; Nilsen, AJ; Osmundsen, H, 2008)	0.35
" Recent studies with mice have shown that dosing pregnant dams with PFOA during gestation gives rise to a dose-dependent mortality in the litters, a reduction in neonatal body weight for the surviving pups, and subsequent deficits in mammary gland development when compared to control animals."	( Analysis of PFOA in dosed CD1 mice. Part 1. Methods development for the analysis of tissues and fluids from pregnant and lactating mice and their pups. Delinsky, AD; Fenton, SE; Lindstrom, AB; Nakayama, SF; Reiner, JL; Stanko, JP; Strynar, MJ, 2009)	0.35
" Exposure to 15 mg/kg decreased bw by approximately 10% after 8 days of dosing and until 2 days postdosing in both adx and sham animals; bw of adx animals were still reduced 5 days postdosing."	( Suppression of humoral immunity by perfluorooctanoic acid is independent of elevated serum corticosterone concentration in mice. Copeland, CB; DeWitt, JC; Luebke, RW, 2009)	0.35
" Pregnant CD-1 mice were dosed with 0, 5, or 10mg/kg PFOS from gestation days 1-17."	( Gene expression profiling in the liver and lung of perfluorooctane sulfonate-exposed mouse fetuses: comparison to changes induced by exposure to perfluorooctanoic acid. Das, KP; Lau, C; Rosen, MB; Schmid, JE; Wood, CR; Zehr, RD, 2009)	0.35
" The Benchmark Dose-Uncertainty Factor approach was selected for dose-response for noncancer and cancer."	( Derivation of a drinking water equivalent level (DWEL) related to the maximum contaminant level goal for perfluorooctanoic acid (PFOA), a persistent water soluble compound. Andersen, M; Bevan, C; Carson, ML; Gargas, ML; Kirman, CR; Sweeney, LM; Tan, YM; Tardiff, RG, 2009)	0.35
" Histopathological changes were seen in the stomach in both studies, probably secondary to irritation caused by the dosing method."	( Subchronic oral toxicity of salcaprozate sodium (SNAC) in Sprague-Dawley and Wistar rats. Castelli, MC; Paehler, EA; Riley, MG, )	0.13
"9) and a dose-response gradient."	( Serum levels of perfluorooctanoic acid and perfluorooctane sulfonate and pregnancy outcome. Dougan, M; Savitz, DA; Stein, CR, 2009)	0.35
" In addition, the expression of PPARalpha was increased in all dosed fish, while the mRNAs for PPARgamma and HNF4alpha were significantly altered with 30 and 3mg PFOA/L doses, respectively."	( The identification of apolipoprotein genes in rare minnow (Gobiocypris rarus) and their expression following perfluorooctanoic acid exposure. Dai, J; Fang, X; Liu, Y; Wang, J; Wei, Y, 2010)	0.36
"84 for the three higher quartiles of maternal PFOA levels compared with the lowest, but no dose-response pattern was found."	( Prenatal exposure to PFOA and PFOS and risk of hospitalization for infectious diseases in early childhood. Fei, C; Lipworth, L; McLaughlin, JK; Olsen, J, 2010)	0.36
" To investigate the low-dose effects of PFOA on offspring, timed-pregnant CD-1 mice were gavage dosed with PFOA for all or half of gestation."	( Prenatal perfluorooctanoic acid exposure in CD-1 mice: low-dose developmental effects and internal dosimetry. Fenton, SE; Helfant, L; Macon, MB; Stanko, JP; Strynar, MJ; Tatum-Gibbs, K; Villanueva, LR; White, SS; Zehr, RD, 2011)	0.37
" Both male and female rat models for each chemical were consistent with available PK data resulting from IV, oral, and dietary dosing regimens."	( Comparison and evaluation of pharmacokinetics of PFOA and PFOS in the adult rat using a physiologically based pharmacokinetic model. Andersen, ME; Butenhoff, JL; Campbell, JL; Clewell, HJ; Loccisano, AE, 2012)	0.38
" Trout have critical and unique advantages allowing for cancer studies with 40,000 animals to determine dose-response at levels orders of magnitude lower than possible in rodents."	( The rainbow trout liver cancer model: response to environmental chemicals and studies on promotion and chemoprevention. Williams, DE, 2012)	0.38
" Plasma samples from human subjects dosed with CPI-613 also contained the sulfoxide ± glucuronide metabolites."	( Formation and anti-tumor activity of uncommon in vitro and in vivo metabolites of CPI-613, a novel anti-tumor compound that selectively alters tumor energy metabolism. Boteju, LW; Lee, KC; Maturo, C; Rodriguez, R; Sheldon, A; Shorr, R, 2011)	0.37
" This suggests that inadvertent selection bias may have affected the lowest exposure quartile (control group), making tenuous the dose-response relationship between PFOA/PFOS and risk of high cholesterol."	( Tenuous dose-response correlations for common disease states: case study of cholesterol and perfluorooctanoate/sulfonate (PFOA/PFOS) in the C8 Health Project. Copeland, TL; DeCaprio, AP; Kerger, BD, 2011)	0.37
" In this study, pregnant CD-1 mice were dosed orally from GD1 to 17 with water or 5mg PFOA/kg to examine PPARα, PPARβ, and PPARγ expression and profile the effects of PFOA on PPAR-regulated genes."	( Effects of perfluorooctanoic acid (PFOA) on expression of peroxisome proliferator-activated receptors (PPAR) and nuclear receptor-regulated genes in fetal and postnatal CD-1 mouse tissues. Abbott, BD; Das, KP; Lau, C; Tatum-Gibbs, K; Watkins, AM; Wood, CR, 2012)	0.38
" The combination of Capmul PG-12, Tween 20 and Cremophor RH 40 can produce SEDDS which can be used as an alternative dosage form for poorly water soluble drug."	( Formulation and in vitro evaluation of self-emulsifying formulations of Cinnarizine. Chaw, CS; Sarraf, S; Vithlani, S, 2012)	0.38
" These data do not support a strong role for plasma lipoprotein fractions in explaining the inconsistent dose-response associations reported in cross-sectional epidemiological studies."	( Distribution of perfluorooctanesulfonate and perfluorooctanoate into human plasma lipoprotein fractions. Butenhoff, JL; Chang, SC; Ehresman, DJ; Gorman, GS; Olsen, GW; Pieterman, E; Princen, HM, 2012)	0.38
" Unlike most other well-studied drinking water contaminants, the human dose-response curve for several effects appears to be steepest at the lower exposure levels, including the general population range, with no apparent threshold for some endpoints."	( Perfluorooctanoic acid (PFOA), an emerging drinking water contaminant: a critical review of recent literature. Cohn, PD; Cooper, KR; Post, GB, 2012)	0.38
" Thus, these results suggest that solid SMEDDS could be used as an effective oral solid dosage form to improve dissolution and oral bioavailability of fenofibrate."	( Enhancement of oral bioavailability of fenofibrate by solid self-microemulsifying drug delivery systems. Choi, HG; Hiep, TT; Kim, GG; Kim, JO; Lee, DW; Marasini, N; Poudel, BK; Yang, KY; Yong, CS, 2013)	0.39
" Ex vivo co-cultures of splenic CD4+CD25+ T cells and CD4+CD25- T cells from dosed male offspring produced less IL-10 relative to control cells."	( Does developmental exposure to perflurooctanoic acid (PFOA) induce immunopathologies commonly observed in neurodevelopmental disorders? Bryan, I; DeWitt, JC; Franklin, JN; Hu, Q; Morris, E; Wood, A, 2012)	0.38
" Even lower results were obtained using logarithmic dose-response curves."	( Immunotoxicity of perfluorinated alkylates: calculation of benchmark doses based on serum concentrations in children. Budtz-Jørgensen, E; Grandjean, P, 2013)	0.39
" A dose-response relationship was observed when PFOS levels were categorized into four groups."	( Perfluorinated compound levels in cord blood and neurodevelopment at 2 years of age. Chen, CY; Chen, MH; Chen, PC; Ha, EH; Hsieh, WS; Jeng, SF; Liao, HF; Lien, GW; Su, YN; Wen, TW, 2013)	0.39
"Rainbow trout (Oncorhynchus mykiss) confined to respirometer-metabolism chambers were dosed with perfluorooctanoate (PFOA) by intra-arterial (i."	( Toxicokinetics of perfluorooctanoate (PFOA) in rainbow trout (Oncorhynchus mykiss). Consoer, DM; Fitzsimmons, PN; Hoffman, AD; Kosian, PA; Nichols, JW, 2014)	0.4
" A specific dose-response enrichment of the stomach tissue C8:0 was observed as a function of dietary C8:0, supporting the hypothesis of an early preduodenal hydrolysis of medium chain triglycerides and a direct absorption at the gastric level."	( Dietary Caprylic Acid (C8:0) Does Not Increase Plasma Acylated Ghrelin but Decreases Plasma Unacylated Ghrelin in the Rat. Beauchamp, E; Dayot, S; Duby, C; Legrand, P; Lemarié, F; Rioux, V, 2015)	0.42
"Estimated mean birth weights were lower among women with serum perfluorohexane sulfonate, perfluoroheptane sulfonate, and PFOS concentrations above the lowest exposure quartile, but we found no consistent monotonic dose-response patterns."	( Perfluoroalkyl Acids in Maternal Serum and Indices of Fetal Growth: The Aarhus Birth Cohort. Bach, CC; Bech, BH; Bonefeld-Jørgensen, EC; Bossi, R; Henriksen, TB; Matthiesen, NB; Nohr, EA; Olsen, J, 2016)	0.43
"We found a dose-response relationship of prenatal PFOS, but not PFOA, exposure with glucocorticoid levels after adjusting for potential confounders."	( The Association of Prenatal Exposure to Perfluorinated Chemicals with Glucocorticoid and Androgenic Hormones in Cord Blood Samples: The Hokkaido Study. Araki, A; Goudarzi, H; Itoh, S; Kishi, R; Mitsui, T; Miyashita, C; Nakazawa, H; Nonomura, K; Sasaki, S, 2017)	0.46
" The impact of different factors on persulfate activity, including pH, temperature (25 °C-50 °C), persulfate dosage and reaction time, was evaluated under different experimental conditions."	( Activated Persulfate Oxidation of Perfluorooctanoic Acid (PFOA) in Groundwater under Acidic Conditions. Hu, Z; Lin, N; Liu, J; Song, X; Yin, P, 2016)	0.43
" In this study, we investigated the mechanism of paclitaxel absorption after oral administration of DHP107 in mice and rats by changing the dosing interval, and evaluated the influence of bile excretion."	( Absorption mechanism of DHP107, an oral paclitaxel formulation that forms a hydrated lipidic sponge phase. Chung, H; Chung, HJ; Hong, JW; Jang, Y; Yun, CW, 2017)	0.46
" We found an obvious dose-response relationship between progesterone inhibition rate and PFAA exposure concentration in mLTC-1."	( Inhibition effects of perfluoroalkyl acids on progesterone production in mLTC-1. Cui, R; Dai, J; Wang, J; Zhao, W, 2017)	0.46
" In the present study, mature male mice were exposed to dosed PFOA for 21 days before conducting biochemical tests and immunoassays."	( Adverse bioeffect of perfluorooctanoic acid on liver metabolic function in mice. Wu, W; Wu, X; Xie, G; Xu, X; Yang, B, 2018)	0.48
" Data from live cell measurements were fit to a log-linear dose-response model."	( A Ternary Mixture of Common Chemicals Perturbs Benign Human Breast Epithelial Cells More Than the Same Chemicals Do Individually. Dairkee, SH; Goodson, WH; Jaffee, IM; Luciani-Torres, G; Moore, DH, 2018)	0.48
"Sixteen participants with a diagnosis of EVT were randomized to a 3-week dosing condition of octanoic acid or placebo, followed by a 2-week washout period and crossover to the other condition for an additional 3 weeks."	( The Effect of Octanoic Acid on Essential Voice Tremor: A Double-Blind, Placebo-Controlled Study. Colton, RH; Hosbach-Cannon, CJ; Kelley, RT; Lowell, SY; Mihaila, D; Monahan, M, 2019)	0.51
"Magnitude of amplitude and frequency tremor were significantly lower after 3 weeks of octanoic acid dosing as compared to the placebo condition."	( The Effect of Octanoic Acid on Essential Voice Tremor: A Double-Blind, Placebo-Controlled Study. Colton, RH; Hosbach-Cannon, CJ; Kelley, RT; Lowell, SY; Mihaila, D; Monahan, M, 2019)	0.51
" Further research is needed to determine whether different dosing or treatment combinations can improve functional communication in EVT."	( The Effect of Octanoic Acid on Essential Voice Tremor: A Double-Blind, Placebo-Controlled Study. Colton, RH; Hosbach-Cannon, CJ; Kelley, RT; Lowell, SY; Mihaila, D; Monahan, M, 2019)	0.51
" Four chemicals (L-Arg, L-Leu-L-Leu-OH, L-Leu-L-Ile-OH and suberic acid) induced behavioral avoidance in toad tadpoles at some (but not all) dosage levels, so we then exposed toad larvae to these chemicals over the entire period of larval development."	( The Effects of Conspecific Alarm Cues on Larval Cane Toads (Rhinella marina). Capon, RJ; Crossland, MR; Salim, AA; Shine, R, 2019)	0.51
" It was also found that SNAC is orally bioavailable (almost 40%) when dosed to rats."	( Evaluating the Pharmacokinetics and Systemic Effects of a Permeability Enhancer Sodium N-[8-(2-hydroxybenzoyl)amino] Caprylate in Rats. Chen, JZ; Chiang, PC; Deshmukh, G; Durk, MR; Li, R; Liu, J; Nagapudi, K; Plise, EG; Valle, N, 2020)	0.56
" Non-linear threshold dose-response associations between serum concentrations of PFNA and PFDA and HFHI need further investigation."	( Perfluoroalkyl substances exposure and hearing impairment in US adults. Ding, N; Park, SK, 2020)	0.56
" In this work, liposomes were synthesized and used in an ecotoxicological context, as a tool to assure stable dosing of technically challenging chemicals to zooplankton."	( Liposome-mediated delivery of challenging chemicals to aid environmental assessment of Bioaccumulative (B) and Toxic (T) properties. Castro, M; Lindqvist, D, 2020)	0.56
" This report describes a novel formulation comprising a unique amphiphilic molecule, 8-((2-hydroxybenzoyl)amino)octanoate (SHAO), that non-covalently interacts with payloads to increase drug dispersion and diffusion when dosed intratumorally (IT) into solid tumors."	( Intratumoral Administration of a Novel Cytotoxic Formulation with Strong Tissue Dispersive Properties Regresses Tumor Growth and Elicits Systemic Adaptive Immunity in In Vivo Models. Abbate, F; Bender, LH; Walters, IB, 2020)	0.56
" PFAS have been consistently associated with raised serum lipids, mainly in cross-sectional studies and in background exposure contexts, but the shape of the dose-response relationships has been poorly investigated."	( Associations between perfluoroalkyl substances and lipid profile in a highly exposed young adult population in the Veneto Region. Barbieri, G; Canova, C; Daprà, F; Fabricio, A; Fletcher, T; Gion, M; Pitter, G; Russo, F; Zare Jeddi, M, 2020)	0.56
"PFCs were associated with increased odds of ovarian and breast cancers with a positive dose-response relationship."	( A cross-sectional study of the association between perfluorinated chemical exposure and cancers related to deregulation of estrogen receptors. Liu, Y; Mamudu, HM; Omoike, OE; Pack, RP; Wang, L, 2021)	0.62
" We found a nonlinear dose-response relationship with a "threshold" effect in serum br-PFOS isomers with MetS, in which the odds of MetS increased quickly with increasing serum br-PFOS isomers under low exposure (p for nonlinearity = 0."	( Associations between serum isomers of perfluoroalkyl acids and metabolic syndrome in adults: Isomers of C8 Health Project in China. Chen, ZX; Chu, C; Dong, GH; Kong, ML; Li, QQ; Xie, YQ; Ye, WL; Yu, S; Zeng, XW, 2021)	0.62
"We report new evidence of associations between PFAAs isomers and MetS and the nonlinearity of dose-response relationship with br-PFOS isomers."	( Associations between serum isomers of perfluoroalkyl acids and metabolic syndrome in adults: Isomers of C8 Health Project in China. Chen, ZX; Chu, C; Dong, GH; Kong, ML; Li, QQ; Xie, YQ; Ye, WL; Yu, S; Zeng, XW, 2021)	0.62
"Associations between PFASs and anthropometric outcomes show a dose-response relationship overall."	( PFAS exposure and overweight/obesity among children in a nationally representative sample. Geiger, SD; Qian, Z; Vaughn, MG; Yao, P, 2021)	0.62
" Clinical correlates of treatment response were evaluated, and cumulative effects over a 2-week period of OA drug dosing were assessed."	( Clinical Features of Essential Voice Tremor and Associations with Tremor Severity and Response to Octanoic Acid Treatment. Colton, RH; Dischinat, N; Hosbach-Cannon, CJ; Kelley, RT; Lowell, SY; Mihaila, D; Monahan, M, 2021)	0.62
" Increasing the KOH-CBC dosage is not beneficial for further mitigating the toxicity of PFOA-contaminated sediments."	( Evaluating the potential of KOH-modified composite biochar amendment to alleviate the ecotoxicity of perfluorooctanoic acid-contaminated sediment on Bellamya aeruginosa. Gong, S; Luo, B; Ma, T; Mi, Y; Xiang, J; Zhou, Y, 2021)	0.62
" The significant decrease in the IgM antibody response to the T cell dependent antigen keyhole limpet hemocyanin (KLH) at a dose lower than the previously documented LOAEL was accompanied by a significant reduction of the Th2 serum cytokines IL-5 and IL-13, a non-significant dose-response reduction of IL-4, a significant reduction of the Th1 cytokine IL-12, and a non-significant dose-response increase in IL-2 and IFNγ."	( Suppression of Th2 cytokines as a potential mechanism for reduced antibody response following PFOA exposure in female B6C3F1 mice. De Guise, S; Levin, M, 2021)	0.62
" Taken together, our results indicate that MD simulations are useful for gaining insights relevant to the design of oral dosage forms based around permeability enhancer molecules."	( In Silico-Based Experiments on Mechanistic Interactions between Several Intestinal Permeation Enhancers with a Lipid Bilayer Model. Hossain, S; Kneiszl, R; Larsson, P, 2022)	0.72
" For the in vivo studies, adult CD-1 female mice were orally dosed with vehicle control or 1, 5, 10, or 20 mg/kg/day PFOA for 10 days."	( Perfluorooctanoic Acid Disrupts Ovarian Steroidogenesis and Folliculogenesis in Adult Mice. Chiu, K; Flaws, JA; Gao, L; Lee, Y; Meling, DD; Warner, GR; Yang, M, 2022)	0.72
" Results showed that PFOA inhibited the chemical oxygen demand (COD) removal rate of the sludge and the dosage of 100 mg/L PFOA was more obvious."	( Effects of PFOA on the physicochemical properties of anaerobic granular sludge: Performance evaluation, microbial community and metagenomic analysis. Cao, L; Gao, S; Liao, Y; Qi, Z; Su, C; Tang, L; Wei, L; Wu, J, 2022)	0.72
" However, the in vivo experiments indicate that applying a higher dosage or using other drugs targeting these metabolic pathways might be more promising."	( Targeting pancreatic cancer with combinatorial treatment of CPI-613 and inhibitors of lactate metabolism. Goldstein, L; Joksch, M; Krause, B; Kumstel, S; Lindner, T; Schönrogge, M; Schreiber, T; Stenzel, J; Vollmar, B; Wendt, EHU; Zechner, D; Zhang, X, 2022)	0.72
" Pharmacokinetic analysis showed that stable steady-state concentrations could be achieved with once-daily dosing owing to the long half-life of oral semaglutide."	( A new era for oral peptides: SNAC and the development of oral semaglutide for the treatment of type 2 diabetes. Aroda, VR; Blonde, L; Pratley, RE, 2022)	0.72
" Summary odds ratio (OR), hazard ratio (HR), or β and their 95% confidence intervals (CIs) were respectively calculated to evaluate the association between PFAS and diabetes using random-effects model by the exposure type, and dose-response meta-analyses were also performed when possible."	( Association between per- and polyfluoroalkyl substances exposure and risk of diabetes: a systematic review and meta-analysis. Chen, YN; Gui, SY; Hu, CY; Jiang, ZX; Li, ZL; Qiao, JC; Wu, KJ; Xu, KX, 2023)	0.91
" Dose-response meta-analysis showed a "parabolic-shaped" association between perfluorooctanoate acid (PFOA) exposure and T2DM risk."	( Association between per- and polyfluoroalkyl substances exposure and risk of diabetes: a systematic review and meta-analysis. Chen, YN; Gui, SY; Hu, CY; Jiang, ZX; Li, ZL; Qiao, JC; Wu, KJ; Xu, KX, 2023)	0.91
"Our findings suggest that PFAS exposure may increase the risk of incident T2DM, and that PFOA may exert non-monotonic dose-response effect on T2DM risk."	( Association between per- and polyfluoroalkyl substances exposure and risk of diabetes: a systematic review and meta-analysis. Chen, YN; Gui, SY; Hu, CY; Jiang, ZX; Li, ZL; Qiao, JC; Wu, KJ; Xu, KX, 2023)	0.91
" Concentration-response data obtained from HepaRG cells on triglyceride (TG) accumulation and expression changes of 12 selected genes (some involved in cholesterol homeostasis) were converted into corresponding human dose-response data, using physiologically based kinetic (PBK) model-facilitated reverse dosimetry."	( New approach methodologies: A quantitative in vitro to in vivo extrapolation case study with PFASs. Bokkers, B; Fragki, S; Louisse, J; Luijten, M; Peijnenburg, A; Piersma, AH; Rijkers, D; Zeilmaker, MJ, 2023)	0.91
" After dosing and immunization of subgroups, spleens were prepared to quantify B-cell subsets."	( Quantifying the impact of PFOA exposure on B-cell development and antibody production. Ahmed, A; DeWitt, JC; Duncker, PC; Hu, Q; Taylor, KD; Woodlief, TL, 2023)	0.91

Role	Description
human metabolite	Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metabolite	Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
fatty acid anion 8:0	Any saturated fatty acid anion containing 8 carbons. Formed by deprotonation of the carboxylic acid moiety. Major species at pH 7.3.
straight-chain saturated fatty acid anion	Any saturated fatty acid anion lacking a carbon side-chain.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
6-gingerol analog biosynthesis (engineered)	2	20
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-2	0	490
6-gingerol analog biosynthesis (engineered)	4	20
rhizobactin 1021 biosynthesis	6	22
lipoate biosynthesis and incorporation II	2	11
Octane oxidation	0	1

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Beta-lactoglobulin	Bos taurus (cattle)	Kd	92.6000	92.6000	92.6000	92.6000	AID977611
Chain A, Beta-lactoglobulin	Bos taurus (cattle)	Kd	92.6000	92.6000	92.6000	92.6000	AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB
AID1798322	Ligand Affinity Measurements from Article 10.1016/j.bmc.2007.01.044: \\Amphipathic benzoic acid derivatives: synthesis and binding in the hydrophobic tunnel of the zinc deacetylase LpxC.\\	2007	Bioorganic & medicinal chemistry, Apr-01, Volume: 15, Issue:7	Amphipathic benzoic acid derivatives: synthesis and binding in the hydrophobic tunnel of the zinc deacetylase LpxC.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1077 (21.87)	18.7374
1990's	435 (8.83)	18.2507
2000's	915 (18.58)	29.6817
2010's	1794 (36.43)	24.3611
2020's	704 (14.29)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	100 (1.98%)	5.53%
Reviews	185 (3.66%)	6.00%
Case Studies	45 (0.89%)	4.05%
Observational	2 (0.04%)	0.25%
Other	4,729 (93.44%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acetylcarnitine Acetylcarnitine: An acetic acid ester of CARNITINE that facilitates movement of ACETYL COA into the matrices of mammalian MITOCHONDRIA during the oxidation of FATTY ACIDS.	3.24	6	0	O-acylcarnitine	human metabolite
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	1.96	1	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	2.17	1	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	2.1	1	0	trichlorobenzene
chloroacetaldehyde [no description available]	2	1	0	organochlorine compound
ethylene chlorohydrin Ethylene Chlorohydrin: Used as a solvent, in the manufacture of insecticides, and for treating sweet potatoes before planting. May cause nausea, vomiting, pains in head and chest, stupefaction. Irritates mucous membranes and causes kidney and liver degeneration.. chloroethanol : An organochlorine compound that is ethanol substituted by at least one chloro group.	1.96	1	0	chloroethanol	xenobiotic metabolite
alpha-ketoisovalerate alpha-ketoisovalerate: RN given refers to parent cpd. 3-methyl-2-oxobutanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 3-methyl-2-oxobutanoic acid, arising from deprotonation of the carboxy group.. 3-methyl-2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.	2.88	4	0	2-oxo monocarboxylic acid; branched-chain keto acid	human metabolite; Saccharomyces cerevisiae metabolite
2-keto-4-methylvalerate alpha-ketoisocaproic acid: RN given refers to parent cpd. 4-methyl-2-oxopentanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 4-methyl-2-oxopentanoic acid.. 4-methyl-2-oxopentanoic acid : A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.	4.68	9	0	2-oxo monocarboxylic acid; branched-chain keto acid	algal metabolite; human metabolite
3-hydroxyisobutyric acid 3-hydroxyisobutyric acid: RN given refers to cpd without isomeric designation. 3-hydroxyisobutyric acid : A 4-carbon, branched hydroxy fatty acid and intermediate in the metabolism of valine.	2.37	2	0	3-hydroxy monocarboxylic acid
acetoacetic acid acetoacetic acid : A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.	6.82	15	1	3-oxo fatty acid; ketone body	metabolite
3-phenylpropionic acid 3-phenylpropionic acid: RN given refers to parent cpd. 3-phenylpropionic acid : A monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group.	1.98	1	0	benzenes; monocarboxylic acid	antifungal agent; human metabolite; plant metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	3.9	12	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.11	1	0	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
5-aminovaleric acid 5-aminovaleric acid: from red fox anal secretion; RN given refers to parent cpd. 5-aminopentanoic acid : A delta-amino acid comprising pentanoic acid with an amino substituent at C-5; a methylene homologue of gamma-aminobutyric acid (GABA) that is a weak GABA agonist.	2	1	0	amino acid zwitterion; delta-amino acid; omega-amino fatty acid	human metabolite
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.44	2	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	5.37	22	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	2.89	4	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.75	3	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
acetyl phosphate acetyl dihydrogen phosphate : An acyl monophosphate in which the acyl group specified is acetyl.	2.01	1	0	acyl monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
adenine [no description available]	1.95	1	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	5.39	14	1	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	4.64	28	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	1.94	1	0	aminobenzoic acid	human metabolite; mouse metabolite
arsenic acid arsenic acid: RN given refers to orthoarsenic acid(H3AsO4); see also sodium arsenate. arsenic acid : An arsenic oxoacid comprising one oxo group and three hydroxy groups attached to a central arsenic atom.	2.6	1	0	arsenic oxoacid	Escherichia coli metabolite
benzene [no description available]	2.9	4	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	2.39	2	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	1.99	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.67	3	0	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.66	3	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	3.81	11	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	4.8	32	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	3.26	6	0	amino-acid anion
carbamyl phosphate Carbamyl Phosphate: The monoanhydride of carbamic acid with PHOSPHORIC ACID. It is an important intermediate metabolite and is synthesized enzymatically by CARBAMYL-PHOSPHATE SYNTHASE (AMMONIA) and CARBAMOYL-PHOSPHATE SYNTHASE (GLUTAMINE-HYDROLYZING).	1.96	1	0	acyl monophosphate; one-carbon compound	Escherichia coli metabolite; mouse metabolite
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.35	2	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.45	2	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
aminooxyacetic acid Aminooxyacetic Acid: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.. (aminooxy)acetic acid : A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues.	2.64	3	0	amino acid; hydroxylamines; monocarboxylic acid	anticonvulsant; EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; nootropic agent
carnitine [no description available]	9.52	99	2	amino-acid betaine	human metabolite; mouse metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	5.5	14	1	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chloroacetic acid chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.	2.05	1	0	chlorocarboxylic acid; haloacetic acid	alkylating agent; herbicide
choline [no description available]	3.76	11	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
aconitic acid Aconitic Acid: A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.. aconitic acid : A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.	1.95	1	0	tricarboxylic acid
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	4.27	18	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	3.68	10	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.05	1	0	coumarins	fluorescent dye; human metabolite; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.91	4	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	3.48	8	0	alkane	xenobiotic
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.55	2	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	20.94	1,106	52	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	2.43	2	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
dihydrolipoic acid dihydrolipoic acid: RN given refers to parent cpd without isomeric designation. dihydrolipoic acid : A thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.. dihydrolipoate : The conjugate base of dihydrolipoic acid.	1.98	1	0	thio-fatty acid	antioxidant; human metabolite; neuroprotective agent
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	9.08	35	1	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	2.69	3	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
2-aminoadipic acid 2-Aminoadipic Acid: A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-METHYL-D-ASPARTATE; (NMDA).. 2-aminoadipic acid : An alpha-amino acid that is adipic acid bearing a single amino substituent at position 2. An intermediate in the formation of lysine.	1.95	1	0	amino dicarboxylic acid; dicarboxylic fatty acid; non-proteinogenic alpha-amino acid	Caenorhabditis elegans metabolite; mammalian metabolite
methylmalonic acid Methylmalonic Acid: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA.. methylmalonic acid : A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group.	2	1	0	C4-dicarboxylic acid	human metabolite
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	3.07	5	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
phosphonoacetic acid Phosphonoacetic Acid: A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.. phosphonoacetic acid : A member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl group.	4.42	6	0	monocarboxylic acid; phosphonic acids	antiviral agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	2.95	4	0	catechols; dihydroxyphenylacetic acid	human metabolite
aminocaproic acid Aminocaproic Acid: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.. 6-aminohexanoic acid : An epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator.	2.64	3	0	amino acid zwitterion; epsilon-amino acid; omega-amino fatty acid	antifibrinolytic drug; hematologic agent; metabolite
creatine [no description available]	2.89	4	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	5.97	41	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dihydroxyacetone phosphate Dihydroxyacetone Phosphate: An important intermediate in lipid biosynthesis and in glycolysis.. dihydroxyacetone phosphate : A member of the class of glycerone phosphates that consists of glycerone bearing a single phospho substituent.	1.99	1	0	glycerone phosphates; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dihydroxyacetone [no description available]	2.92	4	0	ketotriose; primary alpha-hydroxy ketone	antifungal agent; Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	3.47	8	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.6	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glutaric acid glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.	2.7	3	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	Daphnia magna metabolite; human metabolite
glycine [no description available]	7.4	25	2	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	1.94	1	0	aldotriose	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	5.98	43	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	2.38	2	0	glycerol monophosphate	algal metabolite; human metabolite
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	2	1	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	3.83	12	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dalteparin Dalteparin: A low-molecular-weight fragment of heparin, prepared by nitrous acid depolymerization of porcine mucosal heparin. The mean molecular weight is 4000-6000 daltons. It is used therapeutically as an antithrombotic agent. (From Merck Index, 11th ed)	2	1	0
histamine [no description available]	1.95	1	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	3.63	9	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.21	1	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.04	1	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
indole [no description available]	2.05	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.05	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.44	2	0	diatomic iodine	nutrient
itaconic acid itaconic acid : A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.	2.31	1	0	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; human metabolite
lipoamide Lipozyme: lipase from Rhizomucor miehei immobilized on anion exchange resin	3.13	5	0	dithiolanes; monocarboxylic acid amide	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	5.8	29	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	2.36	2	0	alpha,omega-dicarboxylic acid	human metabolite
methylmercaptan methylmercaptan: intermediate in the manufacturing of jet fuels, pesticides, fungicides, plastics, synthesis of methionine; odor may cause nausea; narcotic in high concentrations; depresses urea biosynthesis; RN given refers to parent cpd; structure	1.96	1	0	alkanethiol	human metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	4.21	17	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.15	1	0	cyclitol; hexol
melatonin [no description available]	2.41	1	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.49	2	0	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.39	2	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	4.79	7	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	2.07	1	0	nitrogen oxoacid	protic solvent; reagent
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.66	3	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	6.85	8	2	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
hydroxide ion [no description available]	1.99	1	0	oxygen hydride	mouse metabolite
oxaloacetic acid Oxaloacetic Acid: A dicarboxylic acid ketone that is an important metabolic intermediate of the CITRIC ACID CYCLE. It can be converted to ASPARTIC ACID by ASPARTATE TRANSAMINASE.. oxaloacetic acid : An oxodicarboxylic acid that is succinic acid bearing a single oxo group.	2.45	2	0	C4-dicarboxylic acid; oxo dicarboxylic acid	geroprotector; metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	2.97	4	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	3.34	7	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.39	2	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	7.85	70	1	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
pentachlorophenol PENTA: structure given in first source	2.4	2	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenol [no description available]	2.67	3	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.7	3	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	2.1	1	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	2.06	1	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phosphoenolpyruvate Phosphoenolpyruvate: A monocarboxylic acid anion derived from selective deprotonation of the carboxy group of phosphoenolpyruvic acid. It is a metabolic intermediate in GLYCOLYSIS; GLUCONEOGENESIS; and other pathways.. phosphoenolpyruvate : A monocarboxylic acid anion resuting from selective deprotonation of the carboxy group of phosphoenolpyruvic acid.. phosphoenolpyruvic acid : A monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis.	3.45	8	0	carboxyalkyl phosphate; monocarboxylic acid	fundamental metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	2.01	1	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	3.01	4	0	benzenedicarboxylic acid	human xenobiotic metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	3.95	12	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.65	3	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	3.26	6	0	saturated fatty acid; short-chain fatty acid	antifungal drug
purine 1H-purine : The 1H-tautomer of purine.. 3H-purine : The 3H-tautomer of purine.. 9H-purine : The 9H-tautomer of purine.. 7H-purine : The 7H-tautomer of purine.	2.25	1	0	purine
putrescine [no description available]	2.25	1	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	2.02	1	0	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	1.95	1	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	5.01	40	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.4	2	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	2.05	1	0	sulfur oxide; sulfur oxoanion
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.07	1	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
spermidine [no description available]	2.25	1	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	5.16	11	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.04	1	0	sulfur oxoacid	catalyst
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	2.25	1	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	2.38	2	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	2.64	3	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymine [no description available]	2.1	1	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	3.06	5	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethyloxamine trimethyloxamine: used in manufacture of quaternary ammonium cpds; insect attractant; warming agent for gas; oxidant; structure. trimethylamine N-oxide : A tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine.	2.15	1	0	tertiary amine oxide	Escherichia coli metabolite; metabolite; osmolyte
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.38	2	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	4.93	11	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	4.71	30	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.76	3	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
isocitric acid isocitric acid: RN given refers to unlabeled parent cpd. isocitric acid : A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group.	1.97	1	0	secondary alcohol; tricarboxylic acid	fundamental metabolite
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	2.31	1	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1,2-didecanoylglycerol 1,2-didecanoylglycerol: functions as bioregulator of protein kinase C in human platelets; RN given refers to cpd without isomeric designation	2.03	1	0	1,2-diglyceride; decanoate ester
1,2-dioctanoylglycerol 1,2-dioctanoylglycerol: functions as bioregulator of protein kinase C in human platelets	1.97	1	0
1,3-dipropyl-8-cyclopentylxanthine DPCPX : An oxopurine that is 7H-xanthine substituted at positions 1 and 3 by propyl groups and at position 8 by a cyclohexyl group.	2.11	1	0	oxopurine	adenosine A1 receptor antagonist; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	9.09	113	2	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	2.75	3	0	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	2.05	1	0	bipyridine	chelator; ferroptosis inhibitor
2,4,5-trichlorophenoxyacetic acid 2,4,5-Trichlorophenoxyacetic Acid: An herbicide with strong irritant properties. Use of this compound on rice fields, orchards, sugarcane, rangeland, and other noncrop sites was terminated by the EPA in 1985. (From Merck Index, 11th ed). (2,4,5-trichlorophenoxy)acetic acid : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2, 4 and 5 are substituted by chlorines.	1.97	1	0	chlorophenoxyacetic acid; trichlorobenzene	defoliant; phenoxy herbicide; synthetic auxin
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	2.92	4	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
beta-resorcylic acid beta-resorcylic acid: RN given refers to parent cpd; structure	2.08	1	0
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	3.5	8	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	3.33	7	0	alkanethiol; primary alcohol	geroprotector
n-methyl-3,4-methylenedioxyamphetamine N-Methyl-3,4-methylenedioxyamphetamine: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.. 3,4-methylenedioxymethamphetamine : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.	2.05	1	0	amphetamines; benzodioxoles	neurotoxin
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	1.98	1	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	3.06	5	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
beta-phosphonopropionic acid beta-phosphonopropionic acid: structure	2.47	2	0
ro 5-4864 4'-chlorodiazepam: selectively binds peripheral benzodiazepine receptor	1.97	1	0
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.92	4	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
4-nonylphenol 4-nonylphenol: structure in first source; see also record for nonylphenol. 4-nonylphenol : A member of the class of phenols that is phenol which is para-substituted with a nonyl group.	2.1	1	0	phenols	environmental contaminant
phenytoin [no description available]	3.05	5	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5-hydroxydecanoate 5-hydroxydecanoic acid: Potassium Channel Blocker; RN refers to parent cpd	2	1	0	medium-chain fatty acid
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	1.98	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
8-(4-sulfophenyl)theophylline 8-(4-sulfophenyl)theophylline: adenosine antagonist	2	1	0
8-phenyltheophylline 8-phenyltheophylline: purinergic P1 receptor antagonist	1.98	1	0
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	2.25	1	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	4.91	8	1	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
n-acetyltryptophan N-acetyltryptophan : An N-acetylamino acid that is the N-acetyl derivative of tryptophan.	5.33	13	1	N-acetyl-amino acid; tryptophan derivative	metabolite
albendazole [no description available]	2.05	1	0	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
alendronate alendronic acid : A 1,1-bis(phosphonic acid) that is methanebis(phosphonic acid) in which the two methylene hydrogens are replaced by hydroxy and 3-aminopropyl groups.	2.06	1	0	1,1-bis(phosphonic acid); primary amino compound	bone density conservation agent; EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor
alpha-cyano-4-hydroxycinnamate alpha-cyano-4-hydroxycinnamate: specific inhibitor of pyruvate transport in rat liver mitochondria & human erythrocytes; structure	2.68	3	0
alprenolol Alprenolol: One of the ADRENERGIC BETA-ANTAGONISTS used as an antihypertensive, anti-anginal, and anti-arrhythmic agent.. alprenolol : A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.	1.95	1	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	1.96	1	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
p-aminohippuric acid p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.	3.05	5	0	N-acylglycine	Daphnia magna metabolite
theophylline [no description available]	3.66	10	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	2.75	3	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amobarbital Amobarbital: A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565). amobarbital : A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hypnotic properties.	1.94	1	0	barbiturates
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	2.35	2	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	3.47	8	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
atrazine [no description available]	3.21	5	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
azelaic acid nonanedioic acid : An alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.	2.71	3	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	antibacterial agent; antineoplastic agent; dermatologic drug; plant metabolite
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	2.46	2	0	azobenzenes
benserazide Benserazide: An inhibitor of DOPA DECARBOXYLASE that does not enter the central nervous system. It is often given with LEVODOPA in the treatment of parkinsonism to prevent the conversion of levodopa to dopamine in the periphery, thereby increasing the amount that reaches the central nervous system and reducing the required dose. It has no antiparkinson actions when given alone.. benserazide : A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone.	4.41	1	1	carbohydrazide; catechols; primary alcohol; primary amino compound	antiparkinson drug; dopaminergic agent; EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor
benzethonium Benzethonium: Bactericidal cationic quaternary ammonium surfactant used as a topical anti-infective agent. It is an ingredient in medicaments, deodorants, mouthwashes, etc., and is used to disinfect apparatus, etc., in the food processing and pharmaceutical industries, in surgery, and also as a preservative. The compound is toxic orally as a result of neuromuscular blockade.	2.04	1	0	alkylbenzene
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	3.28	6	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
butylbenzyl phthalate spatozoate: structure in first source	2.69	2	0	benzyl ester
berberine [no description available]	2.25	1	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
propiolactone Propiolactone: Disinfectant used in vapor form to sterilize vaccines, grafts, etc. The vapor is very irritating and the liquid form is carcinogenic.	3.82	2	1	propan-3-olide
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2.76	3	0
bronopol [no description available]	1.95	1	0	nitro compound
bunazosin bunazosin: structure	2.37	2	0	quinazolines
bupivacaine Bupivacaine: A widely used local anesthetic agent.. 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide : A piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline.. bupivacaine : A racemate composed of equimolar amounts of dextrobupivacaine and levobupivacaine. Used (in the form of its hydrochloride hydrate) as a local anaesthetic.	2.02	1	0	aromatic amide; piperidinecarboxamide; tertiary amino compound
buspirone Buspirone: An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.. buspirone : An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position.	2.15	1	0	azaspiro compound; N-alkylpiperazine; N-arylpiperazine; organic heteropolycyclic compound; piperidones; pyrimidines	anxiolytic drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; sedative; serotonergic agonist
caffeine [no description available]	5.05	10	1	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.7	3	0	aromatic ether; nitrile; polyether; tertiary amino compound
carbazochrome carbazochrome: a hemostatic which increases capillary resistance & activates platelet factors, Note: Adona is a multimeaning tradename	2.31	1	0
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	1.97	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
carvedilol [no description available]	2.06	1	0	carbazoles; secondary alcohol; secondary amino compound	alpha-adrenergic antagonist; antihypertensive agent; beta-adrenergic antagonist; cardiovascular drug; vasodilator agent
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	1.97	1	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	2.49	2	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	3.13	5	0	quaternary ammonium ion
cetyl alcohol cetyl alcohol: has been used for eczema, skin irritations; RN given refers to parent cpd; structure. hexadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of sixteen carbon atoms.. hexadecan-1-ol : A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1.	2.07	1	0	hexadecanol; long-chain primary fatty alcohol	algal metabolite; flavouring agent; human metabolite; plant metabolite
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2	1	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
chlamydocin chlamydocin: structure	2.07	1	0
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.17	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	3.75	3	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.13	1	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
eucalyptol [no description available]	2.01	1	0
ciprofibrate [no description available]	2.39	2	0	cyclopropanes; monocarboxylic acid; organochlorine compound	antilipemic drug
cisapride Cisapride: A substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed). cisapride : The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere.	2.4	2	0	benzamides
clebopride clebopride: antidopaminergic; RN given refers to parent cpd; structure	2.15	1	0	piperidines
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	5.56	23	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clofibric acid Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.	3.58	9	0	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	3.38	1	1	clonidine; imidazoline
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	9.57	74	3	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	2.46	2	0	primary amine
r 59022 R 59022: diacylglycerol kinase inhibitor; structure given in first source; platelet activator factor antagonist	1.97	1	0	diarylmethane
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.38	2	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	3.14	5	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
dichlorodiphenyl dichloroethylene Dichlorodiphenyl Dichloroethylene: An organochlorine pesticide, it is the ethylene metabolite of DDT.	2.52	2	0	chlorophenylethylene; monochlorobenzenes	human xenobiotic metabolite; persistent organic pollutant
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	2.52	2	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	3.48	2	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
diuron Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.	2.49	2	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	4.28	19	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
domperidone Domperidone: A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.. domperidone : 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used as an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet preparations.	2.15	1	0	benzimidazoles; heteroarylpiperidine	antiemetic; dopaminergic antagonist
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	3.49	8	0
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	3.14	5	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
carbonyl cyanide p-trifluoromethoxyphenylhydrazone Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.	2.87	4	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.48	2	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
fleroxacin Fleroxacin: A broad-spectrum antimicrobial fluoroquinolone. The drug strongly inhibits the DNA-supercoiling activity of DNA GYRASE.. fleroxacin : A fluoroquinolone antibiotic that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6, 7 and 8 by 2-fluoroethyl, carboxy, fluoro, 4-methylpiperazin-1-yl and fluoro groups, respectively. It is active against many Gram-positive and Gram-negative bacteria.	2.31	1	0	difluorobenzene; fluoroquinolone antibiotic; monocarboxylic acid; N-alkylpiperazine; quinolines	antibacterial drug; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	2.21	1	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.01	1	0	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	5.54	5	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	2.03	1	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurazepam Flurazepam: A benzodiazepine derivative used mainly as a hypnotic.. flurazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a 2-(diethylamino)ethyl group, 2-fluorophenyl group and chloro group at positions 1, 5 and 7, respectively. It is a partial agonist of GABAA receptors and used for the treatment of insomnia.	1.96	1	0	1,4-benzodiazepinone; monofluorobenzenes; organochlorine compound; tertiary amino compound	anticonvulsant; anxiolytic drug; GABAA receptor agonist; sedative
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	1.98	1	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gabapentin Gabapentin: A cyclohexane-gamma-aminobutyric acid derivative that is used for the treatment of PARTIAL SEIZURES; NEURALGIA; and RESTLESS LEGS SYNDROME.. gabapentin : A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.	2.06	1	0	gamma-amino acid	anticonvulsant; calcium channel blocker; environmental contaminant; xenobiotic
gemfibrozil [no description available]	1.96	1	0	aromatic ether	antilipemic drug
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	3.24	6	0
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.46	2	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.39	2	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	1.94	1	0
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	2.89	3	0	methoxybenzenes
guanethidine Guanethidine: An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.. guanethidine : A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group.. guanethidine sulfate : A organic sulfate salt composed of two molecules of guanethidine and one of sulfuric acid.	1.96	1	0	azocanes; guanidines	adrenergic antagonist; antihypertensive agent; sympatholytic agent
1-(5-isoquinolinesulfonyl)-2-methylpiperazine 1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine: A specific protein kinase C inhibitor, which inhibits superoxide release from human neutrophils (PMN) stimulated with phorbol myristate acetate or synthetic diacylglycerol.. 1-(5-isoquinolinesulfonyl)-2-methylpiperazine : A member of the class of N-sulfonylpiperazines that is 2-methylpiperazine substituted at position 1 by a 5-isoquinolinesulfonyl group.	1.97	1	0	isoquinolines; N-sulfonylpiperazine	EC 2.7.11.13 (protein kinase C) inhibitor
halothane [no description available]	2.35	2	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
harmaline Harmaline: A beta-carboline alkaloid isolated from seeds of PEGANUM.. harmaline : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.	2.99	1	0	harmala alkaloid	oneirogen
hexachlorophene Hexachlorophene: A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797). hexachlorophene : An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in soaps and creams for the treatment of various skin disorders. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union.	1.96	1	0	bridged diphenyl fungicide; polyphenol; trichlorobenzene	acaricide; antibacterial agent; antifungal agrochemical; antiseptic drug
hexestrol [no description available]	1.94	1	0	stilbenoid
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2.39	2	0	phenanthridines	fluorochrome; intercalator
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.3	6	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	2.94	4	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
idebenone [no description available]	2.11	1	0	1,4-benzoquinones; primary alcohol	antioxidant; ferroptosis inhibitor
ifosfamide [no description available]	1.99	1	0	ifosfamides	alkylating agent; antineoplastic agent; environmental contaminant; immunosuppressive agent; xenobiotic
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	3.17	1	0	indolyl alcohol	antineoplastic agent; plant metabolite
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	3.59	9	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
iodoacetamide [no description available]	2.89	4	0
iofetamine Iofetamine: An amphetamine analog that is rapidly taken up by the lungs and from there redistributed primarily to the brain and liver. It is used in brain radionuclide scanning with I-123.	2.01	1	0
iodipamide Iodipamide: A water-soluble radiographic contrast media for cholecystography and intravenous cholangiography.. adipiodone : An organoiodine compound that is 3-amino-2,4,6-triiodobenzoic acid in which one of the amino hydrogens is substituted by a 6-(3-carboxy-2,4,6-triiodoanilino)-6-oxohexanoyl group. It is a water-soluble radiographic contrast media for cholecystography and intravenous cholangiography.	1.95	1	0	benzoic acids; organoiodine compound; secondary carboxamide	radioopaque medium
iproniazid [no description available]	1.95	1	0	carbohydrazide; pyridines
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	2.89	4	0	3-isobutyl-1-methylxanthine
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2.47	2	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2.03	1	0	secondary alcohol; secondary fatty alcohol	protic solvent
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	3.47	8	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	2.4	2	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
ketorolac Ketorolac: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed). ketorolac : A racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.. 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid : A member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively.	1.98	1	0	amino acid; aromatic ketone; monocarboxylic acid; pyrrolizines; racemate	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
kynurenic acid Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.	2.49	2	0	monohydroxyquinoline; quinolinemonocarboxylic acid	G-protein-coupled receptor agonist; human metabolite; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist; Saccharomyces cerevisiae metabolite
2-phenylglycine 2-phenylglycine: RN given refers to cpd without isomeric designation; structure. alpha-phenylglycine : An amino acid with a structure in which a phenyl ring is bonded to the alpha-carbon of glycine.	1.97	1	0	non-proteinogenic alpha-amino acid	human metabolite
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	6.27	46	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
qx-314 QX-314: triethyl analog of lidocaine; RN & NM refer to ion	2.08	1	0	monocarboxylic acid amide	local anaesthetic
mecamylamine Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.	1.95	1	0	primary aliphatic amine
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	1.94	1	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	2.13	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	6.66	5	2	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	2.02	1	0	alpha,beta-unsaturated monocarboxylic acid
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	2.07	1	0	beta-amino acid ester; methyl ester; piperidines
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	2.42	2	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
mexiletine Mexiletine: Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.. mexiletine : An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.	1.99	1	0	aromatic ether; primary amino compound	anti-arrhythmia drug
mianserin Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.	3.43	1	1	dibenzoazepine	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; H1-receptor antagonist; histamine agonist; sedative; serotonergic antagonist
mirtazapine Mirtazapine: A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.	3.43	1	1	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	4.72	1	1	dihydroxyanthraquinone	analgesic; antineoplastic agent
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	2.01	1	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.03	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nimodipine Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.. nimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.	2.01	1	0	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	4.13	3	1	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
nortriptyline Nortriptyline: A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions.. nortriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline.	3.43	1	1	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.08	1	0	phenylethanolamines; tyramines	neurotransmitter
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	2.1	1	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	3.41	1	1	aromatic ether; benzimidazoles; pyridines; sulfoxide
oxazepam Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.	1.98	1	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	1.96	1	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
oxybenzone oxybenzone : A hydroxybenzophenone that is benzophenone which is substituted at the 2- and 4-positions of one of the benzene rings by hydroxy and methoxy groups respectively.	2.52	2	0	hydroxybenzophenone; monomethoxybenzene	dermatologic drug; environmental contaminant; protective agent; ultraviolet filter; xenobiotic
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.37	2	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
palmidrol palmidrol: a cannabinoid receptor-inactive eCB-related molecule used as prophylactic in helping to prevent respiratory viral infection. palmitoyl ethanolamide : An N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid.	3.06	1	0	endocannabinoid; N-(long-chain-acyl)ethanolamine; N-(saturated fatty acyl)ethanolamine	anti-inflammatory drug; anticonvulsant; antihypertensive agent; neuroprotective agent
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	1.97	1	0	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.04	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pemoline Pemoline: A central nervous system stimulant used in fatigue and depressive states and to treat hyperkinetic disorders in children.. pemoline : A member of the class of 1,3-oxazoles that is 1,3-oxazol-4(5H)-one which is substituted by an amino group at position 2 and by a phenyl group at position 5. A central nervous system stimulant, it was used to treat hyperactivity disorders in children, but withdrawn from use following reports of serious hepatotoxicity.	1.99	1	0	1,3-oxazoles	central nervous system stimulant
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.65	3	0	barbiturates	GABAA receptor agonist
pentoxifylline [no description available]	2.25	1	0	oxopurine
phenmetrazine Phenmetrazine: A sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to DEXTROAMPHETAMINE.. phenmetrazine : A member of the class of morpholines that is morpholine substituted with a phenyl group at position 2 and a methyl group at position 3.	1.99	1	0	morpholines	metabolite; sympathomimetic agent
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	1.99	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	3.06	5	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
phenoxybenzamine Phenoxybenzamine: An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator.	1.94	1	0	aromatic amine
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2.42	2	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	3.96	4	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
phloretin [no description available]	3.76	3	0	dihydrochalcones	antineoplastic agent; plant metabolite
phorate Phorate: A cholinesterase inhibitor that is used as an insecticide.. phosphatidylcholine O-34:2 : A glycerophosphocholine that is an alkyl,acyl-sn-glycero-3-phosphocholine in which the alkyl or acyl groups at positions 1 and 2 contain a total of 34 carbons and 2 double bonds.	2.1	1	0	organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	1.99	1	0	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	3.35	7	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
potassium iodide Potassium Iodide: An inorganic compound that is used as a source of iodine in thyrotoxic crisis and in the preparation of thyrotoxic patients for thyroidectomy. (From Dorland, 27th ed). potassium iodide : A metal iodide salt with a K(+) counterion. It is a scavenger of hydroxyl radicals.	2.06	1	0	potassium salt	expectorant; radical scavenger
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	2.66	3	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
pyranoprofen pyranoprofen: RN given refers to unlabled parent cpd; structure given in first source	2.05	1	0	pyridochromene
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2	1	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	3.9	13	0	benzoic acids; sulfonamide	uricosuric drug
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	2.17	1	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
procaterol Procaterol: A long-acting beta-2-adrenergic receptor agonist.	2.1	1	0	quinolines
propantheline Propantheline: A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking.	2.39	2	0	xanthenes
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	2.47	2	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	2.11	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.38	2	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
rabeprazole Rabeprazole: A 4-(3-methoxypropoxy)-3-methylpyridinyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.	3.82	2	1	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
butyl phosphorotrithioate butyl phosphorotrithioate: a herbicide	2.21	1	0	organic thiophosphate	defoliant
sebacic acid sebacic acid : An alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.	3.91	13	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite; plant metabolite
sulfadiazine Sulfadiazine: One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.. sulfadiazine : A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.. diazine : The parent structure of the diazines.	1.94	1	0	pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; antiprotozoal drug; coccidiostat; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sodium fluoride [no description available]	3.46	2	0	fluoride salt	mutagen
fluoroacetic acid fluoroacetic acid: N1 same as NM; RN given refers to parent cpd. fluoroacetic acid : A haloacetic acid that is acetic acid in which one of the methyl hydrogens is substituted by fluorine.	2.38	2	0	haloacetic acid; organofluorine compound	EC 4.2.1.3 (aconitate hydratase) inhibitor
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	4.5	24	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
sulfamerazine [no description available]	1.94	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen
sulfamethazine Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.	2.38	2	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antibacterial drug; antiinfective agent; antimicrobial agent; carcinogenic agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; ligand; xenobiotic
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	1.98	1	0	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
sulfamethoxypyridazine Sulfamethoxypyridazine: A sulfanilamide antibacterial agent.. sulfamethoxypyridazine : A sulfonamide consisting of pyridazine having a methoxy substituent at the 6-position and a 4-aminobenzenesulfonamido group at the 3-position.	1.94	1	0	pyridazines; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	2.13	1	0
sulfinpyrazone Sulfinpyrazone: A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.	3.45	2	0	pyrazolidines; sulfoxide	uricosuric drug
sulfisomidine Sulfisomidine: A sulfanilamide antibacterial agent.. sulfisomidine : A sulfonamide consisting of pyrimidine having methyl substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	1.94	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent
sulfobromophthalein Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination.	2.66	3	0	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye
suprofen Suprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.. suprofen : An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.	1.98	1	0	aromatic ketone; monocarboxylic acid; thiophenes	antirheumatic drug; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
tegafur [no description available]	1.98	1	0	organohalogen compound; pyrimidines
terbutaline Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.13	1	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
tetracaine Tetracaine: A potent local anesthetic of the ester type used for surface and spinal anesthesia.. tetracaine : A benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia.	3.75	3	0	benzoate ester; tertiary amino compound	local anaesthetic
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	3.05	5	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
tolmetin Tolmetin: A non-steroidal anti-inflammatory agent (ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL) similar in mode of action to INDOMETHACIN.. tolmetin : A monocarboxylic acid that is (1-methylpyrrol-2-yl)acetic acid substituted at position 5 on the pyrrole ring by a 4-methylbenzoyl group. Used in the form of its sodium salt dihydrate as a nonselective nonsteroidal anti-inflammatory drug.	1.98	1	0	aromatic ketone; monocarboxylic acid; pyrroles	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
tranexamic acid Tranexamic Acid: Antifibrinolytic hemostatic used in severe hemorrhage.	1.95	1	0	amino acid
triacetin Triacetin: A triglyceride that is used as an antifungal agent.. triacetin : A triglyceride obtained by acetylation of the three hydroxy groups of glycerol. It has fungistatic properties (based on release of acetic acid) and has been used in the topical treatment of minor dermatophyte infections.	2.94	4	0	triglyceride	adjuvant; antifungal drug; food additive carrier; food emulsifier; food humectant; fuel additive; plant metabolite; solvent
triclosan [no description available]	3.33	6	0	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic
trientine Trientine: An ethylenediamine derivative used as stabilizer for EPOXY RESINS, as ampholyte for ISOELECTRIC FOCUSING and as chelating agent for copper in HEPATOLENTICULAR DEGENERATION.. TETA : An azamacrocyle in which four nitrogen atoms at positions 1, 4, 8 and 11 of a fouteen-membered ring are each substituted with a carboxymethyl group.. 2,2,2-tetramine : A polyazaalkane that is decane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogens.	1.96	1	0	polyazaalkane; tetramine	copper chelator
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	4.09	3	1	chromanes; thiazolidinone	anticoagulant; anticonvulsant; antineoplastic agent; antioxidant; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; hypoglycemic agent; platelet aggregation inhibitor; vasodilator agent
tulobuterol [no description available]	2.13	1	0	organochlorine compound
tyramine [no description available]	2.02	1	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
undecylenic acid undecylenic acid: a fatty acid with a terminal double bond. 10-undecenoic acid : An undecenoic acid having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems.. undecenoic acid : A C11, straight-chain fatty acid carrying a C=C double bond at any position.	2.07	1	0	undecenoic acid	antifungal drug; plant metabolite
urethane [no description available]	2.05	1	0	carbamate ester	fungal metabolite; mutagen
pirinixic acid pirinixic acid: structure	3.98	13	0	aryl sulfide; organochlorine compound; pyrimidines
xanthurenic acid xanthurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.	2.1	1	0	dihydroxyquinoline; quinolinemonocarboxylic acid	animal metabolite; iron chelator; metabotropic glutamate receptor agonist; vesicular glutamate transport inhibitor
xylazine Xylazine: An adrenergic alpha-2 agonist used as a sedative, analgesic and centrally acting muscle relaxant in VETERINARY MEDICINE.. xylazine : A methyl benzene that is 1,3-dimethylbenzene which is substituted by a 5,6-dihydro-4H-1,3-thiazin-2-ylnitrilo group at position 2. It is an alpha2 adrenergic receptor agonist and frequently used in veterinary medicine as an emetic and sedative with analgesic and muscle relaxant properties.	3.39	1	1	1,3-thiazine; methylbenzene; secondary amino compound	alpha-adrenergic agonist; analgesic; emetic; muscle relaxant; sedative
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	1.98	1	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	3.41	7	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	3.79	2	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
lysergic acid diethylamide Lysergic Acid Diethylamide: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.. lysergic acid diethylamide : An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.	1.95	1	0	ergoline alkaloid; monocarboxylic acid amide; organic heterotetracyclic compound	dopamine agonist; hallucinogen; serotonergic agonist
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	3.04	1	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
phentolamine Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.	1.96	1	0	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	3.39	7	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	2.88	4	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	1.95	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	5.56	16	1	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
methacetin methacetin: RN given refers to parent cpd. methacetin : A member of the class of acetamides that is paracetamol in which the hydrogen of phenolic hydroxy group has been replaced by a methyl group.	2.05	1	0	acetamides; aromatic ether
aldosterone [no description available]	1.94	1	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.46	2	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	4.17	5	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	1.97	1	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
adrenochrome Adrenochrome: Pigment obtained by the oxidation of epinephrine.	2.31	1	0	indoles
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	2.78	3	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	4	14	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2.69	3	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	2.34	2	0	dialkyl phosphate
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.36	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	4.7	30	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	5.06	13	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	3.66	10	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	3.78	11	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	4.45	7	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	3.89	13	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	3.95	13	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	2.13	1	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	1.95	1	0	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.41	2	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	2.37	2	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
methyltestosterone Methyltestosterone: A synthetic hormone used for androgen replacement therapy and as an hormonal antineoplastic agent (ANTINEOPLASTIC AGENTS, HORMONAL).. methyltestosterone : A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position.	2.06	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; enone	anabolic agent; androgen; antineoplastic agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	4.4	22	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.39	2	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	2.35	2	0	uridines	drug metabolite; fundamental metabolite; human metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.6	1	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	3.45	8	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	2.53	2	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	3.07	5	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	5.85	4	2	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	7.85	19	1	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tributyrin tributyrin: structure. tributyrin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by butyric acid.	3.83	11	0	butyrate ester; triglyceride	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug; protective agent
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	3.02	4	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	3.08	5	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
phlorhizin [no description available]	3.04	1	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
acepromazine Acepromazine: A phenothiazine that is used in the treatment of PSYCHOSES.. acepromazine : A member of the class of phenothiazines that is 10H-phenothiazine substituted by an acetyl group at position 2 and a 3-(dimethylamino)propyl group at position 10.	3.39	1	1	aromatic ketone; methyl ketone; phenothiazines; tertiary amino compound	phenothiazine antipsychotic drug
methoxamine Methoxamine: An alpha-1 adrenergic agonist that causes prolonged peripheral VASOCONSTRICTION.. methoxamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine .	1.94	1	0	amphetamines	alpha-adrenergic agonist; antihypotensive agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	3.56	9	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.37	2	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	4.6	27	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
aniline [no description available]	2.02	1	0	anilines; primary arylamine
2-aminoisobutyric acid 2-aminoisobutyric acid: RN given refers to unlabeled cpd. 2-aminoisobutyric acid : A rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays.	2.07	1	0	2,2-dialkylglycine zwitterion; 2,2-dialkylglycine
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	2.41	2	0	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.15	1	0	lactose
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	4.22	5	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.4	2	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	3.34	7	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	2.02	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	1.94	1	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
n-hexanal [no description available]	2.49	2	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	2.87	4	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	2.02	1	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	3.97	4	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
sodium citrate, anhydrous Sodium Citrate: Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.. sodium citrate : The trisodium salt of citric acid.	2.02	1	0	organic sodium salt	anticoagulant; flavouring agent
cycloserine Cycloserine: Antibiotic substance produced by Streptomyces garyphalus.. D-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).	2.04	1	0	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist
mannitol [no description available]	3.59	3	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	4.7	2	1	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	3.21	6	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
dinitrofluorobenzene Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.	1.97	1	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.1	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	4.14	6	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	3.42	7	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	2.02	1	0	chloroethanes	polar solvent
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	3.34	7	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.68	3	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
mestranol [no description available]	1.99	1	0	17beta-hydroxy steroid; aromatic ether; terminal acetylenic compound	prodrug; xenoestrogen
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	6.07	29	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	3.58	9	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	3.78	11	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.1	1	0	alkane; gas molecular entity	food propellant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	3.16	5	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.1	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
tert-amyl alcohol 2-methylbutan-2-ol : A tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups.	2	1	0	aliphatic alcohol; tertiary alcohol	protic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.21	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	3.28	6	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
hexadecafluoro-nonanoic acid hexadecafluoro-nonanoic acid: an endocrine disruptor. hexadecafluorononanoic acid : Any derivative of nonanoic acid carrying sixteen fluoro substituents.	5.12	41	0	hexadecafluorononanoic acid
bromthymol blue Bromthymol Blue: A pH sensitive dye that has been used as an indicator in many laboratory reactions.. bromothymol blue : A member of the class of 2,1-benzoxathioles that is 2,1-benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3-bromo-4-hydroxy-5-isopropyl-2-methylphenyl groups.	1.95	1	0	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; polyphenol; sultone	acid-base indicator; dye; two-colour indicator
bromcresol green Bromcresol Green: An indicator and reagent. It has been used in serum albumin determinations and as a pH indicator.	1.95	1	0	benzofurans
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	6.55	33	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
trimethylolpropane [no description available]	2.42	2	0	primary alcohol
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	1.96	1	0	mercaptopropanoic acid	algal metabolite
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	2.05	1	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	2.52	2	0	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
propylene dichloride propylene dichloride: Russian drug; structure. 1,2-dichloropropane : A chloroalkane that is propane in which a hydrogen from each of two adjacent carbons has been replaced by chlorines.	2.1	1	0	chloroalkane; volatile organic compound
2-butanol 2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.	2	1	0	secondary alcohol
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	3.55	8	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
peracetic acid Peracetic Acid: A liquid that functions as a strong oxidizing agent. It has an acrid odor and is used as a disinfectant.. peracetic acid : A peroxy acid that is acetic acid in which the OH group is substituted by a hydroperoxy group. It is a versatile oxidising agent that is used as a disinfectant.	2.97	4	0	a peroxy acid	disinfectant; oxidising agent
isobutyric acid isobutyric acid: RN given refers to parent cpd. isobutyric acid : A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.	2.67	3	0	branched-chain saturated fatty acid; fatty acid 4:0; methyl-branched fatty acid	Daphnia magna metabolite; plant metabolite; volatile oil component
dichloroacetic acid [no description available]	3.35	7	0	monocarboxylic acid; organochlorine compound	astringent; marine metabolite
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	2.4	2	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum metabolite
tetrabromobisphenol a tetrabromobisphenol A: a brominated flame retardant. 3,3',5,5'-tetrabromobisphenol A : A bromobisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups and the phenyl rings are substituted by bromo groups at positions 2, 2', 6 and 6'. It is a brominated flame retardant.	3.23	5	0	brominated flame retardant; bromobisphenol
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	4.71	26	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
bis(4-hydroxyphenyl)sulfone bis(4-hydroxyphenyl)sulfone: structure and RN in first source. 4,4'-sulfonyldiphenol : A sulfone that is diphenyl sulfone in which both of the para hydrogens have been replaced by hydroxy groups.	2.13	1	0	bisphenol; sulfone	endocrine disruptor; metabolite
cumene hydroperoxide cumene hydroperoxide: RN given refers to parent cpd. cumene hydroperoxide : A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.	2.21	1	0	peroxol	environmental contaminant; Mycoplasma genitalium metabolite; oxidising agent
methylmethacrylate Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.	2.06	1	0	enoate ester; methyl ester	allergen; polymerisation monomer
dehydrocholic acid Dehydrocholic Acid: A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.. 3,7,12-trioxo-5beta-cholanic acid : An oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton.	1.96	1	0	12-oxo steroid; 3-oxo-5beta-steroid; 7-oxo steroid; oxo-5beta-cholanic acid	gastrointestinal drug
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	3.2	6	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
skatole [no description available]	2.15	1	0	methylindole	human metabolite; mammalian metabolite
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.05	1	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	3.76	11	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
pyocyanine Pyocyanine: Antibiotic pigment produced by Pseudomonas aeruginosa.. pyocyanine : An iminium betaine that is 5-methylphenazin-5-ium which is substituted at position 1 by an oxidanidyl group. An antibiotic pigment produced by Pseudomonas aeruginosa.	2.13	1	0	iminium betaine; phenazines	antibacterial agent; bacterial metabolite; biological pigment; virulence factor
fluorene [no description available]	2.02	1	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
acetopyrrothine acetopyrrothine: structure. thiolutin : A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases.	1.92	1	0	acetamides; dithiolopyrrolone antibiotic	angiogenesis inhibitor; antibacterial agent; antifungal agent; antineoplastic agent; bacterial metabolite; chelator; EC 2.7.7.6 (RNA polymerase) inhibitor; marine metabolite; protein synthesis inhibitor; toxin
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.4	2	0
2,4,6-trichlorophenol [no description available]	2.06	1	0	trichlorophenol	carcinogenic agent
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.38	2	0	pyrrolidin-2-ones
dinoseb dinoseb: RN given refers to parent cpd; structure. dinoseb : A racemate composed of equimolar amounts of (R)- and (S)-dinoseb.. 2-(butan-2-yl)-4,6-dinitrophenol : A dinitrophenol that is 2,4-dinitrophenol substituted by a butan-2-yl group at position 2.	2.21	1	0	dinitrophenol
picric acid picric acid: used as antiseptic, astringent & stimulant for epitheliazation; structure. picric acid : A C-nitro compound comprising phenol having three nitro substtituents at the 2-, 4- and 6-positions.	1.93	1	0	C-nitro compound	antiseptic drug; explosive; fixative
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	2.89	3	0	monoterpenoid; phenols	volatile oil component
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.04	1	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.82	3	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	2.02	1	0	xylene
3,4-dimethylphenol 3,4-dimethylphenol: RN given refers to parent cpd. 3,4-xylenol : A member of the class of phenols that is phenol substituted by methyl groups at positions 3 and 4.	1.99	1	0	phenols
dilactide dilactide: structure given in first source	2.41	1	0	dioxanes
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.57	2	0	butan-4-olide	metabolite; neurotoxin
2-methylvaleric acid 2-methylvaleric acid : A methyl-branched fatty acid that is pentanoic acid which carries a methyl group at position 2.	1.97	1	0	branched-chain saturated fatty acid; methyl-branched fatty acid; monocarboxylic acid; short-chain fatty acid	flavouring agent; fragrance; plant metabolite
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	2.5	2	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.25	1	0	aldehyde; furans	Maillard reaction product; metabolite
benzenesulfonic acid benzenesulfonic acid: RN given refers to parent cpd. benzenesulfonic acid : The simplest member of the class of a benzenesulfonic acids that consists of a benzene carrying a single sulfo group.	2.05	1	0	benzenesulfonic acids
cyclohexanecarboxylic acid cyclohexanecarboxylic acid: RN given refers to parent cpd. cyclohexanecarboxylic acid : A monocarboxylic acid that consists of cyclohexane substituted by a carboxy group.	1.98	1	0	monocarboxylic acid
sym-trinitrobenzene Trinitrobenzenes: Benzene derivatives which are substituted with three nitro groups in any position.. 1,3,5-trinitrobenzene : A trinitrobenzene in which each of the nitro groups is meta- to the other two.	1.95	1	0	trinitrobenzene	explosive
4-bromophenacyl bromide 4-bromophenacyl bromide: phospholipidase A(2) inhibitor; structure	2.03	1	0
methylparaben methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd. methylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.	2.82	3	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
gamma-terpinene gamma-terpinene: RN given refers to gamma-terpinene; structure. gamma-terpinene : One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.	2.05	1	0	cyclohexadiene; monoterpene	antioxidant; human xenobiotic metabolite; plant metabolite; volatile oil component
4-anisic acid 4-methoxybenzoic acid: structure in first source. 4-methoxybenzoic acid : A methoxybenzoic acid substituted with a methoxy group at position C-4.	2.03	1	0	methoxybenzoic acid	plant metabolite
4-nitroanisole 4-nitroanisole: dye intermediate; organic synthesis; structure. 4-nitroanisole : A member of the class of 4-nitroanisoles that is anisole in which one the hydrogen meta to the methoxy group is replaced by a nitro group.	1.96	1	0	4-nitroanisoles
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.02	1	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
nicotinyl alcohol Nicotinyl Alcohol: Alcohol analog of NICOTINIC ACID which is a direct-acting peripheral vasodilator that causes flushing and may decrease blood pressure. It is used in vasospasm and threatened GANGRENE.. 3-pyridinemethanol : A member of the class of pyridines that is pyridine which is substituted by a hydroxymethyl group at position 3 .	1.99	1	0	aromatic primary alcohol; pyridines	antilipemic drug; vasodilator agent
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	2.03	1	0	quinuclidines; saturated organic heterobicyclic parent
triethanolamine triethanolamine: RN given refers to parent cpd. triethanolamine : A tertiary amino compound that is ammonia in which each of the hydrogens is substituted by a 2-hydroxyethyl group.	2.04	1	0	amino alcohol; tertiary amino compound; triol	buffer; surfactant
2-phenylethyl acetate phenethyl acetate : The acetate ester of 2-phenylethanol.	2.54	2	0	acetate ester	metabolite; Saccharomyces cerevisiae metabolite
ethyl butyrate ethyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of ethanol with the carboxy group of butyric acid.	3.06	4	0	butyrate ester	plant metabolite
citronellal citronellal: aldehyde of citronellol; found in citronella oil. citronellal : A monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma.	2.04	1	0	aldehyde; monoterpenoid	antifungal agent; metabolite
ethyl oenanthate ethyl heptanoate : The fatty acid ethyl ester of heptanoic acid.	1.96	1	0	fatty acid ethyl ester	metabolite
ethyl caprylate ethyl octanoate : A fatty acid ethyl ester resulting from the formal condensation of octanoic acid with ethanol.	4.23	15	0	fatty acid ethyl ester; octanoate ester	metabolite
ethyl laurate ethyl laurate : A fatty acid ethyl ester of lauric acid.	1.97	1	0	fatty acid ethyl ester	metabolite
4-phenylenediamine 4-phenylenediamine: agent hair dye responsible for contact dermatitis; RN given refers to parent cpd. 1,4-phenylenediamine : A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.	2.25	1	0	phenylenediamine	allergen; dye; hapten; reagent
methyl caproate methyl hexanoate : A fatty acid methyl ester derived from hexanoic (caproic acid).	2.01	1	0	fatty acid methyl ester; hexanoate ester	flavouring agent; plant metabolite
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	2.1	1	0	epoxide; organochlorine compound
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	1.97	1	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
melamine melamine: RN given refers to parent cpd; structure. melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton.	2.25	1	0	triamino-1,3,5-triazine	xenobiotic metabolite
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.01	1	0	cyclohexanols; secondary alcohol	solvent
triethylene glycol dimethacrylate [no description available]	2.47	2	0
n-pentanoic acid n-pentanoic acid: RN given refers to unlabeled parent cpd. valeric acid : A straight-chain saturated fatty acid containing five carbon atoms.	2.66	3	0	short-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.39	2	0	alkane; volatile organic compound	non-polar solvent; refrigerant
diethylamine [no description available]	1.93	1	0	secondary aliphatic amine
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	3.46	7	0	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	2.48	2	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	3.16	5	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
isobutyl acetate isobutyl acetate : The acetate ester of isobutanol.	2.05	1	0	acetate ester	Saccharomyces cerevisiae metabolite
isopropyl myristate isopropyl myristate: used for microemulsions; structure	3.65	9	0	fatty acid ester
ethyl decanoate ethyl decanoate : A fatty acid ethyl ester of decanoic acid.	3.16	5	0	decanoate ester; fatty acid ethyl ester	metabolite
2-heptanone heptan-2-one : A dialkyl ketone with methyl and pentyl as the alkyl groups.	2.9	4	0	dialkyl ketone; methyl ketone	mouse metabolite; pheromone
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	2.31	1	0	cycloalkane; volatile organic compound	non-polar solvent
piperidine [no description available]	2.07	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
diisopropanolamine diisopropanolamine: RN given refers to parent cpd. diisopropanolamine : A secondary amino compound that is diethanolamine substituted by methyl groups at positions 1 and 1'. It is a versatile chemical used in a variety of personal care, cosmetic and industrial products.	2.13	1	0	aminodiol; secondary alcohol; secondary amino compound	buffer; emulsifier; surfactant
squalane [no description available]	2.08	1	0
methyl octanoate methyl octanoate : A fatty acid methyl ester resulting from the formal condensation of the carboxy group of octanoic acid with the hydroxy group of methanol.	4.63	8	0	fatty acid methyl ester; octanoate ester	metabolite
methyl heptine carbonate methyl heptine carbonate: structure	4.99	7	0	fatty acid ester
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	3.08	5	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
heptanal heptanal : An n-alkanal resulting from the oxidation of the alcoholic hydroxy group of heptan-1-ol to the corresponding aldehyde. An endogenous aldehyde coming from membrane lipid oxidation, it is found in the blood of lung cancer patients and has been regarded as a potential biomarker of lung cancer.	2.5	2	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	biomarker
lauric acid methyl ester methyl laurate : A fatty acid methyl ester of lauric acid.	2	1	0	dodecanoate ester; fatty acid methyl ester	metabolite
octylamine octylamine: RN given refers to 1-octylamine. octan-1-amine : An 8-carbon primary aliphatic amine.	2.01	1	0	primary aliphatic amine	metabolite
carbitol carbitol: used as lubricating oil & in braking fluid, structure. diethylene glycol monoethyl ether : A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.	3.32	6	0	diether; glycol ether; hydroxypolyether; primary alcohol	protic solvent
pelargonic acid pelargonic acid: K salt acts as cariostatic agent; RN given refers to parent cpd; structure. nonanoic acid : A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.	4	13	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
octyl acetate octyl acetate : The acetate ester of octan-1-ol.	2.05	1	0	acetate ester	plant metabolite
triethylene glycol triethylene glycol : A poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms.	1.97	1	0	diol; poly(ethylene glycol); primary alcohol	plasticiser
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	3.62	3	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
undecanoic acid undecanoic acid : A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.. undecanoate : A medium-chain fatty acid anion that is the conjugate base of undecanoic acid; used in tandem with testosterone cation in the treatment of male hypogonadism. Major species at pH 7.3.	3.11	5	0	medium-chain fatty acid; straight-chain saturated fatty acid	antifungal agent; human metabolite
dodecanol Dodecanol: A saturated 12-carbon fatty alcohol obtained from coconut oil fatty acids. It has a floral odor and is used in detergents, lubricating oils, and pharmaceuticals. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). dodecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of twelve carbon atoms.. dodecan-1-ol : A primary alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certain moths whose larvae destroy crops.	2.05	1	0	dodecanol; primary alcohol	bacterial metabolite; cosmetic; insect attractant; insecticide; pheromone; plant metabolite
behenic acid behenic acid: RN given refers to parent cpd; structure. docosanoic acid : A straight-chain, C22, long-chain saturated fatty acid.	2.39	2	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
bromphenol blue Bromphenol Blue: A dye that has been used as an industrial dye, a laboratory indicator, and a biological stain.. bromophenol blue : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3,5-dibromo-4-hydroxyphenyl groups. It is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as a size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye.	1.95	1	0	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; phenols; sultone	acid-base indicator; dye; two-colour indicator
tetrafluoroethylene tetrafluoroethylene: RN given refers to parent cpd; structure	2.49	2	0	fluorocarbon
2-methylbutanoic acid 2-methylbutanoic acid: RN given refers to parent cpd without isomeric designation. 2-methylbutyric acid : A methylbutyric acid comprising a butyric acid core carrying a 2-methyl substituent. Produced from amino acid leucine during nutrient starvation in bacteria.	2.1	1	0	methylbutyric acid	bacterial metabolite; human metabolite
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	4.22	17	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
hexachlorobenzene Hexachlorobenzene: An agricultural fungicide and seed treatment agent.. hexachlorobenzene : A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stockholm Convention on Persistent Organic Pollutants.	2.15	1	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	2.41	1	0	trinitrotoluene	explosive
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.34	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	1.92	1	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
meglumine Meglumine: 1-Deoxy-1-(methylamino)-D-glucitol. A derivative of sorbitol in which the hydroxyl group in position 1 is replaced by a methylamino group. Often used in conjunction with iodinated organic compounds as contrast medium.. N-methylglucamine : A hexosamine that is D-glucitol in which the hydroxy group at position 1 is substituted by the nitrogen of a methylamino group. A crystalline base, it is used in preparing salts of certain acids for use as diagnostic radiopaque media, while its antimonate is used as an antiprotozoal in the treatment of leishmaniasis.	1.95	1	0	hexosamine; secondary amino compound
monobutyl phthalate monobutyl phthalate: RN given refers to parent cpd	2.06	1	0	phthalic acid monoester
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.69	3	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
2-ethylhexanoic acid 2-ethylhexanoic acid: structure in first source; wood preservative; 2-ethylhexanoic acid is active ingredient in Sinesto B	2.91	4	0	branched-chain fatty acid
dodecyl sulfate dodecyl sulfate: RN given refers to parent cpd; see also SODIUM DODECYL SULFATE	2.4	2	0	alkyl sulfate
benzyl acetate benzyl acetate : The acetate ester of benzyl alcohol.	2.25	1	0	acetate ester; benzyl ester	metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.78	3	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	7.13	43	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	3.02	4	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
isopropyl palmitate isopropyl palmitate : A fatty acid ester obtained by the formal condensation of carboxy group of palmitic acid with propan-2-ol. Metabolite observed in cancer metabolism.	2.11	1	0	fatty acid ester; isopropyl ester	human metabolite
pregnenolone [no description available]	2.37	2	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
3-o-methylglucose 3-O-Methylglucose: A non-metabolizable glucose analogue that is not phosphorylated by hexokinase. 3-O-Methylglucose is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems. (J Neurochem 1993;60(4):1498-504). 3-O-methyl-D-glucose : A D-aldohexose that is D-glucose in which the hydrogen of the hydroxy group at position 3 has been substituted by a methyl group. It is a non-metabolisable glucose analogue that is not phosphorylated by hexokinase and is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems.	2.46	2	0	D-aldohexose derivative
citronellyl acetate citronellyl acetate: RN given refers to cpd without isomeric designation. citronellol acetate : A monoterpenoid that is the acetate ester of citronellol. It has been isolated from Citrus hystrix.	2.21	1	0	acetate ester; monoterpenoid	plant metabolite
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.61	2	0	catechin	antioxidant; plant metabolite
thiamine pyrophosphate Thiamine Pyrophosphate: The coenzyme form of Vitamin B1 present in many animal tissues. It is a required intermediate in the PYRUVATE DEHYDROGENASE COMPLEX and the KETOGLUTARATE DEHYDROGENASE COMPLEX.. thiamine(1+) diphosphate chloride : An organic chloride salt of thiamine(1+) diphosphate.	1.94	1	0	organic chloride salt; vitamin B1
coronene coronene: structure. coronene : A ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.	2.06	1	0	ortho- and peri-fused polycyclic arene
dibenzo(a,l)pyrene dibenzo(a,l)pyrene: structure in first source	3.17	1	0	ortho- and peri-fused polycyclic arene	human metabolite; mutagen
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	2.48	2	0	ortho- and peri-fused polycyclic arene
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.37	2	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	1.94	1	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
norcarane norcarane: structure in first source	2.15	1	0
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.95	4	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
thiazoles [no description available]	3.79	11	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	1.94	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
perfluorooctane perfluorooctane: used in the treatment of giant retinal tears with proliferative vitreoretinopathy	5.63	20	0	fluoroalkane; fluorocarbon
difluorodinitrobenzene sulfone [no description available]	1.97	1	0
perfluoroheptane [no description available]	2.47	2	0	fluorocarbon
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	19.07	1,988	4	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
perfluorodecanoic acid perfluorodecanoic acid : A fluoroalkanoic acid that is perfluorinated decanoic acid.	7.26	90	1	fluoroalkanoic acid	environmental contaminant; xenobiotic
perfluoromethylcyclohexane [no description available]	2.06	1	0
perfluorobutane perfluorobutane: component of the echo contrast agent, BR14, which consists of perfluorobutane gas microbubbles. perflubutane : A fluorocarbon that is butane in which all of the hydrogens have been replaced by fluorines. Microbubbles of preflubutane are used in the ultrasound contrast agent BR14.	6.13	37	0	fluoroalkane; fluorocarbon; gas molecular entity	ultrasound contrast agent
perflexane perfluorohexane : A fluoroalkane that is hexane in which all of the hydrogens have been replaced by fluorines.	7.47	54	0	fluoroalkane; fluorocarbon; volatile organic compound	non-polar solvent; radioopaque medium
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	2.07	1	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite
aminoimidazole carboxamide Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.	2.7	3	0	aminoimidazole; monocarboxylic acid amide	mouse metabolite
methochlorpromazine methochlorpromazine: RN given refers to parent cpd	1.96	1	0
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	3.05	5	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
perfluorobutyric acid perfluorobutyric acid: ion pairing reagent; RN given refers to parent cpd. perfluorobutyric acid : A monocarboxylic acid that is perfluorinated butyric acid.	5.28	47	0	fluoroalkanoic acid	chromatographic reagent; environmental contaminant; xenobiotic
2,3,4,5,6-pentafluorobenzyl alcohol 2,3,4,5,6-pentafluorobenzyl alcohol : An organofluorine compound that is benzyl alcohol substituted by fluoro groups at positions 2, 3, 4, 5 and 6.	2.02	1	0	benzyl alcohols; organofluorine compound
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	2.11	1	0	monofluorobenzenes	NMR chemical shift reference compound
3,3-dimethyl-2-butanol [no description available]	2	1	0
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	2.63	2	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	7.67	9	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.01	1	0	bile acid glycine conjugate	human metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	1.99	1	0
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	1.96	1	0	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
dithiol dithiol: structure	1.93	1	0
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	3.08	4	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
citronellic acid citronellic acid: structure in first source. citronellic acid : A monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7.	4.32	5	0	medium-chain fatty acid; monoterpenoid; monounsaturated fatty acid	flavouring agent; plant metabolite
hexahydrofarnesylacetone hexahydrofarnesylacetone: a C-18 terpene	2.05	1	0	ketone
4-hydroxybutyric acid 4-hydroxybutyric acid: was an entry term to Sodium Oxybate (74-98). 4-hydroxybutyric acid : A 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.	3.12	1	0	4-hydroxy monocarboxylic acid; hydroxybutyric acid	general anaesthetic; GHB receptor agonist; neurotoxin; sedative
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.69	3	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	2.04	1	0	propane-1,3-diols	metabolite; protic solvent
suberic acid suberic acid: used in plastics industry; inhibits activity of some enzymes; RN given refers to parent cpd; structure. suberic acid : An alpha,omega-dicarboxylic acid that is the 1,6-dicarboxy derivative of hexane.	7.58	44	1	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite
arachidic acid icosanoic acid : A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.	2.01	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
cyanogen bromide Cyanogen Bromide: Cyanogen bromide (CNBr). A compound used in molecular biology to digest some proteins and as a coupling reagent for phosphoroamidate or pyrophosphate internucleotide bonds in DNA duplexes.	2.35	2	0
oleanolic acid [no description available]	2.21	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	3.12	5	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	3.38	7	0	organic molecular entity
2-n-butylmalonate 2-n-butylmalonate: structure	1.95	1	0
perillyl alcohol perillyl alcohol: inhibits geranylgeranyl transferase; structure in first source. perillyl alcohol : A limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender.	1.96	1	0	limonene monoterpenoid	plant metabolite; volatile oil component
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	2.47	2	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
tricaprylin tricaprylin: 13C-labeled trioctanoin used in breath tests to detect fat malabsorption. trioctanoin : A triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease.	11.54	130	3	octanoate ester; triglyceride	anticonvulsant; plant metabolite
trilaurin trilaurin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by lauric (dodecanoic) acid.	4.47	7	0	dodecanoate ester; triglyceride
cetyl palmitate palmityl palmitate : A palmitate ester resulting from the formal condensation of palmitic acid with palmityl alcohol. It is used as a thickener and emollient in cosmetics.	2.49	2	0	hexadecanoate ester	metabolite
ethylene bromohydrin ethylene bromohydrin: RN given refers to 2-bromo cpd	1.96	1	0
2,2,4-trimethylpentane 2,2,4-trimethylpentane: nephrotoxic. isooctane : An alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.	1.96	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	5.54	14	1	dialdehyde	biomarker
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	3.95	13	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
n-hexadecane n-hexadecane: structure. hexadecane : A straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper.	2.47	2	0	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
trichloroacetonitrile [no description available]	1.99	1	0	aliphatic nitrile; organochlorine compound
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	2.11	1	0	organic sodium salt; organobromine compound	fluorochrome; histological dye
neutral red Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.	2.1	1	0	hydrochloride	acid-base indicator; dye; two-colour indicator
4,4'-bipyridyl 4,4'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'.	2.05	1	0	bipyridine
tristearin tristearoylglycerol : A triglyceride that is glycerol in which all three hydroxy groups have been formally esterified with stearic acid.	2.84	3	0	triacylglycerol 54:0	Caenorhabditis elegans metabolite; plant metabolite
tripalmitin tripalmitin: structure. tripalmitin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by palmitic (hexadecanoic) acid.	2.66	3	0	triglyceride
trimyristin trimyristin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by myristic (tetradecanoic) acid.	2.39	2	0	tetradecanoate ester; triglyceride
glycyl-glycyl-glycine glycyl-glycyl-glycine : A tripeptide in which three glycine units are linked via peptide bonds in a linear sequence.	2.05	1	0	tripeptide zwitterion; tripeptide
lignoceric acid lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.	1.97	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia tenebrosa metabolite; human metabolite; plant metabolite; volatile oil component
glycerylphosphorylcholine Glycerylphosphorylcholine: A component of PHOSPHATIDYLCHOLINES or LECITHINS, in which the two hydroxy groups of GLYCEROL are esterified with fatty acids. (From Stedman, 26th ed)	2.35	2	0	glycerophosphocholine
docusate Dioctyl Sulfosuccinic Acid: All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.	2.52	2	0	diester; organosulfonic acid
terpinolene [no description available]	2.05	1	0	p-menthadiene	insect repellent; plant metabolite; sedative; volatile oil component
levulinic acid levulinic acid: inhibits 5-aminolevulinic acid dehydratase; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5316. 4-oxopentanoic acid : An oxopentanoic acid with the oxo group in the 4-position.	2	1	0	oxopentanoic acid; straight-chain saturated fatty acid	plant metabolite
1-methylcyclopropane 1-methylcyclopropane: do not confuse with MCP cpd (1-methylcyclopropene)	2.15	1	0
methyl carbamate methyl carbamate : A carbamate ester resulting from the formal condensation of the carboxy group of carbamic acid with methanol.	2.03	1	0	carbamate ester
ethylmalonic acid ethylmalonic acid: don't confuse with diethyl malonate, which is a diester. ethylmalonate : A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of ethylmalonic acid.. ethylmalonic acid : A dicarboxylic acid obtained by substitution of one of the methylene hydrogens of malonic acid by an ethyl group.	2.38	2	0	dicarboxylic acid; dicarboxylic fatty acid	human metabolite
triphenylphosphine triphenylphosphine: RN given refers to parent cpd. triphenylphosphine : A member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.	2	1	0	benzenes; tertiary phosphine	NMR chemical shift reference compound; reducing agent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.4	7	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
dimethyl disulfide [no description available]	3.22	6	0	organic disulfide	xenobiotic metabolite
pentadecane pentadecane : A straight-chain alkane with 15 carbon atoms. It is a component of volatile oils isolated from plants species like Scandix balansae.	2.1	1	0	long-chain alkane	animal metabolite; plant metabolite; volatile oil component
brilliant green brilliant green: RN given refers to sulfate; structure in Merck Index, 9th ed, #1378. brilliant green : An organic hydrogensulfate salt having 4-{[4-(diethylamino)phenyl](phenyl)methylidene}-N,N-diethylcyclohexa-2,5-dien-1-iminium as the counterion.	2	1	0	organic hydrogensulfate salt	antibacterial agent; antiseptic drug; environmental contaminant; fluorochrome; histological dye; poison
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	4.5	5	1	cyclic ketone; erythromycin
isocaproic acid isocaproic acid: RN given refers to parent cpd. isocaproic acid : A methyl-branched fatty acid that is pentanoic acid with a methyl group substituent at position 4. It is a metabolite of 20 alpha-hydroxycholesterol	2.37	2	0	branched-chain saturated fatty acid; medium-chain fatty acid; methyl-branched fatty acid	human metabolite
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	2.25	1	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
dodecanedioic acid dodecanedioic acid: RN given refers to parent cpd. dodecanedioic acid : An alpha,omega-dicarboxylic acid that is dodecane in which the methyl groups have been oxidised to the corresponding carboxylic acids.	2.9	4	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; human metabolite
2,3,4,5,6-pentafluorophenol 2,3,4,5,6-pentafluorophenol: RN given refers to parent cpd; structure given in first source	2.11	1	0
4-nitrophenyl acetate [no description available]	2.42	2	0	C-nitro compound; phenyl acetates
1-phenylazo-2-naphthol 1-phenylazo-2-naphthol: RN given refers to cpd without isomeric designation	2.25	1	0
hydroxyethyl methacrylate hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE. 2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol.	2.47	2	0	enoate ester	allergen; polymerisation monomer
omega-aminoenantic acid [no description available]	2	1	0	medium-chain fatty acid
dodecylamine dodecylamine: RN given refers to parent cpd	2.43	2	0	primary aliphatic amine
deoxycytidine [no description available]	2.13	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2,6-dichloroindophenol 2,6-Dichloroindophenol: A dye used as a reagent in the determination of vitamin C.. 2,6-dichloroindophenol : A quinone imine that is indophenol substituted by chloro groups at positions 2 and 6.. N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine : 1,4-benzoquinone imine having a 3,5-dichloro-4-hydroxyphenyl substituent attached to the nitrogen atom.	1.98	1	0	dichlorobenzene; quinone imine
pentadecanoic acid pentadecanoic acid: in serum as a marker for intake of milk fat. pentadecanoic acid : A straight-chain saturated fatty acid containing fifteen-carbon atoms.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; food component; human blood serum metabolite; plant metabolite
1,3-propane sultone 1,3-propane sultone: sultone is usually defined as a derivative of 1,8-naphtholsulfonic acid; structure	2.1	1	0	sultone
decabromobiphenyl ether decabromobiphenyl ether: a flame retardant. decabromodiphenyl ether : A polybromodiphenyl ether that is diphenyl ether in which all of the hydrogens have been replaced by bromines.	2.13	1	0	polybromodiphenyl ether	neurotoxin
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	2.02	1	0
cadmium sulfide [no description available]	2.41	1	0	cadmium molecular entity
potassium hydroxide potassium hydroxide: RN given refers to cpd with MF of K-OH	2.78	3	0	alkali metal hydroxide
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.89	4	0	alkali metal hydroxide
manganese dioxide [no description available]	2.15	1	0	manganese molecular entity; metal oxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.57	2	0	zinc molecular entity
propyleneglycol monolaurate [no description available]	2.17	1	0
monolaurin monolaurin: RN given refers to cpd with unspecified monolaurin locant. 1-monolauroylglycerol : A 1-monoglyceride with dodecanoyl (lauroyl) as the acyl group.. rac-1-monolauroylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-lauroyl-sn-glycerol and 3-lauroyl-sn-glycerol	2.42	2	0	1-monoglyceride; dodecanoate ester; rac-1-monoacylglycerol
ammonium hydroxide Ammonium Hydroxide: The hydroxy salt of ammonium ion. It is formed when AMMONIA reacts with water molecules in solution.. ammonium hydroxide : A solution of ammonia in water.	2.05	1	0	inorganic hydroxy compound	food acidity regulator
sorbitan monostearate sorbitan monostearate: Stearic Acid was the HM (74-82), no longer an active MH	2.21	1	0
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	2.41	1	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.73	10	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	2.03	1	0
selenomethionine [no description available]	2.21	1	0	selenoamino acid; selenomethionines	plant metabolite
bisphenol a-glycidyl methacrylate Bisphenol A-Glycidyl Methacrylate: The reaction product of bisphenol A and glycidyl methacrylate that undergoes polymerization when exposed to ultraviolet light or mixed with a catalyst. It is used as a bond implant material and as the resin component of dental sealants and composite restorative materials.	2.47	2	0	diarylmethane
methyl tert-butyl ether methyl tert-butyl ether: used to dissolve gallstones; gasoline additive. methyl tert-butyl ether : An ether having methyl and tert-butyl as the two alkyl components.	7.83	27	0	ether	fuel additive; metabolite; non-polar solvent
ioxynil ioxynil: RN given refers to parent cpd; structure. ioxynil : A nitrile that is benzonitrile substituted by a hydroxy group at position 4 and iodo groups at positions 3 and 5.	2.07	1	0	iodophenol; nitrile	environmental contaminant; herbicide; xenobiotic
bromoxynil bromoxynil: RN given refers to parent cpd; structure. 3,5-dibromo-4-hydroxybenzonitrile : A dibromobenzene that is 2,6-dibromophenol substituted by a cyano group at position 4.	2.01	1	0	dibromobenzene; hydroxynitrile; phenols	environmental contaminant; herbicide; xenobiotic
ethyldimethylaminopropyl carbodiimide Ethyldimethylaminopropyl Carbodiimide: Carbodiimide cross-linking reagent.	1.99	1	0
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	2.11	1	0	organic cation	geroprotector; herbicide
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.54	2	0	quaternary ammonium ion
beta-hydroxymyristic acid beta-hydroxymyristic acid: RN given refers to cpd without isomeric designation. 3-hydroxytetradecanoic acid : A 3-hydroxy fatty acid that is tetradecanoic (myristic) acid substituted at position 3 by a hydroxy group	2.47	2	0	3-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; long-chain fatty acid	bacterial metabolite; human metabolite
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	3.23	1	0	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
1,6-diaminohexane 1,6-diaminohexane: Russian drug; RN given refers to parent cpd; structure. hexane-1,6-diamine : A C6 alkane-alpha,omega-diamine.	1.99	1	0	alkane-alpha,omega-diamine	human xenobiotic metabolite
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	3.45	1	1	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
n-isopropylacrylamide N-isopropylacrylamide: can polymerize with glycidyl acrylate to form reactive water-soluble polymer that can react with the amino groups of enzymes-proteins or other ligands	2	1	0
octachloronaphthalene Perna: A genus of freshwater mussel in the family MYTILIDAE, class BIVALVIA. It is found in tropical and warm temperate coastal waters. Most species have green in their shells.	2.8	3	0
5-phenylvaleric acid 5-phenylvaleric acid: from Polygonum salicifolium. 5-phenylpentanoic acid : A monocarboxylic acid that is valeric acid substituted by a phenyl group at the delta-position.	2.42	2	0	benzenes; monocarboxylic acid
gamma-dodecalactone gamma-dodecalactone: structure in first source. gamma-dodecalactone : A gamma-lactone that is oxolan-2-one substituted by an octyl group at position 5.	2.11	1	0	gamma-lactone	bacterial metabolite; fungal metabolite; volatile oil component
fluorescein Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.	2.1	1	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
fucose Fucose: A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.. L-fucopyranose : The pyranose form of L-fucose.. fucose : Any deoxygalactose that is deoxygenated at the 6-position.	2.35	2	0	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
gamma-glycidoxypropyltrimethoxysilane 3-glycidyloxypropyltrimethoxysilane: used to immobilize carbonic anhydrase into mesoporous supports; structure in first source	2.1	1	0
3-(trimethoxysilyl)propyl methacrylate 3-(trimethoxysilyl)propyl methacrylate: structure in first source	2.47	2	0
sulfuryl fluoride sulfuryl fluoride: fumigant	2.25	1	0	sulfuryl halide	fumigant insecticide
sudan red [no description available]	2.25	1	0
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2.83	3	0	fluorescein isothiocyanate
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	3.03	4	0	thujene	plant metabolite
mannose mannopyranose : The pyranose form of mannose.	3.33	7	0	D-aldohexose; D-mannose; mannopyranose	metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	1.95	1	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
nafenopin Nafenopin: A peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an antihyperlipoproteinemic agent.. nafenopin : A racemate comprising equimolar amounts of (R)- and (S)-nafenopin. It is a peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an hypolipidemic agent.. 2-methyl-2-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]propanoic acid : A monocarboxylic acid that is 2-hydroxy-2-methylpropanoic acid in which ther tertiary hydroxy group has been converted into the corresponding p-(1,2,3,4-tetrahydronaphthalen-1-yl)phenyl ether.	3.23	6	0	aromatic ether; monocarboxylic acid
2-pentylfuran 2-pentylfuran: structure in first source. 2-pentylfuran : A member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a pentyl group. It is found in many heat-processed foods and drinks.	2.17	1	0	furans	Aspergillus metabolite; bacterial metabolite; flavouring agent; human urinary metabolite; insect repellent; plant growth stimulator; volatile oil component
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.13	1	0	carbon oxoanion
2-octanol 2-octanol: RN given refers to cpd without isomeric designation. octan-2-ol : An octanol carrying the hydroxy group at position 2.	2.36	2	0	octanol; secondary alcohol	plant metabolite; volatile oil component
mono-(2-ethylhexyl)phthalate mono-(2-ethylhexyl)phthalate: RN given refers to parent cpd. mono(2-ethylhexyl) phthalate : The mono(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	3.01	4	0	phthalic acid monoester
3-phenylbutyric acid 3-phenylbutyric acid : A monocarboxylic acid that is butanoic acid substituted by a phenyl group at position 3.	2	1	0	benzenes; monocarboxylic acid	antibacterial agent; bacterial xenobiotic metabolite
methylene bis(4-cyclohexylisocyanate) methylene bis(4-cyclohexylisocyanate): used in manufacture of polyurethane foam; RN given refers to cpd without isomeric designation. dicyclohexylmethane-4,4'-diisocyanate : A diisocyanate consisting of dicyclohexylmethane with two isocyanate groups at the 4- and 4'-positions.	2.1	1	0	diisocyanate	allergen
trioctylmethylammonium trioctylmethylammonium: used in high performance liquid chromatography for the separation of tRNA; RN given refers to chloride. methyltrioctylammonium : A quaternary ammonium ion with three octyl groups and one methyl group attached to the nitrogen.	2.25	1	0	quaternary ammonium ion
norleucine Norleucine: An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR.. L-norleucine : A non-proteinogenic L-alpha-amino acid comprising hexanoic acid carrying an amino group at C-2. It does not occur naturally.	2.05	1	0	2-aminohexanoic acid; L-alpha-amino acid zwitterion; non-proteinogenic L-alpha-amino acid
diadenosine tetraphosphate P(1),P(4)-bis(5'-adenosyl) tetraphosphate : A diadenosyl tetraphosphate compound having the two 5'-adenosyl residues attached at the P(1)- and P(4)-positions.	1.97	1	0	diadenosyl tetraphosphate	Escherichia coli metabolite; mouse metabolite
isostearate 16-methylheptadecanoic acid : A methyl-branched fatty acid that is heptadecanoic acid (margaric acid) substituted by a methyl group at position 16.	2.13	1	0	branched-chain saturated fatty acid; long-chain fatty acid; methyl-branched fatty acid
2-octynoic acid [no description available]	1.97	1	0	acetylenic fatty acid; monounsaturated fatty acid
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	5.56	7	0	cycloalkene; p-menthadiene	human metabolite
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	1.94	1	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
sodium metasilicate sodium metasilicate: RN given refers to silicic acid, di-Na salt. sodium silicate : An inorganic sodium salt having silicate as the counterion.	2.08	1	0	inorganic sodium salt
tiadenol tiadenol: structure	2.89	4	0	aliphatic sulfide
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.93	4	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	3.31	6	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	1.94	1	0	chromium group element atom	micronutrient
niobium Niobium: A metal element atomic number 41, atomic weight 92.906, symbol Nb.	2.05	1	0	vanadium group element atom
osmium Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.	1.94	1	0	iron group element atom; platinum group metal atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.99	4	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.5	2	0	elemental platinum; nickel group element atom; platinum group metal atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	2.03	1	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	2.03	1	0	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	3.13	5	0	copper group element atom; elemental silver	Escherichia coli metabolite
technetium Technetium: The first artificially produced element and a radioactive fission product of URANIUM. Technetium has the atomic symbol Tc, and atomic number 43. All technetium isotopes are radioactive. Technetium 99m (m=metastable) which is the decay product of Molybdenum 99, has a half-life of about 6 hours and is used diagnostically as a radioactive imaging agent. Technetium 99 which is a decay product of technetium 99m, has a half-life of 210,000 years.	2.76	3	0	manganese group element atom
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	5.76	25	0	titanium group element atom
argon Argon: A noble gas with the atomic symbol Ar, atomic number 18, and atomic weight 39.948. It is used in fluorescent tubes and wherever an inert atmosphere is desired and nitrogen cannot be used.	2.17	1	0	monoatomic argon; noble gas atom; p-block element atom	food packaging gas; neuroprotective agent
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	8.52	8	0	cadmium molecular entity; zinc group element atom
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	2.38	2	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.08	1	0	chromium group element atom; metal allergen	micronutrient
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	3.48	7	0	copper group element atom; elemental gold
helium Helium: A noble gas with the atomic symbol He, atomic number 2, and atomic weight 4.003. It is a colorless, odorless, tasteless gas that is not combustible and does not support combustion. It was first detected in the sun and is now obtained from natural gas. Medically it is used as a diluent for other gases, being especially useful with oxygen in the treatment of certain cases of respiratory obstruction, and as a vehicle for general anesthetics.	1.96	1	0	monoatomic helium; noble gas atom; s-block element atom	food packaging gas
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	2.06	1	0	d-block element atom; rare earth metal atom; scandium group element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	3.01	4	0	titanium group element atom
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	1.95	1	0	N-acetyl-D-glucosamine	epitope
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	4.15	5	0	D-galactosamine; primary amino compound	toxin
diethyl malate diethyl malate: RN given refers to cpd without isomeric designation. diethyl malate : A malate ester obtained by the formal condensation of the two carboxy groups of malic acid with two molecules of ethanol respectively.	2.21	1	0	malate ester	metabolite
phosphoric acid, trisodium salt [no description available]	2.07	1	0	sodium phosphate
sodium nitrate sodium nitrate : The inorganic nitrate salt of sodium.	3.77	2	1	inorganic nitrate salt; inorganic sodium salt	fertilizer; NMR chemical shift reference compound
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.21	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.17	1	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferrous sulfate ferrous sulfate: Ferro-Gradumet is ferrous sulfate in controlled release form; RN given refers to Fe(+2)[1:1] salt. iron(2+) sulfate (anhydrous) : A compound of iron and sulfate in which the ratio of iron(2+) to sulfate ions is 1:1. Various hydrates occur naturally - most commonly the heptahydrate, which loses water to form the tetrahydrate at 57degreeC and the monohydrate at 65degreeC.	2.01	1	0	iron molecular entity; metal sulfate	reducing agent
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	1.94	1	0	diatomic bromine
sodium sulfate [no description available]	2.4	2	0	inorganic sodium salt
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.07	1	0	calcium phosphate
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	1.94	1	0	chromium oxoanion; divalent inorganic anion	oxidising agent
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	2.01	1	0	metal sulfate	emetic; fertilizer; sensitiser
calcium sulfate Calcium Sulfate: A calcium salt that is used for a variety of purposes including: building materials, as a desiccant, in dentistry as an impression material, cast, or die, and in medicine for immobilizing casts and as a tablet excipient. It exists in various forms and states of hydration. Plaster of Paris is a mixture of powdered and heat-treated gypsum.	2.06	1	0	calcium salt; inorganic calcium salt
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	3.8	11	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	6.05	36	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	3.1	5	0	diatomic chlorine; gas molecular entity	bleaching agent
silver iodide silver iodide: RN given refers to silver iodide [1:1]	2.11	1	0
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.42	2	0	deuterated compound; water	NMR solvent
fluorosulfonic acid perfluorosulfonic acid: sulfonated tetrafluoroethylene-based fluoropolymer–copolymer	3.14	1	0	sulfur oxoacid	NMR solvent
glycerol 1-stearate glycerol 1-stearate: isolated from the young fronds of the bracken fern Pteridium aquilinum; structure in first source. rac-1-monostearoylglycerol : A rac-1-monoacylglycerol composed of equal amounts of 3-stearoyl-sn-glycerol and 1-stearoyl-sn-glycerol.. 1-monostearoylglycerol : A 1-monoglyceride that has stearoyl as the acyl group.	2.02	1	0	1-acylglycerol 18:0; rac-1-monoacylglycerol	algal metabolite; Caenorhabditis elegans metabolite
triisopropanolamine triisopropanolamine: RN given refers to parent cpd	2.13	1	0	amino alcohol
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	3.49	8	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.99	4	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
ferric sulfate ferric sulfate: RN given refers to Fe(+3)[3:2] salt). iron(3+) sulfate : A compound of iron and sulfate in which the ratio of iron(3+) to sulfate ions is 3:2.	2.08	1	0	iron molecular entity; metal sulfate	astringent; catalyst; mordant
aluminum sulfate aluminium sulfate (anhydrous) : An aluminium sulfate that contains no water of crystallisation.	2.11	1	0	aluminium sulfate
octyltrimethylammonium octyltrimethylammonium: RN given refers to parent cpd. octyltrimethylammonium ion : A quarternary ammonium cation having one octyl and three methyl substituents around the central nitrogen.	2.4	2	0	quaternary ammonium ion
rhamnose [no description available]	2.87	4	0	L-rhamnose
clodronic acid Clodronic Acid: A diphosphonate which affects calcium metabolism. It inhibits bone resorption and soft tissue calcification.. clodronic acid : An organochlorine compound that is methylene chloride in which both hydrogens are replaced by phosphonic acid groups. It inhibits bone resorption and soft tissue calcification, and is used (often as the disodium salt tetrahydrate) as an adjunct in the treatment of severe hypercalcaemia associated with malignancy, and in the management of osteolytic lesions and bone pain associated with skeletal metastases.	1.96	1	0	1,1-bis(phosphonic acid); one-carbon compound; organochlorine compound	antineoplastic agent; bone density conservation agent
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	3.57	9	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
ancymidol ancymidol : A tertiary alcohol that is methanol in which the hydrogens attached to the carbon are replaced by cyclopropyl, p-methoxyphenyl and pyrimidin-5-yl groups. By inhibiting gibberellin biosynthesis, ancymidol reduces plant growth, resulting in reduced internode elongation and thus more compact plants. It is used in the commercial production of a wide variety of container-grown bedding and foliage plants, including chrysanthemums, Easter lilies and poinsettias.	2.17	1	0	pyrimidines; tertiary alcohol	cellulose synthesis inhibitor; gibberellin biosynthesis inhibitor; plant growth retardant
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	5.33	16	0	titanium oxides	food colouring
tris(1,3-dichloro-2-propyl)phosphate [no description available]	2.55	2	0	trialkyl phosphate
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.7	3	0
myrmicacin myrmicacin: found in secretions of South American leaf-cutting ant; inhibitor for mitotic progression after metaphase. 3-hydroxydecanoic acid : A medium-chain fatty acid that is decanoic acid substituted at position 3 by a hydroxy group.	4.04	4	0	3-hydroxy fatty acid; medium-chain fatty acid	antimitotic; Escherichia coli metabolite
3-hydroxyoctanoic acid 3-hydroxyoctanoic acid : An 8-carbon, beta-hydroxy fatty acid which may be a marker for primary defects of beta-hydroxy fatty acid metabolism. Repeating unit of poly(3-hydroxyoctanoic acid), a biopolymer used by numerous bacterial species as carbon and energy reserves.	5.9	30	0	3-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; medium-chain fatty acid
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2.02	1	0	selegiline; terminal acetylenic compound	geroprotector
cromolyn sodium Cromolyn Sodium: A chromone complex that acts by inhibiting the release of chemical mediators from sensitized MAST CELLS. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack.. disodium cromoglycate : An organic sodium salt that is the disodium salt of cromoglycic acid.	2.04	1	0	organic sodium salt	anti-asthmatic drug; drug allergen
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	3.26	6	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
fluorides [no description available]	5.44	20	0	halide anion; monoatomic fluorine
stannic oxide tin dioxide : A tin oxide compound consisting of tin(IV) covalently bound to two oxygen atoms.	2.47	2	0	tin oxide
dibenz(b,f)(1,4)oxazepine-10(11h)-carboxylic acid, 8-chloro-, 2-acetylhydrazide Dibenz(b,f)(1,4)oxazepine-10(11H)-carboxylic acid, 8-chloro-, 2-acetylhydrazide: Inhibits the activity of prostaglandins.	1.98	1	0
iodine [no description available]	2.66	3	0	halide anion; monoatomic iodine	human metabolite
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	10.57	146	3	benzenes; phenyl acetates
cetylpyridinium chloride anhydrous tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.	5.06	3	1	chloride salt; organic chloride salt	antiseptic drug; surfactant
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	2.1	1	0	phenols	fungal xenobiotic metabolite
vinyl butyrate [no description available]	2.02	1	0
isopentyl alcohol isopentyl alcohol: RN given refers to unlabeled parent cpd. isoamylol : An primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group.	2.15	1	0	alkyl alcohol; primary alcohol; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite; xenobiotic metabolite
ethyl hexanoate ethyl hexanoate : A fatty acid ethyl ester obtained by the formal condensation of hexanoic acid with ethanol.	3.78	10	0	fatty acid ethyl ester; hexanoate ester	metabolite
dioctyl adipate [no description available]	1.96	1	0	carboxylic ester
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	2.1	1	0	acetate ester	metabolite
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.05	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
isoamyl acetate isoamyl acetate: structure in Merck, 9th ed, #4958. isoamyl acetate : The acetate ester of isoamylol.	2.5	2	0	acetate ester	metabolite; Saccharomyces cerevisiae metabolite
thiodiacetic acid thiodiacetic acid: vinyl chloride metabolite in urine of rats	1.99	1	0	dicarboxylic acid
tripelargonin [no description available]	2.05	1	0
tributyl phosphate tributyl phosphate: a detergent. tributyl phosphate : A trialkyl phosphate that is the tributyl ester of phosphoric acid.	2.02	1	0	trialkyl phosphate
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	2.43	2	0	chlorocarbon; chloroethenes	nephrotoxic agent
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	7.42	8	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	1.99	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
algestone acetophenide Algestone Acetophenide: A progesterone that has been used in ESTRUS SYNCHRONIZATION and has been evaluated as an injectable contraceptive in combination with estradiol enanthate. It is also applied topically as an anti-inflammatory and in the treatment of ACNE.	1.95	1	0
aluminum oxide hydroxide aluminum oxide hydroxide: RN given refers to Al2O3.xH2O	2.07	1	0	aluminium hydroxides; aluminium oxides
alkenes [no description available]	3.12	5	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	5.37	18	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
n-(4-methoxybenzylidene)-4-butylaniline [no description available]	2.02	1	0
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.06	5	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
tramadol Tramadol: A narcotic analgesic proposed for severe pain. It may be habituating.. tramadol : A racemate consisting of equal amounts of (R,R)- and (S,S)-tramadol. A centrally acting synthetic opioid analgesic, used (as the hydrochloride salt) to treat moderately severe pain. The (R,R)-enantiomer exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. Originally developed by Gruenenthal GmbH and launched in 1977, it was subsequently isolated from the root bark of the South African tree Nauclea latifolia.. (R,R)-tramadol : A 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuration; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.	2.31	1	0	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor
almitrine Almitrine: A respiratory stimulant that enhances respiration by acting as an agonist of peripheral chemoreceptors located on the carotid bodies. The drug increases arterial oxygen tension while decreasing arterial carbon dioxide tension in patients with chronic obstructive pulmonary disease. It may also prove useful in the treatment of nocturnal oxygen desaturation without impairing the quality of sleep.. almitrine : A triamino-1,3,5-triazine compound having allylamino substituents at the 2- and 4-positions and a 4-(bis(p-fluorophenyl)methyl)-1-piperazinyl group at the 6-position.	1.99	1	0	piperazines; triamino-1,3,5-triazine	central nervous system stimulant
gallium citrate [no description available]	4.31	1	1
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	1.96	1	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
s-adenosylmethionine acylcarnitine: structure in first source. S-adenosyl-L-methioninate : A sulfonium betaine that is a conjugate base of S-adenosyl-L-methionine obtained by the deprotonation of the carboxy group.	2.53	2	0	sulfonium betaine	human metabolite
pcb 118 [no description available]	2.17	1	0	dichlorobenzene; pentachlorobiphenyl; trichlorobenzene
3,4,3',4'-tetrachlorobiphenyl 3,4,3',4'-tetrachlorobiphenyl: RN given refers to parent cpd. 3,3',4,4'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at position 3 and 4 on each phenyl group are replaced by chlorines.	2.05	1	0	dichlorobenzene; tetrachlorobiphenyl
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.33	6	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
substance p [no description available]	1.95	1	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
2,4,5,2',4',5'-hexachlorobiphenyl [no description available]	2.13	1	0	hexachlorobiphenyl
2,5,2',5'-tetrachlorobiphenyl 2,2',5,5'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at the 2 and 5 position of each benzene ring are replaced by chlorines.	2.05	1	0	dichlorobenzene; tetrachlorobiphenyl
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	2.38	2	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
imidazolidinyl urea imidazolidinyl urea: RN given refers to parent cpd	1.95	1	0	ureas	antimicrobial agent
bezafibrate [no description available]	2.66	3	0	aromatic ether; monocarboxylic acid amide; monocarboxylic acid; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	2.38	2	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
triadimefon 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one : A member of the class of triazoles that is 1-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one in which the hydroxyl hydrogen is replaced by a 4-chlorophenyl group.	2.08	1	0	aromatic ether; hemiaminal ether; ketone; monochlorobenzenes; triazoles
2,3,7,8-tetrabromodibenzo-4-dioxin 2,3,7,8-tetrabromodibenzo-4-dioxin: structure given in first source. 2,3,7,8-tetrabromodibenzodioxine : An organobromine compound that is dibenzodioxine carrying four bromo substituents at positions 2, 3, 7 and 8.	2.5	2	0	dibenzodioxine; organobromine compound
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	2.03	1	0
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
cefmetazole Cefmetazole: A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.. cefmetazole : A second-generation cephalosporin antibiotic having N(1)-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7beta and 7alpha respectively of the parent cephem bicyclic structure.	1.97	1	0	cephalosporin	antibacterial drug
enkephalin, methionine Enkephalin, Methionine: One of the endogenous pentapeptides with morphine-like activity. It differs from LEU-ENKEPHALIN by the amino acid METHIONINE in position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.	2.1	1	0
laurocapram laurocapram: enhances percutaneous absorption of different chemicals; structure given in first source	2.39	2	0
dihydroalprenolol Dihydroalprenolol: Hydrogenated alprenolol derivative where the extra hydrogens are often tritiated. This radiolabeled form of ALPRENOLOL, a beta-adrenergic blocker, is used to label the beta-adrenergic receptor for isolation and study.	2.36	2	0
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	2.4	2	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
1-octanesulfonic acid 1-octanesulfonic acid: RN given refers to parent cpd	2.42	2	0	organosulfonic acid	local anaesthetic
cefaclor anhydrous Cefaclor: Semisynthetic, broad-spectrum antibiotic derivative of CEPHALEXIN.. cefaclor : A cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	3.44	1	1	cephalosporin	antibacterial drug; drug allergen
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	2.37	2	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	2.65	3	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
ethyl 2-(5-(4-chlorophenyl)pentyl)oxiran-2-carboxylate [no description available]	2.37	2	0
bm 13505 daltroban: thromboxane antagonist	1.98	1	0
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	2.25	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
idazoxan Idazoxan: A benzodioxane-linked imidazole that has alpha-2 adrenoceptor antagonist activity.. idazoxan : A benzodioxine that is 2,3-dihydro-1,4-benzodioxine in which one of the hydrogens at position 2 has been replaced by a 4,5-dihydro-1H-imidazol-2-yl group.	2.07	1	0	benzodioxine; imidazolines	alpha-adrenergic antagonist
detomidine detomidine: structure given in first source	3.39	1	1
adapalene Adapalene: A naphthalene derivative that has specificity for RETINOIC ACID RECEPTORS. It is used as a DERMATOLOGIC AGENT for the treatment of ACNE.. adapalene : A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.	2.15	1	0	adamantanes; monocarboxylic acid; naphthoic acid	dermatologic drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; non-steroidal anti-inflammatory drug
topotecan Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.	3.51	1	1	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.13	1	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
atorvastatin [no description available]	2.07	1	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
irinotecan [no description available]	4.51	1	1	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
valsartan Valsartan: A tetrazole derivative and ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to treat HYPERTENSION.. valsartan : A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.	2.49	2	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
ibandronic acid Ibandronic Acid: Aminobisphosphonate that is a potent inhibitor of BONE RESORPTION. It is used in the treatment of HYPERCALCEMIA associated with malignancy, for the prevention of fracture and bone complications in patients with breast cancer and bone metastases, and for the treatment and prevention of POSTMENOPAUSAL OSTEOPOROSIS.	3.81	2	1
zanamivir Zanamivir: A guanido-neuraminic acid that is used to inhibit NEURAMINIDASE.	3.57	2	0	guanidines	antiviral agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.69	3	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
4-pentenoic acid 4-pentenoic acid: inhibitor of fatty acid oxidation; RN given refers to parent cpd. pent-4-enoic acid : A pentenoic acid having the double bond at position 4.	2.89	4	0	pentenoic acid
octyl gallate [no description available]	2.11	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
pyranine pyranine: structure	2	1	0	organic sodium salt	fluorochrome
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	1.97	1	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
4-ethyloctanoic acid [no description available]	4.57	7	0	medium-chain fatty acid
4-methyloctanoic acid [no description available]	4.95	11	0	medium-chain fatty acid
cathinone cathinone: alkaloid from khat shrub, Catha edulis; RN given refers to parent cpd without isomeric designation. cathinone : The S stereoisomer of 2-aminopropiophenone.	2.1	1	0	2-aminopropiophenone; monoamine alkaloid	central nervous system stimulant; psychotropic drug
thiolactic acid thiolactic acid: RN given refers to parent cpd	1.96	1	0	mercaptopropanoic acid
scarlet red Scarlet Red: structure. Sudan IV : A bis(azo) compound that is 2-naphthol substituted at position 1 by a {2-methyl-4-[(2-methylphenyl)diazenyl]phenyl}diazenyl group. A fat-soluble dye predominantly used for demonstrating triglycerides in frozen sections, but which may also stain some protein bound lipids in paraffin sections.	2.25	1	0	azobenzenes; bis(azo) compound; naphthols	carcinogenic agent; fluorochrome; histological dye
sudan iii sudan III: structure in first source. Sudan III : A bis(azo) compound that is 2-naphthol substituted at position 1 by a 4-{[(2-methylphenyl)diazenyl]phenyl}diazenyl group. A fat-soluble dye predominantly used for demonstrating triglycerides in frozen sections, but which may also stain some protein bound lipids in paraffin sections.	2.25	1	0	azobenzenes; bis(azo) compound; naphthols	carcinogenic agent; fluorochrome; histological dye
vanillyl alcohol vanillyl alcohol: structure. vanillyl alcohol : A monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4.	2.31	1	0	benzyl alcohols; guaiacols	plant metabolite
perfluoropropionic acid perfluoropropionic acid: ion pairing reagent; RN given refers to parent cpd	2.46	2	0
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.05	1	0	one-carbon compound; perfluoroalkanesulfonic acid
4-ethylguaiacol 4-ethylguaiacol: a constituent of wood creosote; suppresses intestinal smooth muscle contraction	2.1	1	0	methoxybenzenes; phenols
sodium persulfate sodium persulfate: RN given refers to peroxydisulfuric acid, di-Na salt	2.8	3	0
potassium phosphate potassium phosphate: used in dental materials and to treat hypophosphatemia; RN given refers to cpd with unspecified MF. tripotassium phosphate : An inorganic potassium salt that is the tripotassium salt of phosphoric acid.	2.04	1	0	inorganic phosphate salt; inorganic potassium salt
octyl glucoside octyl-beta-D-glucoside: RN given refers to (beta)-isomer. octyl beta-D-glucopyranoside : An beta-D-glucoside in which the anomeric hydrogen of beta-D-glucopyranose is substituted by an octyl group.	1.98	1	0	beta-D-glucoside	plant metabolite
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	3.3	6	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	3.75	10	0	D-glucopyranose	epitope; mouse metabolite
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	2.65	3	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.97	4	0	organic bromide salt	colorimetric reagent; dye
3-methylhistidine 3-methylhistidine: marker for myofibrillar-protein breakdown; RN given refers to (L)-isomer. 3-methylhistidine : A methylhistidine in which the methyl group is located at N-3.. N(pros)-methyl-L-histidine : A L-histidine derivative that is L-histidine substituted by a methyl group at position 3 on the imidazole ring.	1.97	1	0	L-histidine derivative; non-proteinogenic L-alpha-amino acid; zwitterion	human metabolite; Saccharomyces cerevisiae metabolite
oseltamivir Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.	3.57	2	0	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic
5-methylcytosine 5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.	2.1	1	0	methylcytosine; pyrimidines	human metabolite
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.17	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
n-acetylaspartic acid N-acetyl-L-aspartic acid : An N-acyl-L-aspartic acid in which the acyl group is specified as acetyl.	2.01	1	0	N-acetyl-L-amino acid; N-acyl-L-aspartic acid	antioxidant; human metabolite; mouse metabolite; nutraceutical; rat metabolite
cholesteryl sulfate cholesteryl sulfate: component of human seminal plasma & spermatozoa; RN given refers to (3beta)-isomer. cholesterol sulfate : A steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3.	2	1	0	steroid sulfate	human metabolite
5-dimethylaminonaphthalene-1-sulfonamide [no description available]	2.05	1	0
fluorexon fluorexon: structure	2.42	2	0	xanthene dye	fluorochrome
25-hydroxycholesterol [no description available]	1.96	1	0	25-hydroxy steroid; oxysterol	human metabolite
aica ribonucleotide AICA ribonucleotide: purine precursor that has antineoplastic activity. AICA ribonucleotide : A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative.	2.7	3	0	1-(phosphoribosyl)imidazolecarboxamide; aminoimidazole	cardiovascular drug; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nile red nile red : An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.	2.01	1	0	aromatic amine; cyclic ketone; organic heterotetracyclic compound; tertiary amino compound	fluorochrome; histological dye
metaperiodate Periodic Acid: A strong oxidizing agent.	3.46	8	0	iodine oxoacid
fluorophosphate fluorophosphate: inhibits Phosphorylas phosphatase irreversibly; RN given refers to parent cpd	2.17	1	0	fluorine molecular entity; phosphoric acid derivative
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.02	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
octimibate [no description available]	1.97	1	0
sertaconazole sertaconazole : A racemate comprising equimolar amounts of (R)- and (S)-sertaconazole. A broad spectrum antifungal with added antipruritic and anti-inflammatory activity used (as its nitrate salt) for treatment of various skin infections.. 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole : A member of the class of imidazoles that carries a 2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl group at position 1.	2.15	1	0	1-benzothiophenes; dichlorobenzene; ether; imidazoles
dexloxiglumide dexloxiglumide: a CCK receptor antagonist; structure given in first source	3.42	1	1	glutamic acid derivative
methacycline [no description available]	2.15	1	0	1,2-diglyceride
omega-aminocaprylic acid 8-aminooctanoic acid : An omega-amino fatty acid that is octanoic acid which carries an amino group at position 8.	3.72	10	0	medium-chain fatty acid; omega-amino fatty acid	human metabolite
1,7-phenanthroline [no description available]	1.94	1	0	phenanthroline
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	3.07	5	0	1,2,3-triazole
perfluorohexanoic acid perfluorohexanoic acid : A monocarboxylic acid that is perfluorinated hexanoic acid.	5.42	53	0	fluoroalkanoic acid	environmental contaminant; xenobiotic
perfluorododecanoic acid perfluorododecanoic acid: a synthetic perfluorinated chemical containing 12 carbons, has broad industrial applications and has been detected in sera from humans and other animals. perfluorododecanoic acid : A fluoroalkanoic acid that is dodecanoic acid in which all of the hydrogens attached to carbon atoms are replaced by fluorines. It is a highly persistent, bioaccumulative breakdown product of stain- and grease-proof coatings on food packaging, soft furnishings and carpets.	4.08	14	0	fluoroalkanoic acid	environmental contaminant
perfluorohexanesulfonic acid perfluorohexanesulfonic acid : A perfluoroalkanesulfonic acid that is hexane-1-sulfonic acid in which all thirteen of the hydrogens that are attached to carbons have been replaced by fluorines.	9.82	93	1	perfluoroalkanesulfonic acid
perfluorobutane sulfonate perfluorobutanesulfonic acid: a surfactant; structure in first source. perfluorobutanesulfonic acid : A perfluoroalkanesulfonic acid that is butane-1-sulfonic acid in which all of the hydrogens of the butyl group have been replaced by fluorines.	4.24	15	0	perfluoroalkanesulfonic acid	surfactant
perfluoro-n-heptanoic acid perfluoroheptanoic acid : A fluoroalkanoic acid that is perfluorinated heptanoic acid.	3.44	7	0	fluoroalkanoic acid	environmental contaminant; xenobiotic
perfluoro-n-nonanoic acid perfluorononanoic acid : A fluoroalkanoic acid that is nonanoic acid in which all of the hydrogens in the alkyl chain are replaced by fluorines.	6.68	47	0	fluoroalkanoic acid	persistent organic pollutant; surfactant; xenobiotic
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2.25	1	0	anthocyanidin chloride
sesamol sesamol: constituent of sesame oil; RN given refers to parent cpd; structure in first source	2.03	1	0	benzodioxoles
methyl 2-tetradecylglycidate methyl 2-tetradecylglycidate: structure	1.98	1	0
cicloxilic acid cicloxilic acid: RN given refers to (cis)-isomer; structure. cicloxilic acid : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-cicloxilic acid. It is a choleretic agent that has antilithogenic activity.. (1S,2R)-cicloxilic acid : A 2-hydroxy-2-phenylcyclohexanecarboxylic acid that has (1S,2R)-stereoconfiguration.	1.96	1	0	2-hydroxy-2-phenylcyclohexanecarboxylic acid
triheptanoin [no description available]	6.39	4	2
tricaprin tricaprin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by capric (decanoic) acid.	6.11	9	1	decanoate ester; triglyceride
beta-hydroxyisovaleric acid 3-hydroxyisovaleric acid : A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency.	2.38	2	0	3-hydroxy monocarboxylic acid	human metabolite
perfluorooctanesulfonamide perfluorooctanesulfonamide : A perfluorinated compound that is perfluorooctane in which one of the terminal fluorines has been replace by a sulfamoyl group.	4.54	23	0	perfluorinated compound; sulfonamide	persistent organic pollutant
8-hydroxyoctanoic acid 8-hydroxyoctanoic acid: has been identified in the urine of children with medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. 8-hydroxyoctanoic acid : An omega-hydroxy fatty acid that is caprylic acid in which one of the hydrogens of the terminal methyl group is replaced by a hydroxy group.	3.61	8	0	omega-hydroxy-medium-chain fatty acid; straight-chain fatty acid
dansylglycine [no description available]	2.02	1	0
1-methylcyclohexanecarboxylic acid 1-methylcyclohexanecarboxylic acid: inducer of neuroblastoma morphological differentiation; RN given refers to parent cpd	1.98	1	0
tocophersolan tocophersolan: RN given refers to parent cpd	2.46	2	0	tocol
trichlorosucrose trichlorosucrose: sweetness intensity roughly 600 times that of sucrose and is nonnutritive and noncaloric; largely unabsorbed in the gastrointestinal tract. sucralose : A disaccharide derivative consisting of 4-chloro-4-deoxy-alpha-D-galactopyranose and 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranose units linked by a glycosidic bond.	2.57	2	0	disaccharide derivative; organochlorine compound	environmental contaminant; sweetening agent; xenobiotic
dicolinium iodide dicolin: RN given refers to diiodide; structure	1.93	1	0
2-tetradecylglycidic acid 2-tetradecylglycidic acid: structure	3.35	7	0
teleocidin b-4 teleocidins: structure; RN given refers to teleocidin	1.97	1	0
4-nitrophenyl palmitate p-nitrophenyl palmitate : A palmitate ester obtained by condensation of the carboxy group of palmitic acid with the phenolic hydroxy group of p-nitrophenol.	1.96	1	0	C-nitro compound; hexadecanoate ester
ceric oxide ceric oxide: RN given refers to cpd with MF CeO2. ceric oxide : A metal oxide with formula CeO2. It is used for polishing glass, in coatings for infra-red filters to prevent reflection, and as an oxidant and catalyst in organic synthesis.	2.07	1	0	cerium molecular entity; metal oxide
10-hydroxycapric acid 10-hydroxycapric acid : A 10-carbon, omega-hydroxy fatty acid, shown to be the preferred hydroxylation product (together with the 9-OH isomer) of capric acid in biosystems, and used as a standard in lipid assays; reported to have cytotoxic effects.	2.31	1	0	omega-hydroxy-medium-chain fatty acid; straight-chain saturated fatty acid
perfluorooctane sulfonic acid perfluorooctane-1-sulfonic acid : A perfluoroalkanesulfonic acid that is octane-1-sulfonic acid in which all seventeen of the hydrogens that are attached to carbons hvae been replaced by fluorines.	16.88	909	2	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
triphenylmethylphosphonium triphenylmethylphosphonium: RN given refers to parent cpd	2.25	1	0
4-nitrophenyl laurate [no description available]	2.94	4	0
1-hydroxybenzotriazole 1-hydroxybenzotriazole: RN given refers to parent cpd	2.15	1	0	benzotriazoles
octadecyl palmitate octadecyl palmitate: found in psoriatic nail, but not in normal nails. stearyl palmitate : A palmitate ester resulting from the formal condensation of the carboxy group of palmitic acid with the hydroxy group of stearyl alcohol.	1.95	1	0	hexadecanoate ester; wax ester	coral metabolite; cosmetic
4-nitrophenyl butyrate p-nitrophenyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of 4-nitrophenol with the carboxy group of butyric acid.	2.46	2	0	butyrate ester; C-nitro compound
perfluoropentanoic acid perfluoropentanoic acid: an ion-pairing agent. perfluoropentanoic acid : A monocarboxylic acid that is perfluorinated pentanoic acid.	2.17	1	0	fluoroalkanoic acid	environmental contaminant; xenobiotic
n-octadecyltrimethoxysilane n-octadecyltrimethoxysilane: used to form self-assembled monolayers for high contrast patterned adsorption of bovine serum albumin and deriviatives	2.05	1	0
6-carboxyfluorescein 6-carboxyfluorescein: originally sold as 6-carboxyfluorescein, but commercial product is a mixture of two isomers; correct name is 5(6)-carboxyfluorescein	2.68	3	0	monocarboxylic acid
perfluoroundecanoic acid perfluoroundecanoic acid : A fluoroalkanoic acid that is perfluorinated undecanoic acid.	4.48	20	0	fluoroalkanoic acid	environmental contaminant; xenobiotic
sulfluramid sulfluramid: delayed-action insecticide against the cockroach Dyctyoptera; Blattelidae germanica. sulfluramid : A sulfonamide obtained by the formal condensation of perfluorooctane-1-sulfonic acid with ethylamine.	2.61	2	0	sulfonamide	acaricide; environmental contaminant; insecticide; xenobiotic
rosiglitazone [no description available]	3.01	4	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
1,3,6,8-pyrene tetrasulfonate 1,3,6,8-pyrene tetrasulfonate: RN given refers to parent cpd	2.01	1	0
2-bromopalmitate 2-bromopalmitate: inhibitor of fatty acid oxidation; RN given refers to parent cpd. 2-bromohexadecanoic acid : A bromo fatty acid that is hexadecanoic (palmitic) acid carrying a single bromo substituent at position 2.	3.36	7	0	2-bromocarboxylic acid; bromo fatty acid; long-chain fatty acid; straight-chain fatty acid	fatty acid oxidation inhibitor
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	2.11	1	0	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
3-(trimethoxysilyl)propylamine 3-(trimethoxysilyl)propylamine: reagent for making polymers; structure in first source	2.05	1	0
mepanipyrim mepanipyrim : A member of the class of aminopyrimidines that is N-phenylpyrimidin-2-amine carrying additional methyl and 1-propynyl substituents at positions 4 and 6 respectively. A fungicide used to control a wide range of diseases including grey mould on strawberries, tomatoes and cucumabers, and scab on apples and pears.	2.21	1	0	acetylenic compound; aminopyrimidine; anilinopyrimidine fungicide; secondary amino compound	antifungal agrochemical; aryl hydrocarbon receptor agonist; hepatotoxic agent
coenzyme a [no description available]	5.42	63	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
mebeverine gamma-oryzanol: present in rice bran is associated with various physiological functions; RN given refers to gamma-oryzanol	2.21	1	0
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	3.1	5	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	4.87	4	2	iditol	fungal metabolite
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.07	1	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
irgarol 1051 irgarol 1051: a booster biocide; structure given in first source. irgarol 1051 : A diamino-1,3,5-triazine that is 1,3,5-triazine-2,4-diamine carrying a N-tert-butyl, N'-cyclopropyl and a methylsulfanyl group at position 6.	2.07	1	0	aryl sulfide; cyclopropanes; diamino-1,3,5-triazine	antifouling biocide; environmental contaminant; xenobiotic
ethyl 4-methyloctanoate ethyl 4-methyloctanoate: structure given in first source	3.12	5	0	fatty acid ester
acetoacetyl coa [no description available]	1.97	1	0	3-oxo-fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
propionyl-coenzyme a propionyl-coenzyme A: RN given refers to parent cpd	2.4	2	0	acyl-CoA	Escherichia coli metabolite; metabolite; mouse metabolite
annatto annatto: coloring matter from seeds of Bixa orellana L., Bixaceae; contains bixin and pigments that give carotene reactions; induces hyperglycemia	2.06	1	0
firefly luciferin Firefly Luciferin: A benzothaizole which is oxidized by LUCIFERASES, FIREFLY to cause emission of light (LUMINESCENCE).. Photinus luciferin : A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position.	1.94	1	0	1,3-thiazolemonocarboxylic acid; benzothiazoles; imidothioate	luciferin
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	1.95	1	0
quinupramine quinupramine: RN given refers to parent cpd	2.03	1	0	dibenzooxazepine
4-decenoate 4-decenoic acid: RN given refers to (Z)-isomer; RN for cpd without isomeric designation not available 5/88	3.23	6	0
stearoyl-coenzyme a [no description available]	2.03	1	0	11,12-saturated fatty acyl-CoA; long-chain fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
3-hydroxydodecanoic acid 3-hydroxydodecanoic acid: RN given refers to cpd without isomeric designation. 3-hydroxylauric acid : A medium-chain fatty acid that is the 3-hydroxylated derivative of lauric acid; associated with fatty acid metabolic disorders.	2.03	1	0	3-hydroxy fatty acid; medium-chain fatty acid
cortisol octanoate [no description available]	1.95	1	0	corticosteroid hormone
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.13	1	0	D-glucuronic acid	algal metabolite
2,2',4,4'-tetrabromodiphenyl ether [no description available]	2.8	3	0	aromatic ether; organobromine compound
o-methyltyrosine O-methyltyrosine: RN given refers to parent cpd without isomeric designation. O-methyltyrosine : A tyrosine derivative that is tyrosine in which the hydroxy group at position 4 of the phenyl ring is substituted by a methoxy group.	2.02	1	0	monomethoxybenzene; tyrosine derivative
4-nitrophenyloctanoate [no description available]	4.05	14	0
2-bromostearic acid [no description available]	1.98	1	0
n-caproylglycine N-hexanoylglycine : An N-acylglycine in which the acyl group is specified as hexanoyl.	2.89	4	0	N-acylglycine	metabolite
n-hydroxysuccinimide suberic acid ester disuccinimidyl suberate: used as protein cross-linking agent	1.97	1	0
cholesteryl octanoate cholesteryl octanoate: used for breath tests for detection of pancreatic insufficiency in rats	1.99	1	0
2-amino-4-phenylbutyric acid 2-amino-4-phenylbutanoic acid: structure in first source	1.98	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	3.25	6	0	cobalt group element atom; metal allergen	micronutrient
chlorates Chlorates: Inorganic salts of chloric acid that contain the ClO3- ion.	2.5	2	0	chlorine oxoanion; monovalent inorganic anion
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.11	1	0	oligopeptide
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	3.45	1	1
cremophor el cremophor EL: solvent for Althesin & Propanidid implicated as possible cause of similar adverse effects polyethoxylated castor oil; RN given refers to cpd with unknown MF; see also records for cremophor & cremophor A	2.74	3	0
s-nitrosoglutathione [no description available]	2.05	1	0	glutathione derivative; nitrosothio compound	bronchodilator agent; nitric oxide donor; platelet aggregation inhibitor; signalling molecule
bicuculline methiodide [no description available]	1.96	1	0
2-propyl-4-pentenoic acid 2-propyl-4-pentenoic acid: putative toxic metabolite of valproic acid	1.96	1	0	methyl-branched fatty acid
diacetyldichlorofluorescein diacetyldichlorofluorescein: stable storage form of dichlorofluorescein	2.21	1	0
paxilline paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.	2.15	1	0	diterpene alkaloid; enone; organic heterohexacyclic compound; terpenoid indole alkaloid; tertiary alcohol	anticonvulsant; Aspergillus metabolite; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor; genotoxin; geroprotector; mycotoxin; Penicillium metabolite; potassium channel blocker
fructose 2,6-diphosphate fructose 2,6-diphosphate: phosphofructokinase activator synthesized via Mg-ATP & fructose-6-P. beta-D-fructofuranose 2,6-bisphosphate : A D-fructofuranose 2,6-bisphosphate with a beta-configuration at the anomeric centre.	2.38	2	0	D-fructofuranose 2,6-bisphosphate	human metabolite; mouse metabolite
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.45	2	0
fluorocitrate fluorocitrate: competitve inhibitor of aconitase; effects morphology of kidney tubules in fluorocitrate poisoning; RN given refers to cpd with unspecified isomeric designation	3.23	1	0	carbonyl compound
3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate 3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate: a surfactant; structure given in first source	2.44	2	0	1,1-diunsubstituted alkanesulfonate
inositol 1-phosphate 1D-myo-inositol 1-phosphate : An inositol having myo- configuration substituted at position 1 by a phosphate group.	2.11	1	0
propionylcarnitine propionylcarnitine: RN given refers to cpd without isomeric designation	2.13	1	0	O-acylcarnitine	analgesic; antirheumatic drug; cardiotonic drug; human metabolite; peripheral nervous system drug
dimyristoylphosphatidylglycerol [no description available]	2.02	1	0
beta-hydroxyvaleric acid 3-hydroxypentanoic acid : A short-chain fatty acid that is valeric acid in which one of the methylene hydrogens at position 3 has been replaced by a hydroxy group.	2.44	2	0	3-hydroxy fatty acid; ketone body; short-chain fatty acid
triptolide [no description available]	2.03	1	0	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	2.45	2	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.89	4	0
4-hydroxyvaleric acid [no description available]	2	1	0	hydroxy fatty acid
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	5.7	33	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
thromboxanes thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.	2.39	2	0
dodecyl-beta-d-maltoside dodecyl beta-D-maltoside : A glycoside resulting from attachment of a dodecyl group to the reducing-end anomeric centre of a beta-maltose molecule.	2.02	1	0	disaccharide derivative; glycoside	detergent
gastrodin gastrodin: the glucoside of 4-hydroxybenzyl alcohol (gastrodigenin); isolated from Gastrodia elata Blume;	2.31	1	0	glycoside
1-(9-fluorenyl)ethyl chloroformate 1-(9-fluorenyl)ethyl chloroformate: chiral reagent; structure given in first source	2.13	1	0
3-mercaptopicolinic acid 3-mercaptopicolinic acid: gluconeogenesis inhibitor; may also inhibit ATP-dependentphosphoenolpyruvate carboxykinase	2.37	2	0
mono(2-ethyl-5-oxohexyl)phthalate mono(2-ethyl-5-oxohexyl)phthalate: structure given in first source. mono(2-ethyl-5-oxohexyl) phthalate : A phthalic acid monoester obtained by formal condensation of one of the carboxy groups of phthalic acid with the hydroxy group of 2-ethyl-5-oxohexan-1-ol.	1.98	1	0	methyl ketone; phthalic acid monoester	human urinary metabolite; human xenobiotic metabolite
ginsenoside rh2 ginsenoside Rh2: from leaves of Panax ginseng C; structure given in first source. (20S)-ginsenoside Rh2 : A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.21	1	0	12beta-hydroxy steroid; 20-hydroxy steroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	antineoplastic agent; apoptosis inducer; bone density conservation agent; cardioprotective agent; hepatoprotective agent; plant metabolite
tauroglycocholic acid tauroglycocholic acid: RN given refers to cpd with unknown MF	1.96	1	0
mosapride 4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzamide : A benzamide resulting from the formal condensation of the carboxy group of 4-amino-5-chloro-2-ethoxybenzoic acid with the amino group of 1-[4-(4-fluorobenzyl)morpholin-2-yl]methanamine.	3.46	1	1	aromatic ether; benzamides; monochlorobenzenes; monofluorobenzenes; morpholines; secondary carboxamide; substituted aniline; tertiary amino compound
emeriamine emeriamine: derived from fungal metabolite emericedin; structure given in first source	2.37	2	0
1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid: structure given in first source. DOTA : An azamacrocyle in which four nitrogen atoms at positions 1, 4, 7 and 10 of a twelve-membered ring are each substituted with a carboxymethyl group.	2.46	2	0	azamacrocycle	chelator; copper chelator
medica 16 MEDICA 16 : An alpha,omega-dicarboxylic acid that is hexadecanedioic acid carrying methyl groups at positions 3 and 14. It is a free fatty acid 1 (FFA1/GPR40) receptor agonist and an ATP citrate lyase inhibitor, and exhibits hypolipidemic and antidiabetogenic properties.	2.07	1	0	alpha,omega-dicarboxylic acid	antilipemic drug; EC 2.3.3.8 (ATP citrate synthase) inhibitor; EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor; G-protein-coupled receptor agonist; hypoglycemic agent
(20s)-20-hydroxycholesterol 20-hydroxycholesterol: RN given refers to (20S)-isomer. 20-hydroxycholesterol : An oxysterol that is cholesterol substituted by a hydroxy group at position 20.	1.97	1	0	20-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; oxysterol	human metabolite; mouse metabolite
phytosphingosine phytosphingosine: differ with an additional hydroxyl at C-4 & no double bond between C-4 & C-5	2.08	1	0	amino alcohol; sphingoid; triol	mouse metabolite; Saccharomyces cerevisiae metabolite
butyryl-coenzyme a [no description available]	2	1	0	butanoyl-CoAs	Escherichia coli metabolite; mouse metabolite
octanoyl-coenzyme a [no description available]	1.96	1	0
n-acetylputrescine N-acetylputrescine : An N-monoacetylalkane-alpha,omega-diamine that is the N-monoacetyl derivative of putrescine.	2.25	1	0	N-monoacetylalkane-alpha,omega-diamine; N-substituted putrescine	metabolite; mouse metabolite
2-o-rhamnopyranosyl-rhamnopyranosyl-3-hydroxyldecanoyl-3-hydroxydecanoate 2-O-rhamnopyranosyl-rhamnopyranosyl-3-hydroxyldecanoyl-3-hydroxydecanoate: rhamnolipid biosurfactant from Pseudomonas aeruginosa UG2; active in removing hydrophobic cpds from soil; structure in first source	2	1	0
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	2.02	1	0	carbene; methanediyl
perchlorate perchlorate: the explosive component of rocket fuel; an environmental contaminant that disrupts THYROID HORMONES. perchlorate : A monovalent inorganic anion obtained by deprotonation of perchloric acid.	3.12	1	0	chlorine oxoanion; monovalent inorganic anion
fullerene c60 Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.	2.07	1	0	fullerene	geroprotector
prolyl-phenylalanyl-arginine-4-nitroanilide prolyl-phenylalanyl-arginine-4-nitroanilide: chromogenic cpd	3.03	1	0
ro 8-0576 benserazide, levodopa drug combination: combination of L-Dopa and seryltrihydroxybenzylhydrazine; used in treatment of parkinsonism	4.41	1	1
1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone: structure given in first source. 1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one : A differentiation-inducing factor that is hexaphenone bearing two chloro substituents at positions 3 and 5, two hydroxy substituents at positions 2 and 6 as well as a single methoxy substituent at position 4. A secreted, chlorinated molecule that controls cell fate during development of Dictyostelium cells.	1.95	1	0	dichlorobenzene; differentiation-inducing factor; monomethoxybenzene; resorcinols	eukaryotic metabolite; signalling molecule
hydroxycitric acid hydroxycitric acid: RN given refers to cpd without isomeric designation; structure	1.99	1	0	carbonyl compound
subecholine subecholine: dicholinic ester of suberic acid; structure	1.95	1	0
solutol hs 15 Solutol HS 15: multidrug resistance modification agent in tumor cells; polyoxyethylene esters of 12-hydroxystearic acid; previous RN 105109-85-1	2.77	3	0	aliphatic alcohol
tiglic acid tiglic acid : A 2-methylbut-2-enoic acid having its double bond in trans-configuration.. 2-methylbut-2-enoic acid : A branched-chain fatty acid consisting of 2-butenoic acid having a methyl group at position 2.	2.02	1	0	2-methylbut-2-enoic acid	plant metabolite
methotrexate [no description available]	1.99	1	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
ro 32-0432 [no description available]	2.1	1	0
pseudomonas aeruginosa autoinducer Pseudomonas aeruginosa autoinducer: autoinducer required for expression of Pseudomonas aeruginosa virulence genes; structure given in first source. N-(3-oxododecanoyl)homoserine lactone : A N-acyl homoserine lactone that is the monocarboxylic acid amide arising from formal condensation of homoserine lactone with 3-oxododecanoic acid.	2.25	1	0	N-acyl homoserine lactone
5-aminoimidazole-4-carboxamide-1-ribofuranosyl triphosphate [no description available]	2	1	0
cgs 22652 CGS 22652: has thromboxane receptor antagonism combined with thromboxane synthase inhibition; structure given in first source	3.37	7	0
n-hydroxysulfosuccinimide N-hydroxysulfosuccinimide: hydrophilic ligand for preparation of active esters	1.99	1	0
xylose xylopyranose: structure in first source	3.09	5	0	D-xylose
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	1.97	1	0	beta-lactam antibiotic allergen; beta-lactam
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	3.5	8	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
cucurbitaceae Cucurbitaceae: The gourd plant family of the order Violales, subclass Dilleniidae, class Magnoliopsida. It is sometimes placed in its own order, Cucurbitales. 'Melon' generally refers to CUCUMIS; CITRULLUS; or MOMORDICA.	2.05	1	0
1,3-dicapryloylglycerol 1,3-dioctanoylglycerol : A 1,3-diglyceride in which both acyl groups are specified as octanoyl.	2	1	0	1,3-diglyceride	Brassica napus metabolite; excipient
3-hydroxyhexanoic acid 3-hydroxyhexanoic acid: abnormal metabolite in urine & serum of diabetic ketoacidotic patients	2.74	3	0	3-hydroxy monocarboxylic acid
phenylalanyl-glycyl-glycine phenylalanyl-glycyl-glycine: RN given refers to (L-PHe)-isomer. Phe-Gly-Gly : A tripeptide composed of one L-phenylalanine and two glycine residues joined in sequence.	2.05	1	0	tripeptide	metabolite
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	3.8	2	1	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.63	8	0	oxygen hydride; oxygen radical; reactive oxygen species
gallium oxide gallium oxide: RN given refers to unlabeled cpd	2.07	1	0
malvidin malvidin: RN given refers to parent cpd; coloring agent from flowers of Malvaviscus conzatti. malvidin : An anthocyanidin cation that is delphinidin carrying methyl substituents at positions 3' and 5'.	2.17	1	0	5-hydroxyanthocyanidin	biological pigment; metabolite
torcetrapib [no description available]	2.04	1	0	(trifluoromethyl)benzenes; carbamate ester; quinolines	anticholesteremic drug; CETP inhibitor
aristolochene [no description available]	2.01	1	0	aristolochene
rhamnopyranosyl-3-hydroxydecanoyl-3-hydroxydecanoate rhamnopyranosyl-3-hydroxydecanoyl-3-hydroxydecanoate: rhamnolipid biosurfactant from Pseudomonas aeruginosa UG2; active in removing hydrophobic cpds from soil; structure in first source. L-rhamnosyl-3-hydroxydecanoyl-3-hydroxydecanoic acid : A glycolipid, an alpha-L-rhamnoside of 3-[(3-hydroxydecanoyl)oxy]decanoic acid.	2	1	0	alpha-L-rhamnoside; glycolipid	nonionic surfactant
octyl-2-sulfate octyl-2-sulfate: RN refers to Na salt	1.96	1	0
cupric hydroxide copper hydroxide: used as an antifungal agent	2.05	1	0	organic molecular entity
lauroyl-coenzyme a lauroyl-CoA : A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of lauric (dodecanoic) acid.	1.98	1	0	medium-chain fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
phenylacetyl-coenzyme a phenylacetyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of phenylacetic acid.	2	1	0	acyl-CoA	Escherichia coli metabolite; metabolite; mouse metabolite
technetium tc 99m pentetate Technetium Tc 99m Pentetate: A technetium imaging agent used in renal scintigraphy, computed tomography, lung ventilation imaging, gastrointestinal scintigraphy, and many other procedures which employ radionuclide imaging agents.	2.03	1	0
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	2.06	1	0	iodine oxoanion; monovalent inorganic anion
thiophosphoric acid thiophosphoric acid: RN given refers to parent cpd	2.1	1	0	phosphorothioic acid
aminopterin Aminopterin: A folic acid derivative used as a rodenticide that has been shown to be teratogenic.	1.99	1	0	dicarboxylic acid	EC 1.5.1.3 (dihydrofolate reductase) inhibitor; mutagen
5-hydroxyhexanoic acid 5-hydroxyhexanoic acid : A medium-chain fatty acid that is hexanoic acid substituted at position 5 by a hydroxy group.	4.27	4	1	(omega-1)-hydroxy fatty acid; medium-chain fatty acid	human urinary metabolite
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	2.36	2	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.38	2	0	amino acid zwitterion; angiotensin II	human metabolite
ml 236a ML 236A: inhibitor of hydroxymethylglutaryl CoA reductase; structure. compactin diol lactone : A carbobicyclic compound that is ML-236C substituted by a hydroxy group at position 8S. It is a fungal metabolite isolated from Penicillium citrinum and exhibits anticholesteremic activity.	1.95	1	0	2-pyranones; carbobicyclic compound; hexahydronaphthalenes; polyketide; secondary alcohol	antiatherosclerotic agent; anticholesteremic drug; antilipemic drug; antimicrobial agent; EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; fungal metabolite
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	3.21	6	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.49	2	0
clofibric acid-coenzyme a clofibric acid-coenzyme A: rat liver microsomal thioester metabolite	1.98	1	0
sb 203580 [no description available]	2.02	1	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	4.37	6	0	divalent inorganic anion; phosphite ion
nickel monoxide [no description available]	2.07	1	0
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	3.85	3	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
n(alpha)-lauroylarginine ethyl ester N(alpha)-lauroylarginine ethyl ester: an antimicrobial surfactant; RN given refers to (L)-isomer	2.5	2	0
2-aminosuberic acid 2-aminosuberic acid: RN refers to (R)-isomer	1.99	1	0
2-methylbutyrylglycine 2-methylbutyrylglycine: metabolite of L-isoleucine. N-(2-methylbutanoyl)glycine : A N-acylglycine that is glycine substituted by a 2-methylbutanoyl group at the N atom.	1.95	1	0	N-acylglycine	human metabolite
tcp (antiseptic) TCP (antiseptic): contains solution of 0.4% chlorine, 0.11% iodine, 0.63% phenol & 0.045% of salicylic acid in water	2.05	1	0
darunavir Darunavir: An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.. darunavir : An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.	2.11	1	0	carbamate ester; furofuran; sulfonamide	antiviral drug; HIV protease inhibitor
sorafenib [no description available]	2.11	1	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	4.79	10	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
erythritol [no description available]	2.35	2	0	butane-1,2,3,4-tetrol	antioxidant; human metabolite; plant metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	5.28	10	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
cortisone [no description available]	1.94	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
3-octanone 3-octanone : A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group.	2.05	1	0	dialkyl ketone	antifeedant; biomarker; fungal metabolite; human urinary metabolite; insect attractant; plant metabolite; toxin
lanosterol [no description available]	1.99	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
melengestrol acetate Melengestrol Acetate: A 6-methyl PROGESTERONE acetate with reported glucocorticoid activity and effect on ESTRUS.	1.95	1	0	corticosteroid hormone
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.5	2	0
wortmannin [no description available]	2.1	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
o-(chloroacetylcarbamoyl)fumagillol O-(Chloroacetylcarbamoyl)fumagillol: Semisynthetic analog of fumagillin (a cyclohexane-sesquiterpene antibiotic isolated from ASPERGILLUS FUMIGATUS) that inhibits angiogenesis.. O-(chloroacetylcarbamoyl)fumagillol : A carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative.	1.98	1	0	carbamate ester; organochlorine compound; semisynthetic derivative; sesquiterpenoid; spiro-epoxide	angiogenesis inhibitor; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; methionine aminopeptidase 2 inhibitor; retinoic acid receptor alpha antagonist
permanganate [no description available]	2.17	1	0	manganese oxoacid
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.02	1	0
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	4.56	26	0
arabinose [no description available]	2.35	2	0	L-arabinose	Escherichia coli metabolite; mouse metabolite
amylopectin Amylopectin: A highly branched glucan in starch.. amylopectin : A polydisperse highly branched polysaccharide derivative composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage. The chains are joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some 6-phosphate ester groups also may occur. The branches in amylopectin typically contain 24 to 30 glucose residues.	2.6	1	0
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	3.74	11	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
elastin [no description available]	2.17	1	0	oligopeptide
carnosine polaprezinc: stimulates bone growth	2.89	4	0	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	3.56	9	0	3,5-dihydroxy-3-methylpentanoic acid
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	3.9	13	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
allose [no description available]	2.44	2	0	allopyranose; D-allose	antioxidant
puromycin [no description available]	2.35	2	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.21	1	0	taxifolin	metabolite
mannosamine mannosamine: RN given refers to parent cpd without isomeric designation. D-mannosamine : The D-enantiomer of mannosamine.. 2-amino-2-deoxy-D-mannopyranose : A D-mannosamine in cyclic pyranose form.	2.1	1	0	D-mannosamine
pr toxin PR Toxin: mycotoxin from Penicillium roqueforti; structure	2.01	1	0	oxacycle
cefoxitin Cefoxitin: A semisynthetic cephamycin antibiotic resistant to beta-lactamase.. cefoxitin : A semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase.	3.36	1	1	beta-lactam antibiotic allergen; cephalosporin; cephamycin; semisynthetic derivative	antibacterial drug
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	2.36	2	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
pentazocine Pentazocine: The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)	2.05	1	0	benzazocine
terconazole terconazole: structure & RN for (cis)-isomer from first source. terconazole : A racemate consisting of equimolar amounts of (2R,4S)- and (2S,4R)-terconazole. It has broad-spectrum antifungal activitiy and is used for the treatment of vaginal yeast infections (Candida).. (2R,4S)-terconazole : A 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively.	2.33	2	0	1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine
indican [no description available]	2.47	2	0	beta-D-glucoside; exopolysaccharide; indolyl carbohydrate
notoginsenoside r1 notoginsenoside R1 : A ginsenoside found in Panax notoginseng that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions, in which the hydroxy groups at positions 6 and 20 have been converted to the corresponding beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranoside and beta-D-glucopyranoside respectively, and in which a double bond has been introduced at the 24-25 position.	2.17	1	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; disaccharide derivative; ginsenoside; tetracyclic triterpenoid	antioxidant; apoptosis inducer; neuroprotective agent; phytoestrogen; plant metabolite
alpha-copaene alpha-copaene: from Olea europaea; structure in first source. alpha-copaene : A sesquiterpene that is tricyclo[4.4.0.0(2,7)]dec-3-ene bearing an isopropyl substituent at position 8 and two methyl substituents at positions 1 and 3 (the 1S,6S,7S,8S-diastereomer).	2.57	2	0
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	1.99	1	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	2.03	1	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.03	1	0
acetylleucyl-leucyl-norleucinal acetylleucyl-leucyl-norleucinal: a proteasome inhibitor. acetylleucyl-leucyl-norleucinal : A tripeptide composed of N-acetylleucyl, leucyl and norleucinal residues joined in sequence.	2.02	1	0	aldehyde; tripeptide	cysteine protease inhibitor
devazepide Devazepide: A derivative of benzodiazepine that acts on the cholecystokinin A (CCKA) receptor to antagonize CCK-8's (SINCALIDE) physiological and behavioral effects, such as pancreatic stimulation and inhibition of feeding.. devazepide : An indolecarboxamide obtained by formal condensation of the carboxy group of indole-2-carboxylic acid with the exocyclic amino group of (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one. A cholecystokinin antagonist used for treatment of gastrointestinal disorders.	1.98	1	0	1,4-benzodiazepinone; indolecarboxamide	antineoplastic agent; apoptosis inducer; cholecystokinin antagonist; gastrointestinal drug
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.78	10	0	cyclodextrin
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	6.02	45	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.08	1	0	cinnamic acid	plant metabolite
ergosterol [no description available]	2.48	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.01	1	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.94	4	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	3.4	7	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	2.4	2	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
3-hydroxy-3-methylglutaryl-coenzyme a 3-hydroxy-3-methylglutaryl-coenzyme A: RN given refers to cpd without isomeric designation. 3-hydroxy-3-methylglutaryl-CoA : An alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid.. (3S)-3-hydroxy-3-methylglutaryl-CoA : A 3-hydroxy-3-methylglutaryl-CoA where the 3-hydroxy-3-methylglutaryl component has (S)-configuration.	2.21	1	0	3-hydroxy-3-methylglutaryl-CoA; 3-hydroxy fatty acyl-CoA	human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.54	2	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	3.07	5	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
1,2-dilauroylphosphatidylcholine 1,2-dilauroylphosphatidylcholine: RN given refers to cpd without isomeric designation. 1,2-dilauroyl-sn-glycero-3-phosphocholine(1+) : A A 1,2-diacyl-sn-glycero-3-phosphocholine(1+) that is the dilauroyl diester of phosphatidiylcholine.	2.06	1	0	1,2-diacyl-sn-glycero-3-phosphocholine(1+)
palmitoleic acid hexadecenoate : A long-chain unsaturated fatty acid anion that is the conjugate base of hexadecenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	4.03	5	0	hexadec-9-enoic acid	algal metabolite; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; human blood serum metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	9.08	85	2	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.44	2	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.01	1	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	2.59	2	0	D-galactopyranuronic acid
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	4.23	5	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	2.74	3	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	2	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
lycopene [no description available]	2.07	1	0	acyclic carotene	antioxidant; plant metabolite
zithromax Azithromycin: A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.. azithromycin : A macrolide antibiotic useful for the treatment of bacterial infections.	2.17	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; xenobiotic
obeticholic acid obeticholic acid: A farnesoid X receptor agonist and anticholestatic agent that is used in the treatment of chronic liver diseases; structure in first source.. obeticholic acid : A dihydroxy-5beta-cholanic acid that is chenodeoxycholic acid carrying an additional ethyl substituent at the 6alpha-position. A semi-synthetic bile acid which acts as a farnesoid X receptor agonist and is used for treatment of primary biliary cholangitis.	3.12	1	0	3alpha-hydroxy steroid; 7alpha-hydroxy steroid; dihydroxy-5beta-cholanic acid	farnesoid X receptor agonist; hepatoprotective agent
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	2.38	2	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
n-acetylmethionine N-acetylmethionine: RN given refers to L-isomer. N-acetylmethionine : A methionine derivative that is methionine in which one of the amine hydrogens is substituted by an acetyl group.	2.15	1	0	L-methionine derivative; N-acetyl-L-amino acid; N-acetylmethionine	nutraceutical
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.01	1	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.21	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	4.07	3	1	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
laninamivir laninamivir: an antiviral agent	3.57	2	0	acetamides
sodium chlorate sodium chlorate : An inorganic sodium salt that has chlorate as the counter-ion. An oxidising agent, it is used for bleaching paper and as a herbicide. It is also used in the manufacture of dyes, explosives and matches.	2.07	1	0	chlorate salt; inorganic sodium salt	herbicide
sodium acetate, anhydrous Sodium Acetate: The trihydrate sodium salt of acetic acid, which is used as a source of sodium ions in solutions for dialysis and as a systemic and urinary alkalizer, diuretic, and expectorant.	2.03	1	0	organic sodium salt	NMR chemical shift reference compound
sodium benzoate Sodium Benzoate: The sodium salt of BENZOIC ACID. It is used as an antifungal preservative in pharmaceutical preparations and foods. It may also be used as a test for liver function.. sodium benzoate : An organic sodium salt resulting from the replacement of the proton from the carboxy group of benzoic acid by a sodium ion.	2.06	1	0	organic sodium salt	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	2.4	2	0	acetate salt; ammonium salt	buffer; food acidity regulator
3-mercaptohexanol 3-mercaptohexanol: structure in first source. 3-mercaptohexanol : An alkanethiol that is hexane substituted at positions 1 and 3 by hydroxy and sulfanyl groups respectively.	2.05	1	0	alkanethiol; primary alcohol	flavouring agent; plant metabolite; Saccharomyces cerevisiae metabolite
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	1.93	1	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
n-isovalerylglycine N-isovalerylglycine: urinary metabolite of isovaleric acid in isovaleric acidemia (sweaty feet syndrome). N-isovalerylglycine : An N-acylglycine in which the acyl group is specified as isovaleryl.	1.95	1	0	N-acylglycine	human urinary metabolite
2-bromooctanoic acid 2-bromooctanoic acid: RN given refers to cpd without isomeric designation	4.28	19	0
elaidic acid [no description available]	3.34	2	0	octadec-9-enoic acid	food component
geraniol [no description available]	2.51	2	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	3.23	6	0
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	3.74	11	0	isomethyleugenol
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	2.05	1	0	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.38	2	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.1	1	0	stilbene
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	2.66	2	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	2.39	2	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
malonyl coenzyme a Malonyl Coenzyme A: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.. omega-carboxyacyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of any alpha,omega-dicarboxylic acid.	3.49	8	0	malonyl-CoAs	EC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor; Escherichia coli metabolite; metabolite; mouse metabolite
arginine vasopressin Arginine Vasopressin: The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.. argipressin : The predominant form of mammalian vasopressin (antidiuretic hormone). It is a nonapeptide containing an arginine at residue 8 and two disulfide-linked cysteines at residues of 1 and 6.	2.68	3	0	vasopressin	cardiovascular drug; hematologic agent; mitogen
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	1.94	1	0	diphosphate ion
palmitoyl coenzyme a Palmitoyl Coenzyme A: A fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis.. palmitoyl-CoA : A long-chain fatty acyl-CoA resulting from the formal condensation of the carboxy group of hexadecanoic acid with the thiol group of coenzyme A.	3.48	8	0	11,12-saturated fatty acyl-CoA; 3-substituted propionyl-CoA; long-chain fatty acyl-CoA; palmitoyl bioconjugate	Escherichia coli metabolite; mouse metabolite
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.05	1	0	benzamides
isopropyl thiogalactoside Isopropyl Thiogalactoside: A non-metabolizable galactose analog that induces expression of the LAC OPERON.. isopropyl beta-D-thiogalactopyranoside : An S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.	2.25	1	0	S-glycosyl compound
leuprolide Leuprolide: A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.. leuprolide : An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the acetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.	2.1	1	0	oligopeptide	anti-estrogen; antineoplastic agent; gonadotropin releasing hormone agonist
propylthiouracil Propylthiouracil: A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534). 6-propyl-2-thiouracil : A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.	1.99	1	0	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist
sesquiterpenes [no description available]	3.4	7	0
dansylproline dansylproline: RN given refers to L-proline isomer	2.05	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.01	1	0	caffeic acid	geroprotector; mouse metabolite
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	4.43	4	1	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	3	4	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
benztropine Benztropine: A centrally active muscarinic antagonist that has been used in the symptomatic treatment of PARKINSON DISEASE. Benztropine also inhibits the uptake of dopamine.. benzatropine : Tropane in which a hydrogen at position 3 is substituted by a diphenylmethoxy group (endo-isomer). An acetylcholine receptor antagonist, it is used (particularly as its methanesulphonate salt) in the treatment of Parkinson's disease, and to reduce parkinsonism and akathisia side effects of antipsychotic treatments.	2.07	1	0	diarylmethane
cinnarizine Cinnarizine: A piperazine derivative having histamine H1-receptor and calcium-channel blocking activity with vasodilating and antiemetic properties but it induces PARKINSONIAN DISORDERS.	2.54	2	0	diarylmethane; N-alkylpiperazine; olefinic compound	anti-allergic agent; antiemetic; calcium channel blocker; geroprotector; H1-receptor antagonist; histamine antagonist; muscarinic antagonist
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2	1	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
geranyl acetate geranyl acetate: constituted about 90% of the palmarosa oil. geranyl acetate : A monoterpenoid that is the acetate ester derivative of geraniol.	2.21	1	0	acetate ester; monoterpenoid	plant metabolite
3-phenylpropionylglycine 3-phenylpropionylglycine: found in urine of patients suffering from medium-chain acyl-CoA dehydrogenase deficiency; RN refers to HCl	1.98	1	0	aromatic ketone
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.47	2	0	cinnamate ester; tannin	food component; plant metabolite
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.67	3	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
safranine t safranin O : An organic chloride salt having 3,7-diamino-2,8-dimethyl-5-phenylphenazin-5-ium as the counterion. It is commonly used for staining Gram negative bacteria.	1.96	1	0	organic chloride salt	fluorochrome; histological dye
D-fructopyranose [no description available]	4.15	17	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.4	2	0	thiocarboxamide	hepatotoxic agent
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.05	1	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	6.04	3	2	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
fumonisin b1 fumonisin B1: isolated from Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting activity; inhibits ceramide synthase. fumonisin B1 : A diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol.	2.04	1	0	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	2.38	2	0	bile acid taurine conjugate	human metabolite
nadp [no description available]	3.83	12	0
3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2h-tetrazolium 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium: structure given in first source	2.08	1	0
zeranol Zeranol: A non-steroidal estrogen analog.	2.41	1	0	macrolide
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.34	2	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
estrone sulfate estrone sulfate: sulfoconjugated estrone; RN given refers to parent cpd	2.05	1	0	17-oxo steroid; steroid sulfate	human metabolite; mouse metabolite
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.79	3	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
compound 348u87 compound 348U87: structure given in first source; antiherpes cpd	1.98	1	0
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2.91	3	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	3.06	5	0	alkali metal atom
nitrogen dioxide Nitrogen Dioxide: Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	2.15	1	0	nitrogen oxide
decyl glucoside decyl glucoside: a non-ionic surfactant used in rinse-off products	2.15	1	0
monooctanoin monooctanoin: dissolution agent for retained cholesterol bile duct stones; RN in Chemline for octanoic acid, ester with 1,2,3-propanetriol, MF unknown: 11140-04-8; RN for octanoic acid, 2,3-dihydroxypropyl ester (1-monooctanoin): 502-54-5; RN in 9th CI Form Index for (+-)-1-monooctanoin: 19670-49-6. rac-1-monooctanoylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-octanoyl-sn-glycerol and 3-octanoyl-sn-glycerol.. 1-monooctanoylglycerol : A 1-monoglyceride that has octanoyl as the acyl group.	12.76	171	4	1-monoglyceride; octanoate ester; rac-1-monoacylglycerol
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	3.42	1	1	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
octotiamine [no description available]	1.99	1	0
quinine [no description available]	2.35	2	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
2-ketogluconate 2-ketogluconate: RN given refers to parent cpd without isomeric designation. 2-dehydro-D-gluconic acid : A ketoaldonic acid that is D-gluconic acid in which the hydroxy group at position 2 has been oxidised to a keto group.	2.06	1	0	keto-D-gluconic acid	bacterial metabolite
2-(4-isothiocyanatobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid 2-(4-isothiocyanatobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid: structure given in first source	2.07	1	0
cystine [no description available]	2.44	2	0
ferrocenium ferrocenium: structure given in first source	1.98	1	0
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	2.5	2	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.21	1	0
phosphonic acid phosphonic acid : A phosphorus oxoacid that consists of a single pentavalent phosphorus covalently bound via single bonds to a single hydrogen and two hydroxy groups and via a double bond to an oxygen. The parent of the class of phosphonic acids.	3.17	1	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.59	2	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.51	2	0
gw 7647 GW 7647: a PPAR-alpha agonist; structure in first source. GW 7647 : A monocarboxylic acid that is 2-(phenylsulfanyl)isobutyric acid in which the phenyl group is substituted at the para- position by a 3-aza-7-cyclohexylhept-1-yl group in which the nitrogen is acylated by a (cyclohexylamino)carbonyl group.	2.49	2	0	aryl sulfide; monocarboxylic acid; ureas	PPARalpha agonist
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	5.32	21	0	organic sodium salt	detergent; protein denaturant
valyl-leucyl-lysine 4-nitroanilide valyl-leucyl-lysine 4-nitroanilide: chromogenic substrate of plasmin; H-D-Val-Leu-Lys- 4-nitroaniline	3.03	1	0
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2.04	1	0
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	3.49	8	0
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	1.99	1	0	organic cation; xanthene dye	fluorochrome
4-cresol sulfate p-cresol sulfate : An aryl sulfate that is p-cresol in which the phenolic hydrogen has been replaced by a sulfo group.	2.05	1	0	aryl sulfate	gut flora metabolite; human metabolite; uremic toxin
myelin basic protein Myelin Basic Protein: An abundant cytosolic protein that plays a critical role in the structure of multilamellar myelin. Myelin basic protein binds to the cytosolic sides of myelin cell membranes and causes a tight adhesion between opposing cell membranes.	2.07	1	0
2-mercaptoacetate 2-mercaptoacetate: RN given refers to parent cpd	2.39	2	0	monocarboxylic acid anion
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	2.75	3	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	3.11	4	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	4.11	16	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.89	4	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
12-oxophytodienoic acid 12-oxophytodienoic acid: structure given in first source; a jasmonate precursor that induces phytoalexin synthesis	2.01	1	0	carbocyclic fatty acid; olefinic fatty acid; oxo carboxylic acid
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	5.58	28	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	2.86	4	0
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2.47	2	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	2.06	1	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	1.98	1	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
8,11,14-eicosatrienoic acid 8,11,14-Eicosatrienoic Acid: A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.. all-cis-icosa-8,11,14-trienoic acid : An icosatrienoic acid having three cis double bonds at positions 8, 11 and 14.	3.22	5	0	fatty acid 20:3; long-chain fatty acid	fungal metabolite; human metabolite; nutraceutical
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	2.21	1	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.31	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
6-ketoprostaglandin f1 alpha 6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.	1.98	1	0	prostaglandins Falpha	human metabolite; mouse metabolite
gamma-linolenic acid gamma-Linolenic Acid: An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed). gamma-linolenic acid : A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.	2.01	1	0	linolenic acid; omega-6 fatty acid	human metabolite; mouse metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	4.18	6	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
genistein [no description available]	2.01	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.39	2	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
entacapone entacapone: structure given in first source. entacapone : A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group.	3.43	1	1	2-nitrophenols; catechols; monocarboxylic acid amide; nitrile	antidyskinesia agent; antiparkinson drug; central nervous system drug; EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	2.95	4	0	oxo monocarboxylic acid	jasmonates; plant metabolite
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.46	2	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
norbixin norbixin: an annatto compound; RN given refers to all-trans-norbixin (beta-norbixin); 9-cis-norbixin is alpha-norbixin	2.06	1	0	diterpenoid
mezerein mezerein: toxic component of plant Daphne mezereum with anti-leukemic activity against P-388 & P-1210 in mice; can act as a tumor promoter; RN given refers to (12beta(E,E))-isomer; structure	1.97	1	0	diterpenoid
pyrethrosin pyrethrosin: structure	2.13	1	0	gamma-lactone
daidzein [no description available]	2.01	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	2.17	1	0	stilbenoid
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	2.07	1	0	enone; monomethoxybenzene; phenols
ellagic acid [no description available]	2.25	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	2.46	2	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.39	2	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
4-acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic acid 4-Acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic Acid: A non-penetrating amino reagent (commonly called SITS) which acts as an inhibitor of anion transport in erythrocytes and other cells.	1.97	1	0	stilbenoid
4-hydroxyestradiol 4-hydroxyestradiol: catechol estrogen. 4-hydroxy-17beta-estradiol : A 4-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 4.	2.01	1	0	4-hydroxy steroid	metabolite
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	1.98	1	0	thromboxanes B	human metabolite; mouse metabolite
20-hydroxy-5,8,11,14-eicosatetraenoic acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid: stimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer. 20-HETE : A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20.	1.98	1	0	HETE; hydroxy monocarboxylic acid	human metabolite; mouse metabolite
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	2.03	1	0	4-hydroxynon-2-enal; 4-hydroxynonenal
(2e)-decenal (2E)-decenal: structure in first source. (2E)-dec-2-enal : A dec-2-enal in which the olefinic double bond has E configuration.	2.55	2	0	2-decenal	alarm pheromone; mutagen; nematicide
1-monooleoyl-rac-glycerol Peceol: lipid excipient containing readily dispersible mixture of mono- & diglycerides of oleic acid. 1-oleoylglycerol : A 1-monoglyceride where the acyl group is oleoyl.. monooleoylglycerol : A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified.	4.25	17	0	1-acylglycerol 18:1; monooleoylglycerol	plant metabolite
cholesteryl oleate cholesteryl oleate: RN given refers to ((Z)-isomer). cholesteryl oleate : The (Z)-stereoisomer of cholesteryl octadec-9-enoate.	1.99	1	0	CE(18:1); cholesteryl octadec-9-enoate	mouse metabolite
phenylephrine hydrochloride Nose: A part of the upper respiratory tract. It contains the organ of SMELL. The term includes the external nose, the nasal cavity, and the PARANASAL SINUSES.. phenylephrine hydrochloride : A hydrochloride that is the monohydrochloride salt of phenylephrine.	2.36	2	0	hydrochloride
iodopyracet Iodopyracet: An ionic monomeric contrast medium that was formerly used for a variety of diagnostic procedures. (From Martindale, The Extra Pharmacopoeia, 30th ed, p706). diodone : A 4-pyridone in which the pyridone is iodo-substituted at C-3 and -5 and has a carboxymethyl substituent on nitrogen; used as a radiocontrast agent urography.	2.35	2	0
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	1.97	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
vitamin k 1 Vitamin K 1: A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.. phylloquinone : A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.	1.95	1	0	phylloquinones; vitamin K	cofactor; human metabolite; plant metabolite
anthramycin [no description available]	2.17	1	0
istradefylline [no description available]	2.11	1	0	oxopurine
endomorphin 1 endomorphin 1: isolated from bovine brain	2.04	1	0	oligopeptide
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	1.97	1	0	1-O-acyl-sn-glycero-3-phosphocholine
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	2.37	2	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
octadecadienoic acid octadecadienoic acid: location of unsaturation not specified. octadecadienoate : A long-chain, unsaturated fatty acid anion formed by deprotonation of the carboxy group of any octadecadienoic acid; major species at pH 7.3.. octadecadienoic acid : Any straight-chain, C18 polyunsaturated fatty acid having two C=C double bonds.	2.01	1	0
decaprenoic acid decaprenoic acid: synthetic isoprenoid; RN given refers to cpd without isomeric designation; structure given in first source	2.58	2	0	monoterpenoid
10-hydroxy-2-decenoic acid (E)-10-hydroxydec-2-enoic acid : An omega-hydroxy amino acid that is 2-decenoic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group and in which the C=C double bond has E configuration. It is a component of royal jelly.	2.08	1	0	alpha,beta-unsaturated monocarboxylic acid; hydroxy monounsaturated fatty acid; omega-hydroxy-medium-chain fatty acid; straight-chain fatty acid	animal metabolite; geroprotector
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.44	2	0	phosphatidylcholine(1+)
trilinolein trilinolein: RN given refers to (Z,Z)-isomer. 1,2,3-trilinoleoylglycerol : A triglyceride formed by acylation of the three hydroxy groups of glycerol with linoleic acid.	1.97	1	0	1,2-diacyl-3-linoleoylglycerol; 1,3-diacyl-2-linoleoylglycerol; linoleoyl containing 1,2,3-triacyl-sn-glycerol; TG(18:2/18:2/18:2); triglyceride	mouse metabolite
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.11	1	0
fexaramine fexaramine: structure in first source	3.12	1	0	biphenyls
7-hydroxycoumarin-4-acetic acid 7-hydroxycoumarin-4-acetic acid: pH-indicator dye; structure in first source	1.99	1	0
ergothioneine ergothioneine thione form : A L-histidine derivative that is N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a thioxo group.	1.94	1	0	1,3-dihydroimidazole-2-thiones; amino-acid betaine; L-histidine derivative; sulfur-containing amino acid	antioxidant; chelator; fungal metabolite; plant metabolite; xenobiotic metabolite
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	3.64	8	0	carbon group element atom; elemental lead; metal atom	neurotoxin
tin [no description available]	2.4	2	0	carbon group element atom; elemental tin; metal atom	micronutrient
13-hydroperoxy-9,11-octadecadienoic acid 13-hydroperoxy-9,11-octadecadienoic acid: RN given refers to (E,Z)-isomer; RN for unspecified isomer not in Chemline 8/12/83. 13-HPODE : An HPODE (hydroperoxyoctadecadienoic acid) in which the double bonds are at positions 9 and 11 (E and Z geometry, respectively) and the hydroperoxy group is at position 13.	2.01	1	0	hydroperoxy polyunsaturated fatty acid; octadecadienoic acid
bay 11-7085 BAY11-7085 : A sulfone that is benzene substituted by [(E)-2-cyanoethenyl]sulfonyl and tert-butyl groups at position 1 and 4, respectively. It is an irreversible inhibitor of IkappaB-alpha phosphorylation in cells (IC50 = 10 muM) and prevents the activation of NF-kappaB.	2.21	1	0	benzenes; nitrile; sulfone	anti-inflammatory agent; antibacterial agent; antineoplastic agent; apoptosis inducer; autophagy inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; ferroptosis inducer; NF-kappaB inhibitor
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	3.08	5	0
antimony Antimony: A metallic element that has the atomic symbol Sb, atomic number 51, and atomic weight 121.75. It is used as a metal alloy and as medicinal and poisonous salts. It is toxic and an irritant to the skin and the mucous membranes.	2.47	2	0	metalloid atom; pnictogen
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	1.94	1	0	alkali metal atom
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	1.95	1	0	alkaline earth metal atom; elemental barium
rubidium Rubidium: An element that is an alkali metal. It has an atomic symbol Rb, atomic number 37, and atomic weight 85.47. It is used as a chemical reagent and in the manufacture of photoelectric cells.	2.36	2	0	alkali metal atom
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.88	3	0	boron group element atom; elemental aluminium; metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.8	3	0	metal atom; pnictogen
thallium Thallium: A heavy, bluish white metal, atomic number 81, atomic weight [204.382; 204.385], symbol Tl.. thallium : A metallic element first identified and named from the brilliant green line in its flame spectrum (from Greek thetaalphalambdalambdaomicronsigma, a green shoot).	2.67	3	0	boron group element atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	4.16	5	0	metalloid atom; pnictogen	micronutrient
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	3.03	4	0	boron group element atom
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	4.74	2	1	boron group element atom
butorphanol Butorphanol: A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.. butorphanol : Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain.	3.39	1	1	morphinane alkaloid	antitussive; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
lisinopril Lisinopril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure.	5.94	2	2	dipeptide	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	4.48	7	0	chalcogen; nonmetal atom	macronutrient
glyceryl behenate 1-behenoylglycerol : A fatty acid ester resulting from the formal condensation of the hydroxy group at position-1 of glycerol with the carboxy group of docosanoic acid.	2.03	1	0	1-monoglyceride; fatty acid ester	antineoplastic agent; plant metabolite
ethyl oleate [no description available]	1.99	1	0	long-chain fatty acid ethyl ester	acaricide; plant metabolite
monocrotophos Monocrotophos: An organophosphate insecticide that inhibits monoamine oxidase and acetylcholinesterase. It has been shown to be genotoxic.. monocrotophos : An alkenyl phosphate that is the 4-(methylamino)-4-oxobut-2-en-2-yl ester of dimethyl phosphate.	2.31	1	0	alkenyl phosphate; dialkyl phosphate; monocarboxylic acid amide; organophosphate insecticide	acaricide; agrochemical; avicide; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
diphenylhexatriene Diphenylhexatriene: A fluorescent compound that emits light only in specific configurations in certain lipid media. It is used as a tool in the study of membrane lipids.	2.03	1	0	alkatriene	fluorochrome
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.46	2	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
iditol iditol: RN refers to L-isomer. L-iditol : The L-enantiomer of iditol.	2.01	1	0	iditol	fungal metabolite; human metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	5.36	14	1	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	3.69	10	0	cysteinium	fundamental metabolite
isophthalate isophthalate: RN given refers to parent cpd	2	1	0	dicarboxylic acid dianion
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.07	1	0	carbon group element atom; metalloid atom; nonmetal atom
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	3.57	9	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	2.82	3	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
heroin Heroin: A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed). heroin : A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.	2.37	2	0	morphinane alkaloid	mu-opioid receptor agonist; opioid analgesic; prodrug
aliskiren aliskiren: orally active nonpeptidic renin inhibitor. aliskiren : A monomethoxybenzene compound having a 3-methoxypropoxy group at the 2-position and a multi-substituted branched alkyl substituent at the 4-position.	2.46	2	0	monocarboxylic acid amide; monomethoxybenzene	antihypertensive agent
triolein Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester.. triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.	4.27	19	0	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
docosapentaenoic acid docosapentaenoic acid : Any straight-chain, C22 fatty acid having five C=C double bonds.. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid : The all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 7-, 10-, 13-, 16- and 19-positions.	2.15	1	0	docosapentaenoic acid; omega-3 fatty acid	algal metabolite; human metabolite
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.41	1	0	2-trans-abscisic acid
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.05	1	0	cyanine dye; organic iodide salt	fluorochrome
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	6.02	27	1	ammonium salt; inorganic sulfate salt	fertilizer
2-amino-4-methoxy-3-butenoic acid 2-amino-4-methoxy-3-butenoic acid: bacterial toxin isolated from Pseudomonas aeruginosa; RN given refers to (S-(E))-isomer	1.95	1	0
4,4'-diisothiocyanostilbene-2,2'-disulfonic acid 4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid: An inhibitor of anion conductance including band 3-mediated anion transport.	1.97	1	0
rifamycin sv rifamycin SV: RN given refers to parent cpd; structure in Merck Index, 9th ed, #8009. rifamycin SV : A member of the class of rifamycins that exhibits antibiotic and antitubercular properties.	1.93	1	0	acetate ester; cyclic ketal; lactam; macrocycle; organic heterotetracyclic compound; polyphenol; rifamycins	antimicrobial agent; antitubercular agent; bacterial metabolite
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	1.98	1	0	chalcogen; nonmetal atom	micronutrient
bismuth oxychloride bismuth oxychloride: active against rotaviruses and enteric viruses	2.21	1	0
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	2.65	3	0
mevalonolactone mevalonolactone: RN given refers to unlabeled cpd without isomeric designation; structure. mevalonolactone : A racemate comprising equimolar amounts of (R)-mevalonolactone and (S)-mevalonolactone.	2.87	4	0	4-hydroxy-4-methyloxan-2-one	fungal metabolite; plant metabolite
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	2.37	2	0	amidobenzoic acid
calcium fumarate [no description available]	3.45	1	1
4-bromocrotonic acid 4-bromocrotonic acid: inhibitor of fatty acid oxidation & ketone body degradation in rat heart mitochondria; RN given refers to (E)-isomer	1.96	1	0
1-oleoyl-2-acetylglycerol [no description available]	1.97	1	0	1,2-diglyceride
myxothiazol myxothiazol: strobilurin analogue; methoxyacrylamide derivative; antifungal antibiotic from Myxococcus fulvus; structure given in first source. myxothiazol : A 2,4'-bi-1,3-thiazole substituted at the 4-position with a (1E,3S,4R,5E)-7-amino-3,5-dimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl] group and at the 2'-position with a (2S,3E,5E)-7-methylocta-3,5-dien-2-yl group. It is an inhibitor of coenzyme Q - cytochrome c reductase.	1.99	1	0
1,2-dioleoylphosphatidylserine 1,2-dioleoylphosphatidylserine: RN given in first source; RN given refers to (R-(Z,Z))-isomer; RN for cpd without isomeric designation not available 6/90. 1,2-dioleoyl-sn-glycero-3-phospho-L-serine : A 3-sn-phosphatidyl L-serine in which the phosphatidyl acyl groups are both oleoyl.. phosphatidylserine(18:1/18:1) : A 3-sn-phosphatidyl-L-serine in which the 1- and 2-acyl groups are octadecenoyl groups.	2.03	1	0	phosphatidylserine(18:1/18:1)	mouse metabolite
tiglylglycine tiglylglycine: RN is from 9th CI. tiglylglycine : An N-acylglycine that is glycine with an amine hydrogen substituted by a 2-methylbut-2-enoyl (tiglyl) group.	1.95	1	0	N-acylglycine	metabolite
tuberonic acid tuberonic acid: RN given for (1R-(1alpha,2alpha(Z)))-isomer; isolated from the potato Solanum tuberosum; structure in first source. tuberonic acid : An oxo monocarboxylic acid that is (+)-7-isojasmonic acid in which one of the hydrogens of the side-chain methyl group is replaced by a hydroxy group.	2.01	1	0	cyclopentanones; homoallylic alcohol; oxo monocarboxylic acid; primary alcohol	jasmonates; plant metabolite
flexirubins flexirubins: pigments found in the outer membrane of Flexibacter elegans, characterized by non-isoprenoid omega-substituted polyene carboxylic acids esterified with 2,5-dialkylated resorcinols; structure. flexirubin : The parent member of the class of flexirubins obtained by formal condensation of the carboxy group of 17-(4-hydroxy-3-methylphenyl)heptadeca-2,4,6,8,10,12,14,16-octaenoic acid with one of the phenolic hydroxy groups of 2-dodecyl-5-methyl resorcinol.. flexirubins : Flexirubins are a unique type of pigment produced by various bacteria species characterised by a common structure comprising non-isoprenoid omega-substituted polyene carboxylic acids esterified with 2,5-dialkylated resorcinols.	2.01	1	0
i(3)so3-galactosylceramide Sulfoglycosphingolipids: GLYCOSPHINGOLIPIDS with a sulfate group esterified to one of the sugar groups.. 1-(3-O-sulfo-beta-D-galactosyl)-N-tetracosanoylsphingosine : A D-galactosyl-N-acylsphingosine having a sulfo group at the 3-position on the galactose ring and tetracosanoyl as the N-acyl group.	1.94	1	0	galactosylceramide sulfate; N-acyl-beta-D-galactosylsphingosine
suberylglycine suberylglycine: found in urine of patients with C(6)-C(10)-dicarboxylIC aciduria; RN is from 9th CI, Chem Subs Index; structure	2	1	0	N-acylglycine
cefpodoxime proxetil cefpodoxime proxetil: structure given in first source; prodrug for cefpodoxime. cefpodoxime proxetil : The 1-[(isopropoxycarbonyl)oxy]ethyl (proxetil) ester prodrug of cefpodoxime. After swallowing, hydrolysis of the ester group occurs in the intestinal epithelium, to release active cefpodoxime in the bloodstream. It is used to treat acute otitis media, pharyngitis, and sinusitis.	2.08	1	0	carboxylic acid; carboxylic ester; cephalosporin	antibacterial drug; prodrug
paclobutrazol paclobutrazol: RN given refers to (R,R)-(+-)-isomer. paclobutrazol : A racemate comprising equimolar amounts of (2R,3R)- and (2S,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol. It acts as a plant-growth retardant and fungicide via inhibition of gibberellin biosynthesis.	1.99	1	0
beta-escin [no description available]	2.54	2	0
butylscopolammonium bromide Butylscopolammonium Bromide: Antimuscarinic quaternary ammonium derivative of scopolamine used to treat cramps in gastrointestinal, urinary, uterine, and biliary tracts, and to facilitate radiologic visualization of the gastrointestinal tract.	2.03	1	0
edatrexate edatrexate: structure given in first source	1.99	1	0	glutamic acid derivative
bentiromide bentiromide: chymotrypsin labile peptide used diagnostically as an index of exocrine pancreas function. bentiromide : The dipeptide obtained by condensation of N-benzoyl-L-tyrosine with 4-aminobenzoic acid. Used as a noninvasive screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy, it is given by mouth: the amount of 4-aminobenzoic acid and its metabolites excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas.	2.38	2	0	dipeptide	diagnostic agent; indicator; reagent
bufalin bufalin: cardiotonic; powerful anesthetic & one of the active constituents of the Chinese drug ch'an su(senso); in Japan prepared from skin of Bufo bufo garfarizans; RN given refers to (3beta,5beta)-isomer. bufalin : A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.	2.21	1	0	14beta-hydroxy steroid; 3beta-hydroxy steroid	animal metabolite; anti-inflammatory agent; antineoplastic agent; cardiotonic drug
phosphocreatine Phosphocreatine: An endogenous substance found mainly in skeletal muscle of vertebrates. It has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1996). phosphagen : Any of a group of guanidine or amidine phosphates that function as storage depots for high-energy phosphate in muscle with the purpose of regenerating ATP from ADP during muscular contraction.. N-phosphocreatine : A phosphoamino acid consisting of creatine having a phospho group attached at the primary nitrogen of the guanidino group.	3.23	6	0	phosphagen; phosphoamino acid	human metabolite; mouse metabolite
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2.38	2	0
lipstatin lipstatin: isolated from Streptomyces toxytricini; inhibitor of pancreatic lipase; structure given in first source	2	1	0
dp-b99 DP-b99: structure in first source	2.02	1	0
abiraterone acetate Abiraterone Acetate: An androstene derivative that inhibits STEROID 17-ALPHA-HYDROXYLASE and is used as an ANTINEOPLASTIC AGENT in the treatment of metastatic castration-resistant PROSTATE CANCER.. abiraterone acetate : A sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted in vivo into abiraterone. Used for treatment of metastatic castrate-resistant prostate cancer.	4.11	2	1	pyridines; sterol ester	antineoplastic agent; EC 1.14.99.9 (steroid 17alpha-monooxygenase) inhibitor; prodrug
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	2	1	0	oligopeptide
etomoxir [no description available]	2.94	4	0	aromatic ether
efipladib efipladib: structure in first source	2.05	1	0
pentagastrin Pentagastrin: A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid.	1.95	1	0	organic molecular entity
gc 1 compound GC 1 compound: structure in first source	2.25	1	0	diarylmethane
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	1.98	1	0	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
sorbitan monooleate [no description available]	2.51	2	0	fatty acid ester
zeolites [no description available]	2.52	2	0
g(m1) ganglioside G(M1) Ganglioside: A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis.. ganglioside GM1 : A sialotetraosylceramide consisting of a branched pentasaccharide made up from one sialyl residue, two galactose residues, one N-acetylgalactosamine residue and a glucose residue at the reducing end attached to N-stearoylsphingosine via a beta-linkage.	2	1	0	alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine; sialotetraosylceramide
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	3.71	9	0
methionine sulfoxide methionine sulfoxide: RN given refers to cpd without isomeric designation. L-methionine (R)-S-oxide : The (R)-oxido diastereomer of L-methionine S-oxide.	2.25	1	0	amino acid zwitterion; L-methionine S-oxide	Escherichia coli metabolite
decanoylcarnitine decanoylcarnitine: therapeutic agent for diabetic acidosis; RN given refers to cpd without isomeric designation. O-decanoylcarnitine : An O-acylcarnitine compound having decanoyl as the acyl substituent.	1.97	1	0	decanoate ester; O-acylcarnitine	human urinary metabolite
ro 16-0154 iomazenil: potential benzodiazepine receptor imaging tracer for SPECT; structure given in first source; RN given refers to 123I-labeled cpd; RN for unlabeled cpd not avail 10/90	2.01	1	0
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	2.05	1	0
n-isobutyrylglycine N-isobutyrylglycine: found in urine of patients with glyceric acidemia. N-isobutyrylglycine : An N-acylglycine in which the acyl group is specified as isobutryl.	1.95	1	0	N-acylglycine	human urinary metabolite
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	4.7	2	1	alpha-D-glucosyl-(1->4)-D-mannopyranose
pyrrophenone pyrrophenone: structure in first source	2.05	1	0
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	2.37	2	0	nystatins
linoleic acid hydroperoxide linoleic acid hydroperoxide: RN refers to (Z,Z)-isomer. linoleic acid hydroperoxide : A HPODE that is a mono-hydroperoxy derivative of linoleic acid	2.01	1	0
l-arginine alpha-ketoglutarate [no description available]	2.1	1	0
phoslactomycin b phoslactomycin B: structure given in first source; isolated from Streptomyces nigrescens SC-273	2.03	1	0	2-pyranones
murucoidin v murucoidin V: from morning glory; structure in first source	2.08	1	0
ly2109761 [no description available]	2.21	1	0
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.05	1	0
octanoylcarnitine octanoylcarnitine: RN given refers to cpd without isomeric designation. O-octanoyl-L-carnitine : The L-enantiomer of an O-octanoylcarnitine.	4.04	15	0	O-octanoylcarnitine; saturated fatty acyl-L-carnitine	human metabolite
palmitoylcarnitine Palmitoylcarnitine: A long-chain fatty acid ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids.. O-palmitoyl-L-carnitine : An O-acyl-L-carnitine in which the acyl group is specified as palmitoyl (hexadecanoyl).	3.21	6	0	O-palmitoylcarnitine; saturated fatty acyl-L-carnitine	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; human metabolite; mouse metabolite
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	2.38	2	0	benzoxazole
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.37	2	0
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	2.42	2	0
benzoyl-ile-glu-gly-arg-p-nitroanilide benzoyl-Ile-Glu-Gly-Arg-p-nitroanilide: p-nitroanilide deriv of portion of peptide sequence in prothrombin molecule cleaved by Factor X	3.03	1	0
resorcinarene resorcinarene: structure in first source	2.05	1	0
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.76	3	0
rifamycins [no description available]	1.93	1	0
grisorixin grisorixin: ionophorous antibiotic of nigericin group isolated from cultures of a strain of Streptomyces griseus; RN given refers to parent cpd; structure in sixth source	1.96	1	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.64	3	0
ants Ants: Insects of the family Formicidae, very common and widespread, probably the most successful of all the insect groups. All ants are social insects, and most colonies contain three castes, queens, males, and workers. Their habits are often very elaborate and a great many studies have been made of ant behavior. Ants produce a number of secretions that function in offense, defense, and communication. (From Borror, et al., An Introduction to the Study of Insects, 4th ed, p676)	2.38	2	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	4.98	40	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.32	6	0
calcitonin [no description available]	2.01	1	0
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	5.92	9	3
ceruletide Ceruletide: A specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein is similar in action and composition to CHOLECYSTOKININ. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.. ceruletide : A decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction.	2.66	3	0	oligopeptide	diagnostic agent; gastrointestinal drug
motilin Motilin: A peptide of about 22-amino acids isolated from the DUODENUM. At low pH it inhibits gastric motor activity, whereas at high pH it has a stimulating effect.	2.15	1	0
glucagon-like peptide 1 (7-36)amide glucagon-like peptide 1 (7-36)amide: potent stimulator of insulin released in perfused mammalian pancreas	3.43	1	1
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	1.97	1	0
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	7.9	35	2	peptide hormone
neuropeptide y Neuropeptide Y: A 36-amino acid peptide present in many organs and in many sympathetic noradrenergic neurons. It has vasoconstrictor and natriuretic activity and regulates local blood flow, glandular secretion, and smooth muscle activity. The peptide also stimulates feeding and drinking behavior and influences secretion of pituitary hormones.	2.1	1	0
lactoferricin b lactoferricin B: amino acid sequence given in first source	2.17	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	2.65	3	0
oligonucleotides [no description available]	2.74	3	0
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	8.88	10	4
acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ilys-prolyl-alaninamide acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ILys-prolyl-alaninamide: FE-200486 is the acetate salt	2.03	1	0	polypeptide
incretins Incretins: Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially.	3.43	1	1
c-peptide C-Peptide: The middle segment of proinsulin that is between the N-terminal B-chain and the C-terminal A-chain. It is a pancreatic peptide of about 31 residues, depending on the species. Upon proteolytic cleavage of proinsulin, equimolar INSULIN and C-peptide are released. C-peptide immunoassay has been used to assess pancreatic beta cell function in diabetic patients with circulating insulin antibodies or exogenous insulin. Half-life of C-peptide is 30 min, almost 8 times that of insulin.	2.47	2	0
ristocetin Ristocetin: An antibiotic mixture of two components, A and B, obtained from Nocardia lurida (or the same substance produced by any other means). It is no longer used clinically because of its toxicity. It causes platelet agglutination and blood coagulation and is used to assay those functions in vitro.. ristocetin : A heterodetic cyclic peptide that is produced by species of Amycolatopsis and Nocardia.	1.97	1	0	glycopeptide; heterodetic cyclic peptide; macrocycle; tetrasaccharide derivative	antibacterial drug; antimicrobial agent; bacterial metabolite; platelet-activating factor receptor agonist
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3.58	9	0	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	6.22	45	0	1,2-diacyl-sn-glycero-3-phosphocholine
atractyloside Atractyloside: A glycoside of a kaurene type diterpene that is found in some plants including Atractylis gummifera (ATRACTYLIS); COFFEE; XANTHIUM, and CALLILEPIS. Toxicity is due to inhibition of ADENINE NUCLEOTIDE TRANSLOCASE.	2.4	2	0
vx-770 ivacaftor: a CFTR potentiator; structure in first source. ivacaftor : An aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis.	2.07	1	0	aromatic amide; monocarboxylic acid amide; phenols; quinolone	CFTR potentiator; orphan drug
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	3.13	5	0	chlorophyll; methyl ester	cofactor
jsh 23 4-methyl-N1-(3-phenylpropyl)benzene-1,2-diamine: structure in first source. JSH-23 : A diamine that is 1,2-phenylenediamine carrying a methyl substituent at position 4 and a 3-phenylpropyl substituent at position N1.	2.17	1	0	diamine; substituted aniline	NF-kappaB inhibitor
sodium salicylate [no description available]	4.47	5	1	organic molecular entity
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.95	4	0
calpain Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.	1.96	1	0
4-nitro-3-(octanoyloxy)benzoic acid [no description available]	3.1	1	0
n-methylcarbamate N-methylcarbamate: RN given refers to parent cpd	2.06	1	0	amino-acid anion
chitosan [no description available]	3.82	10	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	3.59	9	0	3',5'-cyclic purine nucleotide
osteum [no description available]	2.88	4	0	organic molecular entity
sarkosyl sarkosyl: RN given is for sarkosyl L, the parent cpd; structure	2.07	1	0
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	4.39	8	0
sodium iodate sodium iodate: RN given refers to iodic acid, Na salt	2.05	1	0	organic molecular entity
sodium glutamate Sodium Glutamate: One of the FLAVORING AGENTS used to impart a meat-like flavor.. monosodium glutamate : An organic sodium salt that is the monosodium salt of glutamic acid.	2.08	1	0	monosodium glutamate	flavouring agent
merocyanine dye merocyanine dye: fluorescent dye used for studying axons 2 position on pyrimidine ring may be S or O; RN given refers to Na salt; structure	1.97	1	0
tuberonic acid glucoside tuberonic acid glucoside: isolated from the potato Solanum tuberosum; structure in first source	2.01	1	0	O-acyl carbohydrate
cpi 613 devimistat: has antineoplastic activity; structure in first source	10.1	24	4
ethyl cellulose [no description available]	2.42	2	0	glycoside
mk 2206 MK 2206: a protein kinase inhibitor and antineoplastic agent	2.1	1	0	organic heterotricyclic compound	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
egg white Egg White: The white of an egg, especially a chicken's egg, used in cooking. It contains albumin. (Random House Unabridged Dictionary, 2d ed)	2.21	1	0
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.06	1	0
neurotensin neurotensin, Tyr(11)-: RN given refers to parent cpd & (D)-isomer; RN for cpd without isomeric designation not avail 5/91	2.41	2	0	peptide hormone	human metabolite; mitogen; neurotransmitter; vulnerary
mannans [no description available]	2.13	1	0
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	3.87	2	1
cytochromes c1 Cytochromes c1: The 30-kDa membrane-bound c-type cytochrome protein of mitochondria that functions as an electron donor to CYTOCHROME C GROUP in the mitochondrial and bacterial RESPIRATORY CHAIN. (From Enzyme Nomenclature, 1992, p545)	1.99	1	0
glycolipids [no description available]	3.47	8	0
piperidines Piperidines: A family of hexahydropyridines.	2.42	2	0
bryostatin 1 bryostatin 1: a protein kinase C activator; macrocyclic lactone from marine Bryozoan Bugula neritina; RN given refers to (1S-(1R,3R,5Z,7S,8E,11R,12R(2E,4E),13E,15R,17S(S),21S,23S,25R))-isomer; structure given in first source; activates protein kinase c. bryostatin 1 : A member of the class of bryostatins that is (17E)-2-oxooxacyclohexacos-17-ene which is substituted by hydroxy groups at positions 4, 10, and 20; an acetoxy group at position 8; methyl groups at positions 9, 9, 18, and 19; 2-methoxy-2-oxoethylidene groups at positions 14 and 24; an (E,E)-octa-2,4-dienoyloxy group at position 21; and with oxygen bridges linking positions 6 to 10, 12 to 16, and 20 to 24. It is one of the most abundant member of the class of bryostatins.	2.77	3	0
thymosin Thymosin: Thymosin. A family of heat-stable, polypeptide hormones secreted by the thymus gland. Their biological activities include lymphocytopoiesis, restoration of immunological competence and enhancement of expression of T-cell characteristics and function. They have therapeutic potential in patients having primary or secondary immunodeficiency diseases, cancer or diseases related to aging.	1.98	1	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.44	2	0
operculinic acid operculinic acid: from the leaves of the native North American prairie plant Ipomoea leptophylla (big root morning glory), shows in vitro activity against M. tuberculosis; structure in first source	2.08	1	0
bm 42304 [no description available]	2.37	2	0
mephedrone mephedrone: a beta-keto (bk) designer drug; Central Nervous System Stimulants. mephedrone : An aromatic ketone that is propiophenone substituted at C-4 and at C-beta with methyl and methylamino groups respectively. It is a synthetic stimulant and entactogen drug of the amphetamine and cathinone classes.	2.1	1	0	amphetamines; aromatic ketone; secondary amino compound	environmental contaminant; xenobiotic
colistin Colistin: Cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally.. colistin : A multi-component mixture comprising mostly of colistin A (R = Me) and B (R = H), with small amounts of colistin C and other polymyxins, produced by certain strains of Bacillus polymyxa var. colistinus. An antibiotic, it is used as its sulfate salt (for oral or topical use) or as the sodium salt of the N-methylsulfonic acid derivative (the injectable form) in the treatment of severe Gram-negative infections, partiularly those due to Pseudomonas aeruginosa.	1.96	1	0
exenatide Exenatide: A synthetic form of exendin-4, a 39-amino acid peptide isolated from the venom of the Gila monster lizard (Heloderma suspectum). Exenatide increases CYCLIC AMP levels in pancreatic acinar cells and acts as a GLUCAGON-LIKE PEPTIDE-1 RECEPTOR (GLP-1) agonist and incretin mimetic, enhancing insulin secretion in response to increased glucose levels; it also suppresses inappropriate glucagon secretion and slows gastric emptying. It is used an anti-diabetic and anti-obesity agent.	2.72	2	0
3',5'-diiodothyronine 3',5'-diiodothyronine: RN given refers to (DL)-isomer	1.99	1	0	phenylalanine derivative
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	1.94	1	0
vasoactive intestinal peptide Vasoactive Intestinal Peptide: A highly basic, 28 amino acid neuropeptide released from intestinal mucosa. It has a wide range of biological actions affecting the cardiovascular, gastrointestinal, and respiratory systems and is neuroprotective. It binds special receptors (RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE).	1.97	1	0
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	2.31	1	0	polypeptide
chondroitin Chondroitin: A mucopolysaccharide constituent of chondrin. (Grant & Hackh's Chemical Dictionary, 5th ed)	1.95	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	4.98	8	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	2	1	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	2.36	2	0
chlortetracycline Chlortetracycline: A TETRACYCLINE with a 7-chloro substitution.. chlortetracycline : A member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens.	3.8	1	1
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	5.07	14	0	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	2.35	2	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
piroxicam [no description available]	2.71	3	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
mobiflex tenoxicam : A thienothiazine-derived monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-hydroxy-2-methylthieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide with the amino group of 2-aminopyridine. Used for the treatment of pain and inflammation in osteoarthritis and rheumatoid arthritis. It is also indicated for short term treatment of acute musculoskeletal disorders including strains, sprains and other soft-tissue injuries.	2.04	1	0	heteroaryl hydroxy compound; monocarboxylic acid amide; pyridines; thienothiazine	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	7.01	10	2	benzenes; hydroxycoumarin; methyl ketone
6-o-palmitoylascorbic acid [no description available]	2.46	2	0	fatty acid ester
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2	1	0
antimycin [no description available]	2.37	2	0
microcystin microcystin: microcystins have the general structure cyclo(D-Ala-L-X-D-erythro--methylisoasp-L-Y-Adda-D-isoGlu-N-methyldehydroAla) where X and Y are variable L-amino acids;. microcystin : A family of cyclic heptapeptide hepatotoxins produced by a number of cyanobacteria, the most notable of which is Microcystis, from which the name of the family is derived. Microcystins consist of a heptapeptide macrocycle made up of five non-protein amino acids and two protein amino acids.	2	1	0	peptide
kaolinite Kaolin: The most common mineral of a group of hydrated aluminum silicates, approximately H2Al2Si2O8-H2O. It is prepared for pharmaceutical and medicinal purposes by levigating with water to remove sand, etc. (From Merck Index, 11th ed) The name is derived from Kao-ling (Chinese: high ridge), the original site. (From Grant & Hackh's Chemical Dictionary, 5th ed). kaolin : An aluminosilicate soft white mineral named after the hill in China (Kao-ling) from which it was mined for centuries. In its natural state kaolin is a white, soft powder consisting principally of the mineral kaolinite, and varying amounts of other minerals such as muscovite, quartz, feldspar, and anatase. It is used in the manufacture of china and porcelain and also widely used in the production of paper, rubber, paint, drying agents, and many other products.	2.1	1	0	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	3.25	5	0
semaglutide [no description available]	8.66	5	3	lipopeptide; polypeptide	anti-obesity agent; appetite depressant; glucagon-like peptide-1 receptor agonist; hypoglycemic agent; neuroprotective agent
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	2.39	2	0	ketal
pyrethrins [no description available]	2.13	1	0
kiss1 protein, human Kisspeptins: Intercellular signaling peptides that were originally characterized by their ability to suppress NEOPLASM METASTASIS. Kisspeptins have since been found to play an important role in the neuroendocrine regulation of REPRODUCTION.	2.63	2	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.37	2	0
laponite laponite: a synthesized hectorite; chemical formula in first source	2.08	1	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	6.02	5	2
technetium tc 99m sulfur colloid Technetium Tc 99m Sulfur Colloid: A gamma-emitting radionuclide imaging agent used for the diagnosis of diseases in many tissues, particularly in the gastrointestinal system, liver, and spleen.	5	3	1
oligomycins Oligomycins: A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).	4.03	15	0
mastoparan x mastoparan X: RN given refers to the all-(L)-isomer. mastoparan-V : A member of the class of mastopyrans that is a 14-amino acid polypeptide comprising isoleucyl, asparaginyl, tryptophyl, lysyl, glycyl, isoleucyl, alanyl, alanyl, methionyl, alanyl, lysyl, lysyl, leucyl, and leucinamide residues coupled in sequence. It is the major active component of the venom of the hornet Vespa velutina and causes degranulation of mast cells. It exhibits antimicrobial activity against both Gram-positive and -negative bacteria as well as haemolytic activity on chicken, human and sheep erythrocytes.	2.06	1	0	mastoparans; peptidyl amide	antibacterial agent
g(m3) ganglioside G(M3) Ganglioside: A ganglioside present in abnormally large amounts in the brain and liver due to a deficient biosynthetic enzyme, G(M3):UDP-N-acetylgalactosaminyltransferase. Deficiency of this enzyme prevents the formation of G(M2) ganglioside from G(M3) ganglioside and is the cause of an anabolic sphingolipidosis.. alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/24:1(15Z)) : A sialotriaosylceramide consisting of beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-Glc attached to the primary hydroxy function of ceramide(d18:1/24:1(15Z)).	2.1	1	0	alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-ceramide; sialodiosylceramide; sialotriaosylceramide	mouse metabolite
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	3.82	12	0
glucagon-like peptide 2 Glucagon-Like Peptide 2: A 33-amino acid peptide derived from the C-terminal of PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. It stimulates intestinal mucosal growth and decreased apoptosis of ENTEROCYTES. GLP-2 enhances gastrointestinal function and plays an important role in nutrient homeostasis.	3.87	2	1
hyaluronoglucosaminidase Hyaluronoglucosaminidase: An enzyme that catalyzes the random hydrolysis of 1,4-linkages between N-acetyl-beta-D-glucosamine and D-glucuronate residues in hyaluronate. (From Enzyme Nomenclature, 1992) There has been use as ANTINEOPLASTIC AGENTS to limit NEOPLASM METASTASIS.	1.95	1	0
carboxyatractyloside carboxyatractyloside: RN given refers to parent cpd; structure	1.96	1	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	4.85	2	1
oxyntomodulin Glucagon-Like Peptides: Peptides derived from proglucagon which is also the precursor of pancreatic GLUCAGON. Despite expression of proglucagon in multiple tissues, the major production site of glucagon-like peptides (GLPs) is the INTESTINAL L CELLS. GLPs include glucagon-like peptide 1, glucagon-like peptide 2, and the various truncated forms.	8.65	6	3
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	3.54	8	0
cytochalasin d Cytochalasin D: A fungal metabolite that blocks cytoplasmic cleavage by blocking formation of contractile microfilament structures resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. Additional reported effects include the inhibition of actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release.. cytochalasin D : An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.	1.96	1	0
peptide yy Peptide YY: A 36-amino acid peptide produced by the L cells of the distal small intestine and colon. Peptide YY inhibits gastric and pancreatic secretion.. peptide YY : A 36-membered human gut polypeptide consisting of Tyr, Pro, Ile, Lys, Pro, Glu, Ala, Pro, Gly, Glu, Asp, Ala, Ser, Pro, Glu, Glu, Leu, Asn, Arg, Tyr, Tyr, Ala, Ser, Leu, Arg, His, Tyr, Leu, Asn, Leu, Val, Thr, Arg, Gln, Arg and Tyr-NH2 residues joined in sequence.	4.67	3	2
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	2.44	2	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	1.95	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	3.41	7	0
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.44	2	0
exudates Malaysia: A parliamentary democracy with a constitutional monarch in southeast Asia, consisting of 11 states (West Malaysia) on the Malay Peninsula and two states (East Malaysia) on the island of BORNEO. It is also called the Federation of Malaysia. Its capital is Kuala Lumpur. Before 1963 it was the Union of Malaya. It reorganized in 1948 as the Federation of Malaya, becoming independent from British Malaya in 1957 and becoming Malaysia in 1963 as a federation of Malaya, Sabah, Sarawak, and Singapore (which seceded in 1965). The form Malay- probably derives from the Tamil malay, mountain, with reference to its geography. (From Webster's New Geographical Dictionary, 1988, p715 & Room, Brewer's Dictionary of Names, 1992, p329)	2.48	2	0
bixin bixin: structure. bixin : A carotenoic acid that is the 6'-monomethyl ester of 9'-cis-6,6'-diapocarotene-6,6'-dioic acid.	2.06	1	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.38	2	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
levoleucovorin Levoleucovorin: A folate analog consisting of the pharmacologically active isomer of LEUCOVORIN.. (6S)-5-formyltetrahydrofolic acid : The pharmacologically active (6S)-stereoisomer of 5-formyltetrahydrofolic acid.	4.51	1	1	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	2.44	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	4.54	5	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.13	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	3.76	3	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	2.44	2	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.96	3	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
7-methylguanine 7-methylguanine: RN given refers to unlabeled cpd; structure. 7-methylguanine : A methylguanine that is guanine substituted by a methyl group at position 7. It is a metabolite obtained during the methylation of DNA.. 2-imino-7-methyl-1,2,3,7-tetrahydro-6H-purin-6-one : A 7-methylguanine that is 1,2,3,7-tetrahydro-6H-purin-6-one substituted by an imino group at position 2 and a methyl group at position 7.. 2-amino-7-methyl-7H-purin-6-ol : A 7-methylguanine that is 7H-purine substituted by an amino group at position 2, a methyl group at position 7 and a hydroxy group at position 6.. 2-amino-7-methyl-1,7-dihydro-6H-purin-6-one : A 7-methylguanine that is 1,7-dihydro-6H-purin-6-one substituted by an amino group at position 2 and a methyl group at position 7.	2.1	1	0	7-methylguanine
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.61	2	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.02	1	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.35	2	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
guanylyl imidodiphosphate Guanylyl Imidodiphosphate: A non-hydrolyzable analog of GTP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It binds tightly to G-protein in the presence of Mg2+. The nucleotide is a potent stimulator of ADENYLYL CYCLASES.. guanosine 5'-[beta,gamma-imido]triphosphate : A nucleoside triphosphate analogue that is GTP in which the oxygen atom bridging the beta- to the gamma- phosphate is replaced by a nitrogen atom A non-hydrolyzable analog of GTP, it binds tightly to G-protein in the presence of Mg(2+).	3.47	2	0	nucleoside triphosphate analogue
thiolactomycin thiolactomycin: from actinomycetes; structure given in first source	2	1	0
peldesine peldesine: potent inhibitor of human CCRF-CEM T-cell proliferation; structure given in first source	2	1	0
8-bromocyclic gmp 8-bromo-3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.	1.99	1	0	3',5'-cyclic purine nucleotide; organobromine compound	muscle relaxant; protein kinase G agonist
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	2.07	1	0	nitroso compound	alkylating agent
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	4.54	5	1	guanosines	biomarker
imidacloprid imidacloprid: systemic & contact insecticide exhibiting low mammalian toxicity; structure given in first source; it is one of the neonicotinoid insecticides, which acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. imidacloprid : An imidazolidine that is N-nitroimidazolidin-2-imine bearing a (6-chloro-3-pyridinyl)methyl substituent at position 1.	2.07	1	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
cholestyramine resin Cholestyramine Resin: A strongly basic anion exchange resin whose main constituent is polystyrene trimethylbenzylammonium Cl(-) anion.	4.15	5	0
eye [no description available]	2.45	2	0
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.01	1	0
carbidopa Carbidopa: An inhibitor of DOPA DECARBOXYLASE that prevents conversion of LEVODOPA to dopamine. It is used in PARKINSON DISEASE to reduce peripheral adverse effects of LEVODOPA. It has no anti-parkinson activity by itself.. carbidopa : The hydrate of 3-(3,4-dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa.	3.43	1	1
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.08	1	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	1.98	1	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	6.33	8	1
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.37	2	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.48	2	0

Condition	Relationship Strength	Studies	Trials
Delayed Effects, Prenatal Exposure [description not available]	8.32	98	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	11.95	299	0
Idiopathic Parkinson Disease [description not available]	8.34	12	4
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	8.34	12	4
Hepatocellular Carcinoma [description not available]	4.13	16	0
Innate Inflammatory Response [description not available]	4.31	17	0
Insulin Sensitivity [description not available]	5.49	14	1
Cancer of Liver [description not available]	4.35	20	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	4.13	16	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	4.31	17	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	5.49	14	1
Liver Neoplasms Tumors or cancer of the LIVER.	4.35	20	0
Enlarged Liver [description not available]	3.72	10	0
Acute Liver Injury, Drug-Induced [description not available]	4.69	26	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	4.69	26	0
Cancer of Kidney [description not available]	4.83	4	0
Cancer, Embryonal [description not available]	3.23	1	0
Cancer of Testis [description not available]	5.35	7	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	4.83	4	0
Neoplasms, Germ Cell and Embryonal Neoplasms composed of primordial GERM CELLS of embryonic GONADS or of elements of the germ layers of the EMBRYO, MAMMALIAN. The concept does not refer to neoplasms located in the gonads or present in an embryo or FETUS.	3.23	1	0
Testicular Neoplasms Tumors or cancer of the TESTIS. Germ cell tumors (GERMINOMA) of the testis constitute 95% of all testicular neoplasms.	5.35	7	0
Birth Weight The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.	8.49	41	0
Lipid Metabolism, Inborn Error [description not available]	8.95	22	4
Metabolic Acidosis [description not available]	3.23	6	0
Benign Neoplasms [description not available]	7.87	24	1
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	3.23	6	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	7.87	24	1
Blood Poisoning [description not available]	2.46	2	0
Lung Injury, Acute [description not available]	2.41	1	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.46	2	0
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	2.41	1	0
Colorectal Cancer [description not available]	3.05	4	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	3.05	4	0
Diathesis [description not available]	4.78	2	1
Acne [description not available]	2.4	2	0
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	2.4	2	0
Mastitis INFLAMMATION of the BREAST, or MAMMARY GLAND.	2.41	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.82	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	8.22	45	0
Cancer of Head [description not available]	2.31	1	0
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.31	1	0
Allergic Encephalomyelitis [description not available]	2.31	1	0
MS (Multiple Sclerosis) [description not available]	2.31	1	0
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	2.31	1	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	5.84	14	0
Breast Cancer [description not available]	4.22	15	0
Breast Neoplasms Tumors or cancer of the human BREAST.	4.22	15	0
Cancer of Pancreas [description not available]	7.68	19	1
Carcinoma, Ductal, Pancreatic [description not available]	2.41	1	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	7.68	19	1
Carcinoma, Pancreatic Ductal Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.	2.41	1	0
Pancreatic Fistula Abnormal passage communicating with the PANCREAS.	2.41	1	0
Complication, Postoperative [description not available]	4.74	7	1
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	4.74	7	1
Edema-Proteinuria-Hypertension Gestosis [description not available]	3.62	8	0
Pre-Eclampsia A complication of PREGNANCY, characterized by a complex of symptoms including maternal HYPERTENSION and PROTEINURIA with or without pathological EDEMA. Symptoms may range between mild and severe. Pre-eclampsia usually occurs after the 20th week of gestation, but may develop before this time in the presence of trophoblastic disease.	3.62	8	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	3.39	7	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3.24	5	0
Animal Mammary Carcinoma [description not available]	2.53	2	0
Experimental Mammary Neoplasms [description not available]	2.41	1	0
Gastric Stasis [description not available]	10.73	19	4
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	8.47	26	0
Gastroparesis Chronic delayed gastric emptying. Gastroparesis may be caused by motor dysfunction or paralysis of STOMACH muscles or may be associated with other systemic diseases such as DIABETES MELLITUS.	10.73	19	4
Abortion, Tubal [description not available]	3.52	7	0
Abortion, Spontaneous Expulsion of the product of FERTILIZATION before completing the term of GESTATION and without deliberate interference.	3.52	7	0
Eczema, Atopic [description not available]	2.94	3	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.94	3	0
Acute Myelogenous Leukemia [description not available]	4.69	2	1
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	4.69	2	1
Chemical and Drug Induced Liver Injury, Chronic Liver disease lasting six months or more, caused by an adverse effect of a drug or chemical. The adverse effect may be caused by drugs, drug metabolites, chemicals from the environment, or an idiosyncratic response.	2.76	2	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.41	1	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.41	1	0
Fetal Growth Restriction [description not available]	3.23	5	0
Fetal Growth Retardation Failure of a FETUS to attain expected GROWTH.	3.23	5	0
Blood Pressure, High [description not available]	3.84	11	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	3.84	11	0
Diabetes Mellitus, Adult-Onset [description not available]	8.78	17	4
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	8.78	17	4
2019 Novel Coronavirus Disease [description not available]	3.3	4	0
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	2.41	1	0
Rheumatoid Arthritis [description not available]	4.89	7	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	4.89	7	1
Carcinoma, Anaplastic [description not available]	2.45	2	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.45	2	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	2.63	2	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	10.62	97	2
Disbacteriosis [description not available]	2.76	2	0
Adenocarcinoma Of Kidney [description not available]	3.33	1	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	3.33	1	0
Dysplastic Nevus Syndrome, Hereditary [description not available]	2.41	1	0
Malignant Melanoma [description not available]	4.07	5	0
Cancer of Skin [description not available]	2.92	4	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	4.07	5	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.92	4	0
Dermatomycoses Superficial infections of the skin or its appendages by any of various fungi.	2.64	3	0
Canine Diseases [description not available]	3.94	2	1
Cat Diseases Diseases of the domestic cat (Felis catus or F. domesticus). This term does not include diseases of the so-called big cats such as CHEETAHS; LIONS; tigers, cougars, panthers, leopards, and other Felidae for which the heading CARNIVORA is used.	2.61	2	0
Sterility, Male [description not available]	4.32	6	0
Varicocele A condition characterized by the dilated tortuous veins of the SPERMATIC CORD with a marked left-sided predominance. Adverse effect on male fertility occurs when varicocele leads to an increased scrotal (and testicular) temperature and reduced testicular volume.	2.41	1	0
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	4.32	6	0
Cardiac Toxicity [description not available]	4.4	15	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	4.4	15	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	7.9	27	1
Clostridium tetani Infection [description not available]	2.59	2	0
Tetanus A disease caused by tetanospasmin, a powerful protein toxin produced by CLOSTRIDIUM TETANI. Tetanus usually occurs after an acute injury, such as a puncture wound or laceration. Generalized tetanus, the most common form, is characterized by tetanic muscular contractions and hyperreflexia. Localized tetanus presents itself as a mild condition with manifestations restricted to muscles near the wound. It may progress to the generalized form.	2.59	2	0
Autism Spectrum Disorder Wide continuum of associated cognitive and neurobehavioral disorders, including, but not limited to, three core-defining features: impairments in socialization, impairments in verbal and nonverbal communication, and restricted and repetitive patterns of behaviors. (from DSM-V)	2.89	3	0
Autism [description not available]	4.21	3	1
Autistic Disorder A disorder beginning in childhood. It is marked by the presence of markedly abnormal or impaired development in social interaction and communication and a markedly restricted repertoire of activity and interest. Manifestations of the disorder vary greatly depending on the developmental level and chronological age of the individual. (DSM-V)	4.21	3	1
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	3.11	4	0
Liver Dysfunction [description not available]	4.69	11	0
Liver Diseases Pathological processes of the LIVER.	4.69	11	0
Black Fever [description not available]	2.41	1	0
Leishmaniasis, Visceral A chronic disease caused by LEISHMANIA DONOVANI and transmitted by the bite of several sandflies of the genera Phlebotomus and Lutzomyia. It is commonly characterized by fever, chills, vomiting, anemia, hepatosplenomegaly, leukopenia, hypergammaglobulinemia, emaciation, and an earth-gray color of the skin. The disease is classified into three main types according to geographic distribution: Indian, Mediterranean (or infantile), and African.	2.41	1	0
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	4.25	6	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	2.58	2	0
Cognitive Decline [description not available]	2.6	1	0
Acute Confusional Senile Dementia [description not available]	5.17	10	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	5.17	10	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.6	1	0
Cancer of Prostate [description not available]	3.47	7	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.47	7	0
Acute Kidney Failure [description not available]	2.71	3	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.71	3	0
Fatty Liver, Nonalcoholic [description not available]	3.12	4	0
Lipid Metabolism Disorders Pathological conditions resulting from abnormal anabolism or catabolism of lipids in the body.	2.6	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	3.12	4	0
Adenocarcinoma, Basal Cell [description not available]	5.84	8	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	5.84	8	1
Adverse Drug Event [description not available]	4.95	4	2
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	4.95	4	2
Gestational Weight Gain Increase in body weight of the mother during the course of her PREGNANCY.	2.63	2	0
Chronic Kidney Diseases [description not available]	3.99	4	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	3.99	4	0
Acrania [description not available]	2.21	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	3.52	8	0
Neural Tube Defects Congenital malformations of the central nervous system and adjacent structures related to defective neural tube closure during the first trimester of pregnancy generally occurring between days 18-29 of gestation. Ectodermal and mesodermal malformations (mainly involving the skull and vertebrae) may occur as a result of defects of neural tube closure. (From Joynt, Clinical Neurology, 1992, Ch55, pp31-41)	2.21	1	0
Experimental Neoplasms [description not available]	3.98	14	0
ADDH [description not available]	5.21	10	0
Attention Deficit Disorder with Hyperactivity A behavior disorder originating in childhood in which the essential features are signs of developmentally inappropriate inattention, impulsivity, and hyperactivity. Although most individuals have symptoms of both inattention and hyperactivity-impulsivity, one or the other pattern may be predominant. The disorder is more frequent in males than females. Onset is in childhood. Symptoms often attenuate during late adolescence although a minority experience the full complement of symptoms into mid-adulthood. (From DSM-V)	5.21	10	0
Anti-MuSK Myasthenia Gravis [description not available]	3.59	1	1
Myasthenia Gravis A disorder of neuromuscular transmission characterized by fatigable weakness of cranial and skeletal muscles with elevated titers of ACETYLCHOLINE RECEPTORS or muscle-specific receptor tyrosine kinase (MuSK) autoantibodies. Clinical manifestations may include ocular muscle weakness (fluctuating, asymmetric, external ophthalmoplegia; diplopia; ptosis; and weakness of eye closure) and extraocular fatigable weakness of facial, bulbar, respiratory, and proximal limb muscles. The disease may remain limited to the ocular muscles (ocular myasthenia). THYMOMA is commonly associated with this condition.	3.59	1	1
Respiration Disorders Diseases of the respiratory system in general or unspecified or for a specific respiratory disease not available.	3.7	3	0
Anoxemia [description not available]	3.08	5	0
Absence Seizure [description not available]	4.49	8	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	3.08	5	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	4.49	8	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	2.57	2	0
Infant, Small for Gestational Age An infant having a birth weight lower than expected for its gestational age.	3.31	6	0
Thyroid Diseases Pathological processes involving the THYROID GLAND.	4.99	8	0
Colitis Gravis [description not available]	5.92	14	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	5.92	14	0
Colitis, Mucous [description not available]	3.17	1	0
Colitis, Granulomatous [description not available]	6.75	8	1
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	6.75	8	1
Irritable Bowel Syndrome A disorder with chronic or recurrent colonic symptoms without a clearcut etiology. This condition is characterized by chronic or recurrent ABDOMINAL PAIN, bloating, MUCUS in FECES, and an erratic disturbance of DEFECATION.	3.17	1	0
Tuberculosis, Drug-Resistant [description not available]	2.25	1	0
Pulmonary Consumption [description not available]	2.66	3	0
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	2.66	3	0
Tuberculosis, Multidrug-Resistant Tuberculosis resistant to chemotherapy with two or more ANTITUBERCULAR AGENTS, including at least ISONIAZID and RIFAMPICIN. The problem of resistance is particularly troublesome in tuberculous OPPORTUNISTIC INFECTIONS associated with HIV INFECTIONS. It requires the use of second line drugs which are more toxic than the first line regimens. TB with isolates that have developed further resistance to at least three of the six classes of second line drugs is defined as EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS.	2.25	1	0
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	3.63	8	0
Adolescent Obesity [description not available]	5.24	6	0
Bacterial Disease [description not available]	2.69	3	0
Bacterial Infections Infections by bacteria, general or unspecified.	2.69	3	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	2.66	2	0
Liver Steatosis [description not available]	4.68	11	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	4.68	11	0
Preterm Birth [description not available]	4.27	6	0
Premature Birth CHILDBIRTH before 37 weeks of PREGNANCY (259 days from the first day of the mother's last menstrual period, or 245 days after FERTILIZATION).	4.27	6	0
Acute Brain Injuries [description not available]	2.54	2	0
Brain Hemorrhage, Cerebral [description not available]	2.72	2	0
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.54	2	0
Cerebral Hemorrhage Bleeding into one or both CEREBRAL HEMISPHERES including the BASAL GANGLIA and the CEREBRAL CORTEX. It is often associated with HYPERTENSION and CRANIOCEREBRAL TRAUMA.	2.72	2	0
Deafness, Transitory [description not available]	2.25	1	0
Hearing Loss A general term for the complete or partial loss of the ability to hear from one or both ears.	2.25	1	0
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	3.4	6	0
Benign Neoplasms, Brain [description not available]	3.66	3	0
Astrocytoma, Grade IV [description not available]	3.48	2	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	3.66	3	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	3.48	2	0
Gout Metabolic disorder characterized by recurrent acute arthritis, hyperuricemia and deposition of sodium urate in and around the joints, sometimes with formation of URIC ACID calculi.	2.25	1	0
Cancer of Colon [description not available]	3.41	7	0
Colonic Neoplasms Tumors or cancer of the COLON.	3.41	7	0
Complications, Pregnancy [description not available]	3.77	3	0
Puerperal Disorders Disorders or diseases associated with PUERPERIUM, the six-to-eight-week period immediately after PARTURITION in humans.	2.25	1	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	2.39	2	0
Bone Cancer [description not available]	2.25	1	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.25	1	0
Cancer of Stomach [description not available]	2.78	3	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.78	3	0
Envenomation, Snakebite [description not available]	5.6	6	3
Motor Disorders Motor skills deficits that significantly and persistently interfere with ACTIVITIES OF DAILY LIVING appropriate to chronological age. (from DSM-5)	2.63	2	0
Left Ventricular Hypertrophy [description not available]	2.61	2	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	2.7	3	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	2.7	3	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.92	4	0
Hypertrophy, Left Ventricular Enlargement of the LEFT VENTRICLE of the heart. This increase in ventricular mass is attributed to sustained abnormal pressure or volume loads and is a contributor to cardiovascular morbidity and mortality.	2.61	2	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	3.49	7	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	3.49	7	0
Diseases, Occupational [description not available]	3.41	7	0
Alveolitis, Fibrosing [description not available]	2.25	1	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	2.25	1	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	3.28	6	0
Infectious Diseases [description not available]	2.79	3	0
Communicable Diseases An illness caused by an infectious agent or its toxins that occurs through the direct or indirect transmission of the infectious agent or its products from an infected individual or via an animal, vector or the inanimate environment to a susceptible animal or human host.	2.79	3	0
Diseases, Metabolic [description not available]	2.67	3	0
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	2.67	3	0
Adenoma, Basal Cell [description not available]	3.1	5	0
Adenoma A benign epithelial tumor with a glandular organization.	3.1	5	0
Cancer of Lung [description not available]	4.9	8	1
Lung Neoplasms Tumors or cancer of the LUNG.	4.9	8	1
Asthma, Bronchial [description not available]	4.45	8	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	4.45	8	0
Bone Loss, Osteoclastic [description not available]	2.45	2	0
Nephrotic Syndrome A condition characterized by severe PROTEINURIA, greater than 3.5 g/day in an average adult. The substantial loss of protein in the urine results in complications such as HYPOPROTEINEMIA; generalized EDEMA; HYPERTENSION; and HYPERLIPIDEMIAS. Diseases associated with nephrotic syndrome generally cause chronic kidney dysfunction.	2.31	1	0
Benign Essential Tremor [description not available]	9.56	11	8
Action Tremor [description not available]	2.63	2	0
Neurologic Voice Disorder [description not available]	4.04	2	1
Tremor Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.	2.63	2	0
Voice Disorders Pathological processes that affect voice production, usually involving VOCAL CORDS and the LARYNGEAL MUCOSA. Voice disorders can be caused by organic (anatomical), or functional (emotional or psychological) factors leading to DYSPHONIA; APHONIA; and defects in VOICE QUALITY, loudness, and pitch.	4.04	2	1
Essential Tremor A relatively common disorder characterized by a fairly specific pattern of tremors which are most prominent in the upper extremities and neck, inducing titubations of the head. The tremor is usually mild, but when severe may be disabling. An autosomal dominant pattern of inheritance may occur in some families (i.e., familial tremor). (Mov Disord 1988;13(1):5-10)	9.56	11	8
Esophageal Squamous Cell Carcinoma A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.	2.31	1	0
Cancer of Esophagus [description not available]	2.31	1	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.31	1	0
Dyslipidemia [description not available]	3.53	2	0
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	3.53	2	0
Cholera Infantum [description not available]	6.21	9	4
Dry Eye [description not available]	2.31	1	0
Dry Eye Syndromes Corneal and conjunctival dryness due to deficient tear production, predominantly in menopausal and post-menopausal women. Filamentary keratitis or erosion of the conjunctival and corneal epithelium may be caused by these disorders. Sensation of the presence of a foreign body in the eye and burning of the eyes may occur.	2.31	1	0
Endometrioma An enlarged area of ENDOMETRIOSIS that resembles a tumor. It is usually found in the OVARY. When it is filled with old blood, it is known as a chocolate cyst.	2.51	2	0
Endometriosis A condition in which functional endometrial tissue is present outside the UTERUS. It is often confined to the PELVIS involving the OVARY, the ligaments, cul-de-sac, and the uterovesical peritoneum.	2.51	2	0
Allergic Contact Dermatitis [description not available]	5.37	8	0
Hand Dermatosis [description not available]	2.15	1	0
Hand Dermatoses Skin diseases involving the HANDS.	2.15	1	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	5.37	8	0
Indigestion [description not available]	7.03	16	2
Dyspepsia Impaired digestion, especially after eating.	7.03	16	2
Luft Disease [description not available]	7.58	4	4
Cardiomyopathies, Primary [description not available]	7.79	6	4
Nervous System Disorders [description not available]	8.62	5	4
Cardiomyopathies A group of diseases in which the dominant feature is the involvement of the CARDIAC MUSCLE itself. Cardiomyopathies are classified according to their predominant pathophysiological features (DILATED CARDIOMYOPATHY; HYPERTROPHIC CARDIOMYOPATHY; RESTRICTIVE CARDIOMYOPATHY) or their etiological/pathological factors (CARDIOMYOPATHY, ALCOHOLIC; ENDOCARDIAL FIBROELASTOSIS).	7.79	6	4
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	8.62	5	4
Rhabdomyolysis Necrosis or disintegration of skeletal muscle often followed by myoglobinuria.	7.58	4	4
Mitochondrial Myopathies A group of muscle diseases associated with abnormal mitochondria function.	7.58	4	4
Impaired Glucose Tolerance [description not available]	2.15	1	0
Diabetes Mellitus, Gestational [description not available]	2.58	2	0
Diabetes, Gestational Diabetes mellitus induced by PREGNANCY but resolved at the end of pregnancy. It does not include previously diagnosed diabetics who become pregnant (PREGNANCY IN DIABETICS). Gestational diabetes usually develops in late pregnancy when insulin antagonistic hormones peaks leading to INSULIN RESISTANCE; GLUCOSE INTOLERANCE; and HYPERGLYCEMIA.	2.58	2	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.15	1	0
Deficiency, Mental [description not available]	2.17	1	0
Intellectual Disability Subnormal intellectual functioning which originates during the developmental period. This has multiple potential etiologies, including genetic defects and perinatal insults. Intelligence quotient (IQ) scores are commonly used to determine whether an individual has an intellectual disability. IQ scores between 70 and 79 are in the borderline range. Scores below 67 are in the disabled range. (from Joynt, Clinical Neurology, 1992, Ch55, p28)	2.17	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	11.37	62	4
Cancer of Ovary [description not available]	2.39	2	0
Invasiveness, Neoplasm [description not available]	3.23	5	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.39	2	0
Cardiac Remodeling, Ventricular [description not available]	2.57	2	0
Cardiac Diseases [description not available]	2.42	2	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.42	2	0
Clear Cell Sarcoma of Soft Tissue [description not available]	2.17	1	0
Sarcoma, Clear Cell A sarcoma of young adults occurring in the lower extremities and acral regions. It is found intimately bound to tendons as a circumscribed but unencapsulated melanin-bearing tumor of neuroectodermal origin. Clear cell sarcoma is associated with a specific t(12;22)(q13;q12) translocation.	2.17	1	0
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	4.27	19	0
Anorexia Nervosa An eating disorder that is characterized by the lack or loss of APPETITE, known as ANOREXIA. Other features include excess fear of becoming OVERWEIGHT; BODY IMAGE disturbance; significant WEIGHT LOSS; refusal to maintain minimal normal weight; and AMENORRHEA. This disorder occurs most frequently in adolescent females. (APA, Thesaurus of Psychological Index Terms, 1994)	2.17	1	0
FMR1-Related Primary Ovarian Insufficiency [description not available]	2.17	1	0
Primary Ovarian Insufficiency Cessation of ovarian function after MENARCHE but before the age of 40, without or with OVARIAN FOLLICLE depletion. It is characterized by the presence of OLIGOMENORRHEA or AMENORRHEA, elevated GONADOTROPINS, and low ESTRADIOL levels. It is a state of female HYPERGONADOTROPIC HYPOGONADISM. Etiologies include genetic defects, autoimmune processes, chemotherapy, radiation, and infections. The most commonly known genetic cause is the expansion of a CGG repeat to 55 to 199 copies in the 5' untranslated region in the X-linked FMR1 gene.	2.17	1	0
Uremia A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.	2.17	1	0
Hyperthyroid [description not available]	3.08	5	0
Hyperthyroidism Hypersecretion of THYROID HORMONES from the THYROID GLAND. Elevated levels of thyroid hormones increase BASAL METABOLIC RATE.	3.08	5	0
Measles, German [description not available]	2.17	1	0
E coli Infections [description not available]	3.46	7	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	3.46	7	0
Interstitial Cell Tumor [description not available]	2.93	4	0
Weight Gain Increase in BODY WEIGHT over existing weight.	3.54	8	0
Metastase [description not available]	2.17	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.17	1	0
Bowel Diseases, Inflammatory [description not available]	3.75	3	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	3.75	3	0
Disease Exacerbation [description not available]	2.5	2	0
Sterility, Female [description not available]	3.22	5	0
Polycystic Ovarian Syndrome [description not available]	2.54	2	0
Infertility, Female Diminished or absent ability of a female to achieve conception.	3.22	5	0
Polycystic Ovary Syndrome A complex disorder characterized by infertility, HIRSUTISM; OBESITY; and various menstrual disturbances such as OLIGOMENORRHEA; AMENORRHEA; ANOVULATION. Polycystic ovary syndrome is usually associated with bilateral enlarged ovaries studded with atretic follicles, not with cysts. The term, polycystic ovary, is misleading.	2.54	2	0
Caries, Dental [description not available]	2.21	1	0
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	2.21	1	0
Tick Infestations Infestations with soft-bodied (Argasidae) or hard-bodied (Ixodidae) ticks.	2.21	1	0
Urinary Tract Infections Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.	2.21	1	0
Coronary Heart Disease [description not available]	2.89	4	0
Diabetic Angiopathies VASCULAR DISEASES that are associated with DIABETES MELLITUS.	2.21	1	0
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	2.89	4	0
Mastitis, Bovine INFLAMMATION of the UDDER in cows.	2.72	3	0
Infections, Staphylococcal [description not available]	2.57	2	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.57	2	0
Allodynia [description not available]	2.21	1	0
Nerve Pain [description not available]	2.21	1	0
Injuries, Spinal Cord [description not available]	2.79	3	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.21	1	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.79	3	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	3.58	9	0
Follicular Thyroid Carcinoma [description not available]	2.21	1	0
Adenocarcinoma, Follicular An adenocarcinoma of the thyroid gland, in which the cells are arranged in the form of follicles. (From Dorland, 27th ed)	2.21	1	0
Dermatitis, Eczematous [description not available]	2.85	3	0
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	2.85	3	0
Prediabetes [description not available]	2.39	2	0
Prediabetic State The time period before the development of symptomatic diabetes. For example, certain risk factors can be observed in subjects who subsequently develop INSULIN RESISTANCE as in type 2 diabetes (DIABETES MELLITUS, TYPE 2).	2.39	2	0
Encephalopathy, Toxic [description not available]	2.52	2	0
Anoxia-Ischemia, Brain [description not available]	2.21	1	0
Age-Related Memory Disorders [description not available]	2.78	3	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	2.78	3	0
Hypoxia-Ischemia, Brain A disorder characterized by a reduction of oxygen in the blood combined with reduced blood flow (ISCHEMIA) to the brain from a localized obstruction of a cerebral artery or from systemic hypoperfusion. Prolonged hypoxia-ischemia is associated with ISCHEMIC ATTACK, TRANSIENT; BRAIN INFARCTION; BRAIN EDEMA; COMA; and other conditions.	2.21	1	0
Breathing Sounds [description not available]	2.21	1	0
Infections, Respiratory [description not available]	3.43	2	0
Respiratory Sounds Noises, normal and abnormal, heard on auscultation over any part of the RESPIRATORY TRACT.	2.21	1	0
Respiratory Tract Infections Invasion of the host RESPIRATORY SYSTEM by microorganisms, usually leading to pathological processes or diseases.	3.43	2	0
Arthritis, Degenerative [description not available]	2.48	2	0
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.48	2	0
Critical Illness A disease or state in which death is possible or imminent.	2.77	3	0
Apoplexy [description not available]	6.07	6	1
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	6.07	6	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	4.3	19	0
Hematoma, Subdural, Acute Accumulation of blood in the SUBDURAL SPACE with acute onset of neurological symptoms. Symptoms may include loss of consciousness, severe HEADACHE, and deteriorating mental status.	2.08	1	0
Anterior Cerebral Circulation Infarction [description not available]	2.08	1	0
Brain Swelling [description not available]	3.6	3	0
Brain Edema Increased intracellular or extracellular fluid in brain tissue. Cytotoxic brain edema (swelling due to increased intracellular fluid) is indicative of a disturbance in cell metabolism, and is commonly associated with hypoxic or ischemic injuries (see HYPOXIA, BRAIN). An increase in extracellular fluid may be caused by increased brain capillary permeability (vasogenic edema), an osmotic gradient, local blockages in interstitial fluid pathways, or by obstruction of CSF flow (e.g., obstructive HYDROCEPHALUS). (From Childs Nerv Syst 1992 Sep; 8(6):301-6)	3.6	3	0
Brain Infarction Tissue NECROSIS in any area of the brain, including the CEREBRAL HEMISPHERES, the CEREBELLUM, and the BRAIN STEM. Brain infarction is the result of a cascade of events initiated by inadequate blood flow through the brain that is followed by HYPOXIA and HYPOGLYCEMIA in brain tissue. Damage may be temporary, permanent, selective or pan-necrosis.	2.08	1	0
Glial Cell Tumors [description not available]	2.92	4	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.92	4	0
Chronic Illness [description not available]	5.1	6	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	5.1	6	0
Injury, Ischemia-Reperfusion [description not available]	2.47	2	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.47	2	0
Gestational Hypertension [description not available]	2.48	2	0
Hypertension, Pregnancy-Induced A condition in pregnant women with elevated systolic (	2.48	2	0
Health Care Associated Infection [description not available]	2.39	2	0
Cross Infection Any infection which a patient contracts in a health-care institution.	2.39	2	0
Abnormality, Heart [description not available]	2.08	1	0
Heart Defects, Congenital Developmental abnormalities involving structures of the heart. These defects are present at birth but may be discovered later in life.	2.08	1	0
Child Development Deviations [description not available]	2.08	1	0
Developmental Coordination Disorder [description not available]	2.08	1	0
Developmental Disabilities Disorders in which there is a delay in development based on that expected for a given age level or stage of development. These impairments or disabilities originate before age 18, may be expected to continue indefinitely, and constitute a substantial impairment. Biological and nonbiological factors are involved in these disorders. (From American Psychiatric Glossary, 6th ed)	2.08	1	0
Hypomenorrhea [description not available]	2.1	1	0
Abdominal Cryptorchidism [description not available]	2.38	2	0
Grippe [description not available]	3.64	3	0
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	3.64	3	0
Behavior Disorders [description not available]	2.47	2	0
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	2.47	2	0
Dyskinesia Syndromes [description not available]	2.45	2	0
Movement Disorders Syndromes which feature DYSKINESIAS as a cardinal manifestation of the disease process. Included in this category are degenerative, hereditary, post-infectious, medication-induced, post-inflammatory, and post-traumatic conditions.	2.45	2	0
Allergic Reaction [description not available]	2.99	4	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.99	4	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	4.75	2	1
Pneumonia Infection of the lung often accompanied by inflammation.	4.75	2	1
Reproductive Sterility [description not available]	1.93	1	0
Infertility A reduced or absent capacity to reproduce.	1.93	1	0
Experimental Hepatoma [description not available]	5.27	12	0
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	2.49	2	0
Hepatitis INFLAMMATION of the LIVER.	2.1	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.46	2	0
Abnormalities, Congenital [description not available]	2.47	2	0
Pouch Ileitis [description not available]	3.03	1	0
Pouchitis Acute INFLAMMATION in the INTESTINAL MUCOSA of the continent ileal reservoir (or pouch) in patients who have undergone ILEOSTOMY and restorative proctocolectomy (PROCTOCOLECTOMY, RESTORATIVE).	3.03	1	0
Bladder Cancer [description not available]	2.74	3	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.74	3	0
Cancer of Intestines [description not available]	2.1	1	0
Intestinal Neoplasms Tumors or cancer of the INTESTINES.	2.1	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.71	3	0
ALS - Amyotrophic Lateral Sclerosis [description not available]	3.69	3	0
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	3.69	3	0
Biliary Calculi [description not available]	9.97	51	3
Gallstones Solid crystalline precipitates in the BILIARY TRACT, usually formed in the GALLBLADDER, resulting in the condition of CHOLELITHIASIS. Gallstones, derived from the BILE, consist mainly of calcium, cholesterol, or bilirubin.	9.97	51	3
Hepatic Insufficiency Conditions in which the LIVER functions fall below the normal ranges. Severe hepatic insufficiency may cause LIVER FAILURE or DEATH. Treatment may include LIVER TRANSPLANTATION.	2.1	1	0
Cerebral Palsy, Athetoid [description not available]	5.64	3	2
Cerebral Palsy A heterogeneous group of nonprogressive motor disorders caused by chronic brain injuries that originate in the prenatal period, perinatal period, or first few years of life. The four major subtypes are spastic, athetoid, ataxic, and mixed cerebral palsy, with spastic forms being the most common. The motor disorder may range from difficulties with fine motor control to severe spasticity (see MUSCLE SPASTICITY) in all limbs. Spastic diplegia (Little disease) is the most common subtype, and is characterized by spasticity that is more prominent in the legs than in the arms. Pathologically, this condition may be associated with LEUKOMALACIA, PERIVENTRICULAR. (From Dev Med Child Neurol 1998 Aug;40(8):520-7)	5.64	3	2
Hematologic Malignancies [description not available]	4.4	1	1
Leucocythaemia [description not available]	5.16	4	1
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	5.16	4	1
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	4.4	1	1
Bleeding [description not available]	5.17	6	2
Hemorrhage Bleeding or escape of blood from a vessel.	5.17	6	2
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.7	3	0
Hyperphagia Ingestion of a greater than optimal quantity of food.	3.48	1	1
Arteriosclerosis, Coronary [description not available]	2.5	2	0
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	2.5	2	0
Anasarca [description not available]	3.38	7	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	3.38	7	0
Astheno Teratozoospermia [description not available]	2.11	1	0
Aneuploid [description not available]	2.11	1	0
Abnormalities, Autosome [description not available]	2.69	3	0
Hypospermatogenesis [description not available]	2.11	1	0
Salmonella Infections, Animal Infections in animals with bacteria of the genus SALMONELLA.	2.97	4	0
B16 Melanoma [description not available]	2.11	1	0
Elevated Cholesterol [description not available]	4.62	6	1
Central Hypothyroidism [description not available]	3.24	6	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	4.62	6	1
Hypothyroidism A syndrome that results from abnormally low secretion of THYROID HORMONES from the THYROID GLAND, leading to a decrease in BASAL METABOLIC RATE. In its most severe form, there is accumulation of MUCOPOLYSACCHARIDES in the SKIN and EDEMA, known as MYXEDEMA. It may be primary or secondary due to other pituitary disease, or hypothalamic dysfunction.	3.24	6	0
Ebola Hemorrhagic Fever [description not available]	3.03	1	0
Hemorrhagic Fever, Ebola A highly fatal, acute hemorrhagic fever caused by EBOLAVIRUS.	3.03	1	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.41	2	0
Glaucoma An ocular disease, occurring in many forms, having as its primary characteristics an unstable or a sustained increase in the intraocular pressure which the eye cannot withstand without damage to its structure or impairment of its function. The consequences of the increased pressure may be manifested in a variety of symptoms, depending upon type and severity, such as excavation of the optic disk, hardness of the eyeball, corneal anesthesia, reduced visual acuity, seeing of colored halos around lights, disturbed dark adaptation, visual field defects, and headaches. (Dictionary of Visual Science, 4th ed)	2.11	1	0
Malnourishment [description not available]	3.37	2	0
Paraneoplastic Syndromes In patients with neoplastic diseases a wide variety of clinical pictures which are indirect and usually remote effects produced by tumor cell metabolites or other products.	3.03	1	0
Anastomotic Leak Breakdown of the connection and subsequent leakage of effluent (fluids, secretions, air) from a SURGICAL ANASTOMOSIS of the digestive, respiratory, genitourinary, and cardiovascular systems. Most common leakages are from the breakdown of suture lines in gastrointestinal or bowel anastomosis.	3.03	1	0
Malnutrition An imbalanced nutritional status resulting from insufficient intake of nutrients to meet normal physiological requirement.	3.37	2	0
Morbid Obesity [description not available]	2.11	1	0
Weight Reduction [description not available]	2.45	2	0
Obesity, Morbid The condition of weighing two, three, or more times the ideal weight, so called because it is associated with many serious and life-threatening disorders. In the BODY MASS INDEX, morbid obesity is defined as having a BMI greater than 40.0 kg/m2.	2.11	1	0
Weight Loss Decrease in existing BODY WEIGHT.	2.45	2	0
Corynebacterium diphtheriae Infection [description not available]	2.11	1	0
Diphtheria A localized infection of mucous membranes or skin caused by toxigenic strains of CORYNEBACTERIUM DIPHTHERIAE. It is characterized by the presence of a pseudomembrane at the site of infection. DIPHTHERIA TOXIN, produced by C. diphtheriae, can cause myocarditis, polyneuritis, and other systemic toxic effects.	2.11	1	0
Age-Related Osteoporosis [description not available]	2.45	2	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.45	2	0
Allergy, Drug [description not available]	2.49	2	0
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	2.49	2	0
Testicular Diseases Pathological processes of the TESTIS.	2.11	1	0
Food Poisoning [description not available]	3.76	2	1
Extravascular Hemolysis [description not available]	3.37	7	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	3.37	7	0
Bright Disease A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.	2.11	1	0
Chronic Kidney Failure [description not available]	3.88	4	0
Anti-GBM Disease [description not available]	2.11	1	0
Glomerulonephritis Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.	2.11	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	3.88	4	0
Anti-Glomerular Basement Membrane Disease An autoimmune disease of the KIDNEY and the LUNG. It is characterized by the presence of circulating autoantibodies targeting the epitopes in the non-collagenous domains of COLLAGEN TYPE IV in the basement membranes of kidney glomeruli (KIDNEY GLOMERULUS) and lung alveoli (PULMONARY ALVEOLI), and the subsequent destruction of these basement membranes. Clinical features include pulmonary alveolar hemorrhage and glomerulonephritis.	2.11	1	0
Pancreatic Insufficiency [description not available]	3.83	4	0
Exocrine Pancreatic Insufficiency A malabsorption condition resulting from greater than 10% reduction in the secretion of pancreatic digestive enzymes (LIPASE; PROTEASES; and AMYLASE) by the EXOCRINE PANCREAS into the DUODENUM. This condition is often associated with CYSTIC FIBROSIS and with chronic PANCREATITIS.	3.83	4	0
Angiogenesis, Pathologic [description not available]	2.73	3	0
Diseases of Immune System [description not available]	3.04	1	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	3.04	1	0
Degenerative Diseases, Central Nervous System [description not available]	2.47	2	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	2.47	2	0
Symptom Cluster [description not available]	2.42	2	0
Colicky Pain [description not available]	2.79	3	0
Syndrome A characteristic symptom complex.	2.42	2	0
Abdominal Pain Sensation of discomfort, distress, or agony in the abdominal region.	2.79	3	0
Adrenocortical Carcinoma A malignant neoplasm of the ADRENAL CORTEX. Adrenocortical carcinomas are unencapsulated anaplastic (ANAPLASIA) masses sometimes exceeding 20 cm or 200 g. They are more likely to be functional than nonfunctional, and produce ADRENAL CORTEX HORMONES that may result in hypercortisolism (CUSHING SYNDROME); HYPERALDOSTERONISM; and/or VIRILISM.	2.13	1	0
Celiac Sprue [description not available]	3.07	5	0
Celiac Disease A malabsorption syndrome that is precipitated by the ingestion of foods containing GLUTEN, such as wheat, rye, and barley. It is characterized by INFLAMMATION of the SMALL INTESTINE, loss of MICROVILLI structure, failed INTESTINAL ABSORPTION, and MALNUTRITION.	3.07	5	0
Catheter-Associated Infections [description not available]	2.13	1	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.13	1	0
Fasciolopsiasis [description not available]	2.13	1	0
Cancer of Endometrium [description not available]	2.13	1	0
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	2.13	1	0
Pyrexia [description not available]	2.13	1	0
Infection [description not available]	5.03	3	1
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	2.13	1	0
Infections Invasion of the host organism by microorganisms or their toxins or by parasites that can cause pathological conditions or diseases.	5.03	3	1
Anaphylactic Reaction [description not available]	2.15	1	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	2.15	1	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	2.13	1	0
Carcinoma, Small Cell Lung [description not available]	3.51	1	1
Local Neoplasm Recurrence [description not available]	3.51	1	1
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	3.51	1	1
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	2.67	3	0
Neonatal Death The death of a live-born INFANT less than 28 days of age.	3.04	1	0
Atelectasis [description not available]	3.04	1	0
Alloxan Diabetes [description not available]	4.21	18	0
Respiratory Tract Diseases Diseases involving the RESPIRATORY SYSTEM.	2.04	1	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	2.67	3	0
Campylobacter Infection [description not available]	4.53	5	1
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	5.02	9	1
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	3.43	1	1
Erythrophagocytic Lymphohistiocytosis, Familial [description not available]	2.05	1	0
Lymphohistiocytosis, Hemophagocytic A group of related disorders characterized by LYMPHOCYTOSIS; HISTIOCYTOSIS; and hemophagocytosis. The two major forms are familial and reactive.	2.05	1	0
Elevated ICP (Intracranial Pressure) [description not available]	2.89	1	0
Hepatic Failure [description not available]	3.6	3	0
Liver Failure Severe inability of the LIVER to perform its normal metabolic functions, as evidenced by severe JAUNDICE and abnormal serum levels of AMMONIA; BILIRUBIN; ALKALINE PHOSPHATASE; ASPARTATE AMINOTRANSFERASE; LACTATE DEHYDROGENASES; and albumin/globulin ratio. (Blakiston's Gould Medical Dictionary, 4th ed)	3.6	3	0
Intracranial Hypertension Increased pressure within the cranial vault. This may result from several conditions, including HYDROCEPHALUS; BRAIN EDEMA; intracranial masses; severe systemic HYPERTENSION; PSEUDOTUMOR CEREBRI; and other disorders.	2.89	1	0
Hyperammonemia Elevated level of AMMONIA in the blood. It is a sign of defective CATABOLISM of AMINO ACIDS or ammonia to UREA.	2.89	1	0
Chronic Inflammatory Demyelinating Polyradiculoneuropathy [description not available]	11.22	12	11
Polyradiculoneuropathy, Chronic Inflammatory Demyelinating A slowly progressive autoimmune demyelinating disease of peripheral nerves and nerve roots. Clinical manifestations include weakness and sensory loss in the extremities and enlargement of peripheral nerves. The course may be relapsing-remitting or demonstrate a step-wise progression. Protein is usually elevated in the spinal fluid and cranial nerves are typically spared. GUILLAIN-BARRE SYNDROME features a relatively rapid progression of disease which distinguishes it from this condition. (Adams et al., Principles of Neurology, 6th ed, p1337)	11.22	12	11
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.73	3	0
Cachexia General ill health, malnutrition, and weight loss, usually associated with chronic disease.	3.38	2	0
Lymphocytopenia [description not available]	2.05	1	0
Lymphopenia Reduction in the number of lymphocytes.	2.05	1	0
Neutropenia A decrease in the number of NEUTROPHILS found in the blood.	2.05	1	0
Disease A definite pathologic process with a characteristic set of signs and symptoms. It may affect the whole body or any of its parts, and its etiology, pathology, and prognosis may be known or unknown.	3.58	3	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	4.22	18	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	3.21	6	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	3.21	6	0
Astrocytosis [description not available]	2.44	2	0
Bile Duct Obstruction, Extrahepatic [description not available]	3.59	3	0
Cirrhoses, Experimental Liver [description not available]	2.05	1	0
Acute Disease Disease having a short and relatively severe course.	6.37	8	2
Alcoholic Hepatitis [description not available]	2.05	1	0
Hepatitis, Alcoholic INFLAMMATION of the LIVER due to ALCOHOL ABUSE. It is characterized by NECROSIS of HEPATOCYTES, infiltration by NEUTROPHILS, and deposit of MALLORY BODIES. Depending on its severity, the inflammatory lesion may be reversible or progress to LIVER CIRRHOSIS.	2.05	1	0
Hepatorenal Syndrome Functional KIDNEY FAILURE in patients with liver disease, usually LIVER CIRRHOSIS or portal hypertension (HYPERTENSION, PORTAL), and in the absence of intrinsic renal disease or kidney abnormality. It is characterized by intense renal vasculature constriction, reduced renal blood flow, OLIGURIA, and sodium retention.	2.05	1	0
Primary Peritonitis [description not available]	2.05	1	0
Peritonitis INFLAMMATION of the PERITONEUM lining the ABDOMINAL CAVITY as the result of infectious, autoimmune, or chemical processes. Primary peritonitis is due to infection of the PERITONEAL CAVITY via hematogenous or lymphatic spread and without intra-abdominal source. Secondary peritonitis arises from the ABDOMINAL CAVITY itself through RUPTURE or ABSCESS of intra-abdominal organs.	2.05	1	0
Anemia, Hemolytic, Acquired [description not available]	2.96	1	0
Anemia, Hemolytic A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).	2.96	1	0
Complications, Labor [description not available]	2.05	1	0
Cancer of the Thyroid [description not available]	2.05	1	0
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	2.05	1	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.72	3	0
Cerebral Ischemia [description not available]	6.3	8	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	6.3	8	1
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.72	3	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	4.29	4	1
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	4.29	4	1
Arrhythmia [description not available]	2.34	2	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.34	2	0
Fibroadenoma An adenoma containing fibrous tissue. It should be differentiated from ADENOFIBROMA which is a tumor composed of connective tissue (fibroma) containing glandular (adeno-) structures. (From Dorland, 27th ed)	2.05	1	0
Condition, Preneoplastic [description not available]	2.05	1	0
Multiple Primary Neoplasms [description not available]	2.05	1	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.05	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.05	1	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.15	5	0
Amentia [description not available]	2.05	1	0
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	2.05	1	0
Thromboembolism Obstruction of a blood vessel (embolism) by a blood clot (THROMBUS) in the blood stream.	4.29	4	0
Brain Vascular Disorders [description not available]	2.97	1	0
Cerebrovascular Disorders A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.	2.97	1	0
Gastric Diseases [description not available]	3.85	2	1
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.42	2	0
Chromosome-Defective Micronuclei [description not available]	2.06	1	0
Candida Infection [description not available]	3.77	4	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	3.77	4	0
Fungal Diseases [description not available]	1.92	1	0
Mycoses Diseases caused by FUNGI.	1.92	1	0
Amyloid Deposits [description not available]	2.06	1	0
Body Weight, Fetal [description not available]	2.06	1	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	2.06	1	0
Injury, Myocardial Reperfusion [description not available]	3.63	3	0
Alcohol Abuse [description not available]	2.66	3	0
Malabsorption Syndromes General term for a group of MALNUTRITION syndromes caused by failure of normal INTESTINAL ABSORPTION of nutrients.	3.35	7	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	2.66	3	0
Equine Diseases [description not available]	2.72	3	0
Bacterial Skin Diseases [description not available]	2.06	1	0
Actinomycetales Infections Infections with bacteria of the order ACTINOMYCETALES.	2.06	1	0
Skin Diseases, Bacterial Skin diseases caused by bacteria.	2.06	1	0
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	2.06	1	0
Circulatory Collapse [description not available]	2.39	2	0
Shock A pathological condition manifested by failure to perfuse or oxygenate vital organs.	2.39	2	0
Cruveilhier-Baumgarten Syndrome Liver cirrhosis with intrahepatic portal obstruction, HYPERTENSION, and patent UMBILICAL VEINS.	4.07	3	1
Cirrhosis, Liver [description not available]	5.98	15	2
Hypertension, Portal Abnormal increase of resistance to blood flow within the hepatic PORTAL SYSTEM, frequently seen in LIVER CIRRHOSIS and conditions with obstruction of the PORTAL VEIN.	4.07	3	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	5.98	15	2
Infectious Endophthalmitis Infectious condition of the internal eye.	2.06	1	0
Endophthalmitis Suppurative inflammation of the tissues of the internal structures of the eye frequently associated with an infection.	2.06	1	0
Adrenal Cortex Cancer [description not available]	2.06	1	0
Adrenal Cortex Neoplasms Tumors or cancers of the ADRENAL CORTEX.	2.06	1	0
Adjuvant Arthritis [description not available]	2.41	2	0
Cytomegalic Inclusion Disease [description not available]	2.98	1	0
Infections, Helicobacter [description not available]	4.54	9	0
Urination Disorders Abnormalities in the process of URINE voiding, including bladder control, frequency of URINATION, as well as the volume and composition of URINE.	2.98	1	0
Cytomegalovirus Infections Infection with CYTOMEGALOVIRUS, characterized by enlarged cells bearing intranuclear inclusions. Infection may be in almost any organ, but the salivary glands are the most common site in children, as are the lungs in adults.	2.98	1	0
Urinary Incontinence Involuntary loss of URINE, such as leaking of urine. It is a symptom of various underlying pathological processes. Major types of incontinence include URINARY URGE INCONTINENCE and URINARY STRESS INCONTINENCE.	2.98	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	4.54	9	0
Dumping Syndrome Gastrointestinal symptoms resulting from an absent or nonfunctioning pylorus.	2.06	1	0
Avian Flu [description not available]	2.98	1	0
Influenza in Birds Infection of domestic and wild fowl and other BIRDS with INFLUENZA A VIRUS. Avian influenza usually does not sicken birds, but can be highly pathogenic and fatal in domestic POULTRY.	2.98	1	0
Coagulation Disorders, Blood [description not available]	4.4	2	2
Blood Coagulation Disorders Hemorrhagic and thrombotic disorders that occur as a consequence of abnormalities in blood coagulation due to a variety of factors such as COAGULATION PROTEIN DISORDERS; BLOOD PLATELET DISORDERS; BLOOD PROTEIN DISORDERS or nutritional conditions.	4.4	2	2
Behavior Disorder, Rapid Eye Movement Sleep [description not available]	3.45	1	1
REM Sleep Behavior Disorder A disorder characterized by episodes of vigorous and often violent motor activity during REM sleep (SLEEP, REM). The affected individual may inflict self injury or harm others, and is difficult to awaken from this condition. Episodes are usually followed by a vivid recollection of a dream that is consistent with the aggressive behavior. This condition primarily affects adult males. (From Adams et al., Principles of Neurology, 6th ed, p393)	3.45	1	1
Aura [description not available]	3.39	7	0
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	3.39	7	0
Stillbirth The event that a FETUS is born dead or stillborn.	2.07	1	0
Fetal Macrosomia A condition of fetal overgrowth leading to a large-for-gestational-age FETUS. It is defined as BIRTH WEIGHT greater than 4,000 grams or above the 90th percentile for population and sex-specific growth curves. It is commonly seen in GESTATIONAL DIABETES; PROLONGED PREGNANCY; and pregnancies complicated by pre-existing diabetes mellitus.	2.07	1	0
Hyperhomocysteinemia Condition in which the plasma levels of homocysteine and related metabolites are elevated (	2.07	1	0
Cataract, Membranous [description not available]	2.38	2	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	2.38	2	0
Intraocular Pressure The pressure of the fluids in the eye.	2.08	1	0
Atherogenesis [description not available]	2.07	1	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.07	1	0
Mesothelioma A tumor derived from mesothelial tissue (peritoneum, pleura, pericardium). It appears as broad sheets of cells, with some regions containing spindle-shaped, sarcoma-like cells and other regions showing adenomatous patterns. Pleural mesotheliomas have been linked to exposure to asbestos. (Dorland, 27th ed)	2.07	1	0
Absence Status [description not available]	2.08	1	0
Status Epilepticus A prolonged seizure or seizures repeated frequently enough to prevent recovery between episodes occurring over a period of 20-30 minutes. The most common subtype is generalized tonic-clonic status epilepticus, a potentially fatal condition associated with neuronal injury and respiratory and metabolic dysfunction. Nonconvulsive forms include petit mal status and complex partial status, which may manifest as behavioral disturbances. Simple partial status epilepticus consists of persistent motor, sensory, or autonomic seizures that do not impair cognition (see also EPILEPSIA PARTIALIS CONTINUA). Subclinical status epilepticus generally refers to seizures occurring in an unresponsive or comatose individual in the absence of overt signs of seizure activity. (From N Engl J Med 1998 Apr 2;338(14):970-6; Neurologia 1997 Dec;12 Suppl 6:25-30)	2.08	1	0
Emesis [description not available]	2.67	3	0
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	2.67	3	0
Moniliasis, Oral [description not available]	2.07	1	0
Candidiasis, Oral Infection of the mucous membranes of the mouth by a fungus of the genus CANDIDA. (Dorland, 27th ed)	2.07	1	0
Acetonemia [description not available]	5.21	6	0
Arthritides, Bacterial [description not available]	2.08	1	0
Viral Diseases [description not available]	4.31	4	1
Virus Diseases A general term for diseases caused by viruses.	4.31	4	1
Cystic Fibrosis of Pancreas [description not available]	4.3	4	1
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	4.3	4	1
Hepatitis B Virus Infection [description not available]	2.66	3	0
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.66	3	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.01	1	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.01	1	0
Dementias, Transmissible [description not available]	2.01	1	0
Antibody Deficiency Syndrome [description not available]	6.94	6	3
Asthenia Clinical sign or symptom manifested as debility, or lack or loss of strength and energy.	4.31	1	1
Immunologic Deficiency Syndromes Syndromes in which there is a deficiency or defect in the mechanisms of immunity, either cellular or humoral.	6.94	6	3
ANS (Autonomic Nervous System) Diseases [description not available]	4.72	2	1
Autoimmune Diabetes [description not available]	5.39	5	1
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	5.39	5	1
Sinus Infections [description not available]	4.31	1	1
Sinusitis Inflammation of the NASAL MUCOSA in one or more of the PARANASAL SINUSES.	4.31	1	1
Blood Clot [description not available]	3.76	2	1
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	3.76	2	1
Drug Withdrawal Symptoms [description not available]	2.41	2	0
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	2.41	2	0
Candidiasis, Genital [description not available]	1.93	1	0
Candidiasis, Vulvovaginal Infection of the VULVA and VAGINA with a fungus of the genus CANDIDA.	1.93	1	0
Infections, Trichomonas [description not available]	1.93	1	0
Trichomoniasis, Human [description not available]	1.93	1	0
Trichomonas Infections Infections in birds and mammals produced by various species of Trichomonas.	1.93	1	0
Trichomonas Vaginitis Inflammation of the vagina, marked by a purulent discharge. This disease is caused by the protozoan TRICHOMONAS VAGINALIS.	1.93	1	0
Vaginal Diseases Pathological processes of the VAGINA.	1.93	1	0
Leukorrhea A clear or white discharge from the VAGINA, consisting mainly of MUCUS.	2.84	4	0
Deficiency, Pyridoxine [description not available]	1.93	1	0
Erythroblastosis Fetalis [description not available]	1.93	1	0
Blood Diseases [description not available]	1.93	1	0
Hematologic Diseases Disorders of the blood and blood forming tissues.	1.93	1	0
Koch's Disease [description not available]	1.93	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	1.93	1	0
Deficiency, Vitamin A [description not available]	2.65	3	0
Vitamin A Deficiency A nutritional condition produced by a deficiency of VITAMIN A in the diet, characterized by NIGHT BLINDNESS and other ocular manifestations such as dryness of the conjunctiva and later of the cornea (XEROPHTHALMIA). Vitamin A deficiency is a very common problem worldwide, particularly in developing countries as a consequence of famine or shortages of vitamin A-rich foods. In the United States it is found among the urban poor, the elderly, alcoholics, and patients with malabsorption. (From Cecil Textbook of Medicine, 19th ed, p1179)	2.65	3	0
Deficiency Diseases A condition produced by dietary or metabolic deficiency. The term includes all diseases caused by an insufficient supply of essential nutrients, i.e., protein (or amino acids), vitamins, and minerals. It also includes an inadequacy of calories. (From Dorland, 27th ed; Stedman, 25th ed)	2.34	2	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.34	2	0
EHS Tumor [description not available]	1.94	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	1.94	1	0
Biotinidase Deficiency The late onset form of MULTIPLE CARBOXYLASE DEFICIENCY (deficiency of the activities of biotin-dependent enzymes propionyl-CoA carboxylase, methylcrotonyl-CoA carboxylase, and PYRUVATE CARBOXYLASE) due to a defect or deficiency in biotinidase which is essential for recycling BIOTIN.	1.93	1	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	2.01	1	0
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	2.01	1	0
Postgastrectomy Syndromes Sequelae of gastrectomy from the second week after operation on. Include recurrent or anastomotic ulcer, postprandial syndromes (DUMPING SYNDROME and late postprandial hypoglycemia), disordered bowel action, and nutritional deficiencies.	2.01	1	0
Esophageal Dysmotility [description not available]	4.31	1	1
Ache [description not available]	4.3	4	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	4.3	4	1
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.02	1	0
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	2.02	1	0
Autoimmune Thrombocytopenia [description not available]	5.58	3	2
Purpura, Thrombocytopenic, Idiopathic Thrombocytopenia occurring in the absence of toxic exposure or a disease associated with decreased platelets. It is mediated by immune mechanisms, in most cases IMMUNOGLOBULIN G autoantibodies which attach to platelets and subsequently undergo destruction by macrophages. The disease is seen in acute (affecting children) and chronic (adult) forms.	5.58	3	2
Deep Vein Thrombosis [description not available]	4.09	3	0
Venous Thrombosis The formation or presence of a blood clot (THROMBUS) within a vein.	4.09	3	0
A-alphalipoprotein Neuropathy [description not available]	2.02	1	0
Bile Duct Obstruction [description not available]	4.45	5	0
Hyperlipemia [description not available]	3.97	5	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	4.45	5	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	3.97	5	0
MPTP Neurotoxicity Syndrome [description not available]	2.43	2	0
Precordial Catch [description not available]	2.02	1	0
Chest Pain Pressure, burning, or numbness in the chest.	2.02	1	0
Brain Damage, Chronic A condition characterized by long-standing brain dysfunction or damage, usually of three months duration or longer. Potential etiologies include BRAIN INFARCTION; certain NEURODEGENERATIVE DISORDERS; CRANIOCEREBRAL TRAUMA; ANOXIA, BRAIN; ENCEPHALITIS; certain NEUROTOXICITY SYNDROMES; metabolic disorders (see BRAIN DISEASES, METABOLIC); and other conditions.	2.94	1	0
Autoimmune Disease [description not available]	2.02	1	0
Autoimmune Diseases Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.	2.02	1	0
Giardia duodenalis Infection [description not available]	2.02	1	0
Giardiasis An infection of the SMALL INTESTINE caused by the flagellated protozoan GIARDIA. It is spread via contaminated food and water and by direct person-to-person contact.	2.02	1	0
Esophageal Reflux [description not available]	3.8	2	1
Gastric Ulcer [description not available]	3.82	2	1
Gastroesophageal Reflux Retrograde flow of gastric juice (GASTRIC ACID) and/or duodenal contents (BILE ACIDS; PANCREATIC JUICE) into the distal ESOPHAGUS, commonly due to incompetence of the LOWER ESOPHAGEAL SPHINCTER.	3.8	2	1
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	3.82	2	1
Heart Disease, Ischemic [description not available]	2.7	3	0
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	2.7	3	0
Canine Distemper [description not available]	2.02	1	0
Academic Disorder, Developmental [description not available]	2.03	1	0
Learning Disabilities Conditions characterized by a significant discrepancy between an individual's perceived level of intellect and their ability to acquire new language and other cognitive skills. These may result from organic or psychological conditions. Relatively common subtypes include DYSLEXIA, DYSCALCULIA, and DYSGRAPHIA.	2.03	1	0
Recrudescence [description not available]	12.25	17	10
Amyloidosis A group of sporadic, familial and/or inherited, degenerative, and infectious disease processes, linked by the common theme of abnormal protein folding and deposition of AMYLOID. As the amyloid deposits enlarge they displace normal tissue structures, causing disruption of function. Various signs and symptoms depend on the location and size of the deposits.	2.03	1	0
Adhesions, Tissue [description not available]	2.03	1	0
Respiratory Syndrome, Acute, Severe [description not available]	2.03	1	0
Severe Acute Respiratory Syndrome A viral disorder characterized by high FEVER, dry COUGH, shortness of breath (DYSPNEA) or breathing difficulties, and atypical PNEUMONIA. A virus in the genus CORONAVIRUS is the suspected agent.	2.03	1	0
Anterior Circulation Transient Ischemic Attack [description not available]	3.8	2	1
Ischemic Attack, Transient Brief reversible episodes of focal, nonconvulsive ischemic dysfunction of the brain having a duration of less than 24 hours, and usually less than one hour, caused by transient thrombotic or embolic blood vessel occlusion or stenosis. Events may be classified by arterial distribution, temporal pattern, or etiology (e.g., embolic vs. thrombotic). (From Adams et al., Principles of Neurology, 6th ed, pp814-6)	3.8	2	1
Zoonoses Diseases of non-human animals that may be transmitted to HUMANS or may be transmitted from humans to non-human animals.	2.03	1	0
Airway Hyper-Responsiveness [description not available]	2.03	1	0
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	2.03	1	0
Anterior Choroidal Artery Infarction [description not available]	2.94	1	0
Cerebral Infarction The formation of an area of NECROSIS in the CEREBRUM caused by an insufficiency of arterial or venous blood flow. Infarcts of the cerebrum are generally classified by hemisphere (i.e., left vs. right), lobe (e.g., frontal lobe infarction), arterial distribution (e.g., INFARCTION, ANTERIOR CEREBRAL ARTERY), and etiology (e.g., embolic infarction).	2.94	1	0
Blastocyst Disintegration [description not available]	2.03	1	0
Gastritis, Atrophic GASTRITIS with atrophy of the GASTRIC MUCOSA, the GASTRIC PARIETAL CELLS, and the mucosal glands leading to ACHLORHYDRIA. Atrophic gastritis usually progresses from chronic gastritis.	2.03	1	0
Enterocolitis Inflammation of the MUCOSA of both the SMALL INTESTINE and the LARGE INTESTINE. Etiology includes ISCHEMIA, infections, allergic, and immune responses.	2.04	1	0
Brain Disorders [description not available]	2.39	2	0
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	2.39	2	0
Acute Edematous Pancreatitis [description not available]	3.58	3	0
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	3.58	3	0
Angle's Classification [description not available]	3.43	1	1
Malocclusion Such malposition and contact of the maxillary and mandibular teeth as to interfere with the highest efficiency during the excursive movements of the jaw that are essential for mastication. (Jablonski, Illustrated Dictionary of Dentistry, 1982)	3.43	1	1
Gastroduodenal Ulcer [description not available]	1.94	1	0
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	1.94	1	0
Encephalopathy, Hepatic [description not available]	4.04	15	0
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	4.04	15	0
Gallstone Disease [description not available]	11.17	70	3
Cholelithiasis Presence or formation of GALLSTONES in the BILIARY TRACT, usually in the gallbladder (CHOLECYSTOLITHIASIS) or the common bile duct (CHOLEDOCHOLITHIASIS).	11.17	70	3
Insulin Coma Severe HYPOGLYCEMIA induced by a large dose of exogenous INSULIN resulting in a COMA or profound state of unconsciousness from which the individual cannot be aroused.	1.96	1	0
Cholangitis Inflammation of the biliary ductal system (BILE DUCTS); intrahepatic, extrahepatic, or both.	3.57	3	0
Fatty Liver with Encephalopathy [description not available]	3.91	13	0
Gall Bladder Diseases [description not available]	1.96	1	0
Ulcer A lesion on the surface of the skin or a mucous surface, produced by the sloughing of inflammatory necrotic tissue.	1.96	1	0
Bile Duct Diseases Diseases in any part of the ductal system of the BILIARY TRACT from the smallest BILE CANALICULI to the largest COMMON BILE DUCT.	6.41	16	0
Coma A profound state of unconsciousness associated with depressed cerebral activity from which the individual cannot be aroused. Coma generally occurs when there is dysfunction or injury involving both cerebral hemispheres or the brain stem RETICULAR FORMATION.	3.35	7	0
Besnoitiasis [description not available]	1.96	1	0
Curling Ulcer Acute stress DUODENAL ULCER, usually observed in patients with extensive third-degree burns.	2.66	3	0
Duodenal Ulcer A PEPTIC ULCER located in the DUODENUM.	2.66	3	0
Biliary or Urinary Stones [description not available]	1.96	1	0
Delayed Hypersensitivity [description not available]	2.65	3	0
Bile Reflux Retrograde bile flow. Reflux of bile can be from the duodenum to the stomach (DUODENOGASTRIC REFLUX); to the esophagus (GASTROESOPHAGEAL REFLUX); or to the PANCREAS.	1.96	1	0
Common Bile Duct Diseases Diseases of the COMMON BILE DUCT including the AMPULLA OF VATER and the SPHINCTER OF ODDI.	2.88	4	0
Biliary Tract Diseases Diseases in any part of the BILIARY TRACT including the BILE DUCTS and the GALLBLADDER.	2.36	2	0
Fetal Resorption The disintegration and assimilation of the dead FETUS in the UTERUS at any stage after the completion of organogenesis which, in humans, is after the 9th week of GESTATION. It does not include embryo resorption (see EMBRYO LOSS).	2.38	2	0
Dental Fluoroses [description not available]	2.87	1	0
Bone Diseases Diseases of BONES.	2.87	1	0
Fluorosis, Dental A chronic endemic form of hypoplasia of the dental enamel caused by drinking water with a high fluorine content during the time of tooth formation, and characterized by defective calcification that gives a white chalky appearance to the enamel, which gradually undergoes brown discoloration. (Jablonski's Dictionary of Dentistry, 1992, p286)	2.87	1	0
Abscess, Hepatic [description not available]	1.96	1	0
Liver Abscess Solitary or multiple collections of PUS within the liver as a result of infection by bacteria, protozoa, or other agents.	1.96	1	0
Hematochezia The passage of bright red blood from the rectum. The blood may or may not be mixed with formed stool in the form of blood, blood clots, bloody stool or diarrhea.	2.87	1	0
Gastrointestinal Hemorrhage Bleeding in any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM.	2.87	1	0
Intestinal Polyps Discrete abnormal tissue masses that protrude into the lumen of the INTESTINE. A polyp is attached to the intestinal wall either by a stalk, pedunculus, or by a broad base.	2.87	1	0
Intestinal Diseases Pathological processes in any segment of the INTESTINE from DUODENUM to RECTUM.	2.36	2	0
Bile Duct Cancer [description not available]	2.38	2	0
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	2.38	2	0
Icterus Gravis Neonatorum [description not available]	2.36	2	0
Jaundice, Neonatal Yellow discoloration of the SKIN; MUCOUS MEMBRANE; and SCLERA in the NEWBORN. It is a sign of NEONATAL HYPERBILIRUBINEMIA. Most cases are transient self-limiting (PHYSIOLOGICAL NEONATAL JAUNDICE) occurring in the first week of life, but some can be a sign of pathological disorders, particularly LIVER DISEASES.	2.36	2	0
Infant, Newborn, Diseases Diseases of newborn infants present at birth (congenital) or developing within the first month of birth. It does not include hereditary diseases not manifesting at birth or within the first 30 days of life nor does it include inborn errors of metabolism. Both HEREDITARY DISEASES and METABOLISM, INBORN ERRORS are available as general concepts.	1.96	1	0
Palsy [description not available]	2.35	2	0
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	2.35	2	0
Disease, Pulmonary [description not available]	1.96	1	0
Lung Diseases Pathological processes involving any part of the LUNG.	1.96	1	0
Anorexia The lack or loss of APPETITE accompanied by an aversion to food and the inability to eat. It is the defining characteristic of the disorder ANOREXIA NERVOSA.	1.95	1	0
Amino Acid Metabolism Disorders, Inborn [description not available]	2.36	2	0
Addison Disease and Cerebral Sclerosis [description not available]	1.98	1	0
Adult Refsum Disease [description not available]	2.36	2	0
Cerebro-Hepato-Renal Syndrome [description not available]	1.98	1	0
Adrenoleukodystrophy An X-linked recessive disorder characterized by the accumulation of saturated very long chain fatty acids in the LYSOSOMES of ADRENAL CORTEX and the white matter of CENTRAL NERVOUS SYSTEM. This disease occurs almost exclusively in the males. Clinical features include the childhood onset of ATAXIA; NEUROBEHAVIORAL MANIFESTATIONS; HYPERPIGMENTATION; ADRENAL INSUFFICIENCY; SEIZURES; MUSCLE SPASTICITY; and DEMENTIA. The slowly progressive adult form is called adrenomyeloneuropathy. The defective gene ABCD1 is located at Xq28, and encodes the adrenoleukodystrophy protein (ATP-BINDING CASSETTE TRANSPORTERS).	1.98	1	0
Zellweger Syndrome An autosomal recessive disorder due to defects in PEROXISOME biogenesis which involves more than 13 genes encoding peroxin proteins of the peroxisomal membrane and matrix. Zellweger syndrome is typically seen in the neonatal period with features such as dysmorphic skull; MUSCLE HYPOTONIA; SENSORINEURAL HEARING LOSS; visual compromise; SEIZURES; progressive degeneration of the KIDNEYS and the LIVER. Zellweger-like syndrome refers to phenotypes resembling the neonatal Zellweger syndrome but seen in children or adults with apparently intact peroxisome biogenesis.	1.98	1	0
Goldblatt Syndrome [description not available]	1.98	1	0
Hypertension, Renovascular Hypertension due to RENAL ARTERY OBSTRUCTION or compression.	1.98	1	0
Muscular Dystrophy, Animal MUSCULAR DYSTROPHY that occurs in VERTEBRATE animals.	1.98	1	0
Death, Sudden The abrupt cessation of all vital bodily functions, manifested by the permanent loss of total cerebral, respiratory, and cardiovascular functions.	2.38	2	0
Cot Death [description not available]	2.89	4	0
Alkalosis A pathological condition that removes acid or adds base to the body fluids.	1.98	1	0
Cancer of Pituitary [description not available]	1.98	1	0
Pituitary Neoplasms Neoplasms which arise from or metastasize to the PITUITARY GLAND. The majority of pituitary neoplasms are adenomas, which are divided into non-secreting and secreting forms. Hormone producing forms are further classified by the type of hormone they secrete. Pituitary adenomas may also be characterized by their staining properties (see ADENOMA, BASOPHIL; ADENOMA, ACIDOPHIL; and ADENOMA, CHROMOPHOBE). Pituitary tumors may compress adjacent structures, including the HYPOTHALAMUS, several CRANIAL NERVES, and the OPTIC CHIASM. Chiasmal compression may result in bitemporal HEMIANOPSIA.	1.98	1	0
Coronary Thrombosis Coagulation of blood in any of the CORONARY VESSELS. The presence of a blood clot (THROMBUS) often leads to MYOCARDIAL INFARCTION.	1.98	1	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	1.98	1	0
Di Guglielmo Disease [description not available]	1.98	1	0
Acute Promyelocytic Leukemia [description not available]	1.98	1	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	1.98	1	0
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	1.98	1	0
Inborn Errors of Metabolism [description not available]	2.4	2	0
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	2.4	2	0
Calcification, Pathologic [description not available]	1.99	1	0
Calcinosis Pathologic deposition of calcium salts in tissues.	1.99	1	0
Basedow Disease [description not available]	1.99	1	0
Graves Disease A common form of hyperthyroidism with a diffuse hyperplastic GOITER. It is an autoimmune disorder that produces antibodies against the THYROID STIMULATING HORMONE RECEPTOR. These autoantibodies activate the TSH receptor, thereby stimulating the THYROID GLAND and hypersecretion of THYROID HORMONES. These autoantibodies can also affect the eyes (GRAVES OPHTHALMOPATHY) and the skin (Graves dermopathy).	1.99	1	0
Anaplastic Astrocytoma [description not available]	1.99	1	0
Astrocytoma Neoplasms of the brain and spinal cord derived from glial cells which vary from histologically benign forms to highly anaplastic and malignant tumors. Fibrillary astrocytomas are the most common type and may be classified in order of increasing malignancy (grades I through IV). In the first two decades of life, astrocytomas tend to originate in the cerebellar hemispheres; in adults, they most frequently arise in the cerebrum and frequently undergo malignant transformation. (From Devita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2013-7; Holland et al., Cancer Medicine, 3d ed, p1082)	1.99	1	0
Chronic Progressive External Ophthalmoplegia [description not available]	1.99	1	0
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	1.99	1	0
Chemical Dependence [description not available]	1.99	1	0
Substance-Related Disorders Disorders related to substance use or abuse.	1.99	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	1.99	1	0
Adipocere [description not available]	1.99	1	0
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	2.91	1	0
Phlegmasia Alba Dolens Inflammation that is characterized by swollen, pale, and painful limb. It is usually caused by DEEP VEIN THROMBOSIS in a FEMORAL VEIN, following PARTURITION or an illness. This condition is also called milk leg or white leg.	1.99	1	0
Thrombophlebitis Inflammation of a vein associated with a blood clot (THROMBUS).	1.99	1	0
Hyperoxia An abnormal increase in the amount of oxygen in the tissues and organs.	1.99	1	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	2.66	3	0
Niemann-Pick Disease [description not available]	1.99	1	0
Niemann-Pick Diseases A group of autosomal recessive disorders in which harmful quantities of lipids accumulate in the viscera and the central nervous system. They can be caused by deficiencies of enzyme activities (SPHINGOMYELIN PHOSPHODIESTERASE) or defects in intracellular transport, resulting in the accumulation of SPHINGOMYELINS and CHOLESTEROL. There are various subtypes based on their clinical and genetic differences.	1.99	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	3.38	1	1
Dermatoses [description not available]	2.37	2	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.37	2	0
Angina Pectoris with Normal Coronary Arteriogram [description not available]	2	1	0
Colonic Inertia Symptom characterized by the passage of stool once a week or less.	2	1	0
Constipation Infrequent or difficult evacuation of FECES. These symptoms are associated with a variety of causes, including low DIETARY FIBER intake, emotional or nervous disturbances, systemic and structural disorders, drug-induced aggravation, and infections.	2	1	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	2.88	4	0
Wasting Disease [description not available]	2	1	0
Gastroenteritis INFLAMMATION of any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM. Causes of gastroenteritis are many including genetic, infection, HYPERSENSITIVITY, drug effects, and CANCER.	2	1	0
Complications of Diabetes Mellitus [description not available]	2	1	0
Nutritional Disorders [description not available]	2.92	1	0
Nutrition Disorders Disorders caused by nutritional imbalance, either overnutrition or undernutrition.	2.92	1	0
Diseases in Twins Disorders affecting TWINS, one or both, at any age.	1.95	1	0
Acidosis, Diabetic [description not available]	2.64	3	0
Diabetic Ketoacidosis A life-threatening complication of diabetes mellitus, primarily of TYPE 1 DIABETES MELLITUS with severe INSULIN deficiency and extreme HYPERGLYCEMIA. It is characterized by KETOSIS; DEHYDRATION; and depressed consciousness leading to COMA.	2.64	3	0
Soft Tissue Neoplasms Neoplasms of whatever cell type or origin, occurring in the extraskeletal connective tissue framework of the body including the organs of locomotion and their various component structures, such as nerves, blood vessels, lymphatics, etc.	1.95	1	0
Endotoxin Shock [description not available]	1.95	1	0
Cardiac Tamponade Compression of the heart by accumulated fluid (PERICARDIAL EFFUSION) or blood (HEMOPERICARDIUM) in the PERICARDIUM surrounding the heart. The affected cardiac functions and CARDIAC OUTPUT can range from minimal to total hemodynamic collapse.	1.95	1	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	1.95	1	0
Newcastle Disease An acute febrile, contagious, viral disease of birds caused by an AVULAVIRUS called NEWCASTLE DISEASE VIRUS. It is characterized by respiratory and nervous symptoms in fowl and is transmissible to man causing a severe, but transient conjunctivitis.	1.95	1	0
Infections, Legionella pneumophila [description not available]	2.65	3	0
Leukemia L 1210 [description not available]	1.95	1	0
Bilirubin Encephalopathy [description not available]	1.95	1	0
Kernicterus A term used pathologically to describe BILIRUBIN staining of the BASAL GANGLIA; BRAIN STEM; and CEREBELLUM and clinically to describe a syndrome associated with HYPERBILIRUBINEMIA. Clinical features include athetosis, MUSCLE SPASTICITY or hypotonia, impaired vertical gaze, and DEAFNESS. Nonconjugated bilirubin enters the brain and acts as a neurotoxin, often in association with conditions that impair the BLOOD-BRAIN BARRIER (e.g., SEPSIS). This condition occurs primarily in neonates (INFANT, NEWBORN), but may rarely occur in adults. (Menkes, Textbook of Child Neurology, 5th ed, p613)	1.95	1	0
Hyperventilation A pulmonary ventilation rate faster than is metabolically necessary for the exchange of gases. It is the result of an increased frequency of breathing, an increased tidal volume, or a combination of both. It causes an excess intake of oxygen and the blowing off of carbon dioxide.	2.37	2	0
Enteric Fever [description not available]	1.95	1	0
Typhoid Fever An acute systemic febrile infection caused by SALMONELLA TYPHI, a serotype of SALMONELLA ENTERICA.	1.95	1	0
Alcoholic Cirrhosis [description not available]	1.95	1	0
Liver Cirrhosis, Alcoholic FIBROSIS of the hepatic parenchyma due to chronic excess ALCOHOL DRINKING.	1.95	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.64	3	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.64	3	0
Alcoholic Intoxication An acute brain syndrome which results from the excessive ingestion of ETHANOL or ALCOHOLIC BEVERAGES.	1.95	1	0
Bacterial Overgrowth Syndrome [description not available]	1.95	1	0
Biliary Fistula Abnormal passage in any organ of the biliary tract or between biliary organs and other organs.	2.64	3	0
Pancreatic Diseases Pathological processes of the PANCREAS.	1.97	1	0
Abnormalities, Multiple Congenital abnormalities that affect more than one organ or body structure.	1.97	1	0
Empyema, Gall Bladder [description not available]	1.97	1	0
Cholecystitis Inflammation of the GALLBLADDER; generally caused by impairment of BILE flow, GALLSTONES in the BILIARY TRACT, infections, or other diseases.	1.97	1	0
Germinoblastoma [description not available]	2.36	2	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.36	2	0
Deficiency, Riboflavin [description not available]	2.38	2	0
Embolism, Fat Blocking of a blood vessel by fat deposits in the circulation. It is often seen after fractures of large bones or after administration of CORTICOSTEROIDS.	1.97	1	0
Embolism, Pulmonary [description not available]	1.97	1	0
Pulmonary Embolism Blocking of the PULMONARY ARTERY or one of its branches by an EMBOLUS.	1.97	1	0
Alkalosis, Respiratory A state due to excess loss of carbon dioxide from the body. (Dorland, 27th ed)	1.97	1	0
Contact Dermatitis [description not available]	1.97	1	0
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	1.97	1	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	1.97	1	0
Edema, Pulmonary [description not available]	3.97	5	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	3.97	5	0
Infantile Respiratory Distress Syndrome [description not available]	1.97	1	0
Respiratory Distress Syndrome, Newborn A condition of the newborn marked by DYSPNEA with CYANOSIS, heralded by such prodromal signs as dilatation of the alae nasi, expiratory grunt, and retraction of the suprasternal notch or costal margins, mostly frequently occurring in premature infants, children of diabetic mothers, and infants delivered by cesarean section, and sometimes with no apparent predisposing cause.	1.97	1	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	1.97	1	0
Cerebral Pseudosclerosis [description not available]	1.96	1	0
Hepatolenticular Degeneration A rare autosomal recessive disease characterized by the deposition of copper in the BRAIN; LIVER; CORNEA; and other organs. It is caused by defects in the ATP7B gene encoding copper-transporting ATPase 2 (EC 3.6.3.4), also known as the Wilson disease protein. The overload of copper inevitably leads to progressive liver and neurological dysfunction such as LIVER CIRRHOSIS; TREMOR; ATAXIA and intellectual deterioration. Hepatic dysfunction may precede neurologic dysfunction by several years.	1.96	1	0
Urinary Calculi Low-density crystals or stones in any part of the URINARY TRACT. Their chemical compositions often include CALCIUM OXALATE, magnesium ammonium phosphate (struvite), CYSTINE, or URIC ACID.	1.96	1	0
Kidney Stones [description not available]	1.96	1	0
Abscess Accumulation of purulent material in tissues, organs, or circumscribed spaces, usually associated with signs of infection.	1.96	1	0
Empyema Presence of pus in a hollow organ or body cavity.	1.96	1	0
Kidney Calculi Stones in the KIDNEY, usually formed in the urine-collecting area of the kidney (KIDNEY PELVIS). Their sizes vary and most contains CALCIUM OXALATE.	1.96	1	0
Eye Abnormalities Congenital absence of or defects in structures of the eye; may also be hereditary.	1.96	1	0
Erythema Redness of the skin produced by congestion of the capillaries. This condition may result from a variety of disease processes.	1.96	1	0
Renal Artery Stenosis [description not available]	1.94	1	0
Renal Artery Obstruction Narrowing or occlusion of the RENAL ARTERY or arteries. It is due usually to ATHEROSCLEROSIS; FIBROMUSCULAR DYSPLASIA; THROMBOSIS; EMBOLISM, or external pressure. The reduced renal perfusion can lead to renovascular hypertension (HYPERTENSION, RENOVASCULAR).	1.94	1	0
Lymphatic Diseases Diseases of LYMPH; LYMPH NODES; or LYMPHATIC VESSELS.	1.95	1	0
Lymph Node Metastasis [description not available]	1.95	1	0
Flatus [description not available]	1.95	1	0
Flatulence Production or presence of gas in the gastrointestinal tract which may be expelled through the anus.	1.95	1	0
Far East Scarlet-like Fever [description not available]	1.95	1	0
Bacteroides Infections Infections with bacteria of the genus BACTEROIDES.	1.94	1	0
Fusobacterium Infections Infections with bacteria of the genus FUSOBACTERIUM.	1.94	1	0
Toxemia A condition produced by the presence of toxins or other harmful substances in the BLOOD.	1.94	1	0
Diabetic Coma A state of unconsciousness as a complication of diabetes mellitus. It occurs in cases of extreme HYPERGLYCEMIA or extreme HYPOGLYCEMIA as a complication of INSULIN therapy.	1.95	1	0
BCKD Deficiency [description not available]	1.95	1	0
Maple Syrup Urine Disease An autosomal recessive inherited disorder with multiple forms of phenotypic expression, caused by a defect in the oxidative decarboxylation of branched-chain amino acids (AMINO ACIDS, BRANCHED-CHAIN). These metabolites accumulate in body fluids and render a maple syrup odor. The disease is divided into classic, intermediate, intermittent, and thiamine responsive subtypes. The classic form presents in the first week of life with ketoacidosis, hypoglycemia, emesis, neonatal seizures, and hypertonia. The intermediate and intermittent forms present in childhood or later with acute episodes of ataxia and vomiting. (From Adams et al., Principles of Neurology, 6th ed, p936)	1.95	1	0
Sarcoma 37 An experimental sarcoma of mice.	1.94	1	0
Autosomal Hemophilia A [description not available]	2.35	2	0
Hepatitis, Infectious [description not available]	1.94	1	0
Granuloma, Hodgkin [description not available]	1.94	1	0
Hemophilia A The classic hemophilia resulting from a deficiency of factor VIII. It is an inherited disorder of blood coagulation characterized by a permanent tendency to hemorrhage.	2.35	2	0
Hepatitis A INFLAMMATION of the LIVER in humans caused by a member of the HEPATOVIRUS genus, HUMAN HEPATITIS A VIRUS. It can be transmitted through fecal contamination of food or water.	1.94	1	0
Hodgkin Disease A malignant disease characterized by progressive enlargement of the lymph nodes, spleen, and general lymphoid tissue. In the classical variant, giant usually multinucleate Hodgkin's and REED-STERNBERG CELLS are present; in the nodular lymphocyte predominant variant, lymphocytic and histiocytic cells are seen.	1.94	1	0
Deficiency, Thiamine [description not available]	2.86	4	0
Thiamine Deficiency A nutritional condition produced by a deficiency of THIAMINE in the diet, characterized by anorexia, irritability, and weight loss. Later, patients experience weakness, peripheral neuropathy, headache, and tachycardia. In addition to being caused by a poor diet, thiamine deficiency in the United States most commonly occurs as a result of alcoholism, since ethanol interferes with thiamine absorption. In countries relying on polished rice as a dietary staple, BERIBERI prevalence is very high. (From Cecil Textbook of Medicine, 19th ed, p1171)	2.86	4	0
Congenital Familial Lymphedema [description not available]	1.94	1	0
Lymphedema Edema due to obstruction of lymph vessels or disorders of the lymph nodes.	1.94	1	0
Kahler Disease [description not available]	1.94	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	1.94	1	0
Myxedema A condition characterized by a dry, waxy type of swelling (EDEMA) with abnormal deposits of MUCOPOLYSACCHARIDES in the SKIN and other tissues. It is caused by a deficiency of THYROID HORMONES. The skin becomes puffy around the eyes and on the cheeks. The face is dull and expressionless with thickened nose and lips.	1.94	1	0
Embolus [description not available]	1.94	1	0
Embolism Blocking of a blood vessel by an embolus which can be a blood clot or other undissolved material in the blood stream.	1.94	1	0
Hemoglobinuria The presence of free HEMOGLOBIN in the URINE, indicating hemolysis of ERYTHROCYTES within the vascular system. After saturating the hemoglobin-binding proteins (HAPTOGLOBINS), free hemoglobin begins to appear in the urine.	1.94	1	0
BH4 Deficiency [description not available]	1.94	1	0
Phenylketonurias A group of autosomal recessive disorders marked by a deficiency of the hepatic enzyme PHENYLALANINE HYDROXYLASE or less frequently by reduced activity of DIHYDROPTERIDINE REDUCTASE (i.e., atypical phenylketonuria). Classical phenylketonuria is caused by a severe deficiency of phenylalanine hydroxylase and presents in infancy with developmental delay; SEIZURES; skin HYPOPIGMENTATION; ECZEMA; and demyelination in the central nervous system. (From Adams et al., Principles of Neurology, 6th ed, p952).	1.94	1	0
Deficiency, Vitamin E [description not available]	1.94	1	0

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