naphthalene profile

ID Source	ID
PubMed CID	931
CHEMBL ID	16293
CHEBI ID	16482
MeSH ID	M0099457

Synonym
BIDD:ER0665
naftaleno
naftalina
CHEBI:16482 ,
naphthalen
naphtaline
naphtalene
white tar
dezodorator
nsc-37565
wln: l66j
naphthalin
naphthene
moth balls
camphor tar
albocarbon
naftalen
naphthaline
moth flakes
tar camphor
nsc37565
nci-c52904
mothballs
na-cemmix
inchi=1/c10h8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8
NCGC00090793-01
caswell no. 587
un1334
mighty rd1
rcra waste number u165
naphthalene, crude or refined
einecs 202-049-5
ccris 1838
hsdb 184
naphthalene (molten)
naphtalene [iso:french]
naphthalene, molten
un2304
rcra waste no. u165
mighty 150
c10h8
epa pesticide chemical code 055801
nsc 37565
naphthalene, pure
naphthalene [bsi:iso]
naftalen [polish]
ai3-00278
C00829
naphthalene ,
91-20-3
naphthalene, analytical standard
naphthalene, 99%
naphthalene, suitable for scintillation, >=99%
NCGC00090793-02
MLS001055498
smr000677944
L001166
CHEMBL16293 ,
naphthalinum
bdbm50159249
FT-0651884
N0004
AKOS000119977
NCGC00090793-03
NCGC00090793-04
HMS3039N15
tox21_202004
NCGC00254058-01
NCGC00259553-01
tox21_300008
N0885
dtxcid00913
cas-91-20-3
dtxsid8020913 ,
tox21_111023
68412-25-9
STL282720
FT-0672611
FT-0672612
ec 202-049-5
naphthalene, molten [un2304] [flammable solid]
naphthalene, crude or refined [un1334] [flammable solid]
unii-2166in72un
2166in72un ,
naphtalinum
25135-16-4
naphthalene-1,2,3,4-13c4
287399-39-7
naphthalene [mi]
naphthalene [usp-rs]
naphthalene [mart.]
naphthalene [iarc]
naphthalinum [hpus]
naphthalene [iso]
naphthalene [hsdb]
naphthalene [who-dd]
napthalene
NCGC00090793-05
un 1334
un 2304
mfcd00001742
F0001-2217
naphthalene, certified reference material, tracecert(r)
sr-01000854997
SR-01000854997-2
naphthalene, saj first grade, >=98.0%
melting point standard 79-81c, analytical standard
naphthalene, 98%
naphthalene, united states pharmacopeia (usp) reference standard
naphthalene, for synthesis, 98.5%
naphthalene, pharmaceutical secondary standard; certified reference material
naphthalene 10 microg/ml in cyclohexane
naphthalene 100 microg/ml in acetonitrile
naphthalene 10 microg/ml in acetonitrile
naphthalene-1,4-d2
72931-45-4
naphthalene,(s)
naphthalene 100 microg/ml in methanol
Q179724
AMY22299
naphthalene (1,2,3,4,5,6,7,8-d8)
1-naphthalene
2-naphthalen
2-naphthalene
D97670
BS-22320
EN300-21626
naphthalene (mart.)
naphthalene (usp-rs)
naphthalene, refined
usepa/opp pesticide code 055801
naphtalene (iso:french)
naphthalene (iarc)
Z104506008

Excerpt	Reference	Relevance
"Naphthalene exposure is a common cause of toxicity in older children, but is rarely described in neonates."	( Newborn with Perinatal Naphthalene Toxicity after Maternal Ingestion of Mothballs during Pregnancy. Arunachalam, A; Lohmann, P; Shafer, G, 2020)	1.59
"Naphthalene is a good structural replacement for the isovanillin moiety (i.e. "	( Synthesis and Evaluation of 2-Naphthaleno trans-Stilbenes and Cyanostilbenes as Anticancer Agents. Crooks, PA; Eoff, RL; Guzman, ML; Ketkar, A; Madadi, NR; Penthala, NR; Trujullo-Alonso, V, 2018)	1.92
"Naphthalene-etomidate is a very low-efficacy etomidate analog that exhibits the pharmacology of an anesthetic competitive antagonist at the γ-aminobutyric acid type A receptor."	( Competitive Antagonism of Anesthetic Action at the γ-Aminobutyric Acid Type A Receptor by a Novel Etomidate Analog with Low Intrinsic Efficacy. Cohen, JB; Jayakar, SS; Ma, C; McGrath, M; Miller, KW; Pejo, E; Raines, DE; Zhou, X, 2017)	1.9
"Naphthalene poisoning is an uncommon poisoning due to its pungent smell, taste, insolubility in water, and poor absorption from the gut. "	( Acute kidney injury: A rare complication of mothball (Naphthalene) poisoning. Chandan Kumar, KM; Ekambaram, S; Mahalingam, V, )	1.82
"Naphthalene (NA) is a ubiquitous environmental pollutant and possible human carcinogen that forms tumors in rodents with tissue/regional and species selectivity. "	( Naphthalene genotoxicity: DNA adducts in primate and mouse airway explants. Buchholz, BA; Carratt, SA; Collette, NM; Ding, X; Hartog, M; Kuhn, EA; Van Winkle, LS, 2019)	3.4
"Naphthalene (mothball) is a commonly used deodorizer in the Indian subcontinent, including Sri Lanka. "	( Acute intravascular hemolysis due to naphthalene toxicity: a case report. Fernando, AHN; Jayasinghe, CS; Uthuman, AAA, 2019)	2.23
"Naphthalene chlorination is an important formation mechanism of polychlorinated naphthalenes (PCNs) in combustion flue gas. "	( Electrophilic Chlorination of Naphthalene in Combustion Flue Gas. Cao, R; Chen, J; Fan, Y; Ren, M; Wang, D; Zhang, H, 2019)	2.25
"Naphthalene vapor is a nasal cytotoxicant in the rat and mouse but is a nasal carcinogen in only the rat. "	( Nasal dosimetry of inspired naphthalene vapor in the male and female B6C3F1 mouse. Morris, JB, 2013)	2.13
"Naphthalene is a ubiquitous environmental pollutant to which humans are exposed. "	( Characterization of the biochemical effects of naphthalene on the mouse respiratory system using NMR-based metabolomics. Chien, CL; Hong, JH; Hsu, YM; Lee, WC; Liang, HJ; Lin, CY; Wan, CH, 2014)	2.1
"Naphthalene is a nasal carcinogen, inducing respiratory adenomas in male and olfactory neuroblastomas in female rats, respectively. "	( Sex differences in the acute nasal antioxidant/antielectrophilic response of the rat to inhaled naphthalene. Buckpitt, AR; Cichocki, JA; Mendoza, R; Morris, JB; Smith, GJ; Van Winkle, LS, 2014)	2.06
"Naphthalene ingestion is a rare cause of hemolysis."	( [Hemolytic anemia due to naphthalene poisoning]. Bagnères, D; Bernard, F; Frances, Y; Jego, L; Jouve, A; Maurice, F; Rossi, P; Roumieu, S; Vieillard, M, 2015)	2.16
"Naphthalene is an environmental toxicant to which humans are exposed. "	( Simultaneous quantification of multiple urinary naphthalene metabolites by liquid chromatography tandem mass spectrometry. Ayala, DC; Buckpitt, AR; Morin, D, 2015)	2.12
"Naphthalene is a global environmental concern, because this substance is assumed to contribute considerably to human cancer risk."	( Enhancement of naphthalene tolerance in transgenic Arabidopsis plants overexpressing the ferredoxin-like protein (ADI1) from rice. Fu, XY; Han, HJ; Peng, RH; Tian, YS; Yao, QH; Zhao, W; Zhu, B, 2016)	1.51
"Naphthalene (NA) is a ubiquitous pollutant to which humans are widely exposed. "	( Naphthalene cytotoxicity in microsomal epoxide hydrolase deficient mice. Buckpitt, AR; Carratt, SA; Edwards, PC; Morin, D; Van Winkle, LS, 2016)	3.32
"Naphthalene is a nasal toxicant and carcinogen in the rat. "	( Upper respiratory tract uptake of naphthalene. Buckpitt, AR; Morris, JB, 2009)	2.07
"Naphthalene (NA) is a semivolatile aromatic hydrocarbon to which humans are exposed from a variety of sources. "	( Protein thiol oxidation in murine airway epithelial cells in response to naphthalene or diethyl maleate. Buckpitt, AR; Morin, D; Spiess, PC; Williams, CR, 2010)	2.03
"Naphthalene is a volatile hydrocarbon that causes dose-, species-, and cell type-dependent cytotoxicity after acute exposure and hyperplasia/neoplasia after lifetime exposures in rodents. "	( Formation of covalently bound protein adducts from the cytotoxicant naphthalene in nasal epithelium: species comparisons. Buckpitt, A; DeStefano-Shields, C; Morin, D, 2010)	2.04
"Naphthalene is an interesting candidate to study in the framework of organic delivery to planetary surfaces as well as in the origin of life. "	( Radiolytic studies of naphthalene in the presence of water. Keheyan, Y; ten Kate, IL, 2012)	2.14
"Naphthalene is a volatile polycyclic aromatic hydrocarbon generated during combustion and is a ubiquitous chemical in the environment. "	( Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry. Buckpitt, AR; Jewell, WT; Jones, AD; Morin, D; Pham, NT, 2012)	2.05
"Naphthalene is an important contaminant in indoor and outdoor air. "	( Naphthalene biomarkers and relationship with hemoglobin and hematocrit in White, Black, and Hispanic adults: results from the 2003-2004 National Health and Nutrition Examination Survey. Cardenas, A; Harding, A; Smit, E; Sudakin, DL, 2013)	3.28
"Naphthalene is a bicyclic aromatic compound that has wide industrial and commercial applications. "	( Naphthalene toxicity and antioxidant nutrients. Bagchi, D; Ohia, S; Stohs, SJ, 2002)	3.2
"Naphthalene is a toxicant with unusual species and tissue specificity that has been the subject of in vitro studies. "	( A preliminary physiologically based pharmacokinetic model for naphthalene and naphthalene oxide in mice and rats. Babish, JG; Quick, DJ; Shuler, ML; Sweeney, LM, )	1.81
"Naphthalene is an aromatic hydrocarbon that, at the dose used in this study, selectively destroys nonciliated bronchial epithelial cells (Clara cells) through cytochrome P-450-mediated metabolic activation into cytotoxic epoxides."	( Cell proliferation contributes to PNEC hyperplasia after acute airway injury. McBride, JT; Peake, JL; Pinkerton, KE; Stevens, TP; Stripp, BR, 1997)	1.02
"Naphthalene is a bicyclic aromatic compound that is widely used in various domestic and commercial applications including lavatory scent disks, soil fumigants and moth balls. "	( Naphthalene-induced oxidative stress and DNA damage in cultured macrophage J774A.1 cells. Bagchi, D; Bagchi, M; Balmoori, J; Stohs, SJ; Ye, X, 1998)	3.19
"Naphthalene is a bicyclic aromatic compound that is widely used in various domestic and commercial applications including lavatory scent disks, soil fumigants and moth balls. "	( Induction of oxidative stress and DNA damage by chronic administration of naphthalene to rats. Bagchi, D; Bagchi, M; Balmoori, J; Stohs, SJ; Vuchetich, PJ, 1998)	1.97
"Naphthalene is a component of crude and refined oil, and may be found in the marine environment following acute events such as oil spills."	( Development and characterization of a cell line from Pacific herring, Clupea harengus pallasi, sensitive to both naphthalene cytotoxicity and infection by viral hemorrhagic septicemia virus. Bols, NC; Ganassin, RC; Joyce, EM; Kennedy, CJ; Sanders, SM, 1999)	1.24
"Naphthalene is a bicyclic aromatic compound that is widely used in various domestic and commercial applications. "	( Protective effect of melatonin on naphthalene-induced oxidative stress and DNA damage in cultured macrophage J774A.1 cells. Bagchi, D; Bagchi, M; Balmoori, J; Ray, SD; Stohs, SJ; Ye, X, 2001)	2.03
"Naphthalene is a polyaromatic hydrocarbon (PAH) present in many sediment-water systems. "	( Naphthalene removal from aqueous systems by Sagittarius sp.. Maillacheruvu, K; Safaai, S, 2002)	3.2

Excerpt	Reference	Relevance
"Naphthalene has remained a challenge how to eradicate it from the water because of its carcinogenic risk to humans. "	( Embryotoxicity assessment and efficient removal of naphthalene from water by irradiated graphene aerogels. Bai, J; Li, G; Li, S; Liu, Y; Si, J; Yao, H; Zhang, H; Zhang, L; Zhang, T; Zhou, R, 2020)	2.25
"Naphthalene has been regarded as a model PAH compound for investigating the mechanisms of bacterial PAH biodegradation."	( Genome Analysis of Naphthalene-Degrading Kim, J; Park, W, 2018)	1.53
"Naphthalene has been used worldwide as a commercial insecticide for decades, which when detected in the environment can have various negative effects on non-target organism, such as hepatotoxicity. "	( Investigation of the molecular mechanisms of hepatic injury upon naphthalene exposure in zebrafish (Danio rerio). Bian, H; Chen, H; Gong, Z; Ru, S; Sheng, L, 2018)	2.16
"Naphthalene has been widely used to study the role of soil fauna, but its potential non-target effects on soil enzyme activity remain unknown in subalpine forests. "	( Effects of naphthalene on soil fauna abundance and enzyme activity in the subalpine forest of western Sichuan, China. Chen, Y; Lan, L; Liu, Y; Ni, X; Tan, B; Wu, F; Xu, Z; Yang, F; Yang, W; Yue, K; Zhang, L, 2019)	2.35
"Naphthalene has been widely used to test the functional roles of soil fauna, but its nontarget effects remain uncertain in various soils. "	( Naphthalene exerts substantial nontarget effects on soil nitrogen mineralization processes in a subalpine forest soil: A microcosm study. Lan, L; Li, H; Liu, Y; Tan, B; Xu, Z; Yang, F; You, C; Zhang, J; Zhang, L, 2019)	3.4
"Naphthalene use has been associated with intravascular haemolysis especially in patients with glucose-6-phoshate dehydrogenase (G6PD) deficiency but its unorthodox use for the treatment of urethritis in a young man and its associated acute kidney injury has not been described in Ghana."	( Naphthalene induced acute kidney injury in an African patient in Ghana: a case report. Hutton-Mensah, KA; Tannor, EK, 2019)	2.68
"Naphthalene has emission in the ultraviolet (UV) region, limiting its trace level determination in biological and environmental samples due to detrimental effect of UV light on the living cell and interference from other substances having emission in the UV region. "	( Tuning FRET efficiency as a novel approach for improved detection of naphthalene: application to environmental samples. Adhikari, S; Banerjee, A; Das, D; Mandal, S; Nandi, S, 2016)	2.11
"Naphthalene has been shown to be a weak carcinogen in rats. "	( Depurinating naphthalene-DNA adducts in mouse skin related to cancer initiation. Cavalieri, E; Chakravarti, D; Gaikwad, N; Higginbotham, S; Rogan, E; Saeed, M, 2009)	2.16
"Naphthalene dipeptides have been shown to be useful low-molecular-weight gelators. "	( On crystal versus fiber formation in dipeptide hydrogelator systems. Adams, DJ; Chen, L; Houton, KA; Jones, JT; Lloyd, GO; Morris, KL; Schmidtmann, M; Serpell, LC, 2012)	1.82
"Naphthalene has been well studied in both fields."	( Radiolytic studies of naphthalene in the presence of water. Keheyan, Y; ten Kate, IL, 2012)	1.41

Excerpt	Reference	Relevance
"Naphthalene ingestion can cause acute tubular necrosis from haemoglobinuria and timely interventions are necessary to restore renal and maintain good renal functions."	( Naphthalene induced acute kidney injury in an African patient in Ghana: a case report. Hutton-Mensah, KA; Tannor, EK, 2019)	2.68
"Naphthalene did not cause a chemically-induced phase shift in the circadian rhythm of black pigment dispersion but reduced the daytime peak of that dispersion."	( A mechanism of action for the inhibition of black pigment dispersion in the fiddler crab, Uca pugilator, by naphthalene. Fingerman, M; Staub, GC, 1984)	1.2

Excerpt	Reference	Relevance
"Naphthalene treatment had maximal effects on BMC retention when given 2 days before cell delivery."	( Optimization of targeted cell replacement therapy: a new approach for lung disease. Duchesneau, P; Waddell, TK; Wong, AP, 2010)	1.08
"Naphthalene treatment produced in previtellogenic fish decreased 17beta-estradiol levels in plasma, increased plasma glucose or decreased liver gluconeogenic capacity whereas no major effects were noticed on parameters involved in lipid, amino acid and lactate metabolism."	( Interactive effects of naphthalene treatment and the onset of vitellogenesis on energy metabolism in liver and gonad, and plasma steroid hormones of rainbow trout Oncorhynchus mykiss. Alvarez, R; Gesto, M; Míguez, JM; Soengas, JL; Tintos, A, 2006)	1.37
"Naphthalene treatment resulted in a 2.1-fold increase in lipid peroxidation in liver and brain mitochondria at the 24-h time point."	( Naphthalene-induced oxidative stress in rats and the protective effects of vitamin E succinate. Bagchi, D; Bagchi, M; Hassoun, EA; Stohs, SJ; Tang, L; Vuchetich, PJ, 1996)	2.46
"Treatment of naphthalene intoxicated rats with plant extract reversed these distorted parameters to near normal levels. "	( Protective effect of Coleus aromaticus Benth (Lamiaceae) against naphthalene-induced hepatotoxicity. Anbuselvam, C; Ashokkumar, B; Vijayavel, K, 2013)	1
"Mice treated with naphthalene were used for the bronchiolar epithelium injury model, and mice treated with bleomycin were used for the alveolar epithelium injury model."	( A change in the number of CCSP(pos)/SPC(pos) cells in mouse lung during development, growth, and repair. Ishiguro, A; Kijima, H; Nukiwa, T; Saijo, Y; Sun, R; Takahata, T; Ye, X; Zhou, Q, 2013)	0.71

Excerpt	Reference	Relevance
" LD50 values indicate that SS, NAP, and PNP were more toxic (8."	( Developmental toxicity of nine selected compounds following prenatal exposure in the mouse: naphthalene, p-nitrophenol, sodium selenite, dimethyl phthalate, ethylenethiourea, and four glycol ether derivatives. Booth, GM; Bradshaw, WS; Carter, MW; Hardin, BD; Plasterer, MR; Schuler, RL, 1985)	0.49
" The acute oral LD50 of naphthalene was 533 and 710 mg/kg in male and female mice, respectively."	( Naphthalene toxicity in CD-1 mice: general toxicology and immunotoxicology. Anderson, AC; Barnes, DW; Borzelleca, JF; Condie, LW; Duke, SS; Hayes, JR; Holsapple, MP; Shopp, GM; White, KL, 1984)	2.02
" The rates of photomodification of the three PAHs were rapid enough for the photooxidized compounds to contribute to toxicity, and the photomodified PAHs were more toxic than the parent compounds."	( Photoinduced toxicity of three polycyclic aromatic hydrocarbons (fluoranthene, pyrene, and naphthalene) to the duckweed Lemna gibba L. G-3. Dixon, DG; Greenberg, BM; Huang, XD; McConkey, BJ; Ren, L, 1994)	0.51
" These procedures lead to a fractionation of the toxicity, which may underestimate or overestimate exposure routes and consequently potential adverse environmental effects."	( Microbial bioassays to assess the toxicity of solid-associated contaminants. Ahlf, W; Liss, W; Rönnpagel, K, 1995)	0.29
" This has decisive toxicological implications, which could be demonstrated by comparing the lung-specific toxic effects of naphthalenes in mouse: the lack of ring oxidation correlates well with lack of lung toxicity while, vice versa, the extent of enzymatic oxidative attack at the aromatic ring structure results in a toxic pattern that is observed with naphthalene and its monomethyl derivatives."	( Metabolism and toxicity of diisopropylnaphthalene as compared to naphthalene and monoalkyl naphthalenes: a minireview. Höke, H; Zellerhoff, R, 1998)	0.78
"In this study we evaluated specific and nonspecific toxic effects of aeration and trichloroethylene (TCE) oxidation on methanotrophic bacteria grown with different nitrogen sources (nitrate, ammonia, and molecular nitrogen)."	( Evaluation of toxic effects of aeration and trichloroethylene oxidation on methanotrophic bacteria grown with different nitrogen sources. Alvarez-Cohen, L; Chu, KH, 1999)	0.3
"50 median lethal doses (LD(50)) of 2,3,7, 8-tetrachlorodibenzo-p-dioxin (TCDD), endrin, naphthalene, and sodium dichromate (VI) [Cr(VI)] on lipid peroxidation, DNA fragmentation, and enhanced production of superoxide anion (cytochrome c reduction) in liver and brain tissues of p53-deficient and standard C57BL/6NTac mice to determine the role of p53 gene in the toxic manifestations produced by these diverse xenobiotics."	( Role of p53 tumor suppressor gene in the toxicity of TCDD, endrin, naphthalene, and chromium (VI) in liver and brain tissues of mice. Bagchi, D; Bagchi, M; Balmoori, J; Stohs, SJ; Williams, CB; Ye, X, 2000)	0.77
" To explain the different responses of the two CCA designs, PBPKs of the two reactors were tested with variations in physical and kinetic parameters, and toxic mechanism."	( Combining cell culture analogue reactor designs and PBPK models to probe mechanisms of naphthalene toxicity. Ghanem, A; Shuler, ML, )	0.35
"The occurrence and potential adverse effects of select semivolatile organic compounds (SVOCs) in streambed sediment were assessed at 536 sites in 20 major river basins across the United States from 1992 to 1995."	( Occurrence and potential adverse effects of semivolatile organic compounds in streambed sediment, United States, 1992-1995. Furlong, ET; Lopes, TJ, 2001)	0.31
" In addition to lens opacification (cataracts) and histological changes associated with pneumotoxicity, other biomarkers of toxic effects include glutathione depletion, lipid peroxidation, DNA fragmentation and the production of the active oxygen species as superoxide anion and hydroxyl radical."	( Naphthalene toxicity and antioxidant nutrients. Bagchi, D; Ohia, S; Stohs, SJ, 2002)	1.76
" While multiple exposure is widely acknowledged, arguments are raised that adverse combined effects might not be evoked by mixtures of substances with dissimilar modes of action and being present at only low concentrations."	( Mixture toxicity of priority pollutants at no observed effect concentrations (NOECs). Altenburger, R; Consolaro, F; Gramatica, P; Scholze, M; Walter, H, 2002)	0.31
" The intent of this review is to outline some of the work conducted on the site and species selective toxicity and metabolism of the volatile lung toxic aromatic hydrocarbon, naphthalene."	( Naphthalene-induced respiratory tract toxicity: metabolic mechanisms of toxicity. Baldwin, R; Boland, B; Buckpitt, A; Chan, K; Fanucchi, M; Isbell, M; Karlsson, A; Lin, C; Morin, D; Plopper, C; Shultz, M; Taff, A; Van Winkle, L; West, J, 2002)	1.95
"Treatment plants may be exposed to a whole range of toxic organic and inorganic compounds that may inhibit the removal of organic matter and nitrogen."	( Monitoring toxicity of industrial wastewater and specific chemicals to a green alga, nitrifying bacteria and an aquatic bacterium. Arvin, E; Eilersen, AM; Henze, M, 2004)	0.32
" These results suggest that a gender-specific 1,4-naphthoquinone metabolic pathway may exist, which gives rise to unknown toxic metabolites."	( In vitro toxicity of naphthalene, 1-naphthol, 2-naphthol and 1,4-naphthoquinone on human CFU-GM from female and male cord blood donors. Croera, C; Ferrario, D; Gribaldo, L, 2008)	0.66
" Results showed that naphthalene was less toxic under N,P-starved condition."	( The toxicity of naphthalene to marine Chlorella vulgaris under different nutrient conditions. Kong, Q; Shen, X; Zhu, L, 2010)	1.03
"The short-term (96 h) toxic effects of two polycyclic aromatic hydrocarbons (PAHs), naphthalene (NAP) and pyrene (PYR), on the common prawn (Palaemon serratus) were investigated in laboratory bioassays, including a fitness related assay based on the post-exposure swimming velocity."	( Short-term toxic effects of naphthalene and pyrene on the common prawn (Palaemon serratus) assessed by a multi-parameter laboratorial approach: mechanisms of toxicity and impairment of individual fitness. Guilhermino, L; Luís, LG, 2012)	0.9
" We recommend that the users of household pesticides be educated about the health hazards and about safe practices and non-chemical methods of pest control be promoted."	( High prevalence of household pesticides and their unsafe use in rural South India. Bhatnagar, T; Chitra, GA; Kaur, P; Manickam, P; Murhekar, MV, 2013)	0.39
" However, a number of such indices testified to attenuation of naphthalene's adverse effects under the impact of lead."	( Does a concomitant exposure to lead influence unfavorably the naphthalene subchronic toxicity and toxicokinetics? Beresneva, TA; Degtyareva, TD; Katsnelson, BA; Minigaliyeva, IA; Privalova, LI, 2014)	0.88
" Can reliable predictions of the aquatic toxicity of crude oil, a multi-component mixture, be described from toxicity data on individual PAH compounds? Naphthalene, the most abundant PAH compound, and benzo(a)pyrene, a highly toxic PAH compound, were selected as model compounds to quantify toxicity of crude oil on two phytoplankton species, Ditylum brightwellii and Heterocapsa triquetra, by analyzing the effects of different concentrations of these PAHs on growth rate."	( Can crude oil toxicity on phytoplankton be predicted based on toxicity data on benzo(a)pyrene and naphthalene? Bargu, S; Ozhan, K, 2014)	0.82
" Naphthalene was a low potency cytotoxicant in vitro, with 500 μM frequently observed as a no-observed adverse effect concentration or lowest observed adverse effect concentration."	( Cytotoxicity of naphthalene toward cells from target and non-target organs in vitro. Kedderis, GL; Recio, L; Shepard, KG, 2014)	1.66

Excerpt	Reference	Relevance
" We describe a preliminary physiologically based pharmacokinetic (PBPK) model for naphthalene constructed solely from in vitro data for comparison to animal data without the use of adjustable parameters."	( A preliminary physiologically based pharmacokinetic model for naphthalene and naphthalene oxide in mice and rats. Babish, JG; Quick, DJ; Shuler, ML; Sweeney, LM, )	0.6
"A physiologically based pharmacokinetic (PBPK) model with five tissue groups (lung, liver, fat, richly perfused, and poorly perfused tissues plus venous and arterial blood compartments) has been developed from in vitro data and models of primary cell cultures for naphthalene toxicity in mice and rats."	( Use of in vitro data for construction of a physiologically based pharmacokinetic model for naphthalene in rats and mice to probe species differences. Quick, DJ; Shuler, ML, )	0.53
" A clearance study conducted for the grain showed the half-life of clearance was approximately 20 days for all compounds studied."	( Controlled exposure chamber study of uptake and clearance of airborne polycyclic aromatic hydrocarbons by wheat grain. Cahill, TM; Kado, NY; Kobayashi, R; Maddalena, RL; Okamoto, RA, 2007)	0.34
" Significant potency gains were appreciated by inverting the polarity of the thione of the parent triazolothione 1, resulting in potent compounds with attractive pharmacokinetic profiles."	( Highly selective c-Jun N-terminal kinase (JNK) 3 inhibitors with in vitro CNS-like pharmacokinetic properties II. Central core replacement. Anderson, J; Bard, F; Chereau, D; Griswold-Prenner, I; Konradi, AW; Lorentzen, C; Nakamura, D; Neitz, RJ; Powell, K; Qin, A; Quinn, KP; Ren, Z; Ruslim, L; Sauer, JM; Sham, HL; Wong, K; Yednock, TA; Zmolek, W, 2011)	0.37

Excerpt	Reference	Relevance
"The dynamics of a ferroelectric liquid crystal with a naphthalene ring (FLC-3) during the electric-field-induced switching between two surface-stabilized ferroelectric liquid crystal states were investigated by time-resolved infrared (IR) spectroscopy combined with two-dimensional (2D) correlation spectroscopy."	( Dynamics of a ferroelectric liquid crystal with a naphthalene ring during electric-field-induced switching studied by time-resolved infrared spectroscopy combined with two-dimensional correlation spectroscopy. Jiang, J; Ozaki, Y; Siesler, HW; Yoshihara, T; Zhao, J, 2003)	0.82

Excerpt	Reference	Relevance
" Bioavailability assays with two bacterial species (Pseudomonas putida ATCC 17484 and a gram-negative soil isolate, designated NP-Alk) gave dramatically different results."	( Differential bioavailability of soil-sorbed naphthalene to two bacterial species. Boyd, SA; Guerin, WF, 1992)	0.54
" In addition, a naphthalene-lux reporter system was used to determine bioavailability of naphthalene within these soils."	( Molecular diagnostics of polycyclic aromatic hydrocarbon biodegradation in manufactured gas plant soils. Applegate, B; Fleming, J; King, JM; Sanseverino, J; Sayler, GS; Werner, C, )	0.48
"The principal objective of this study was to quantify the bioavailability of micelle-solubilized naphthalene to naphthalene-degrading microorganisms comprising a mixed population isolated from contaminated waste and soils."	( Biodegradation of naphthalene in aqueous nonionic surfactant systems. Jacobson, AM; Liu, Z; Luthy, RG, 1995)	0.84
"An optical whole-cell biosensor based on a genetically engineered bioluminescent catabolic reporter bacterium was developed for continuous on-line monitoring of naphthalene and salicylate bioavailability and microbial catabolic activity potential in waste streams."	( Optical biosensor for environmental on-line monitoring of naphthalene and salicylate bioavailability with an immobilized bioluminescent catabolic reporter bacterium. Bienkowski, PR; Heitzer, A; Malachowsky, K; Sayler, GS; Thonnard, JE; White, DC, 1994)	0.73
"Due to the effects that sediment or soil matrices have on the bioavailability of compounds, it has been difficult to screen toxicity of solid-associated contaminants."	( Microbial bioassays to assess the toxicity of solid-associated contaminants. Ahlf, W; Liss, W; Rönnpagel, K, 1995)	0.29
" The biomass formation rate under mass transfer limited conditions, which is related to the naphthalene biodegradation rate, was correlated to the dimensionless Reynolds number, indicating increased bioavailability at increased mixing in the reactor liquid."	( Influence of hydrodynamic conditions on naphthalene dissolution and subsequent biodegradation. Breure, AM; Grotenhuis, JT; Mulder, H; Rulkens, WH; Van Andel, JG, 1998)	0.79
"The bioavailability of naphthalene present as a component of a complex nonaqueous phase liquid (NAPL) comprised by nine aromatic compounds was investigated."	( Mass transfer effects on microbial uptake of naphthalene from complex NAPLs. Mukherji, S; Weber, WJ, 1998)	0.87
" Although the nature of the oil does have a deep effect on the phase behavior of the micellar systems, in the present investigation no differences in the yields and in the rates of product formation of the enzymatic system were observed on changing the oil, thus showing that in this case the substrate concentration or bioavailability is not the rate-limiting step."	( Direct micellar systems as a tool to improve the efficiency of aromatic substrate conversion for fine chemicals production. Baglioni, P; Berti, D; Bestetti, G; Briganti, F; Di Gennaro, P; Galli, E; Randazzo, D; Scozzafava, A, 2000)	0.31
"Use of chemical dispersants as oil spill clean-up agents may alter the normal behavior of petroleum hydrocarbons (PH) by increasing their functional water solubility, resulting in increased bioavailability and altered interactions between dispersant, oil, and biological membranes."	( Influence of dispersants on the bioavailability and trophic transfer of petroleum hydrocarbons to larval topsmelt (Atherinops affinis). Mielbrecht, EE; Schwartz, GJ; Singaram, S; Sowby, ML; Tjeerdema, RS; Wolfe, MF, 2001)	0.31
" The results suggest that chemically dispersing oil may have the greatest effect on bioavailability of hydrocarbons, both through waterborne and food chain exposures."	( The effect of different oil spill remediation techniques on petroleum hydrocarbon elimination in Australian bass (Macquaria novemaculeata). Cohen, AM; Gagnon, MM; Nugegoda, D, 2001)	0.31
"The degradation of naphthalene was studied in soil-slurry systems, and a quantitative model was developed to evaluate the bioavailability of sorbed-phase contaminant."	( Biodegradation of non-desorbable naphthalene in soils. Park, JH; Voice, TC; Zhao, X, 2001)	0.92
" Finally, the net absorption rate increased because the solubilization effects of micelles exceeded the reduction effects of mass transfer coefficient above the CMC."	( Enhanced naphthalene solubility in the presence of sodium dodecyl sulfate: effect of critical micelle concentration. Huang, HL; Lee, WM, 2001)	0.73
"The bioavailability of naphthalene present as a component of a complex nonaqueous phase liquid(NAPL) comprised by nine aromatic compounds was investigated."	( Mass transfer effects on microbial uptake of naphthalene from complex NAPLs. Mukherji, S; Weber, WJ, 2001)	0.88
" As the magnitude of the micelle solubilization effect was greater than the reduction of the mass transfer coefficient in the presence of the surfactant, the total gas absorption rate increased."	( Simultaneous absorption of vapor phase polycyclic aromatic hydrocarbon and carbon dioxide in anionic surfactant solutions. Huang, HL; Lee, WM, 2001)	0.31
" Bioavailability assays, inoculated soil slurries, were conducted and both liquid- and sorbed-phase naphthalene concentrations were measured over time."	( Development of a kinetic basis for bioavailability of sorbed naphthalene in soil slurries. Park, JH; Voice, TC; Zhao, X, 2002)	0.77
" The bioavailability of many organic contaminants is controlled in part by the nature, magnitude, and rate of sorption/desorption processes."	( Biodegradation during contaminant transport in porous media: 6. Impact of sorption on coupled degradation-transport behavior. Brusseau, ML; Famisan, GB, 2003)	0.32
" The solubilization effect exceeded that of the reduced mass transfer coefficient, increasing the rate of absorption of vaporous naphthalene."	( Removal of vaporous naphthalene using polyoxyethylenated nonionic surfactants. Huang, HL; Lee, WM, 2003)	0.85
" To date, these studies have only considered bioavailability in a single soil type."	( Non-exhaustive extraction techniques (NEETs) for the prediction of naphthalene mineralisation in soil. Paton, GI; Patterson, CJ; Semple, KT, 2004)	0.56
" Potent and specific inhibitors of the CYP2A6 enzyme can be used in the future to increase nicotine bioavailability and thus make oral nicotine administration feasible in smoking cessation therapy."	( Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme. Juvonen, RO; Poso, A; Rahnasto, M; Raunio, H; Wittekindt, C, 2005)	0.33
" To investigate the roles of medium composition and metal bioavailability on these different degrees and patterns of inhibition, we assessed the impact of cadmium on naphthalene biodegradation by a newly isolated strain of Comamonas testosteroni in three chemically-defined minimal salts media (MSM): Tris-buffered MSM, PIPES-buffered MSM, and Bushnell-Haas medium."	( Medium composition affects the degree and pattern of cadmium inhibition of naphthalene biodegradation. Hoffman, DR; Okon, JL; Sandrin, TR, 2005)	0.75
" In addition, high adsorption capacity of PAHs by carbon nanotubes may add to their high environmental risks once released to the environment, and result in potential alteration of PAHs fate and bioavailability in the environment."	( Adsorption of polycyclic aromatic hydrocarbons by carbon nanomaterials. Xing, B; Yang, K; Zhu, L, 2006)	0.33
" Here we describe a gfp-bearing bioreporter that is sensitive to naphthalene (a poorly water soluble pollutant behaving like a large class of hydrophobic compounds), is suitable for use in chemical assays and bioavailability studies, and has detection limits comparable to lux-bearing bioreporters for higher efficiency detection strategies."	( Bioreporters: gfp versus lux revisited and single-cell response. Harms, H; Kohlmeier, S; Mancuso, M; Tecon, R; van der Meer, JR; Wells, M, 2007)	0.58
" The combined biological action was optimized in micellar and microemulsion systems able to increase the bioavailability of the hydrophobic aromatic pollutants."	( Combined action of a bacterial monooxygenase and a fungal laccase for the biodegradation of mono- and poly-aromatic hydrocarbons. Branciamore, S; Briganti, F; Caño, MF; Duchi, I; Giardina, P; Gullotto, A; Randazzo, D; Sannia, G; Scozzafava, A; Tilli, S, 2008)	0.35
"A rapid biological method for the determination of the bioavailability of naphthalene was developed and its value as an alternative to extraction-based chemical approaches demonstrated."	( Comparison of naphthalene bioavailability determined by whole-cell biosensing and availability determined by extraction with Tenax. Deepthike, U; Harms, H; Kohlmeier, S; Mancuso, M; Tecon, R; van der Meer, JR; Wells, M, 2008)	0.94
" Results indicate that non-linearity would not significantly affect bioavailability in low f(oc) geosorbents."	( Naphthalene and phenanthrene sorption to very low organic content diatomaceous earth: modeling implications for microbial bioavailability. Mittal, M; Rockne, KJ, 2009)	1.8
" Even for coals with high PAH content (approximately 4000 ppm total PAHs), a PAH-sensitive bacterial biosensor demonstrates nondetectable bioavailability as quantified, based on naphthalene as a test calibrant."	( Unlike PAHs from Exxon Valdez crude oil, PAHs from Gulf of Alaska coals are not readily bioavailable. Deepthike, HU; Harms, H; Short, J; Tecon, R; Van der Meer, JR; Van Kooten, G; Wells, M, 2009)	0.55
" The surface concentration as depicted using three-dimensional plots showed that there is occlusion of the aromatics (naphthalene and anthracene) within the soil micropores, thereby limiting their bioavailability and in the long run increasing their toxicity."	( Estimation of transport and degradation parameters for naphthalene and anthracene: influence of mass transfer on kinetics. Ogbeide, SE; Owabor, CN; Susu, AA, 2010)	0.82
" This study supports the use of bile fluorescence in Nile tilapia by fixed wavelength fluorescence and synchronous fluorescence spectrometry with non-normalized data as a simple method for screening bioavailability of these PAHs."	( Assessment of bile fluorescence patterns in a tropical fish, Nile tilapia (Oreochromis niloticus) exposed to naphthalene, phenanthrene, pyrene and chrysene using fixed wavelength fluorescence and synchronous fluorescence spectrometry. Hemachandra, CK; Pathiratne, A; Pathiratne, KA, 2010)	0.57
" Diffusion of VOC in the vapor-phase is much more efficient than in water and results in effective VOC transport and high bioavailability despite restricted mobility of bacteria in the vadose zone."	( Microbial growth with vapor-phase substrate. Hanzel, J; Harms, H; Thullner, M; Wick, LY, 2011)	0.37
" Bioavailability of contaminants for nutrition and toxicity has opposite consequences which may have resulted in quite different bacterial adaptation mechanisms; these may particularly interfere when a growth substrate causes toxicity at high bioavailability."	( Walking the tightrope of bioavailability: growth dynamics of PAH degraders on vapour-phase PAH. Hanzel, J; Harms, H; Thullner, M; Wick, LY, 2012)	0.38
"Sediment remediation techniques to limit the bioavailability of contaminants are of special interest due to related acute or chronic toxicities associated with sediment contaminants."	( Effect of reactive core mat application on bioavailability of hydrophobic organic compounds. Alshawabkeh, AN; Barbuto, SM; Meric, D; Sheahan, TC; Shine, JP, 2012)	0.38
" These inverse relationships may reflect a slower rate of absorption or a faster rate of expiration of benzene in the lung."	( Detection of DNA damage in workers exposed to JP-8 jet fuel. B'hymer, C; Butler, MA; Clark, JC; Gibson, RL; Krieg, EF; Marlow, KL; Mathias, PI; Singh, NP; Toennis, CA, 2012)	0.38
" We investigated whether root exudates could enhance desorption of residual pollutants, thus improving bioavailability and subsequent biodegradation potential."	( Root exudate enhanced contaminant desorption: an abiotic contribution to the rhizosphere effect. Hozalski, RM; LeFevre, GH; Novak, PJ, 2013)	0.39
" During enrichment on hydrocarbons, strain TG409(T) emulsified n-tetradecane and crude oil, and cells were found to be preferentially attached to oil droplets, indicating an ability by the strain to express cell surface amphiphilic substances (biosurfactants or bioemulsifiers) as a possible strategy to increase the bioavailability of hydrocarbons."	( Polycyclic aromatic hydrocarbon degradation of phytoplankton-associated Arenibacter spp. and description of Arenibacter algicola sp. nov., an aromatic hydrocarbon-degrading bacterium. Aitken, MD; Berry, D; Gutierrez, T; Mishamandani, S; Nichols, PD; Rhodes, G; Semple, KT; Whitman, WB, 2014)	0.4
"In this letter, we reported the design and synthesis of three potent, selective, and orally bioavailable 11β-HSD1 inhibitors labeled with (14)C: AMG 456 (1), AM-6949 (2), and AM-7715 (3)."	( Synthesis, in Vitro Covalent Binding Evaluation, and Metabolism of (14)C-Labeled Inhibitors of 11β-HSD1. Fan, P; He, X; Jiang, M; McMinn, DL; Monshouwer, M; Powers, JP; Rew, Y; Sun, D; Tu, H; Yan, X; Ye, Q, 2014)	0.4
" Ultimately a compound with oral bioavailability of 100% in rat, and a long half-life in plasma was obtained."	( The discovery and optimization of naphthalene-linked P2-P4 Macrocycles as inhibitors of HCV NS3 protease. Bowsher, M; Friborg, J; Hernandez, D; Hiebert, S; Klei, H; Knipe, JO; Li, R; McPhee, F; Meanwell, NA; Mosure, K; Rajamani, R; Scola, PM; Wang, AX; Wang, YK; Yu, F, 2018)	0.76
" A direct plant exposure assay in combination with an organic solvent extraction experiment was carried out in this study to investigate the bioavailability of polycyclic aromatic hydrocarbons (PAHs) with the application of pine needle biochars pyrolyzed under different temperatures (100, 300, 400, and 700 °C; referred as P100-P700 accordingly)."	( Reduced bioavailability and plant uptake of polycyclic aromatic hydrocarbons from soil slurry amended with biochars pyrolyzed under various temperatures. Chen, B; Wang, Y; Zhang, Y; Zhu, X, 2018)	0.48
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51
"The presence of surfactants may affect the bioavailability of polycyclic aromatic hydrocarbons."	( Antagonism or synergism? Responses of Hydrocharis dubia (Bl.) Backer to linear alkylbenzene sulfonate, naphthalene and their joint exposure. Chai, L; Wang, F; Wu, Z; Yang, L; Zhang, Y; Zhou, Y, 2020)	0.77

Excerpt	Relevance	Reference
" A 5-day-old calf dosed orally with 14C-propachlor excreted 70% dose in the urine as the cysteine conjugate; no mercapturic acid was detected."	( Evidence for the absence of cysteine S-conjugate N-acetyltransferase activity in the metabolism of propachlor, naphthalene, and dichlobanil in calves. Bakke, JE; Davison, KL; Larsen, GL, 1990)	0.49
" This suggests in vivo activation to a metabolic intermediate forming a complex with cerebral cytochrome P-450, which 2 hr after dosing is fully insensitive to stiripentol added to incubates."	( Ex vivo inhibition of rat brain cytochrome P-450 activity by stiripentol. Jenner, P; Mesnil, M; Testa, B, 1988)	0.27
" Appreciable quantities of 1- and 2-naphthol (7-20% of dose) and 1,2-dihydro-1-hydroxy-2-methylthionaphthalene (1-35% of dose) were in urine from rats dosed orally or intracecally with 1,2-dihydro-1-hydroxy-2-S-cysteinylnaphthalene and 1,2-dihydro-1-hydroxy-2-S-(N-acetyl)cysteinylnaphthalene."	( Catabolism of premercapturic acid pathway metabolites of naphthalene to naphthols and methylthio-containing metabolites in rats. Bakke, J; Gustafsson, B; Gustafsson, JA; Struble, C, 1985)	0.73
" Other organ weights were unaffected at any dosage level."	( Naphthalene toxicity in CD-1 mice: general toxicology and immunotoxicology. Anderson, AC; Barnes, DW; Borzelleca, JF; Condie, LW; Duke, SS; Hayes, JR; Holsapple, MP; Shopp, GM; White, KL, 1984)	1.71
" Dose-response curves based on chemical concentration and light intensity revealed that the order of phytotoxic strength was fluoranthene > pyrene > naphthalene."	( Photoinduced toxicity of three polycyclic aromatic hydrocarbons (fluoranthene, pyrene, and naphthalene) to the duckweed Lemna gibba L. G-3. Dixon, DG; Greenberg, BM; Huang, XD; McConkey, BJ; Ren, L, 1994)	0.71
" It was found that at the same dosage of 10 mg/kg/day, both AL01576 and AL04114 completely prevented all morphological and biochemical changes in the lenses of naphthalene-fed rats."	( Inhibition of naphthalene cataract in rats by aldose reductase inhibitors. Lou, MF; Xu, GT; York, B; Zigler, S, 1996)	0.85
" The prototypical PBPK model containing five lumped tissue compartments was developed to describe the uptake and metabolism of naphthalene by mice and rats dosed intraperitoneally (i."	( A preliminary physiologically based pharmacokinetic model for naphthalene and naphthalene oxide in mice and rats. Babish, JG; Quick, DJ; Shuler, ML; Sweeney, LM, )	0.58
" In contrast, deposition within dosed skin showed the reverse pattern."	( Dermal absorption and distribution of topically dosed jet fuels jet-A, JP-8, and JP-8(100). Brooks, JD; Budsaba, K; Monteiro-Riviere, NA; Riviere, JE; Smith, CE, 1999)	0.3
" In the prototype system using cells attached to glass dilution bottles, naphthalene dosing resulted in generation of a circulating metabolite from the "liver" compartment (based on H4IIE cells from a rat hepatoma) that caused cell death in the "lung" compartment (L2 cells from a rat lung), as well as depletion of glutathione in the L2 cells."	( Combining cell culture analogue reactor designs and PBPK models to probe mechanisms of naphthalene toxicity. Ghanem, A; Shuler, ML, )	0.59
" Studies of this CCA bioreactor presented here include mixing profiles, effect of reactor environment on cell viability and intracellular glutathione, naphthalene distribution profile, and initial naphthalene dosing studies."	( Characterization of a perfusion reactor utilizing mammalian cells on microcarrier beads. Ghanem, A; Shuler, ML, )	0.33
" We measured cysteinyl adducts of these metabolites in hemoglobin (Hb) and albumin (Alb) from F344 rats dosed with 100-800 mg naphthalene per kg body weight."	( Measurement of hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone after administration of naphthalene to F344 rats. Lindstrom, AB; Rappaport, SM; Troester, MA; Waidyanatha, S, 2002)	0.78
" The 8Q405 significantly reduced naphthalene contents in dosed silastic and skin indicating a direct interaction between additive and marker hydrocarbons."	( Comparative mixture effects of JP-8(100) additives on the dermal absorption and disposition of jet fuel hydrocarbons in different membrane model systems. Brooks, JD; Muhammad, F; Riviere, JE, 2004)	0.6
" A supralinear dose-response relationship was observed between urinary naphthols and naphthalene exposure."	( Dose-dependent production of urinary naphthols among workers exposed to jet fuel (JP-8). Egeghy, PP; Gibson, R; Rappaport, SM; Serdar, B, 2004)	0.55
" To study the prodrugs in Clara cells without the influence of hepatic naphthalene metabolism and circulating glutathione, dose-response and time-course studies were conducted with intrapulmonary airway explant cultures."	( Prevention of naphthalene-induced pulmonary toxicity by glutathione prodrugs: roles for glutathione depletion in adduct formation and cell injury. Buckpitt, AR; Nagasawa, HT; Phimister, AJ; Plopper, CG, 2005)	0.92
" Two of the compounds showed good activity in vivo in the STIB900 model for acute African trypanosomiasis; one gave 3/4 cures and the other gave 4/4 cures on ip dosage of 20 mg/kg for 4 days."	( Dicationic DNA-targeted antiprotozoal agents: naphthalene replacement of benzimidazole. Boykin, DW; Brun, R; Chackal-Catoen, S; Miao, Y; Wenzler, T; Wilson, WD, 2006)	0.59
" Probabilities are assigned to alternative model components, including the determination of human carcinogenicity, mode of action, the dosimetry measure for exposure, the mathematical form of the dose-response relationship, the experimental data set(s) used to fit the relationship, and the formula used for interspecies extrapolation."	( Methods for assessing uncertainty in fundamental assumptions and associated models for cancer risk assessment. Small, MJ, 2008)	0.35
" As specific health effect mechanisms and dose-response are obscured bythe complex composition of DE, the linkage from exposure to internal dose can presumably be improved by use of specific biomarkers and metabolites in blood, breath, or urine."	( Identification of surrogate measures of diesel exhaust exposure in a controlled chamber study. Funk, WE; Hubbard, HF; Madden, MC; Pleil, JD; Rappaport, SM; Sobus, JR, 2008)	0.35
" rhodesiense in vivo, curing three of four infected mice dosed intraperitoneally at 5 mg/kg x 4 days."	( Synthesis and antiprotozoal activities of dicationic bis(phenoxymethyl)benzenes, bis(phenoxymethyl)naphthalenes, and bis(benzyloxy)naphthalenes. Bakunov, SA; Bakunova, SM; Barzcz, T; Brun, R; Chen, H; Jones, SK; Kumar, EV; Patrick, DA; Tidwell, RR; Wenzler, T; Werbovetz, KA, 2009)	0.57
" Based on the current results, and with further work on characterising the dose-response and seasonal variation in this species, mud crabs have great potential as indicator species for water quality and ecosystem monitoring programs across tropical coastal regions of Australia."	( Investigation of the mud crab (Scylla serrata) as a potential bio-monitoring species for tropical coastal marine environments of Australia. Codi King, S; Humphrey, C; Mondon, J; Negri, A; van Oosterom, J, 2010)	0.36
" To obtain mechanistic insight into NA-induced nasal carcinogenesis, NA dose-response was characterized in nasal epithelium using a tumor-relevant endpoint."	( p53 codon 271 CGT to CAT mutant fraction does not increase in nasal respiratory and olfactory epithelia of rats exposed to inhaled naphthalene. Clewell, HJ; Dodd, DE; Gross, EA; Meng, F; Myers, MB; Parsons, BL; Wang, Y; Wong, BA, 2011)	0.57
"5ppm) and EtOH(500ppm) + NAA(10ppm)), was then applied to six diverse species of microalgae to determine if the treatment dosage was effective for other freshwater and marine green algae, cyanobacteria, coccolithophore, and diatoms."	( The effect of naphthalene-acetic acid on biomass productivity and chlorophyll content of green algae, coccolithophore, diatom, and cyanobacterium cultures. Chinnasamy, S; Das, KC; Hunt, RW, 2011)	0.73
" In this method, the sole substrate naphthalene is dosed passively via gaseous phase to liquid medium and the detection of growth is based on the automated measurement of turbidity using an absorbance reader."	( Simplified MPN method for enumeration of soil naphthalene degraders using gaseous substrate. Lappi, K; Lehtinen, T; Mikkonen, A; Suominen, L; Vaalama, A; Wallenius, K; Wickström, A, 2012)	0.91
" Hemolytic anemia was also found in G6PD-deficient mice at this dosage of naphthalene."	( Development of a novel mouse model of severe glucose-6-phosphate dehydrogenase (G6PD)-deficiency for in vitro and in vivo assessment of hemolytic toxicity to red blood cells. Fok, TF; Fung, KP; Gu, GJ; James, AE; Ko, CH; Li, CL; Li, K; Ng, PC; Wong, RP, 2011)	0.6
"The dose-response relationship for the induction of micronuclei (MN) and the impact of glutathione (GSH) detoxication on naphthalene-induced cytotoxicity and genotoxicity were investigated in human TK6 cells."	( Dose-response assessment of naphthalene-induced genotoxicity and glutathione detoxication in human TK6 lymphoblasts. Hernández, LG; Kedderis, GL; Recio, L; Shepard, KG, 2012)	0.88
" Field experiments performed in sediments where strain CJ2 was isolated showed nitrogenase activity in response to dosing with naphthalene."	( Role of nitrogen fixation in the autecology of Polaromonas naphthalenivorans in contaminated sediments. Hanson, BT; Jeon, CO; Madsen, EM; Yagi, JM, 2012)	0.58
"In dose-response analysis, regression analysis and hypothesis testing are the main tools of choice."	( Reconsidering sufficient and optimal test design in acute toxicity testing. Jager, T, 2014)	0.4
" The present studies characterized the dose-response relationships for naphthalene-induced glutathione (GSH) depletion, effects on cellular ATP, and cytotoxicity in cells from both target (lung, nasal epithelium) and non-target (liver) organs in vitro using cells from F-344 rats, B6C3F1 mice and humans."	( Cytotoxicity of naphthalene toward cells from target and non-target organs in vitro. Kedderis, GL; Recio, L; Shepard, KG, 2014)	0.98
" Male ICR mice were intraperitoneally dosed with olive oil (vehicle), and a low dose and a high dose (100 and 200 mg kg(-1) body wt, respectively) of naphthalene."	( NMR- and MS-based metabolomics: various organ responses following naphthalene intervention. Chung, MH; Liang, HJ; Lin, CY; Lin, MH; Ling, YS, 2014)	0.84
" We also conducted a dose-response analysis, based on the likely MoA, which suggests that the rat nasal MoA is not relevant in human respiratory tissues at typical environmental exposures."	( Hypothesis-based weight-of-evidence evaluation and risk assessment for naphthalene carcinogenesis. Bailey, LA; Kerper, LE; Nascarella, MA; Rhomberg, LR, 2016)	0.67
" The adsorption capacity (7210 μg g(-1)) of OWNS at the temperature of 298 K was observed for an initial naphthalene concentration of 25 mg L(-1) with contact time of 40 h, sorbent dosage of 1 g L(-1), and in neutral condition."	( Adsorption of naphthalene from aqueous solution onto fatty acid modified walnut shells. Dong, L; Sun, J; Yao, J; Zhu, M, 2016)	1.01
" The results showed that only compounds 5b and 5c met the criteria for subsequent testing to determine growth inhibition values (GI50) in dose-response studies."	( Synthesis and Evaluation of 2-Naphthaleno trans-Stilbenes and Cyanostilbenes as Anticancer Agents. Crooks, PA; Eoff, RL; Guzman, ML; Ketkar, A; Madadi, NR; Penthala, NR; Trujullo-Alonso, V, 2018)	0.48
" Water pipe smoking was linked to urinary OH-PAH metabolite in a dose-response function."	( Environmental and lifestyle factors affecting exposure to polycyclic aromatic hydrocarbons in the general population in a Middle Eastern area. Delgado-Saborit, JM; Faridi, S; Hassanvand, MS; Hoseini, M; Nabizadeh, R; Naddafi, K; Parmy, S; Rafiee, A; Yaghmaeian, K; Yunesian, M, 2018)	0.48
" Multiple linear regression analysis was used to analyze the relationship between the concentrations of 2-OH NAP and birth outcomes, and restricted cubic spline models were further used to examine the shapes of the dose-response association."	( Maternal urinary 2-hydroxynaphthalene and birth outcomes in Taiyuan, China. Cheng, L; Deng, Y; Duan, L; Li, J; Li, Y; Nie, J; Niu, Q; Perera, F; Tang, D; Yan, Z, 2018)	0.78
" Pulsing frequency as well as dosage concentration had a large impact on the degradation efficiency."	( Dosage concentration and pulsing frequency affect the degradation efficiency in simulated bacterial polycyclic aromatic hydrocarbon-degrading cultures. Kleindienst, S; Thompson, KJ; Vogel, AL; Zarfl, C, 2023)	0.91

Role	Description
volatile oil component	Any plant metabolite that is found naturally as a component of a volatile oil.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
environmental contaminant	Any minor or unwanted substance introduced into the environment that can have undesired effects.
carcinogenic agent	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
mouse metabolite	Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
apoptosis inhibitor	Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
[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
naphthalenes	Any benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
ortho-fused bicyclic arene
[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
naphthalene degradation (aerobic)	9	29
naphthalene degradation (anaerobic)	5	14
superpathway of aromatic compound degradation via 2-hydroxypentadienoate	50	95
naphthalene degradation to acetyl-CoA	11	38

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
thioredoxin reductase	Rattus norvegicus (Norway rat)	Potency	89.1251	0.1000	20.8793	79.4328	AID588453
phosphopantetheinyl transferase	Bacillus subtilis	Potency	89.1251	0.1413	37.9142	100.0000	AID1490
AR protein	Homo sapiens (human)	Potency	63.0957	0.0002	21.2231	8,912.5098	AID588515
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	15.2929	0.0030	41.6115	22,387.1992	AID1159555
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	28.4060	0.0008	17.5051	59.3239	AID1159527; AID1159531
pregnane X nuclear receptor	Homo sapiens (human)	Potency	31.6228	0.0054	28.0263	1,258.9301	AID720659
polyunsaturated fatty acid lipoxygenase ALOX12	Homo sapiens (human)	Potency	39.8107	1.0000	12.2326	31.6228	AID1452
parathyroid hormone/parathyroid hormone-related peptide receptor precursor	Homo sapiens (human)	Potency	4.4668	3.5481	19.5427	44.6684	AID743266
geminin	Homo sapiens (human)	Potency	1.2995	0.0046	11.3741	33.4983	AID624296
Spike glycoprotein	Severe acute respiratory syndrome-related coronavirus	Potency	11.2202	0.0096	10.5250	35.4813	AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Cytochrome P450 1A2	Homo sapiens (human)	IC50 (µMol)	700.0000	0.0001	1.7740	10.0000	AID241334
Cytochrome P450 2A6	Homo sapiens (human)	IC50 (µMol)	25.0017	0.0044	3.8895	10.0000	AID241172; AID420671
Cytochrome P450 2A5	Mus musculus (house mouse)	IC50 (µMol)	73.9803	1.0000	4.2025	9.7051	AID241174; AID420670
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
steroid catabolic process	Cytochrome P450 1A2	Homo sapiens (human)
porphyrin-containing compound metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
toxin biosynthetic process	Cytochrome P450 1A2	Homo sapiens (human)
post-embryonic development	Cytochrome P450 1A2	Homo sapiens (human)
alkaloid metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
regulation of gene expression	Cytochrome P450 1A2	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
dibenzo-p-dioxin metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 1A2	Homo sapiens (human)
lung development	Cytochrome P450 1A2	Homo sapiens (human)
methylation	Cytochrome P450 1A2	Homo sapiens (human)
monocarboxylic acid metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 1A2	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 1A2	Homo sapiens (human)
cellular respiration	Cytochrome P450 1A2	Homo sapiens (human)
aflatoxin metabolic process	Cytochrome P450 1A2	Homo sapiens (human)
hydrogen peroxide biosynthetic process	Cytochrome P450 1A2	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 1A2	Homo sapiens (human)
cellular response to cadmium ion	Cytochrome P450 1A2	Homo sapiens (human)
omega-hydroxylase P450 pathway	Cytochrome P450 1A2	Homo sapiens (human)
xenobiotic metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 2A6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2A6	Homo sapiens (human)
coumarin catabolic process	Cytochrome P450 2A6	Homo sapiens (human)
epoxygenase P450 pathway	Cytochrome P450 2A6	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
monooxygenase activity	Cytochrome P450 1A2	Homo sapiens (human)
iron ion binding	Cytochrome P450 1A2	Homo sapiens (human)
protein binding	Cytochrome P450 1A2	Homo sapiens (human)
electron transfer activity	Cytochrome P450 1A2	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 1A2	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Cytochrome P450 1A2	Homo sapiens (human)
enzyme binding	Cytochrome P450 1A2	Homo sapiens (human)
heme binding	Cytochrome P450 1A2	Homo sapiens (human)
demethylase activity	Cytochrome P450 1A2	Homo sapiens (human)
caffeine oxidase activity	Cytochrome P450 1A2	Homo sapiens (human)
aromatase activity	Cytochrome P450 1A2	Homo sapiens (human)
estrogen 16-alpha-hydroxylase activity	Cytochrome P450 1A2	Homo sapiens (human)
estrogen 2-hydroxylase activity	Cytochrome P450 1A2	Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activity	Cytochrome P450 1A2	Homo sapiens (human)
iron ion binding	Cytochrome P450 2A6	Homo sapiens (human)
coumarin 7-hydroxylase activity	Cytochrome P450 2A6	Homo sapiens (human)
enzyme binding	Cytochrome P450 2A6	Homo sapiens (human)
heme binding	Cytochrome P450 2A6	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Cytochrome P450 2A6	Homo sapiens (human)
arachidonic acid epoxygenase activity	Cytochrome P450 2A6	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
endoplasmic reticulum membrane	Cytochrome P450 1A2	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 1A2	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 1A2	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2A6	Homo sapiens (human)
cytoplasmic microtubule	Cytochrome P450 2A6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2A6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2A6	Homo sapiens (human)
virion membrane	Spike glycoprotein	Severe acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504749	qHTS profiling for inhibitors of Plasmodium falciparum proliferation	2011	Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043	Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID513076	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2433) mutant carrying nis96 transgene assessed as number of extra VC- cells in postembryonic stage at 250 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID29421	Partition coefficient (logP) (HPLC)	2000	Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15	ElogPoct: a tool for lipophilicity determination in drug discovery.
AID513078	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-4(n1162) mutant assessed as number of cell corpses in 4-fold stage of transgenic line-1 embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513053	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at comma stage of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513065	Antiapoptotic activity against hermaphroditic wild type Caenorhabditis elegans carrying smls26 transgene assessed as inhibition of male-specific CEM neurons death at 200 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID603957	Octanol-water partition coefficient, log P of the compound	2008	European journal of medicinal chemistry, Apr, Volume: 43, Issue:4	QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.
AID19424	Partition coefficient (logD7.4)	2001	Journal of medicinal chemistry, Jul-19, Volume: 44, Issue:15	ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.
AID512728	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx at 75 uM dissolved in water	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513083	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-1(e1735) mutant assessed as number of cell corpses in 4-fold stage of (smls111) transgenic embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513077	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-1(e1735) mutant assessed as number of cell corpses in 4-fold stage of transgenic line-1 embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513081	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-1(e1735) mutant assessed as number of cell corpses in 4-fold stage of transgenic line-3 embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513060	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at comma 4-fold of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1331299	1-octanol/D2O distribution coefficient, log D of the compound at pH 7.4 by 1H NMR spectroscopic analysis
AID513064	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at comma 4-fold of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1081379	Repellent activity against Eysarcoris ventralis assessed as reduction in number of bugs at 0.003 umol measured after 30 min	2010	Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5	3-(4-Methylfuran-3-yl)propan-1-ol: a white-spotted Stinkbug ( Eysarcoris ventralis ) repellent produced by an endophyte isolated from green foxtail.
AID513067	Antiapoptotic activity against hermaphroditic Caenorhabditis elegans ced-3(n2433) mutant carrying smls26 transgene assessed as inhibition of male-specific CEM neurons death at 200 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1125765	Partition coefficient, log P of the compound in methanol-water mixture at 0.25 mg/ml by HPLC analysis	2014	Bioorganic & medicinal chemistry, Apr-15, Volume: 22, Issue:8	Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands.
AID513062	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at 1.5-fold stage of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512727	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx at 50 uM dissolved in water	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513073	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2433) mutant carrying nis96 transgene assessed as number of extra VC- cells in postembryonic stage at 200 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512726	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2433) mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513066	Antiapoptotic activity against hermaphroditic Caenorhabditis elegans ced-3(n2438) mutant carrying smls26 transgene assessed as inhibition of male-specific CEM neurons death at 200 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512729	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx at 100 uM dissolved in water	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513085	Octanol-water partition coefficient, log P of the compound	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1331301	n-Octanol/water partition coefficient, log P of the compound by HPLC method
AID19262	Aqueous solubility	2000	Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11	Prediction of drug solubility from Monte Carlo simulations.
AID513080	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-4(n1162) mutant assessed as number of cell corpses in 4-fold stage of transgenic line-2 embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID19427	HPLC capacity factor (k)	2000	Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15	ElogPoct: a tool for lipophilicity determination in drug discovery.
AID376055	Antifungal activity against Microsporum canis C 112 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID203473	Binding constant against bovine serum albumin	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography.
AID1331300	Lipophilicity, log D of the compound at pH 7.4 by HPLC method
AID376050	Antifungal activity against Saccharomyces cerevisiae ATCC 9763 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID376051	Antifungal activity against Cryptococcus neoformans ATCC 32264 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID512733	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx kept in drug exposed air tight plastic storage box at 0.6 g/L in air	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID241334	Inhibitory concentration against recombinant human cytochrome P450 1A2	2005	Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11	Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors.
AID512741	Antiapoptotic activity against Caenorhabditis elegans ced-4(n2273) mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513068	Antiapoptotic activity against hermaphroditic wild type Caenorhabditis elegans carrying smls26 transgene assessed as inhibition of male-specific CEM neurons death at 250 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513054	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at 1.5 fold stage of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID460406	Partition coefficient, log P by RP-HPLC	2010	Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3	Conjugates of desferrioxamine B (DFOB) with derivatives of adamantane or with orally available chelators as potential agents for treating iron overload.
AID460407	Partition coefficient, log P by shake flask method	2010	Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3	Conjugates of desferrioxamine B (DFOB) with derivatives of adamantane or with orally available chelators as potential agents for treating iron overload.
AID513063	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at 2-fold stage of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID242975	Ratio of IC50 for human CYP2A6 to that of mouse CYP2A5 was determined	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID513084	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-4(n1162) mutant assessed as number of cell corpses in 4-fold stage of (smls111) transgenic embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513050	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at 1.5 fold stage of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513074	Antiapoptotic activity against Caenorhabditis elegans carrying nis96 transgene assessed as number of extra VC- cells in postembryonic stage at 250 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID241174	Inhibitory concentration against mouse cytochrome P450 2A5	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID1171393	Oxidative metabolism in human liver microsomes assessed as protein covalent binding measured per mg protein at 10 uM after 1 hr in presence of NADPH	2014	ACS medicinal chemistry letters, Nov-13, Volume: 5, Issue:11	Synthesis, in Vitro Covalent Binding Evaluation, and Metabolism of (14)C-Labeled Inhibitors of 11β-HSD1.
AID512740	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2436) L269 mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512730	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx at 125 uM dissolved in water	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512742	Antiapoptotic activity against Caenorhabditis elegans ced-8(n1891) mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512735	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx at 100 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID376049	Antifungal activity against Candida albicans ATCC 10231 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID1081376	Repellent activity against Eysarcoris ventralis assessed as reduction in number of bugs at 1 umol measured after 30 min	2010	Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5	3-(4-Methylfuran-3-yl)propan-1-ol: a white-spotted Stinkbug ( Eysarcoris ventralis ) repellent produced by an endophyte isolated from green foxtail.
AID24226	Partition coefficient (logP)	1985	Journal of medicinal chemistry, Sep, Volume: 28, Issue:9	Quantitative evaluation of the beta 2-adrenoceptor affinity of phenoxypropanolamines and phenylethanolamines.
AID513059	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at 2-fold stage of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID376046	Antifungal activity against Trichophyton mentagrophytes ATCC by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID376052	Antifungal activity against Aspergillus flavus ATCC 9170 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID376054	Antifungal activity against Aspergillus niger ATCC 9029 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID513069	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant carrying smls26 transgene assessed as survival of CEM neurons at 250 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512739	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2447) S446L mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID420671	Inhibition of human CYP2A6	2009	European journal of medicinal chemistry, May, Volume: 44, Issue:5	Exploring QSAR and QAAR for inhibitors of cytochrome P450 2A6 and 2A5 enzymes using GFA and G/PLS techniques.
AID513058	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at 1.5-fold stage of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513079	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-1(e1735) mutant assessed as number of cell corpses in 4-fold stage of transgenic line-2 embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID23676	Partition coefficient (logP)	1981	Journal of medicinal chemistry, Nov, Volume: 24, Issue:11	Acidic epinephrine analogues derived from 1H, 3H-2,1,3-benzothiadiazole 2,2-dioxide and from trifluoromethanesulfonanilide. A new synthesis of 1H,3H-2,1,3-benzothiadiazole 2,2-dioxide.
AID513052	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at 4-fold stage of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1081377	Repellent activity against Eysarcoris ventralis assessed as reduction in number of bugs at 0.1 umol measured after 30 min	2010	Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5	3-(4-Methylfuran-3-yl)propan-1-ol: a white-spotted Stinkbug ( Eysarcoris ventralis ) repellent produced by an endophyte isolated from green foxtail.
AID460408	Partition coefficient, log P in presence of Fe(3+) by RP-HPLC	2010	Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3	Conjugates of desferrioxamine B (DFOB) with derivatives of adamantane or with orally available chelators as potential agents for treating iron overload.
AID513047	Inhibition of human caspase-3-mediated apoptosis assessed as appearance of [35]S methionine-labeled PARP cleavage product at 100 uM after 2 hrs by fluorescence assay	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513048	Inhibition of human caspase-3-mediated apoptosis assessed as Ac-DEVD-7-amino-4-methylcoumarin cleavage product at 100 uM by fluorescence assay	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID376045	Antifungal activity against Microsporum gypseum C 115 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID27580	Partition coefficient (logP)	2000	Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15	ElogPoct: a tool for lipophilicity determination in drug discovery.
AID513056	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at 4-fold stage of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1179091	Retention time of the compound in 75% MeOH by HPLC analysis	2014	Bioorganic & medicinal chemistry, Jul-15, Volume: 22, Issue:14	Sulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation.
AID513075	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant carrying nis96 transgene assessed as number of extra VC- cells in postembryonic stage at 250 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513046	Inhibition of Caenorhabditis elegans CED-3-mediated apoptosis assessed as [35]S methionine labeled CED-9 cleavage product at 100 uM after 2 hrs by fluorescence assay	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1179092	Lipophilicity, log K of the compound by HPLC analysis	2014	Bioorganic & medicinal chemistry, Jul-15, Volume: 22, Issue:14	Sulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation.
AID513072	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant carrying nis96 transgene assessed as number of extra VC- cells in postembryonic stage at 200 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID241172	Inhibitory concentration against human cytochrome P450 2A6	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID1149946	Inhibition of alpha-chymotrypsin (unknown origin)	1977	Journal of medicinal chemistry, Nov, Volume: 20, Issue:11	Quantitative structure-activity relationship of chymotrypsin-ligand interactions.
AID376053	Antifungal activity against Aspergillus fumigatus ATCC 26934 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID644414	Lipophilicity, log D of the compound in octanol-water at pH 7.4 by reverse-phase HPLC analysis	2012	Bioorganic & medicinal chemistry, Feb-15, Volume: 20, Issue:4	QSAR study and synthesis of new phenyltropanes as ligands of the dopamine transporter (DAT).
AID513051	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at 2-fold stage of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513070	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2433) mutant carrying smls26 transgene assessed as survival of CEM neurons at 250 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513049	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at comma stage of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512731	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx at 150 uM dissolved in water	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID23714	Partition coefficient (logP)	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography.
AID1371097	Octanol-water partition coefficient, log P of the compound at 1 mg by RP-HPLC analysis	2017	Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8	Adamantyl- and other polycyclic cage-based conjugates of desferrioxamine B (DFOB) for treating iron-mediated toxicity in cell models of Parkinson's disease.
AID513057	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at comma stage of embryo at 200 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512734	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells kept in anterior pharynx in gaseous compound exposed air tight plastic storage box at 4 uM	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512743	Antiapoptotic activity against Caenorhabditis elegans ced-9(n1950) mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID376047	Antifungal activity against Trichophyton rubrum C 113 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID420670	Inhibition of mouse CYP2A5	2009	European journal of medicinal chemistry, May, Volume: 44, Issue:5	Exploring QSAR and QAAR for inhibitors of cytochrome P450 2A6 and 2A5 enzymes using GFA and G/PLS techniques.
AID512737	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID512736	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as number of extra cells in anterior pharynx compound dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513071	Antiapoptotic activity against wild type Caenorhabditis elegans carrying nis96 transgene assessed as number of extra VC- cells in postembryonic stage at 200 mM after 2 hrs	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1818269	Antifungal activity against Candida albicans SC5314 assessed as reduction in fungal growth incubated for 72 hrs by CLSI protocol based broth microdilution method
AID512738	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) G474R mutant assessed as number of extra cells in anterior pharynx L3 and L4 larvae at 200 mM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID1081378	Repellent activity against Eysarcoris ventralis assessed as reduction in number of bugs at 0.01 umol measured after 30 min	2010	Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5	3-(4-Methylfuran-3-yl)propan-1-ol: a white-spotted Stinkbug ( Eysarcoris ventralis ) repellent produced by an endophyte isolated from green foxtail.
AID23978	Capacity ratio (log k'w)	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography.
AID212400	Toxicity determined using Tadpole Narcosis Test	1991	Journal of medicinal chemistry, May, Volume: 34, Issue:5	Using theoretical descriptors in quantitative structure-activity relationships: some toxicological indices.
AID512732	Antiapoptotic activity against Caenorhabditis elegans ced-3(n2438) mutant assessed as increase in number of extra cells in anterior pharynx kept in drug exposed air tight plastic storage box at 0.06 g/L in air	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513055	Antiapoptotic activity against wild-type Caenorhabditis elegans assessed as reduction in number of cell cropses at 2-fold stage of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID376048	Antifungal activity against Epidermophyton floccosum C 114 by agar dilution method	1999	Journal of natural products, Oct, Volume: 62, Issue:10	In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.
AID513082	Suppression of activated CED-3-induced apoptosis expressed in Caenorhabditis elegans ced-4(n1162) mutant assessed as number of cell corpses in 4-fold stage of transgenic line-3 embryo in absence of CED-4	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
AID513061	Antiapoptotic activity against Caenorhabditis elegans engulfment-deffective ced-1(e1735) mutant assessed as reduction in number of cell cropses at comma stage of embryo at 250 uM dissolved in soybean oil	2006	Nature chemical biology, Jun, Volume: 2, Issue:6	The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	492 (19.45)	18.7374
1990's	249 (9.84)	18.2507
2000's	751 (29.68)	29.6817
2010's	887 (35.06)	24.3611
2020's	151 (5.97)	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	5 (0.19%)	5.53%
Reviews	53 (2.00%)	6.00%
Case Studies	35 (1.32%)	4.05%
Observational	0 (0.00%)	0.25%
Other	2,557 (96.49%)	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
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.	4.02	4	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.	9.21	5	0	trichlorobenzene
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.	1.95	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.	2.59	2	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
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.	2.75	3	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.	3.37	7	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	2.44	2	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	9.5	7	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	8.26	6	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.	2.1	1	0	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.	3.11	5	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
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.	2.08	1	0	arsenic oxoacid	Escherichia coli metabolite
beta-alanine [no description available]	1.93	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzaldehyde [no description available]	2.72	3	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	8.19	105	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.	8.23	6	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.	4.35	6	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
2,3-dihydroxybiphenyl 2,3-dihydroxybiphenyl: structure in first source. biphenyl-2,3-diol : A member of the class of hydroxybiphenyls that is 1,1'-biphenyl substituted by hydroxy groups at positions 2 and 3.	7.01	1	0	catechols; hydroxybiphenyls
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)	8.16	5	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.	3.07	1	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.	1.92	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	2.44	2	0	amino-acid anion
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.	2.93	4	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
catechol [no description available]	4.03	14	0	catechols	allelochemical; genotoxin; plant 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).	5.87	30	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	3.35	7	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	9.83	10	0	coumarins	fluorescent dye; human metabolite; plant metabolite
2-cresol 2-cresol: RN given refers to parent cpd. o-cresol : A cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene.	3.48	2	0	cresol	human xenobiotic 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).	10.52	22	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
3-methylcatechol 3-methylbenzene-1,2-diol: structure in first source. dihydroxytoluene : Any hydroxytoluene that has two hydroxy substituents. 3-methylcatechol : A methylcatechol carrying a methyl substituent at position 3. It is a xenobiotic metabolite produced by some bacteria capable of degrading nitroaromatic compounds present in pesticide-contaminated soil samples.	2.01	1	0	methylcatechol	bacterial xenobiotic metabolite
3-cresol 3-cresol: RN given refers to parent cpd. m-cresol : A cresol with the methyl substituent at position 3. It is a minor urinary metabolite of toluene.	3.07	1	0	cresol	human xenobiotic 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.	2.92	4	0	alkane	xenobiotic
1,2-dihydroxy-1,2-dihydronaphthalene 1,2-dihydroxy-1,2-dihydronaphthalene: naphthalene metabolite; RN given refers to cpd without isomeric designation. 1,2-dihydronaphthalene-1,2-diol : A member of the class of naphthalenediols that is 1,2-dihydronaphthalene substituted by hydroxy groups at positions 1 and 2 respectively.	2.4	2	0	dihydronaphthalenes; naphthalenediols	bacterial xenobiotic metabolite; mouse 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.	7.78	3	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
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.	3.69	10	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2	1	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
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.	2.03	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
dibenzofuran Dibenzofurans: Compounds that include the structure of dibenzofuran.. dibenzofurans : Any organic heterotricyclic compound based on a dibenzofuran skeleton and its substituted derivatives thereof.. dibenzofuran : A mancude organic heterotricyclic parent that consists of a furan ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	3.56	8	0	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
cytosine [no description available]	2.72	3	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
alanine [no description available]	2	1	0	alpha-amino acid; amino acid zwitterion	fundamental metabolite
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.	3.13	5	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	2.03	1	0	alpha-diketone	Escherichia coli 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.	3.4	7	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	8.31	6	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
formamide formimidic acid : A carboximidic acid that is formic acid in which the carbonyl oxygen is replaced by an imino group.. primary carboxamide : A carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2.	2.49	2	0	carboximidic acid; formamides; monocarboxylic acid amide; one-carbon compound	solvent
hexachlorocyclohexane Lindane: An organochlorine insecticide made up of greater than 99% gamma-Hexachlorocyclohexane. It has been used as a pediculicide and scabicide, and shown to cause cancer.. beta-hexachlorocyclohexane : The beta-isomer of hexachlorocyclohexane.	2	1	0	chlorocyclohexane
glutaconyl-coenzyme a [no description available]	2.15	1	0
glycine [no description available]	3.06	5	0	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
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.13	1	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
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.	2.6	1	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	2.88	4	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
homogentisic acid Homogentisic Acid: Dihydroxyphenylacetic acid with hydroxyls at the 2 and 5 positions of the phenyl ring.. homogentisic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions.	2.08	1	0	dihydroxyphenylacetic acid; hydroquinones	human metabolite; plant metabolite
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.	4.47	22	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.37	2	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.	1.97	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
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.68	3	0	imidazole
indole [no description available]	4.01	14	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.	2.84	4	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..	1.98	1	0	diatomic iodine	nutrient
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.	2.05	1	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
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	2.11	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.	4.92	12	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.	2.08	1	0	cyclitol; hexol
melatonin [no description available]	3.81	3	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
acetanilide acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.	2.69	3	0	acetamides; anilide	analgesic
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.	3.94	12	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.	2.49	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
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.37	2	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.81	11	0	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.	2.44	2	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)	2.42	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	7.11	1	0	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
n,n-dimethylaniline N,N-dimethylaniline: RN given refers to parent cpd; structure. dimethylaniline : A methylaniline carrying at least two methyl groups.. N,N-dimethylaniline : A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.	2.95	4	0	dimethylaniline; tertiary amine
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.	4.03	4	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2.04	1	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse 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.	2.04	1	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.	4.01	4	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.	1.96	1	0	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
parathion [no description available]	3.51	2	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; avicide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; mouse metabolite
pentachlorophenol PENTA: structure given in first source	2.96	4	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	10.92	212	1	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	5.72	26	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.	2.03	1	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.	2.37	2	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.	2.48	2	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	7.04	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.	7.76	3	0	benzenedicarboxylic acid	human xenobiotic metabolite
picolinic acid picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206. picolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.	2.46	2	0	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
diphosphoric acid diphosphoric acid : An acyclic phosphorus acid anhydride obtained by condensation of two molecules of phosphoric acid.	2.08	1	0	acyclic phosphorus acid anhydride; phosphorus oxoacid	Escherichia coli 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.	2.02	1	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.	4.01	4	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.	1.93	1	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	2.74	3	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	4.83	10	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	2.03	1	0	benzenetriol; phenolic donor	plant 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.	2.73	3	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.	2.42	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.	2.21	1	0	sulfur oxide; sulfur oxoanion
selenious acid Selenious Acid: A selenium compound with the molecular formula H2SO3. It used as a source of SELENIUM, especially for patients that develop selenium deficiency following prolonged PARENTERAL NUTRITION.	1.96	1	0	selenium oxoacid
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.33	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermine [no description available]	2.02	1	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
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.	2.96	4	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
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.	2.49	2	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
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.	2.04	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymine [no description available]	7.02	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.	7.94	81	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethylamine [no description available]	2	1	0	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	4.45	21	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.	2.41	1	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.	3.26	6	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).	2.03	1	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	2.02	1	0	xanthine	Saccharomyces cerevisiae metabolite
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	3.75	3	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.05	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) 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.	2.08	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
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
2,4,6-tribromophenol [no description available]	2.04	1	0	bromophenol	environmental contaminant; fungicide; marine metabolite
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.	4.23	5	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
4-(2,4-dichlorophenoxy)butyric acid 4-(2,4-dichlorophenoxy)butyric acid: structure. 2,4-DB : A monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a 2,4-dichlorophenoxy group. A selective post-emergence herbicide.	2.05	1	0	aromatic ether; monocarboxylic acid; organochlorine compound	agrochemical; phenoxy herbicide; synthetic auxin
2-aminofluorene [no description available]	1.93	1	0
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.	1.99	1	0	alkanethiol; primary alcohol	geroprotector
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.	3.76	3	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
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.	2.11	1	0	phenols	environmental contaminant
phenytoin [no description available]	2	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
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.	2.03	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	2	1	0	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
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.	7.91	4	0	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
salophen salophen: structure given in first source	7.21	1	0	carbonyl compound
albuterol Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).	1.96	1	0	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic
alprazolam Alprazolam: A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of PANIC DISORDERS, with or without AGORAPHOBIA, and in generalized ANXIETY DISORDERS. (From AMA Drug Evaluations Annual, 1994, p238). alprazolam : A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.	2	1	0	organochlorine compound; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA agonist; muscle relaxant; sedative; xenobiotic
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.	2	1	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
ambroxol Ambroxol: A metabolite of BROMHEXINE that stimulates mucociliary action and clears the air passages in the respiratory tract. It is usually administered as the hydrochloride.	7.02	1	0	aromatic amine
theophylline [no description available]	2.71	3	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
amiodarone Amiodarone: An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.. amiodarone : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.	2	1	0	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug
amlodipine Amlodipine: A long-acting dihydropyridine calcium channel blocker. It is effective in the treatment of ANGINA PECTORIS and HYPERTENSION.. amlodipine : A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.	2	1	0	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
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.	2.41	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.	2.38	2	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]	3.53	8	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
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.	7.4	2	0	azobenzenes
barbital 5,5-diethylbarbituric acid : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).	2	1	0	barbiturates	drug allergen
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.43	2	0	benzamides
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.	6.73	43	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzocaine Benzocaine: A surface anesthetic that acts by preventing transmission of impulses along NERVE FIBERS and at NERVE ENDINGS.. dextran sulfate sodium : An organic sodium salt of dextran sulfate. It induces colitis in mice.. benzocaine : A benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina.	2	1	0	benzoate ester; substituted aniline	allergen; antipruritic drug; sensitiser; topical anaesthetic
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	3.27	6	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
betaxolol [no description available]	1.96	1	0	propanolamine	antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
bay h 4502 bifonazole : A racemate comprising equimolar amounts of R- and S-bifonazole. It is a broad spectrum antifungal drug used for the treatment of fungal skin and nail infections.. 1-[biphenyl-4-yl(phenyl)methyl]imidazole : A member of the class of imidazoles carrying an alpha-(biphenyl-4-yl)benzyl substituent at position 1.	2.69	3	0	biphenyls; imidazoles
bromazepam Bromazepam: One of the BENZODIAZEPINES that is used in the treatment of ANXIETY DISORDERS.	2.69	3	0	organic molecular entity
caffeine [no description available]	3.27	6	0	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.	2.41	2	0	aromatic ether; nitrile; polyether; tertiary amino compound
camphor, (+-)-isomer [no description available]	4.83	10	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	7.93	4	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
carbamazepine epoxide carbamazepine epoxide: metabolite of carbamazepine; RN given refers to unlabeled cpd. carbamazepine-10,11-epoxide : An epoxide and metabolite of carbamazepine.	1.99	1	0	dibenzoazepine; epoxide; ureas	allergen; drug metabolite; marine xenobiotic metabolite
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.	1.96	1	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
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.	3.45	7	0	quaternary ammonium ion
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	2.08	1	0	pyridinium ion
chloral hydrate [no description available]	2.01	1	0	aldehyde hydrate; ethanediol; organochlorine compound	general anaesthetic; mouse metabolite; sedative; xenobiotic
chlorambucil Chlorambucil: A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed). chlorambucil : A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.	2.69	3	0	aromatic amine; monocarboxylic acid; nitrogen mustard; organochlorine compound; tertiary amino compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	2	1	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
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.	2.66	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.	2.95	4	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
chlorthalidone Chlorthalidone: A benzenesulfonamide-phthalimidine that tautomerizes to a BENZOPHENONES form. It is considered a thiazide-like diuretic.	2	1	0	isoindoles; monochlorobenzenes; sulfonamide
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
eucalyptol [no description available]	2.07	1	0
clenbuterol Clenbuterol: A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma.. clenbuterol : A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.	1.96	1	0	amino alcohol; dichlorobenzene; ethanolamines; primary arylamine; secondary amino compound; substituted aniline	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent
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.	2	1	0	clonidine; imidazoline
clotrimazole [no description available]	2.41	2	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.69	3	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
cyclothiazide cyclothiazide: inhibits the desensitization of AMPA-type receptors; structure. cyclothiazide : 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted at positions 3, 5 and 6 by a 2-norbornen-5-yl group, chlorine, and a sulfonamide group, respectively. A thiazide diuretic, it has been used in the management of hypertension and oedema.	2	1	0	benzothiadiazine	antihypertensive agent; diuretic
dapi DAPI: RN given refers to parent cpd.	2.06	1	0	indoles	fluorochrome
deferiprone Deferiprone: A pyridone derivative and iron chelator that is used in the treatment of IRON OVERLOAD in patients with THALASSEMIA.. deferiprone : A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.	2.05	1	0	4-pyridones	iron chelator; protective agent
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	2.49	2	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	2.41	2	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
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.	2.02	1	0	primary amine
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.	2.69	3	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diazinon Diazinon: A cholinesterase inhibitor that is used as an organothiophosphorus insecticide.. diazinon : A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.	2.76	3	0	organic thiophosphate; pyrimidines	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; nematicide; xenobiotic
dibenzothiophene dibenzothiophene : A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	3.41	7	0	dibenzothiophenes; mancude organic heterotricyclic parent	keratolytic drug
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	2.02	1	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
dichlobanil 2,6-dichlorobenzonitrile : A nitrile that is benzonitrile which is substituted by chlorines at positions 2 and 6. A cellulose synthesis inhibitor, it is used as a pre-emergent and early post-emergent herbicide.	6.97	1	0	dichlorobenzene; nitrile	agrochemical; cellulose synthesis inhibitor; environmental contaminant; herbicide; 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.	2.17	1	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
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	2	1	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
dichlorvos Dichlorvos: An organophosphorus insecticide that inhibits ACETYLCHOLINESTERASE.. dichlorvos : An alkenyl phosphate that is the 2,2-dichloroethenyl ester of dimethyl phosphate.	2.7	3	0	alkenyl phosphate; dialkyl phosphate; organochlorine acaricide; organophosphate insecticide	anthelminthic drug; antibacterial agent; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
pentetic acid Pentetic Acid: An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.	2.08	1	0	pentacarboxylic acid	copper chelator
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	2.4	2	0	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
benzophenone benzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.	3.66	9	0	benzophenones	photosensitizing agent; plant metabolite
disopyramide Disopyramide: A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties.. disopyramide : A monocarboxylic acid amide that is butanamide substituted by a diisopropylamino group at position 4, a phenyl group at position 2 and a pyridin-2-yl group at position 2. It is used as a anti-arrhythmia drug.	2	1	0	monocarboxylic acid amide; pyridines; tertiary amino compound	anti-arrhythmia drug
stallimycin [no description available]	3.16	1	0
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.	2.42	2	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
endosulfan Endosulfan: A polychlorinated compound used for controlling a variety of insects. It is practically water-insoluble, but readily adheres to clay particles and persists in soil and water for several years. Its mode of action involves repetitive nerve-discharges positively correlated to increase in temperature. This compound is extremely toxic to most fish. (From Comp Biochem Physiol (C) 1993 Jul;105(3):347-61). endosulfan : A cyclic sulfite ester that is 1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine 3-oxide substituted by chloro groups at positions 6, 7, 8, 9, 10 and 10.	1.99	1	0	cyclic sulfite ester; cyclodiene organochlorine insecticide	acaricide; agrochemical; GABA-gated chloride channel antagonist; persistent organic pollutant
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.	3.49	2	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
fenbufen fenbufen: structure; RN given refers to parent cpd	2	1	0	4-oxo monocarboxylic acid; biphenyls	non-steroidal anti-inflammatory drug
flecainide Flecainide: A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial ARRHYTHMIAS and TACHYCARDIAS.. flecainide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid with the primary amino group of piperidin-2-ylmethylamine. An antiarrhythmic agent used (in the form of its acetate salt) to prevent and treat tachyarrhythmia (abnormal fast rhythm of the heart).	2	1	0	aromatic ether; monocarboxylic acid amide; organofluorine compound; piperidines	anti-arrhythmia drug
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.	2.69	3	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	2	1	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	2.03	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	3.12	5	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
guaiazulene guaiazulene: structure	2.01	1	0	sesquiterpene
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.53	2	0	carboxamidine; guanidines; one-carbon compound
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.74	3	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	1.96	1	0	barbiturates
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.	2.47	2	0	phenanthridines	fluorochrome; intercalator
hydralazine Hydralazine: A direct-acting vasodilator that is used as an antihypertensive agent.. hydralazine : The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent.	1.98	1	0	azaarene; hydrazines; ortho-fused heteroarene; phthalazines	antihypertensive agent; vasodilator agent
hydroxyurea [no description available]	1.99	1	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.41	2	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.	2.71	3	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.71	3	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
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.	7.7	3	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
indoprofen Indoprofen: A drug that has analgesic and anti-inflammatory properties. Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p21). indoprofen : A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.	2	1	0	gamma-lactam; isoindoles; monocarboxylic acid	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
iodoacetamide [no description available]	1.96	1	0
iproniazid [no description available]	1.93	1	0	carbohydrazide; pyridines
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).	2.62	3	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.	3.81	3	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.	1.96	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.42	2	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
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	1	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
kinetin Kinetin: A furanyl adenine found in PLANTS and FUNGI. It has plant growth regulation effects.. cytokinin : A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.. kinetin : A member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group.	7.67	3	0	6-aminopurines; furans	cytokinin; geroprotector
loratadine Loratadine: A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.. loratadine : A benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders.	2	1	0	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	2.69	3	0	benzodiazepine
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	1.98	1	0	diester; ethyl ester; organic thiophosphate
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	3.18	6	0	nitrogen mustard; organochlorine compound	alkylating agent
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.04	1	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
metaproterenol Metaproterenol: A beta-2 adrenergic agonist used in the treatment of ASTHMA and BRONCHIAL SPASM.. orciprenaline : A racemate composed of equimolar amounts of (R)- and (S)-orciprenaline. Used (as its sulfate salt) to relax the airway muscles and improve breathing for patients suffering from asthma or bronchitis.. 5-[1-hydroxy-2-(isopropanylamino)ethyl]benzene-1,3-diol : A member of the class of resorcinols bearing an additional 1-hydroxy-2-(isopropanylamino)ethyl substituent at position 5 of resorcinol itself.	1.96	1	0	aralkylamino compound; phenylethanolamines; resorcinols; secondary alcohol; secondary amino compound
methyl parathion Methyl Parathion: The methyl homolog of parathion. An effective, but highly toxic, organothiophosphate insecticide and cholinesterase inhibitor.. parathion-methyl : A C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4.	7.05	1	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; genotoxin
metoclopramide Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.	2	1	0	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	2	1	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
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.	2.73	3	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	2.05	1	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
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.	2	1	0	aromatic ether; primary amino compound	anti-arrhythmia drug
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	2	1	0	organic molecular entity	metabolite
deet N,N-diethyl-m-toluamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of m-toluic acid with the nitrogen of diethylamine. First developed by the U.S. Army in 1946 for use by military personnel in insect-infested areas, it is the most widely used insect repellent worldwide.	7.5	2	0	benzamides; monocarboxylic acid amide	environmental contaminant; insect repellent; xenobiotic
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	2	1	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.69	3	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nizatidine [no description available]	2	1	0	1,3-thiazoles; C-nitro compound; carboxamidine; organic sulfide; tertiary amino compound	anti-ulcer drug; cholinergic drug; H2-receptor antagonist
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.	2.1	1	0	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
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.	2	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
1,2-cyclohexanediamine 1,2-cyclohexanediamine: RN given refers to cpd without isomeric designation	2.08	1	0	primary aliphatic amine
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.	2	1	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; 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).	7.94	4	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
4-chlorophenol 4-chlorophenol: used as a root canal irrigant. 4-chlorophenol : A monochlorophenol substituted at the pare position by a chlorine atom.	2.4	2	0	monochlorophenol
4-dichlorobenzene dichlorobenzene : Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.. 1,4-dichlorobenzene : A dichlorobenzene carrying chloro groups at positions 1 and 4.	11.29	28	0	dichlorobenzene	insecticide
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	1.98	1	0	aromatic amine
pentoxifylline [no description available]	2.41	2	0	oxopurine
perphenazine Perphenazine: An antipsychotic phenothiazine derivative with actions and uses similar to those of CHLORPROMAZINE.. perphenazine : A phenothiazine derivative in which the phenothiazine tricycle carries a chloro substituent at the 2-position and a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at N-10.	2	1	0	N-(2-hydroxyethyl)piperazine; N-alkylpiperazine; organochlorine compound; phenothiazines	antiemetic; dopaminergic antagonist; phenothiazine antipsychotic drug
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2	1	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
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.	2.67	3	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
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.	1.95	1	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
o-phthalaldehyde o-Phthalaldehyde: A reagent that forms fluorescent conjugation products with primary amines. It is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.. phthalaldehyde : A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.	7.8	3	0	benzaldehydes; dialdehyde	epitope
pirenzepine Pirenzepine: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.	2	1	0	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
practolol Practolol: A beta-1 adrenergic antagonist that has been used in the emergency treatment of CARDIAC ARRYTHMIAS.. practolol : N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythmias.	1.96	1	0	acetamides; ethanolamines; propanolamine; secondary alcohol; secondary amino compound	anti-arrhythmia drug; beta-adrenergic antagonist
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2.36	2	0	diarylmethane
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	2	1	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	2.42	2	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	2	1	0	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
pronethalol pronethalol: was heading 1964-94 (Prov 1964-66); NAPHTHYLISOPROTERENOL was see PRONETHALOL 1977-94; use ETHANOLAMINES to search PRONETHALOL 1966-94	1.96	1	0	naphthalenes
propachlor propachlor: structure. propachlor : An anilide that consists of 2-chloroacetanilide bearing an N-isopropyl substituent.	6.97	1	0	anilide; monocarboxylic acid amide; organochlorine compound	environmental contaminant; herbicide; xenobiotic
propafenone Propafenone: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.. propafenone : An aromatic ketone that is 3-(propylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is replaced by a 2-(3-phenylpropanoyl)phenyl group. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used as the hydrochloride salt in the management of supraventricular and ventricular arrhythmias.	2	1	0	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug
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.	2.43	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
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	2	1	0
ranitidine [no description available]	2	1	0	aralkylamine
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	3.49	8	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
risperidone Risperidone: A selective blocker of DOPAMINE D2 RECEPTORS and SEROTONIN 5-HT2 RECEPTORS that acts as an atypical antipsychotic agent. It has been shown to improve both positive and negative symptoms in the treatment of SCHIZOPHRENIA.. risperidone : A member of the class of pyridopyrimidines that is 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.	2	1	0	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine	alpha-adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; psychotropic drug; second generation antipsychotic; serotonergic antagonist
salicyl alcohol salicyl alcohol: RN given refers to parent cpd; saligenin is the aglycone of salicin; structure; it is oxidatively metabolized to gentisic acid. salicyl alcohol : A hydroxybenzyl alcohol that is phenol substituted by a hydroxymethyl group at C-2.	1.96	1	0	aromatic primary alcohol; hydroxybenzyl alcohol	human urinary metabolite
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	1.96	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
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.	1.98	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
simazine Simazine: A triazine herbicide.. simazine : A diamino-1,3,5-triazine that is N,N'-diethyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6.	2.1	1	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
sotalol Sotalol: An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.. sotalol : A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.	2.38	2	0	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic
fenofibrate [no description available]	2.02	1	0	benzochromenone; delta-lactone; naphtho-alpha-pyrone	platelet aggregation inhibitor; Sir2 inhibitor
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.	1.98	1	0	pyridazines; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor
sulfanilamide [no description available]	2.62	3	0	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sulfobromophthalein Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination.	1.93	1	0	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye
sumatriptan Sumatriptan: A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of MIGRAINE DISORDERS.. sumatriptan : A sulfonamide that consists of N,N-dimethyltryptamine bearing an additional (N-methylsulfamoyl)methyl substituent at position 5. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used (in the form of its succinate salt) for the acute treatment of migraine with or without aura in adults.	2	1	0	sulfonamide; tryptamines	serotonergic agonist; vasoconstrictor agent
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.	2.02	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
suramin Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.	1.93	1	0	naphthalenesulfonic acid; phenylureas; secondary carboxamide	angiogenesis inhibitor; antinematodal drug; antineoplastic agent; apoptosis inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; GABA antagonist; GABA-gated chloride channel antagonist; purinergic receptor P2 antagonist; ryanodine receptor agonist; trypanocidal drug
tegafur [no description available]	2.02	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.	1.96	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.	2	1	0	benzoate ester; tertiary amino compound	local anaesthetic
thiabendazole Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate	2.02	1	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
thioridazine Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.	2.41	2	0	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
tiapride [no description available]	2	1	0	benzamides
tolnaftate [no description available]	2.41	2	0	monothiocarbamic ester	antifungal drug
trazodone Trazodone: A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309). trazodone : An N-arylpiperazine in which one nitrogen is substituted by a 3-chlorophenyl group, while the other is substituted by a 3-(3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl group.	2	1	0	monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazolopyridine	adrenergic antagonist; antidepressant; anxiolytic drug; H1-receptor antagonist; sedative; serotonin uptake inhibitor
triamterene Triamterene: A pteridinetriamine compound that inhibits SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS.. triamterene : Pteridine substituted at positions 2, 4 and 7 with amino groups and at position 6 with a phenyl group. A sodium channel blocker, it is used as a diuretic in the treatment of hypertension and oedema.	2	1	0	pteridines	diuretic; sodium channel blocker
trichlormethiazide Trichlormethiazide: A thiazide diuretic with properties similar to those of HYDROCHLOROTHIAZIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p830). trichlormethiazide : A benzothiadiazine, hydrogenated at positions 2, 3 and 4 and substituted with an aminosulfonyl group at C-7, a chloro substituent at C-6 and a dichloromethyl group at C-3 and with S-1 as an S,S-dioxide. A sulfonamide antibiotic, it is used as a diuretic to treat oedema (including that associated with heart failure) and hypertension.	2	1	0	benzothiadiazine; sulfonamide antibiotic	antihypertensive agent; diuretic
trifluoperazine [no description available]	2	1	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	2.41	2	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
tulobuterol [no description available]	1.96	1	0	organochlorine compound
urethane [no description available]	7.33	2	0	carbamate ester	fungal metabolite; mutagen
fr 74366 [no description available]	1.97	1	0
hydrocortisone acetate hydrocortisone acetate: RN given refers to cpd without isomeric designation	2.41	2	0	cortisol ester; tertiary alpha-hydroxy ketone
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.	2	1	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	2	1	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.	2.41	2	0	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
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	2.13	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
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.	1.93	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
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.43	2	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	6.93	1	0	pyrimidone	hyperglycemic agent; metabolite
piperonyl butoxide [no description available]	2.38	2	0	benzodioxoles	pesticide synergist
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	7.8	3	0	benzimidazole; polycyclic heteroarene
2-aminophenol [no description available]	2.4	2	0	aminophenol	bacterial metabolite
bromouracil Bromouracil: 5-Bromo-2,4(1H,3H)-pyrimidinedione. Brominated derivative of uracil that acts as an antimetabolite, substituting for thymine in DNA. It is used mainly as an experimental mutagen, but its deoxyriboside (BROMODEOXYURIDINE) is used to treat neoplasms.. 5-bromouracil : A pyrimidine having keto groups at the 2- and 4-positions and a bromo group at the 5-position. Used mainly as an experimental mutagen.	2.05	1	0	nucleobase analogue; pyrimidines	mutagen
trichlorfon Trichlorfon: An organochlorophosphate cholinesterase inhibitor that is used as an insecticide for the control of flies and roaches. It is also used in anthelmintic compositions for animals. (From Merck, 11th ed). trichlorfon : A phosphonic ester that is dimethyl phosphonate in which the hydrogen atom attched to the phosphorous is substituted by a 2,2,2-trichloro-1-hydroxyethyl group.	1.98	1	0	organic phosphonate; organochlorine compound; phosphonic ester	agrochemical; anthelminthic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; insecticide
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	2.69	3	0	11-oxo 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; immunosuppressive agent; prodrug
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	2.04	1	0	ortho-fused polycyclic arene	mutagen
adrenochrome Adrenochrome: Pigment obtained by the oxidation of epinephrine.	1.93	1	0	indoles
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.	4.35	6	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.	7.92	4	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
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	5.25	9	0	ortho-fused polycyclic arene; tetraphenes
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.69	3	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
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.	6.94	1	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
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.	2.76	3	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.	3.1	5	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.	2.54	2	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.	7.02	1	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
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.	3.48	2	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
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.	3.43	7	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	2.76	3	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.	2.06	1	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	3.1	5	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.	3.03	4	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.	2.11	1	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
benzoxazolone benzoxazolone: RN given refers to parent cpd; structure. 2-benzoxazolinone : A member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2.	2.02	1	0	benzoxazole	allelochemical; phytoalexin
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.	2.45	2	0	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.	2	1	0	butyrate ester; triglyceride	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug; protective agent
p-dimethylaminoazobenzene p-Dimethylaminoazobenzene: A reagent used mainly to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens (NTP 85-002, p. 89) published in 1985, this compound may reasonably be anticipated to be a carcinogen. (Merck, 11th ed)	7.33	2	0	azobenzenes
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.04	1	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.	3.84	3	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.	2.03	1	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
methacholine chloride Methacholine Chloride: A quaternary ammonium parasympathomimetic agent with the muscarinic actions of ACETYLCHOLINE. It is hydrolyzed by ACETYLCHOLINESTERASE at a considerably slower rate than ACETYLCHOLINE and is more resistant to hydrolysis by nonspecific CHOLINESTERASES so that its actions are more prolonged. It is used as a parasympathomimetic bronchoconstrictor agent and as a diagnostic aid for bronchial asthma. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1116)	2.07	1	0	quaternary ammonium salt
aniline [no description available]	10.1	14	0	anilines; primary arylamine
carbaryl Carbaryl: A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.. carbaryl : A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.	3.51	8	0	carbamate ester; naphthalenes	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant growth retardant
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.	1.99	1	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.	2.42	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.	3.31	6	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	7.33	2	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
2-naphthaldehyde 2-naphthaldehyde: structure. 2-naphthaldehyde : A naphthaldehyde that is naphthalene substituted by a formyl group at position 2.	1.94	1	0	naphthaldehyde	mouse metabolite
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.	4.21	5	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	3.5	2	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
mannitol [no description available]	7.4	2	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
4-toluenesulfonamide 4-toluenesulfonamide: RN given refers to parent cpd. toluene-4-sulfonamide : A sulfonamide that is benzenesulfonamide bearing a methyl group at position 4.	2	1	0	sulfonamide
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.	7.17	1	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.	3.07	1	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.	3.79	3	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.	2.04	1	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
methaqualone Methaqualone: A quinazoline derivative with hypnotic and sedative properties. It has been withdrawn from the market in many countries because of problems with abuse. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). methaqualone : A member of the class of quinazolines that is quinazolin-4-one substituted at positions 2 and 3 by methyl and o-tolyl groups respectively. A depressant that increases the activity of the GABA receptors in the brain and nervous system, it is used as a sedative and hypnotic medication. It became popular as a recreational drug and club drug in the late 1960s and 1970s.	1.98	1	0	quinazolines	GABA agonist; sedative
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.	3.56	8	0	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.	1.93	1	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
nifenalol nifenalol: adrenergic beta-blocker with good antiarrhythmic properties; also tends to lower blood pressure & provide protection against angina; minor descriptor (75-86); on-line & INDEX MEDICUS search ETHANOLAMINES (75-86); RN given refers to parent cpd without isomeric designation	1.96	1	0	C-nitro compound
methyl bromide methyl bromide: used in ionization chambers, degreasing wool, extracting oils; insect fumigant; high concentrations can produce pulmonary edema,narcosis; chronic exposure can cause CNS depression,kidney injury; RN given refers to parent cpd; structure. bromomethane : A one-carbon compound in which the carbon is attached by single bonds to three hydrogen atoms and one bromine atom. It is produced naturally by marine algae.	3.53	2	0	bromohydrocarbon; bromomethanes; methyl halides	algal metabolite; fumigant insecticide; marine metabolite
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	2.43	2	0	alkane; gas molecular entity	plant metabolite; refrigerant
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	3.09	5	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	8.73	10	0	alkyne; gas molecular entity; terminal acetylenic compound
methyl iodide methyl iodide: RN given refers to unlabeled cpd with MF of CH3-I. iodomethane : A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.	1.97	1	0	iodomethanes; methyl halides	fumigant insecticide
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	6.92	1	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.05	1	0	alkane; gas molecular entity	food propellant
ethyl chloride Ethyl Chloride: A gas that condenses under slight pressure. Because of its low boiling point ethyl chloride sprayed on skin produces an intense cold by evaporation. Cold blocks nerve conduction. Ethyl chloride has been used in surgery but is primarily used to relieve local pain in sports medicine.. chloroethane : The simplest and least toxic member of the class of chloroethanes, that is ethane in which a single hydrogen is substituted by a chlorine. A colourless gas at room temperature and pressure (boiling point 12degreeC), it is used as a mild topical anaesthetic to numb the skin prior to ear piercing, skin biopsies, etc., and is also used in the treatment of sports injuries. It was formerly used in the production of tetraethyllead.	3.5	2	0	chloroethanes	antipruritic drug; inhalation anaesthetic; local anaesthetic
vinyl chloride Vinyl Chloride: A gas that has been used as an aerosol propellant and is the starting material for polyvinyl resins. Toxicity studies have shown various adverse effects, particularly the occurrence of liver neoplasms.. chloroethene : A monohaloethene that is ethene in which one of the hydrogens has been replaced by a chloro group.	1.96	1	0	chloroethenes; gas molecular entity; monohaloethene	carcinogenic agent
vinyl fluoride [no description available]	2.05	1	0	gas molecular entity; monohaloethene
ethylamine ethylamine : A two-carbon primary aliphatic amine.	2	1	0	primary aliphatic amine	human metabolite
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.	4.87	10	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.	3.82	3	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
methylene iodide methylene iodide: RN given refers to parent cpd	2.78	3	0
1,1-dichloroethane [no description available]	3.07	1	0	organochlorine compound
vinylidene chloride vinylidene chloride: potent hepatotoxin. 1,1-dichloroethene : A member of the class of chloroethenes that is ethene in which both of the hydrogens attached to one of the carbons are replaced by chlorines.	1.98	1	0	chloroethenes	carcinogenic agent; mouse metabolite; mutagen
nitromethane nitromethane: structure. nitromethane : A primary nitroalkane that is methane in which one of the hydrogens is replace by a nitro group. A polar solvent (b.p. 101 degreeC), it is an important starting material in organic synthesis. It is also used as a fuel for rockets and radio-controlled models.	3.49	2	0	primary nitroalkane; volatile organic compound	EC 4.3.1.3 (histidine ammonia-lyase) inhibitor; explosive; NMR chemical shift reference compound; polar aprotic solvent
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	3.49	2	0	tertiary alcohol	human xenobiotic metabolite
trichlorofluoromethane trichlorofluoromethane: refrigerant, aerosol propellant; RN given refers to parent cpd; structure. trichlorofluoromethane : A one-carbon compound that is methane in which the hydrogens have been replaced by three chlorine and one fluorine atom.	2.04	1	0	chlorofluorocarbon; halomethane	environmental contaminant; NMR chemical shift reference compound; NMR solvent; refrigerant
methanesulfonic acid [no description available]	2.01	1	0	alkanesulfonic acid; one-carbon compound	Escherichia coli metabolite
trimethylchlorosilane trimethylsilyl chloride: structure in first source. chlorotrimethylsilane : A silyl chloride consisting of a central silicon atom covalently bound to one chloro and three methyl groups. Chlorotrimethylsilane is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2	1	0	silyl chloride	chromatographic reagent
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.	3.07	1	0	aliphatic alcohol; tertiary alcohol	protic solvent
pentachloroethane [no description available]	2.48	2	0	chloroethanes	non-polar solvent
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	6.93	1	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
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.	3.01	2	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
isophorone isophorone : A cyclic ketone, the structure of which is that of cyclohex-2-en-1-one substituted by methyl groups at positions 3, 5 and 5.	1.97	1	0	cyclic ketone; enone	plant metabolite; solvent
isopentane [no description available]	2.04	1	0	alkane	refrigerant
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	3.09	5	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	3.07	1	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.	3.07	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.	3.07	1	0	secondary alcohol
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	3.49	2	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
1,1,2-trichloroethane 1,1,2-trichloroethane: RN given refers to cpd with locants as specified. 1,1,2-trichloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1 and 2.	3.07	1	0	chloroethanes
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	4.7	9	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	2.17	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
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.	2.33	2	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
methyl acetate methyl acetate : An acetate ester resulting from the formal condensation of acetic acid with methanol. A low-boiling (57 degreeC) colourless, flammable liquid, it is used as a solvent for many resins and oils.	2	1	0	acetate ester; methyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; fragrance; polar aprotic solvent
nitroethane nitroethane : A nitroalkane that is ethane substituted by a nitro group.	2	1	0	primary nitroalkane
1,1,2,2-tetrachloroethane 1,1,2,2-tetrachloroethane: see also record for tetrachloroethane. 1,1,2,2-tetrachloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1, 2 and 2.	3.5	2	0	chloroethanes
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.	2.04	1	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum metabolite
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.	8.94	3	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
alpha-pinene [no description available]	3.58	2	0	pinene	plant metabolite
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.	2.25	1	0	enoate ester; methyl ester	allergen; polymerisation monomer
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.	2.06	1	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
acenaphthenequinone acenaphthoquinone : An orthoquinone that is the 1,2-dioxo derivative of acenaphthene.	1.93	1	0	orthoquinones	chain carrier; epitope
acenaphthene [no description available]	4.44	22	0	acenaphthenes
skatole [no description available]	4.01	4	0	methylindole	human metabolite; mammalian metabolite
3-methylsalicylic acid 3-methylsalicylic acid : A monohydroxybenzoic acid consisting of salicylic acid carrying a methyl group at the 3-position.	2.02	1	0	monohydroxybenzoic acid	bacterial xenobiotic metabolite
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	1.99	1	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione [no description available]	2.04	1	0	flavin
9,10-phenanthrenequinone 9,10-phenanthrenequinone: structure	1.96	1	0	phenanthrenes
diethyl phthalate diethyl phthalate: structure. diethyl phthalate : The diethyl ester of benzene-1,2-dicarboxylic acid.	7.76	3	0	diester; ethyl ester; phthalate ester	neurotoxin; plasticiser; teratogenic agent
naphthionic acid naphthionic acid: RN given refers to parent cpd; structure in Merck Index & Negwer	2.33	2	0	aminonaphthalenesulfonic acid
phthalic anhydride phthalic anhydride : The cyclic dicarboxylic anhydride that is the anhydride of phthalic acid.	2.07	1	0	2-benzofurans; cyclic dicarboxylic anhydride	allergen
1-(2-pyridylazo)-2-naphthol [no description available]	7	1	0
1-hydroxy-2-naphthoic acid 1-hydroxy-2-naphthoic acid: RN given refers to parent cpd. 1-hydroxy-2-naphthoic acid : A naphthoic acid with the carboxy group at position 2 and carrying a hydroxy substituent at the 1-position. It is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.	2.38	2	0	hydroxy monocarboxylic acid; naphthoic acid; naphthols	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
1-naphthoic acid naphthoic acid : An aromatic carboxylic acid that consists of a naphthalene skeleton substituted by one or more carboxy groups.	3.45	8	0	naphthoic acid	bacterial xenobiotic metabolite; fungal xenobiotic metabolite
1-nitronaphthalene 1-nitronaphthalene: RN given refers to cpd with locant for nitro moiety in 1 position. 1-nitronaphthalene : A mononitronaphthalene substituted by a nitro group at position 1.. mononitronaphthalene : A nitronaphthalene carrying a single nitro group at unspecified position.. nitronaphthalene : A nitroarene that is naphthalene substituted by at least one nitro group.	3.13	5	0	mononitronaphthalene	environmental contaminant; mouse metabolite
fluorene [no description available]	6.28	46	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
carbazole carbazole: structure in first source	2.74	3	0	carbazole
1-naphthaleneacetic acid 1-naphthaleneacetic acid: a plant growth regulator; RN given refers to parent cpd. naphthylacetic acid : A monocarboxylic acid that is naphthalene substituted by a carboxymethyl group at any position.. 1-naphthaleneacetic acid : A naphthylacetic acid substituted by a carboxymethyl group at position 1.	2.62	3	0	naphthylacetic acid	synthetic auxin
2,4,6-trichloroanisole 2,4,6-trichloroanisole: Cork taint compound. 2,4,6-trichloroanisole : A monomethoxybenzene that is 1,3,5-trichlorobenzene in which one of the hydrogens is replaced by a methoxy group.	2.02	1	0	monomethoxybenzene; trichlorobenzene
1,2,3-trichlorobenzene trichlorobenzene: commercial grade of trichlorobenzene containing 70% 1,2,4-trichlorobenzene & 30% 1,2,3-trichlorobenzene; see also record for 1,2,4-trichlorobenzene. trichlorobenzene : Any member of the class of chlorobenzenes carrying three chloro substituents at unspecified positions.. 1,2,3-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 2 and 3.	3.81	3	0	trichlorobenzene
2,6-dichlorophenol 2,6-dichlorophenol: RN given refers to unlabeled cpd. 2,6-dichlorophenol : A dichlorophenol with the chloro substituents at positions 2 and 6.	2.4	2	0	dichlorophenol
hexamethylbenzene hexamethylbenzene : A methylbenzene that is benzene in which all six hydrogens have been replaced by methyl groups.	2.42	2	0	methylbenzene
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	7.15	1	0
2-nitrotoluene nitrotoluene : Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.	4.01	4	0	mononitrotoluene	carcinogenic agent; environmental contaminant
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.	2.08	1	0	C-nitro compound	antiseptic drug; explosive; fixative
2,4-dinitrobenzenesulfonic acid 2,4-dinitrobenzenesulfonic acid: RN given refers to parent cpd; structure. 2,4-dinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with two nitro substituents in the 2- and 4-positions.	2.21	1	0	arenesulfonic acid; C-nitro compound
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.	4.17	5	0	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.68	3	0	hydroxybenzaldehyde	nematicide; plant metabolite
1-methylnaphthalene 1-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 1.	3.75	10	0	methylnaphthalene	carcinogenic agent; plant metabolite
1-chloronaphthalene 1-chloronaphthalene: word preservative; in xylamon the active ingredient is 60% 1-chloronaphthalene; structure in Merck Index, 9th ed, #2126	8.25	6	0
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	5.09	43	0	naphthol	genotoxin; human xenobiotic metabolite
decalin decalin: RN given refers to cpd without isomeric designation; don't confuse with decaline which has a nitrogen at the juncture of the two rings;. trans-decalin : The trans-stereoisomer of decalin.. decalin : An ortho-fused bicyclic hydrocarbon that is the decahydro- derivative of naphthalene.	2.64	3	0	ortho-fused bicyclic hydrocarbon	solvent
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.99	4	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	6.16	24	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	2.08	1	0	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
2-methylnaphthalene 2-methylnaphthalene: RN given refers to parent cpd. 2-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 2.	4.53	24	0	methylnaphthalene
2-chloronaphthalene 2-chloronaphthalene: structure in first source	2.73	3	0
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	5.81	31	0	naphthylamine	carcinogenic agent
2-methylquinoline 2-methylquinoline: RN given refers to parent cpd. methylquinoline : Any member of the class of quinolines carrying at least one methyl substituent.. quinaldine : A quinoline compound in which the quinoline skeleton is substituted at C-2 with a methyl group.	2.72	3	0	quinolines
naphthacene tetracene : An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.	2.95	4	0	acene; tetracenes
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	10.01	39	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
phenylpiperazine phenylpiperazine: RN given refers to parent cpd	2.17	1	0
3-hydroxy-2-naphthoic acid 3-hydroxy-2-naphthoic acid: RN given refers to parent cpd	2.63	3	0	naphthoic acid
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2	1	0	xanthene
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	3.03	5	0	biphenyls; substituted aniline	carcinogenic agent
2-methoxynaphthalene [no description available]	8.09	5	0	naphthalenes
2-naphthoic acid 2-naphthoic acid: RN given refers to parent cpd. 2-naphthoic acid : A naphthoic acid that is naphthalene carrying a carboxy group at position 2.	3.58	9	0	naphthoic acid	mouse metabolite; xenobiotic metabolite
methyleugenol methyleugenol: structure	2	1	0	phenylpropanoid
2-(2-naphthyloxy)ethanol 2-(2-naphthyloxy)ethanol: may be used in treatment of rosacea; structure in Merck Index, 9th ed, #6241	1.93	1	0
methyl benzoate methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.	2.43	2	0	benzoate ester; methyl ester	insect attractant; metabolite
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)	2.48	2	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
indene indene: structure in first source. 1H-indene : An ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.	3.51	8	0	indene; ortho-fused bicyclic arene
benzothiophene [no description available]	7.97	4	0	1-benzothiophenes; benzothiophene
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	2.77	3	0	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	4.72	9	0	xylene
2-chlorotoluene 2-chlorotoluene: RN given refers to parent cpd	2.04	1	0
2-dichlorobenzene 2-dichlorobenzene: structure. 1,2-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 2.	3.82	3	0	dichlorobenzene	hepatotoxic agent; metabolite
2-bromophenol bromophenol : A halophenol that is any phenol containing one or more covalently bonded bromine atoms.	2.03	1	0	bromophenol	marine metabolite
2-chlorophenol chlorophenol : A halophenol that is any phenol containing one or more covalently bonded chlorine atoms.	2.03	1	0	2-halophenol; monochlorophenol
pseudocumene 1,2,4-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 4.	2.42	2	0	trimethylbenzene	neurotoxin
durene durene: structure. durene : A tetramethylbenzene carrying methyl groups at positions 1, 2, 4 and 5.	2.04	1	0	tetramethylbenzene
1,2,4,5-tetrachlorobenzene 1,2,4,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.	3.5	2	0	tetrachlorobenzene
2,4,5-trichlorophenol 2,4,5-trichlorophenol: RN given refers to parent cpd; structure. 2,4,5-trichlorophenol : A trichlorophenol carrying chloro groups at positions 2, 4 and 5.	2.01	1	0	trichlorophenol
diethyl ketone diethyl ketone: RN given refers to unlabeled parent cpd. pentan-3-one : A pentanone that is pentane carrying an oxo group at position 3. It has been isolated from Triatoma brasiliensis and Triatoma infestans.	3.07	1	0	pentanone	animal metabolite
cyclopentanol [no description available]	3.07	1	0	cyclopentanols
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.	2.43	2	0	butan-4-olide	metabolite; neurotoxin
sulfosalicylic acid 5-sulfosalicylic acid : An arenesulfonic acid that is benzoic acid substituted by a hydroxy at position C-2 and a sulfo group at C-5.	6.93	1	0	arenesulfonic acid; benzoic acids; phenols	metabolite
ethyl 2-methylpropanoate ethyl isobutyrate : A fatty acid ethyl ester obtained by the formal condensation of isobutyric acid with ethanol.	3.07	1	0	fatty acid ethyl ester	plant metabolite
butyl methacrylate [no description available]	2.03	1	0	enoate ester
tert-butylbenzene [no description available]	2.04	1	0
benzotrifluoride alpha,alpha,alpha-trifluorotoluene: structure in first source. (trifluoromethyl)benzene : A fluorohydrocarbon that is fluoroform in which the hydrogen is substituted by a phenyl group.	2	1	0	(trifluoromethyl)benzenes; fluorohydrocarbon	environmental contaminant; NMR chemical shift reference compound; solvent
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	1	0	benzenesulfonic acids
3-trifluoromethylphenol 3-trifluoromethylphenol: structure in first source	1.97	1	0	(trifluoromethyl)benzenes
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.49	2	0	phenols	allergen
4-tert-butylbenzoic acid 4-tert-butylbenzoic acid: RN given refers to parent cpd	1.95	1	0	alkylbenzene
cumene cumene : An alkylbenzene that is benzene carrying an isopropyl group.	2.42	2	0	alkylbenzene
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	4.72	9	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	4.47	7	0	nitroarene; nitrobenzenes
3-toluic acid 3-toluic acid: RN given refers to parent cpd; structure	2.37	2	0	methylbenzoic acid	human xenobiotic metabolite
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.11	1	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	2	1	0	botanical anti-fungal agent; carvones	allergen
3-dinitrobenzene dinitrobenzene : Any member of the class of nitrobenzenes that consists of a benzene ring substituted by two nitro groups. A closed class.. 1,3-dinitrobenzene : A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.	2.8	3	0	dinitrobenzene	neurotoxin
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.04	1	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
4-hydroxyacetophenone 4-hydroxyacetophenone: promotes secretion of bile & bile salts, which promotes griseofulvin absorption in the duodenum. 4'-hydroxyacetophenone : A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.	2.02	1	0	monohydroxyacetophenone	fungal metabolite; mouse metabolite; plant metabolite
4-toluic acid 4-toluic acid: RN given refers to parent cpd; structure. p-toluic acid : A methylbenzoic acid in which the methyl substituent is located at position 4.	2.37	2	0	methylbenzoic acid
4-nitrotoluene 4-nitrotoluene: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6470. mononitrotoluene : A nitrotoluene bearing a single nitro substituent at any position. A "closed class".. 4-nitrotoluene : A mononitrotoluene that consists of toluene bearing a nitro substituent at the 4-position.	2.76	3	0	mononitrotoluene
4-chloronitrobenzene [no description available]	2.4	2	0	C-nitro compound
4-nitroaniline [no description available]	2.1	1	0	nitroaniline	bacterial xenobiotic 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.	1.97	1	0	4-nitroanisoles
2-diethylaminoethanol 2-diethylaminoethanol: RN given refers to unlabeled parent cpd. 2-diethylaminoethanol : A member of the class of ethanolamines that is aminoethanol in which the hydrogens of the amino group are replaced by ethyl groups.	2.01	1	0	ethanolamines; primary alcohol; tertiary amino compound
ethylbenzene [no description available]	3.99	13	0	alkylbenzene
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.	4.74	9	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
benzyl chloride benzyl chloride: RN given refers to unlabeled cpd. chlorophenylmethane : A chlorohydrocarbon that is phenylmethane substituted by a chloro group at unspecified position.. benzyl chloride : A member of the class of benzyl chlorides that is toluene substituted on the alpha-carbon with chlorine.	2.49	2	0	benzyl chlorides
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.03	1	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
benzonitrile benzonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group.	8.4	7	0	benzenes; nitrile
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	3.77	3	0	monomethoxybenzene	plant metabolite
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	2.06	1	0	quinuclidines; saturated organic heterobicyclic parent
1,2-dihydrostilbene 1,2-dihydrostilbene: intermdiate in biosynthesis of dihydrophenanthrenes from phenylalanine. 1,2-dihydrostilbene : A diphenylethane that is the 1,2-dihydro derivative of stilbene.	2.04	1	0	diphenylethane
n-propylbenzene n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.	2.93	4	0	alkylbenzene
n-butylbenzene butylbenzene : An alkylbenzene that is benzene substituted by a butyl group at position 1.	2.44	2	0	alkylbenzene
xi-gamma-Undecalactone [no description available]	2.02	1	0	lactone
4-methylbenzaldehyde p-tolualdehyde : A tolualdehyde compound with the methyl substituent at the 4-position.	2.02	1	0	tolualdehyde	plant metabolite
4-anisidine 4-anisidine: RN given refers to parent cpd. p-anisidine : A substituted aniline that is aniline in which the hydrogen para to the amino group has been replaced by a methoxy group. It is used as a reagent for the detection of oxidation products such as aldehydes and ketones in fats and oils.	1.97	1	0	methoxybenzenes; primary amino compound; substituted aniline	genotoxin; reagent
anisyl alcohol anisyl alcohol: structure given in first source	1.97	1	0	benzyl alcohols
ethyl propionate ethyl propionate: cholesterol gallstone solvent. ethyl propionate : A propanoate ester of ethanol.	3.07	1	0	propanoate ester	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.	3.07	1	0	butyrate ester	plant metabolite
2,4-dimethylphenol 2,4-dimethylphenol: RN given refers to parent cpd. 2,4-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 2 and 4.	3.07	1	0	aromatic fungicide; phenols	disinfectant; volatile oil component
1,4-dibromobenzene [no description available]	2.73	3	0	dibromobenzene
4-bromoaniline 4-bromoaniline: RN given refers to parent cpd; structure given in Merck Index, 9th ed, #1403	1.97	1	0
4-bromophenol 4-bromophenol : A bromophenol containing only hydroxy and bromo substituents that are para to one another.	1.97	1	0	bromophenol	human urinary metabolite; human xenobiotic metabolite; marine metabolite; mouse metabolite; persistent organic pollutant; rat metabolite
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	3.31	6	0	xylene
4-chlorotoluene 4-chlorotoluene: RN given refers to unlabeled cpd	2.04	1	0	monochlorobenzenes
4-chloroaniline 4-chloroaniline: RN given refers to parent cpd; structure. 4-chloroaniline : A chloroaniline in which the chloro atom is para to the aniline amino group.	7.92	4	0	chloroaniline; monochlorobenzenes
4-toluidine 4-toluidine: RN given refers to parent cpd. p-toluidine : An aminotoluene in which the amino substituent is para to the methyl group.	2.4	2	0	aminotoluene
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	3.1	5	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.04	1	0	alkane; gas molecular entity	food propellant; refrigerant
1-butene but-1-ene : A butene with unsaturation at position 1.	2.42	2	0	butene
1,3-butadiene buta-1,3-diene : A butadiene with unsaturation at positions 1 and 3.	7.44	2	0	butadiene	carcinogenic agent; mutagen
allyl chloride [no description available]	2.47	2	0	organochlorine compound
propionitrile propionitrile: structure. propionitrile : A nitrile that is acrylonitrile in which the carbon-carbon double bond has been reduced to a single bond.	2	1	0	aliphatic nitrile; volatile organic compound	polar aprotic solvent
propargyl alcohol propargyl alcohol: irreversibly inactivates alcohol oxidase; RN given refers to parent cpd. prop-2-yn-1-ol : A terminal acetylenic compound that is prop-2-yne substituted by a hydroxy group at position 1.	2.06	1	0	propynol; terminal acetylenic compound; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite
methyl formate methyl formate: RN given refers to parent cpd. methyl formate : A formate ester resulting from the formal condensation of formic acid with methanol. A low-boiling (31.5 degreeC) colourless, flammable liquid, it has been used as a fumigant and larvicide for tobacco and food crops.	3.07	1	0	formate ester; methyl ester; volatile organic compound	fumigant; insecticide; polar aprotic solvent; refrigerant
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	3.3	6	0	alkane
2-pentanone pentanone : Any ketone that is pentane substituted by an oxo group at unspecified position.	3.07	1	0	methyl ketone; pentanone	plant metabolite
methyl isobutyl ketone [no description available]	3.07	1	0	ketone
gamma-valerolactone gamma-valerolactone: metabolite of n-hexane; RN given refers to cpd with methyl moiety in position 5. gamma-valerolactone : A butan-4-olide that is dihydrofuran-2(3H)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to n-hexane.	2.02	1	0	butan-4-olide	flavouring agent; human xenobiotic metabolite
maleic anhydride Maleic Anhydrides: Used in copolymerization reactions, in the Diels-Alder(diene)synthesis, in the preparation of resins, pharmaceuticals and agricultural chemicals. It is a powerful irritant and causes burns.. maleic anhydride : A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.	1.93	1	0	cyclic dicarboxylic anhydride; furans	allergen
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	3.78	3	0	xylene
3-chlorophenol 3-chlorophenol : A monochlorophenol carrying the chloro substituent at position 3.	2.68	3	0	monochlorophenol
mesitylene mesitylene: structure. 1,3,5-trimethylbenzene : A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.	2.04	1	0	trimethylbenzene
3,5-xylenol 3,5-xylenol: RN given refers to 3,5-isomer. 3,5-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 3 and 5.	2.03	1	0	phenols	xenobiotic metabolite
1,3,5-trichlorobenzene 1,3,5-trichlorobenzene: structure in first source. 1,3,5-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.	3.5	2	0	trichlorobenzene
bromobenzene [no description available]	2.72	3	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
chlorobenzene [no description available]	4.84	6	0	monochlorobenzenes	solvent
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.	3.81	3	0	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	3.07	1	0	cyclohexanones	human xenobiotic metabolite
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	2.21	1	0	aryl thiol
triethylene glycol dimethacrylate [no description available]	2.47	2	0
propyl acetate propyl acetate: affects aggression without affecting motor activity; RN given refers to parent cpd. propyl acetate : An acetate ester obtained by the formal condensation of acetic acid with propanol.	3.07	1	0	acetate ester	fragrance; 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.	4.19	5	0	alkane; volatile organic compound	non-polar solvent; refrigerant
1-pentene 1-pentene: structure in first source	3.5	2	0
butyl chloride butyl chloride: structure	3.5	2	0
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	2.13	1	0	aliphatic nitrile; dinitrile
dimethoxymethane dimethoxymethane : An acetal that is the dimethyl acetal derivative of formaldehyde.	2	1	0	acetal; diether
diethylamine [no description available]	1.93	1	0	secondary aliphatic amine
ethyl formate ethyl formate : A formate ester resulting from the formal condensation of formic acid with ethanol.. ethoxycarbonyl group : An organyl group of formula -COOEt.	3.07	1	0	ethyl ester; formate ester	fumigant; plant metabolite
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.	2.5	2	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.	4.03	4	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	2.44	2	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	4.3	18	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
isobutyl acetate isobutyl acetate : The acetate ester of isobutanol.	3.07	1	0	acetate ester	Saccharomyces cerevisiae metabolite
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.71	3	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
1,4-butanediol butane-1,4-diol : A butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16degreeC) with a high boiling point (230degreeC), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF).	2.02	1	0	butanediol; glycol	neurotoxin; prodrug; protic solvent
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.	8.39	7	0	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	2.68	3	0	cycloalkene
piperidine [no description available]	2.15	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
morpholine [no description available]	2.35	2	0	morpholines; saturated organic heteromonocyclic parent	NMR chemical shift reference compound
2-octanone 2-octanone : A methyl ketone that is octane substituted by an oxo group at position 2.	3.07	1	0	methyl ketone	metabolite
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.	3.07	1	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
n-butyl vinyl ether vinilin: RN given refers to cpd with unknown MF; no further information available 10/91	2.03	1	0
heptanol Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.	3.07	1	0	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.76	3	0	alkane	plant metabolite; volatile oil component
n-dodecane dodecane : A straight-chain alkane with 12 carbon atoms. It has been isolated from the essential oils of various plants including Zingiber officinale (ginger).	3.65	9	0	alkane	plant metabolite
lauryl acetate [no description available]	2.05	1	0	carboxylic ester
ergotamine Ergotamine: A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.. ergotamine : A peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10.	3.54	9	0	peptide ergot alkaloid	alpha-adrenergic agonist; mycotoxin; non-narcotic analgesic; oxytocic; serotonergic agonist; vasoconstrictor agent
propylene propylene: structure	2.76	3	0	alkene; gas molecular entity	refrigerant; xenobiotic
dimethyl ether dimethyl ether : An ether in which the oxygen atom is connected to two methyl groups.	6.92	1	0	ether
1-amino-2-naphthol-4-sulfonic acid 4-amino-3-hydroxynaphthalene-1-sulfonic acid: reagent for removal of chromium(VI) from aqueous solution	2.33	2	0	aminonaphthalene; naphthalenesulfonic acid	mutagen
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.	2.68	3	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
ortho-hydroxybenzophenone ortho-hydroxybenzophenone: structure in first source. hydroxybenzophenone : Any benzophenone into which is substituted one or more hydroxy groups.	2.13	1	0
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.	8.3	6	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
chloranil Chloranil: A quinone fungicide used for treatment of seeds and foliage.. tetrachloro-1,4-benzoquinone : A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.	7.02	1	0	1,4-benzoquinones; organochlorine compound	EC 2.7.1.33 (pantothenate kinase) inhibitor; metabolite
tetralin tetralin: structure given in first source. tetralin : An ortho-fused bicyclic hydrocarbon that is 1,2,3,4-tetrahydro derivative of naphthalene.	8.2	6	0	ortho-fused bicyclic hydrocarbon; tetralins
isoquinoline [no description available]	3.01	4	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	7.82	93	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
2-naphthalenesulfonic acid naphthalene-2-sulfonic acid : A naphthalenesulfonic acid in which the sulfo group is linked to position 2 of the naphthalene ring.	6.93	1	0	naphthalenesulfonic acid	environmental contaminant; xenobiotic
2-naphthoxyacetic acid 2-naphthoxyacetic acid: used as plant hormone to promote the growth of roots on clippings, to prevent fruit from falling prematurely; structure	2.05	1	0	naphthyloxyacetic acid
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	2	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
dimethyl 4-phthalate dimethyl 4-phthalate: solvent; structure. dimethyl terephthalate : A diester resulting from the formal condensation of the carboxy groups of terephthalic acid with methanol. It is a primary ingredient widely used in the manufacture of polyesters and industrial plastics.	2.02	1	0	diester; methyl ester; phthalate ester
2,4-dichlorophenol 2,4-dichlorophenol: RN given refers to unlabeled parent+ cpd; structure. 2,4-dichlorophenol : A dichlorophenol that is phenol carrying chloro substituents at positions 2 and 4.	7.48	2	0	dichlorophenol
cyclopentanone [no description available]	3.07	1	0	cyclopentanones	Maillard reaction product
n-methylpyrrolidine N-methylpyrrolidine: RN given refers to parent cpd	1.97	1	0
2,4-dinitrotoluene 2,4-dinitrotoluene : A dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.	3.1	5	0	dinitrotoluene
3-nitrobenzoic acid 3-nitrobenzoic acid: RN given refers to parent cpd	2	1	0
1,4-naphthoquinone naphthoquinone : A polycyclic aromatic ketone metabolite of naphthalene.. 1,4-naphthoquinone : The parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties.	3.52	8	0	1,4-naphthoquinones
dimethyl phthalate dimethyl phthalate: used as plasticizer in computer mouse; structure	7.71	3	0	diester; methyl ester; phthalate ester
naphthoresorcinol naphthoresorcinol: RN given refers to parent cpd	2.33	2	0
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	2.08	1	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant metabolite
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	3.66	10	0	naphthylamine	human xenobiotic metabolite
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.	7.06	107	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
pentacene [no description available]	2.05	1	0	acene; pentacenes
sec-butylbenzene sec-butylbenzene : An alkylbenzene that is benzene substituted by a butan-2-yl group.	1.96	1	0	alkylbenzene
ziram Ziram: An industrial fungicide with low mammalian toxicity, although it does possess an irritant capacity for skin and mucous membranes.. ziram : A dithiocarbamate salt that is the zinc salt of dimethyldithiocarbamic acid. It is a broad-spectrum fungicide and bird and animal repellent that is also used to accelerate the vulcanisation of rubber.	7.02	1	0	dithiocarbamate salt; zinc molecular entity	antifungal agrochemical; apoptosis inducer
zephiramine [no description available]	1.97	1	0
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	3.79	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
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).	7.46	2	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
dibutyl ether [no description available]	3.07	1	0
tetraphenylborate Tetraphenylborate: An anionic compound that is used as a reagent for determination of potassium, ammonium, rubidium, and cesium ions. It also uncouples oxidative phosphorylation and forms complexes with biological materials, and is used in biological assays.	7.01	1	0
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	2.62	3	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
3-hydroxyanisole 3-hydroxyanisole: structure in first source. 3-methoxyphenol : A member of the class of phenols that is phenol having a methoxy-substituent at the 3-position.	1.97	1	0	monomethoxybenzene; phenols
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	1.97	1	0	methoxybenzenes; phenols	metabolite
o,o,o-trimethyl phosphorothioate [no description available]	1.99	1	0
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.	2.41	1	0	catechin	antioxidant; plant metabolite
coronene coronene: structure. coronene : A ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.	7.77	3	0	ortho- and peri-fused polycyclic arene
1,12-benzoperylene 1,12-benzoperylene: structure; see also record for benzoperylene	2.42	2	0	ortho- and peri-fused polycyclic arene
benzo(e)pyrene benzo(e)pyrene: RN given refers to parent cpd. benzo[e]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. It is listed as a Group 3 carcinogen by the IARC.	2.04	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mutagen
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	5.04	12	0	ortho- and peri-fused polycyclic arene; perylenes
benzo(j)fluoranthene benzo(j)fluoranthene: dihydrodiol metabolites identified as mutagens; structure given in first source	2.04	1	0	naphthalenes
benzo(b)fluoranthene benzo[b]fluoranthene : An ortho- and peri-fused polycyclic arene that consists of a benzene ring fused with a acephenanthrylene ring.	3.85	3	0	ortho- and peri-fused polycyclic arene	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.	4.24	17	0	ortho- and peri-fused polycyclic arene
benzo(k)fluoranthene [no description available]	7.52	2	0	naphthalenes
acenaphthylene acenaphthylene: RN given refers to parent cpd. acenaphthylene : A ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar.	4.76	9	0	acenaphthylenes; ortho- and peri-fused polycyclic arene; ortho- and peri-fused tricyclic hydrocarbon
triphenylene triphenylene: structure. triphenylene : An ortho-fused polycyclic arene consisting of four fused benzene rings.	2.74	3	0	ortho-fused polycyclic arene
chrysene chrysene: structure in Merck Index, 9th ed, #2252. chrysene : An ortho-fused polycyclic arene found commonly in the coal tar.	3.83	11	0	ortho-fused polycyclic arene	plant metabolite
dibenzo(aj)anthracene dibenzo(aj)anthracene: structure in first source	2.04	1	0	phenanthrenes
benzo(a)fluorene benzo(a)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
benzo(b)fluorene benzo(b)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
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.	3.45	7	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.	3.74	3	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
dibenzo(1,4)dioxin dibenzo(1,4)dioxin: structure	2.75	3	0	dibenzodioxine; heteranthrene; mancude organic heterotricyclic parent; oxacycle; polycyclic heteroarene
phenoxathiin phenoxathiin: structure given in first source	2	1	0
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.05	1	0	indazole
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	7.75	3	0	1-benzofurans; benzofuran
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.5	2	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
azulene [no description available]	3.08	5	0	azulenes; mancude carbobicyclic parent; ortho-fused bicyclic arene	plant metabolite; volatile oil component
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.46	2	0	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	3.25	6	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.47	2	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	4.21	5	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.75	3	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
cyclooctane [no description available]	2.04	1	0
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.	2	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
hydrazine diamine : Any polyamine that contains two amino groups.	2.74	3	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
monocrotaline Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.	3.51	2	0	pyrrolizidine alkaloid
methylthioinosine Methylthioinosine: 6-(Methylthio)-9-beta-D-ribofuranosylpurine. An analog of inosine with a methylthio group replacing the hydroxyl group in the 6-position.	2.41	2	0	purine ribonucleoside; thiopurine
diethyl sulfide ethyl sulfide : An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.. diethyl sulfide : An ethyl sulfide compound having two ethyl groups attached to a sulfur atom.	2.04	1	0	ethyl sulfide
fluocinonide Fluocinonide: A topical glucocorticoid used in the treatment of ECZEMA.	2.13	1	0	organic molecular entity
phenylbenzoquinone phenylbenzoquinone: RN given refers to parent cpd	2.15	1	0
4-fluorophenol 4-fluorophenol: structure given in first source. 4-fluorophenol : A fluorophenol that is phenol in which the hydrogen para- to the hydroxy group has been replaced by a fluorine.	1.97	1	0	fluorophenol; monofluorobenzenes
3-fluoroaniline 3-fluoroaniline: structure given in first source. 3-fluoroaniline : A derivative of aniline in which the hydrogen at position 3 has been substituted by fluorine. It is used as a pharmaceutical intermediate.	1.97	1	0	fluoroaniline; primary arylamine
3-fluorophenol 3-fluorophenol: structure in first source	1.97	1	0
silicon carbide silicon carbide: fibers used for reinforcement of porcelain crowns; a feldspathic body (gingival) porcelain; used to coat titanium hip prostheses	2.05	1	0	organosilicon compound
1,2-dihydronaphthalene 1,2-dihydronaphthalene : A dihydronaphthalene hydrogenated at C-1 and C-2.	7.43	2	0	dihydronaphthalene
4-methylcatechol [no description available]	2.01	1	0	methylcatechol	antioxidant; carcinogenic agent; hapten; human metabolite; plant metabolite
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	8.06	5	0	imidazolidine-2,4-dione
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.	2.42	2	0	monofluorobenzenes	NMR chemical shift reference compound
propadiene [no description available]	2.45	2	0	allenes
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.	2.02	1	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
pinane pinane: RN given refers to cpd without isomeric designation. pinane : A monoterpene that is bicyclo[3.1.1]heptane substituted by methyl groups at positions 2, 6 and 6.	1.97	1	0	carbobicyclic compound; monoterpene; terpenoid fundamental parent	plant metabolite
naphthazarin naphthazarin: fish toxin; isolated for first time from the walnut onigurmi, Juglans mandshurica maxim var. Sieboldiana Makino; structure. naphthazarin : A naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 5 and 8 are replaced by hydroxy groups.	2.03	1	0	hydroxy-1,4-naphthoquinone	acaricide; antibacterial agent; antineoplastic agent; apoptosis inducer; geroprotector; plant metabolite
cholanthrene cholanthrene: structure given in first source	2.04	1	0
indirubin [no description available]	2	1	0
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	2.03	1	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
menadiol [no description available]	2.04	1	0	methylnaphthalenes; naphthalenediols; naphthohydroquinone
9-fluorenone fluoren-9-one : The simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9.	2.6	1	0	fluoren-9-ones	fungal xenobiotic metabolite
elemicin [no description available]	2	1	0	olefinic compound
indan indan: structure in first source. indane : An ortho-fused bicyclic hydrocarbon consisting of a benzene ring fused to a cyclopentane ring; a high-boiling (176 (o)C) colourless liquid.	2.44	2	0	indanes; ortho-fused bicyclic hydrocarbon
indoline indoline: structure given in first source	2	1	0	indoles
coumaran 2,3-dihydrobenzofuran : A member of the class of 1-benzofurans that is the 2,3-dihydroderivative of benzofuran.	2.02	1	0	1-benzofurans	metabolite
biphenylacetylene biphenylacetylene : An arylacetylene that is acetylene in which the hydrogens are replaced by phenyl groups.	2.5	2	0	arylacetylene; benzenes	fluorochrome
caprolactone hexano-6-lactone : A epsilon-lactone that is oxepane substituted by an oxo group at position 2.	2.02	1	0	epsilon-lactone
phorone phorone: an industrial solvent; structure	1.97	1	0	dialkenyl ketone
trimethyl phosphate trimethyl phosphate: request from searcher; structure. trimethyl phosphate : A trialkyl phosphate that is the trimethyl ester of phosphoric acid.	1.97	1	0	trialkyl phosphate	insect attractant; NMR chemical shift reference compound
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.01	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
1,2-naphthoquinone-4-sulfonate 1,2-naphthoquinone-4-sulfonic acid: a nonpermeable electron acceptor. 1,2-naphthoquinone-4-sulfonic acid : An arenesulfonic acid that is 1,2-naphthoquinone substituted at position 4 with a sulfonic acid group. Used principally as a reagent in colorimetric determinations.	1.93	1	0	arenesulfonic acid; naphthalenone	colorimetric reagent
1,2-naphthoquinone naphthalene-1,2-dione: structure given in first source. 1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.	3.41	7	0	1,2-naphthoquinones	aryl hydrocarbon receptor agonist; carcinogenic agent
1-nitroso-3,6-disulfonate [no description available]	1.97	1	0
hemimellitene hemimellitene: structure. 1,2,3-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 3. It has been found in Centaurium erythraea.	2.46	2	0	trimethylbenzene	neurotoxin; 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.	2.05	1	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2.05	1	0	organic molecular entity
tetralol tetralol: structure	6.92	1	0
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	3.15	5	0	benzenes
4-chloroacetanilide 4-chloroacetanilide : Acetamide substituted on nitrogen by a para-chlorophenyl group.	2	1	0	acetamides; monochlorobenzenes
Ethyl pentanoate ethyl valerate: a green apple flavoring agent	3.07	1	0	fatty acid ester
4-iodophenol [no description available]	1.97	1	0	iodophenol
1-chloropropane 1-chloropropane: structure in first source	2.42	2	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.	2.04	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
1,3-dichlorobenzene 1,3-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 3.	3.5	2	0	dichlorobenzene
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.	3.45	7	0	dialdehyde	biomarker
1-chlorohexane [no description available]	2.04	1	0
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.	3.73	10	0	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
phenalen-1-one phenalen-1-one: fossil fuel combustion product	2.06	1	0
1-naphthylisothiocyanate 1-Naphthylisothiocyanate: A tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. It may cause skin and kidney damage.	1.93	1	0	isothiocyanate	insecticide
3-nitrophenol [no description available]	2.49	2	0	3-nitrophenols
glycidol glycidol: structure given in first source	1.98	1	0	epoxide; primary alcohol
1,4-dimethylnaphthalene 1,4-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 4.	2.44	2	0	dimethylnaphthalene
1,4-naphthohydroquinone naphthohydroquinone : A hydroxynaphthalene that is naphthalene-1,4-diol and its C-substituted derivatives.	1.98	1	0	naphthalenediol; naphthohydroquinone
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	2.02	1	0	bis(azo) compound
1,2-dimethylnaphthalene 1,2-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 2.. dimethylnaphthalene : Any member of the class of naphthalenes carrying two methyl groups at unspecified positions.	7.95	4	0	dimethylnaphthalene
1,2-dihydroxynaphthalene 1,2-dihydroxynaphthalene: RN given refers to parent cpd	3.39	7	0	naphthalenediol	mouse metabolite
1,6-dimethylnaphthalene 1,6-dimethylnaphthalene: structure in first source	2.72	3	0	dimethylnaphthalene
2,3-dichlorophenol dichlorophenol : Any chlorophenol carrying chloro substituents.	2	1	0
2,6-dimethylnaphthalene 2,6-dimethylnaphthalene: RN given refers to parent cpd. 2,6-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 2 and 6.	2.95	4	0	dimethylnaphthalene	environmental contaminant
1,2-dibromobenzene dibromobenzene : Any member of the class of bromobenzenes that consists of a benzene or a substituted benzene ring carrying two bromo groups at unspecified positions.	2.04	1	0	dibromobenzene
potassium carbonate potassium carbonate : A potassium salt that is the dipotassium salt of carbonic acid.	2.05	1	0	carbonate salt; potassium salt	catalyst; fertilizer; flame retardant
3,5-dichlorophenol 3,5-dichlorophenol : A dichlorophenol in which the two chloro substituents are located at positions 3 and 5.	2.41	2	0	dichlorophenol
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	2.04	1	0
1-hexene 1-hexene: structure in first source. 1-hexene : An alkene that is hexane carrying a double bond at position 1.	2.04	1	0	alkene
octadecane octadecane: RN given refers to parent cpd. octadecane : A straight-chain alkane carrying 18 carbon atoms.	1.96	1	0	long-chain alkane	bacterial metabolite; plant metabolite
1,1'-binaphthyl 1,1'-binaphthyl: structure in first source	2.07	1	0
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	1.96	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
erythropoietin 1,5-dinitronaphthalene: structure in first source. 1,5-dinitronaphthalene : A dinitronaphthalene carrying nitro groups at positions 1 and 5.	2.13	1	0	dinitronaphthalene	genotoxin
pentachlorobenzene pentachlorobenzene: structure. pentachlorobenzene : A member of the class of pentachlorobenzenes that is benzene in which five of the hydrogens are replaced by chlorines. Now classed as a persistent organic pollutant under the Stockholm Convention.	3.82	3	0	pentachlorobenzenes	persistent organic pollutant
8-methylquinoline [no description available]	2	1	0	methylquinoline
3-methylquinoline [no description available]	2.72	3	0	methylquinoline	xenobiotic
2-methylanthracene 2-methylanthracene: structure given in first source	2.04	1	0
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.6	9	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
3-isopropylphenol 3-isopropylphenol: RN given refers to parent cpd	7.03	1	0
3-nitrobenzonitrile [no description available]	1.97	1	0
3-ethylphenol [no description available]	1.97	1	0	phenols
methyl butyrate [no description available]	2	1	0	fatty acid ester
1,3-dicyanobenzene 1,3-dicyanobenzene: structure in first source	2.21	1	0	nitrile
2-hexanol hexan-2-ol : A hexanol in which the hydroxy group is at position 2.	3.07	1	0	hexanol; secondary alcohol	human metabolite; plant metabolite; semiochemical
amyl acetate amyl acetate: sources do not specify n-isomer. pentyl acetate : An acetate ester of pentanol.	3.07	1	0	acetate ester	metabolite
n-tetradecane tetradecane : A straight chain alkane consisting of 14 carbon atoms.	3.3	6	0	long-chain alkane	plant metabolite; volatile oil component
1,2,3,4-tetrachlorobenzene 1,2,3,4-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4.. tetrachlorobenzene : Any member of the class of chlorobenzenes carrying four chloro groups at unspecified positions.	3.8	3	0	tetrachlorobenzene
1,2,3,5-tetrachlorobenzene 1,2,3,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.	3.5	2	0	tetrachlorobenzene
ethyl tert-butyl ether ethyl tert-butyl ether: gasoline additive. tert-butyl ethyl ether : An ether having ethyl and tert-butyl as the two alkyl components. It is used as an engine fuel additive to reduce emissions of carbon monoxide and soot.	2.05	1	0	ether; volatile organic compound	fuel additive
phytane [no description available]	2.44	2	0	diterpene
tetracosane tetracosane: a pure alkane compound. tetracosane : A straight-chain alkane containing 24 carbon atoms.	2.1	1	0	long-chain alkane	plant metabolite; volatile oil component
hempa Hempa: A chemosterilant agent that is anticipated to be a carcinogen.	2.07	1	0	phosphoramide	insect sterilant; mutagen
4-hexanolide gamma-caprolactone : A gamma-lactone that is oxolan-2-one substituted by an ethyl group at position 5.	2.02	1	0	butan-4-olide	human blood serum metabolite
pentamethylbenzene [no description available]	2.01	1	0	methylbenzene
decan-4-olide gamma-decalactone : A gamma-lactone that is oxolan-2-one substituted by a hexyl group at position 5.	2.02	1	0	gamma-lactone; tetrahydrofuranone	anticonvulsant; flavouring agent; food additive
2-hydroxy-1-naphthaldehyde 2-hydroxynaphthaldehyde: structure in first source. 2-hydroxy-1-naphthaldehyde : A member of the class of naphthaldehydes that is naphthalene-1-carbaldehyde substituted by a hydroxy group at position 2. Active core of sirtinol (CHEBI:73158).	2.49	2	0	naphthaldehydes; naphthols
1,2,4,5-tetracyanobenzene 1,2,4,5-tetracyanobenzene: structure in first source	2.08	1	0
diphenyliodonium diphenyliodonium: RN given refers to the parent coumpound; inhibitor of neutrophil superoxide generating oxidase; structure has been determined	2.07	1	0
3,4-dichloro-1-butene 3,4-dichloro-1-butene: RN given refers to cpd without isomeric designation	2.1	1	0
acetylenedicarboxylic acid dimethyl ester acetylenedicarboxylic acid dimethyl ester: inhibitor of oxidative phosphorylation	2.04	1	0
9-methylanthracene [no description available]	2.04	1	0
9,10-dimethylanthracene 9,10-dimethylanthracene: RN given refers to parent ion	2.04	1	0
4-methylimidazole 4-methylimidazole: RN given refers to parent cpd. 4-methylimidazole : Imidazole substituted at position 4 by a methyl group.	7.25	1	0	imidazoles	carcinogenic agent; reaction intermediate
4-nitrophenyl acetate [no description available]	1.95	1	0	C-nitro compound; phenyl acetates
naphthyl acetate naphthyl acetate: do not confuse with naphthaleneacetic acid; acetic acid ester of naphthol	2.37	2	0
ametryne ametryne: minor descriptor (72-83); on-line & Index Medicus search HERBICIDES, TRIAZINE (75-83) & HERBICIDES (72-74) & TRIAZINES (72-74); RN given refers to unlabeled cpd; structure. ametryn : A methylthio-1,3,5-triazine that is 2-(methylsulfanyl)-1,3,5-triazine substituted by an ethylamino and an isopropylamino group at positions 4 and 6 respectively.	2.11	1	0	diamino-1,3,5-triazine; methylthio-1,3,5-triazine	environmental contaminant; herbicide
2-(2'-hydroxyphenyl)benzoxazole 2-(2'-hydroxyphenyl)benzoxazole: structure in first source. 2-(1,3-benzoxazol-2-yl)phenol : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazole substituted by a 2-hydroxyphenyl group at position 2.	7.1	1	0	1,3-benzoxazoles; phenols	geroprotector
ethyl n-alpha-acetyl-tyrosinate ethyl N-alpha-acetyl-tyrosinate: RN given refers to parent cpd. ethyl N-acetyl-L-tyrosinate : An L-tyrosine derivative that is the ethyl ester of N-acetyltyrosine.	1.95	1	0	acetamides; ethyl ester; L-tyrosine derivative; phenols
lormetazepam lormetazepam: RN given refers to cpd with specified locant for methyl group; structure given in first source. lormetazepam : A 1,4-benzodiazepinone compound having a methyl substituent at the 1-position, a hydroxy substituent at the 3-position, a 2-chlorophenyl group at the 5-position and a chloro substituent at the 7-position.	2.41	2	0	1,4-benzodiazepinone; organochlorine compound	sedative
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
2,6-dimethylquinoline 2,6-dimethylquinoline: from roots of Peucedanum praeruptorum II	2.72	3	0
terbutryne terbutryn : A methylthio-1,3,5-triazine that is 2-(methylsulfanyl)-1,3,5-triazine substituted by a tert-butylamino and an ethylamino group at positions 2 and 4 respectively.	2.11	1	0	diamino-1,3,5-triazine; methylthio-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
2'-deoxyadenosine 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source	7.08	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fentanyl citrate fentanyl citrate : The citric acid salt of fentanyl, comprising equimolar amounts of citric acid and fentanyl. A mu-opioid receptor agonist, it is a potent opioid analgesic used in the management of labour pain, postoperative pain, and chronic intractable cancer pain. It is also widely used as the analgesic component of balanced anaesthesia.	2	1	0	citrate salt	mu-opioid receptor agonist; opioid analgesic
methylphosphonic acid methylphosphonic acid : A one-carbon compound that is phosphonic acid in which the hydrogen attached to the phosphorus is substituted by a methyl group.	7.06	1	0	one-carbon compound; phosphonic acids
diethyl acetamidomalonic acid diethyl acetamidomalonic acid: RN given refers to unlabeled parent cpd	1.95	1	0
phenylhydroquinone phenylhydroquinone: major metabolite of o-phenylphenol; cleaves DNA; structure given in first source	1.97	1	0
1,2-octanediol [no description available]	2.06	1	0	octanediol
undecane undecane : A straight-chain alkane with 11 carbon atoms.	2.73	3	0	alkane
3-vinylpyridine 3-vinylpyridine: structure given in first source; formed from nicotine during smoking of tobacco products	2.05	1	0
methyl hippurate methyl hippurate : A glycine derivative that is the methyl ester of hippuric acid.	1.95	1	0	glycine derivative; methyl ester	metabolite
calcium peroxide [no description available]	7.21	1	0	calcium oxides
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).	2.69	3	0
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.02	1	0	alkali metal hydroxide
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.	2.52	2	0	zinc molecular entity
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.	4.49	7	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]	4.02	4	0
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.	2.77	3	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.	2.05	1	0	ether	fuel additive; metabolite; non-polar solvent
6-methylchrysene 6-methylchrysene: RN given refers to parent cpd; structure given in first source	2.04	1	0	carbopolycyclic compound
1-methylisoquinoline 1-methylisoquinoline : An isoquinoline substituted by a methyl group at position 1.	2.44	2	0	isoquinolines
decane decane : A straight-chain alkane with 10 carbon atoms.	8.27	6	0	alkane
n-benzyloxycarbonylglycine 4-nitrophenyl ester N-benzyloxycarbonylglycine 4-nitrophenyl ester: hydrolyzed by papain	1.95	1	0
popop [no description available]	6.97	1	0	1,3-oxazoles	fluorochrome
Propioveratrone [no description available]	2	1	0	aromatic ketone
stearylamine stearylamine: RN given refers to parent cpd. octadecan-1-amine : An 18-carbon primary aliphatic amine.	2.04	1	0	primary aliphatic amine	film-forming compound
tetrachloroisophthalonitrile tetrachloroisophthalonitrile: structure. chlorothalonil : A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops.	1.99	1	0	aromatic fungicide; dinitrile; tetrachlorobenzene	antifungal agrochemical
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.	2.92	4	0	organic cation	geroprotector; herbicide
pristane pristane: structure. pristane : A norterpene that is an acyclic saturated hydrocarbon derived from phytane by loss of its C-16 terminal methyl group.	2.01	1	0	long-chain alkane; norterpene	biomarker; immunological adjuvant
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	1.98	1	0	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
phenylguanidine phenylguanidine: RN given refers to parent cpd	2.13	1	0
6h-dibenzo-(b,d)-pyran-6-one 6H-dibenzo[b,d]pyran-6-one : A benzochromenone that is 6H-dibenzo[b,d]pyran substituted by an oxo group at position 6.	1.98	1	0	benzochromenone	plant metabolite
2-isopropylnaphthalene 2-isopropylnaphthalene: RN given refers to parent cpd	1.97	1	0
diallyl trisulfide [no description available]	7.11	1	0	organic trisulfide	anti-inflammatory agent; antilipemic drug; antineoplastic agent; antioxidant; antiprotozoal drug; apoptosis inducer; estrogen receptor antagonist; insecticide; platelet aggregation inhibitor; vasodilator agent
decachlorobiphenyl decachlorobiphenyl: structure. decachlorobiphenyl : A polychlorobiphenyl that is biphenyl in which all of the hydrogens are replaced by chlorines.	2	1	0	pentachlorobenzenes; polychlorobiphenyl
4-chlorobiphenyl 4-chlorobiphenyl : A monochlorobiphenyl carrying a chloro substituent at position 4.	8.1	5	0	monochlorobiphenyl
4-chlorocatechol 4-chlorocatechol : A chlorocatechol that is catechol substituted by a chloro group at position 4.	2.01	1	0	chlorocatechol; monochlorobenzenes	bacterial xenobiotic metabolite
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.	6.93	1	0
1,5-naphthalenediamine 1,5-diaminonaphthalene: structure in first source. naphthalene-1,5-diamine : A naphthalenediamine compound having amino substituents in the 1- and 5-positions.	2.04	1	0	naphthalenediamine	carcinogenic agent
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.	2.02	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	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
1-methylpyrene [no description available]	2	1	0	pyrenes
12-methylbenzanthracene [no description available]	2.04	1	0
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.	2.42	2	0	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
2-methylphenanthrene [no description available]	2.37	2	0
7-methylbenzanthracene [no description available]	2.04	1	0
toliprolol toliprolol: was MH 1975-92 (see under PROPANOLAMINES 1981-90, was DOBEROL see under PROPANOLAMINES 1975-80); KOE 592 was see TOLIPROLOL 1975-92; use PROPANOLAMINES to search TOLIPROLOL 1975-92; beta adrenergic blockader with some stimulant action; it has been proposed for angina pectoris	1.96	1	0	aromatic ether
trichloroepoxypropane Trichloroepoxypropane: A potent epoxide hydrase and aryl hydrocarbon hydroxylase inhibitor. It enhances the tumor-initiating ability of certain carcinogens.	2.67	3	0
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	2.21	1	0	primary alcohol
mannose mannopyranose : The pyranose form of mannose.	2.06	1	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.	1.96	1	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
diheptyl phthalate diheptyl phthalate : The diheptyl ester of benzene-1,2-dicarboxylic acid.	2.02	1	0	diester; phthalate ester
5-methylchrysene 5-methylchrysene: methylchrysenes in tobacco smoke are suspected to contribute to tumorigenicity of this inhalant; RN given refers to unlabeled cpd; structure	2.04	1	0	carbopolycyclic compound
5,6-dimethylchrysene 5,6-dimethylchrysene: structure given in first source	2.04	1	0
7-ethylbenz(a)anthracene [no description available]	2.04	1	0
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.	2.72	3	0	carbon oxoanion
strombine N-methyliminodiacetic acid: structure in first source	2.31	1	0
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.4	2	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
1-hydroxypyrene 1-hydroxypyrene: pyrene metabolite; RN given refers to parent cpd	4.21	5	0	pyrenes
1-nitropyrene [no description available]	3.06	1	0	nitroarene	carcinogenic agent
o,o-diethyl o-3,5,6-trichloro-2-pyridyl phosphate [no description available]	2.03	1	0
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.	3.58	2	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.	2.05	1	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
3,5,6-trichloro-2-pyridinol 3,5,6-trichloro-2-pyridinol: RN given refers to parent cpd. 3,5,6-trichloropyridine-2-one : A pyridone that is pyridin-2(1H)-one substituted by chloro groups at positions 3, 5 and 6. It is a metabolite of the agrochemical chlorpyrifos.. 3,5,6-trichloro-2-pyridinol : A hydroxypyridine that is pyridin-2-ol substituted by chloro groups at positions 3,5 and 6. It is a metabolite of the agrochemical chlorpyrifos.	7.49	2	0	chloropyridine; hydroxypyridine; pyridone	human urinary metabolite; human xenobiotic metabolite; marine xenobiotic metabolite
deterenol [no description available]	1.96	1	0
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.15	1	0	cobalt group element atom; platinum group metal atom
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.	3.12	5	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.	3.53	8	0	elemental mercury; zinc group element atom	neurotoxin
neon Neon: A noble gas with the atomic symbol Ne, atomic number 10, and atomic weight 20.18. It is found in the earth's crust and atmosphere as an inert, odorless gas and is used in vacuum tubes and incandescent lamps.	2.38	2	0	monoatomic neon; noble gas atom; p-block element atom
osmium Osmium: A very hard, gray, toxic, and nearly infusible metal element, atomic number 76, atomic weight 190.2, symbol Os.	2.05	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.	4.27	17	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.	3.33	6	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	2.48	2	0	manganese group element 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.	8.16	5	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.	2.74	3	0	iron group element atom; platinum group metal atom
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	2.46	2	0	f-block element atom; lanthanoid 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.	2.97	4	0	copper group element atom; elemental silver	Escherichia coli metabolite
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	2.45	2	0	f-block element atom; lanthanoid 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.	7.83	3	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.	3.41	7	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.	3.52	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.	2.1	1	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.	3.63	9	0	chromium group element atom; metal allergen	micronutrient
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	2.73	3	0	f-block element atom; lanthanoid atom
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.	4.08	14	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.	2	1	0	monoatomic helium; noble gas atom; s-block element atom	food packaging gas
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.46	2	0	elemental vanadium; vanadium group element atom	micronutrient
xenon Xenon: A noble gas with the atomic symbol Xe, atomic number 54, and atomic weight 131.30. It is found in the earth's atmosphere and has been used as an anesthetic.	2.07	1	0	monoatomic xenon; noble gas atom; p-block element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	7.04	1	0	titanium group element atom
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	1.98	1	0	mercury coordination entity	sensitiser
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	1.96	1	0	D-galactosamine; primary amino compound	toxin
cesium chloride cesium chloride: RN given refers to unlabeled cpd. caesium chloride : The inorganic chloride salt of caesium; each caesium ion is coordinated by eight chlorine ions.	2.01	1	0	inorganic caesium salt; inorganic chloride	phase-transfer catalyst; vasoconstrictor agent
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.	2.08	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	8.86	3	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
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.	2.1	1	0	diatomic bromine
chromic acid [no description available]	2.02	1	0	chromium oxoacid	oxidising agent
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.	7.77	3	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.	2.02	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.	2.4	2	0	metal sulfate	emetic; fertilizer; sensitiser
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	3.64	9	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.	3.64	2	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.	3.06	5	0	diatomic chlorine; gas molecular entity	bleaching agent
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	2.45	2	0	nitrogen oxoacid
nickel sulfate nickel sulfate: RN given refers to cpd with MF of Ni(2+)-H2SO4. nickel sulfate : A metal sulfate having nickel(2+) as the metal ion.	2.05	1	0	metal sulfate	allergen
sulfonyl chloride [no description available]	2.37	2	0	sulfuryl halide
desmedipham desmedipham: structure. desmedipham : A carbamate ester that is phenylcarbamic acid in which the hydrogen of the hydroxy group has been replaced by a 3-[(ethoxycarbonyl)amino]phenyl group. It is an agrochemical used as a herbicide.	2	1	0	carbamate ester	agrochemical; environmental contaminant; herbicide; xenobiotic
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.37	2	0
poloxalene Poloxalene: A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.. pluronic : A triblock copolymer composed of a central hydrophobic chain of poly(propylene oxide) flanked by two hydrophilic chains of poly(ethylene oxide).	1.99	1	0	epoxide
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.	3.56	8	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.07	1	0	inorganic sodium salt; selenite salt	nutraceutical
colterol colterol: RN given refers to parent cpd without isomeric designation; structure. colterol : A member of the class of ethanolamines that is catechol in which the hydrogen at position 4 is replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.	1.96	1	0	catechols; ethanolamines; secondary alcohol; secondary amino compound; triol	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent
camphoroquinone camphoroquinone: a natural monoterpene, non-aromatic quinone; structure given in first source. bornane-2,3-dione : A bornane monoterpenoid that is bicyclo[2.2.1]heptane substituted by methyl groups at positions 1, 7 and 7 and oxo groups at positions 2 and 3.	1.97	1	0	bornane monoterpenoid; carbobicyclic compound
rhamnose [no description available]	2.4	2	0	L-rhamnose
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	2.44	2	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
3-hydroxybenzo(a)pyrene 3-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	2.07	1	0	ortho- and peri-fused polycyclic arene
gallium chloride gallium chloride: RN given refers to parent cpd	2.01	1	0
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.	2.55	2	0	titanium oxides	food colouring
menthone menthone : The trans-stereoisomer of p-menthan-3-one.. (-)-menthone : A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer).	2	1	0	menthone
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.	1.97	1	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.	2	1	0	3-hydroxy fatty acid; medium-chain fatty acid	antimitotic; Escherichia coli metabolite
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	1	0	selegiline; terminal acetylenic compound	geroprotector
thiamphenicol [no description available]	2.41	2	0	monocarboxylic acid amide; sulfone	antimicrobial agent; immunosuppressive agent
(2-methoxyethoxy)acetic acid (2-methoxyethoxy)acetic acid: a urinary biomarker; metabolite of 2-(2-methoxyethoxy)ethanol	2.07	1	0
ethephon (2-chloroethyl)phosphonic acid: structure in first source. (2-chloroethyl)phosphonic acid : A phosphonic acid compound having a 2-chloroethyl substituent attached to the P-atom.	2.03	1	0	phosphonic acids	plant growth regulator
fluorides [no description available]	2.99	4	0	halide anion; monoatomic fluorine
stilbene oxide stilbene oxide: inducer of epoxide hydratase; RN given refers to cpd without isomeric designation	7.39	2	0	epoxide
tert-butyldimethylsilyl chloride tert-butyldimethylsilyl chloride: structure in first source. tert-butyldimethylsilyl chloride : A silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2	1	0	silyl chloride	chromatographic reagent
verbenone verbenone: platelet aggregation inhibitor; RN given refers to cpd without isomeric designation. 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one : A carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4.. (S)-(-)-verbenone : A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have S configuration.	2.07	1	0	carbobicyclic compound; cyclic ketone; enone
chromium chromium hexavalent ion: a human respiratory carcinogen	3.21	5	0	chromium cation; monoatomic hexacation
4-amino-2,6-dinitrotoluene 4-amino-2,6-dinitrotoluene : An amino-nitrotoluene that is 2,6-dinitrotoluene substituted at position 4 by an amino group.	7.03	1	0	amino-nitrotoluene	explosive; fungal xenobiotic metabolite; marine metabolite
brilliant orange 3r brilliant orange 3R: RN given refers to di-Na salt; RN for parent cpd not avail 11/92; structure given in first source	2.1	1	0
iodine [no description available]	2.76	3	0	halide anion; monoatomic iodine	human metabolite
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	3.16	1	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial 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.	5.31	18	0	benzenes; phenyl acetates
4-anisaldehyde 4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.	2.43	2	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
acetylacetone acetylacetone : A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.	2.1	1	0	beta-diketone
pyrrolidine [no description available]	2.03	1	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	3.07	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.	2.37	2	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	2.71	3	0	chlorocarbon; chloroethenes	nephrotoxic agent
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	2	1	0	acetamides; monocarboxylic acid amide	human metabolite
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.	2.01	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	5.98	100	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
2,6-diisopropylnaphthalene [no description available]	3.49	2	0	naphthalenes	agrochemical; plant growth retardant
alkenes [no description available]	4.01	13	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.	2.72	3	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.83	3	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
2-aminotetralin 2-aminotetralin: RN given refers to parent cpd without isomeric designation; structure	2.84	4	0	tetralins
pcb 118 [no description available]	2.59	2	0	dichlorobenzene; pentachlorobiphenyl; trichlorobenzene
4-ipomeanol 4-ipomeanol: lung-toxic furanoterpenoid produced in moldy sweet potatoes in response to fungus infection; RN given refers to cpd without isomeric designation; structure	3.99	2	0	aromatic ketone
2,3,4,5-tetrachlorobiphenyl tetrachlorobiphenyl : Any polychlorobiphenyl with molecular formula C12H6Cl4.	2.04	1	0	tetrachlorobenzene; tetrachlorobiphenyl
2,5-dichlorobiphenyl 2,5-dichlorobiphenyl : A dichlorobiphenyl that is p-dichlorobenzene in which one of the hydrogens has been replaced by a phenyl group.	2.04	1	0	dichlorobenzene; dichlorobiphenyl
2,4'-dichlorobiphenyl 2,4'-dichlorobiphenyl: RN given refers to unlabeled cpd. 2,4'-dichlorobiphenyl : A dichlorobiphenyl that is chlorobenzene in which the hydrogen at position 2 has been replaced by a 4-chlorophenyl group.	2.04	1	0	dichlorobiphenyl; monochlorobenzenes
2-amino-4,6-dinitrotoluene 2-amino-4,6-dinitrotoluene : An amino-nitrotoluene that is 4,6-dinitrotoluene substituted at position 2 by an amino group.	7.03	1	0	amino-nitrotoluene	explosive; fungal xenobiotic metabolite
2,4,6-trichlorobiphenyl 2,4,6-trichlorobiphenyl: structure given in first source	2.04	1	0
cicloprofen [no description available]	2.02	1	0
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	1	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
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	1.99	1	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	2.06	1	0	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
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).	1.96	1	0
prenalterol Prenalterol: A partial adrenergic agonist with functional beta 1-receptor specificity and inotropic effect. It is effective in the treatment of acute CARDIAC FAILURE, postmyocardial infarction low-output syndrome, SHOCK, and reducing ORTHOSTATIC HYPOTENSION in the SHY-RAGER SYNDROME.	1.96	1	0	aromatic ether
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.	1.96	1	0
4-(n-methyl-n-nitrosamino)-1-(3-pyridyl)-1-butanone 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone: structure; from tobacco smoke	2.04	1	0	nitrosamine; pyridines
tiotidine tiotidine: UD gives slightly different structure for this cpd; RN given refers to parent cpd; structure in first source	2	1	0	thiazoles
amonafide xanafide: salt formulation of amonafide; DNA-intercalating agent and topoisomerase II inhibitor	2.02	1	0	isoquinolines
fenoxycarb fenoxycarb: used against mosquitoes (Diptera:Culicidae); structure given in first source. fenoxycarb : A carbamate ester that is the O-ethyl carbamate of 2-(4-phenoxyphenoxy)ethylamine.	2	1	0	aromatic ether; carbamate ester	environmental contaminant; insecticide; juvenile hormone mimic; xenobiotic
tolrestat tolrestat: RN & structure given in first source	1.99	1	0	naphthalenes	EC 1.1.1.21 (aldehyde reductase) inhibitor
raloxifene hydrochloride Raloxifene Hydrochloride: A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.. raloxifene hydrochloride : A hydrochloride salt resulting from the reaction of equimolar amounts of raloxifene and hydrogen chloride.	2.03	1	0	hydrochloride	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
zaltidine zaltidine: RN given for parent cpd; structure given in first source	2	1	0
nitroaniline nitroaniline: RN given refers to cpd with unspecified locant for nitro moiety. nitroaniline : A substituted aniline that carries one or more nitro groups.	2.15	1	0
nitrogen chloride nitrogen chloride: strong irritant & lacrimator	1.93	1	0	nitrogen halide
magnesium peroxide [no description available]	2.21	1	0	organic molecular entity
benzylaminopurine benzylaminopurine: a plant growth regulator. N-benzyladenine : A member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group.	2.45	2	0	6-aminopurines	cytokinin; plant metabolite
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.	2.08	1	0	one-carbon compound; perfluoroalkanesulfonic acid
isothiocyanic acid [no description available]	2.33	2	0	hydracid; one-carbon compound
sodium persulfate sodium persulfate: RN given refers to peroxydisulfuric acid, di-Na salt	2.13	1	0
propranolol hydrochloride Inderex: combination of above cpds; used in treatment of hypertension	1.96	1	0	hydrochloride
mandrax Mandrax: contains methaqualone; diphenhydramine	1.98	1	0	diarylmethane
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.	2.37	2	0	D-glucopyranose	epitope; mouse metabolite
iodonitrotetrazolium iodonitrotetrazolium chloride : An organic chloride salt having iodonitrotetrazolium as the counterion.. iodonitrotetrazolium : An organic cation that is the cationic component of iodonitrotetrazolium violet.	1.98	1	0	organic chloride salt	histological dye
cyclen cyclen: macrocyclic polyamine metal-complexing agent. 1,4,7,10-tetraazacyclododecane : An azacycloalkane that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogen atoms.	2.05	1	0	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
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.	2.06	1	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
diacetylfluorescein [no description available]	2.6	1	0
phenylalanylphenylalanine phenylalanylphenylalanine: RN given refers to (L,L)-isomer	2.06	1	0
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.73	3	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
fenclofenac fenclofenac: RN given refers to parent cpd	2	1	0	aromatic ether
imirestat imirestat: structure given in first source	2.89	4	0
boron nitride [no description available]	2.17	1	0	nitride
perylenediimide perylenediimide: structure in first source. perylenediimide : The 3,4,9,10-tetracarboxylic diimide derivative of perylene.	7.06	1	0	dicarboximide; organic heteropolycyclic compound	fluorochrome
naphthalimides Naphthalimides: Compounds with three fused rings that appear like a naphthalene fused to piperidone or like a benz(de)isoquinoline-1,3-dione (not to be confused with BENZYLISOQUINOLINES which have a methyl separating the naphthyl from the benzyl rings). Members are CYTOTOXINS.	2.44	2	0
alpha-naphthyl isocyanate alpha-naphthyl isocyanate: used to separate enantiomers of beta-blockers; structure given in first source	1.93	1	0
divinyl benzene [no description available]	2.04	1	0	styrenes
naphthol as naphthol AS: azo dye coupling component implicated in occupational pigmented contact dermatitis; RN given refers to unlabeled parent cpd; structure	2.62	3	0
benzeneboronic acid [no description available]	2.13	1	0	boronic acids
2-ethoxybenzoic acid [no description available]	2.02	1	0
estradiol-3,4-quinone estradiol-3,4-quinone: structure in first source	2.1	1	0
1,7-phenanthroline [no description available]	3.13	5	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.	7.82	3	0	1,2,3-triazole
1h-tetrazole tetrazole : An azaarene that is a five-membered ring composed of 4 nitrogen and 1 carbon atom.. 2H-tetrazole : A tetrazole tautomer where the proton is located on the 2 position.	2.08	1	0	one-carbon compound; tetrazole
trifluoromethanesulfonanilide [no description available]	1.96	1	0
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.06	1	0	isocoumarins
duroquinone tetramethyl-1,4-benzoquinone: structure in first source. duroquinone : A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which all four hydrogens are substituted by methyl groups.	1.96	1	0	1,4-benzoquinones
beta-tetralone [no description available]	2.44	2	0
alpha-methylene gamma-butyrolactone alpha-methylene gamma-butyrolactone : A butan-4-olide having a methylene group at the 3-position.	1.99	1	0	butan-4-olide	anti-ulcer drug; gastrointestinal drug
2(3h)-benzofuranone 2(3H)-benzofuranone: structure in first source	2.02	1	0
medetomidine Medetomidine: An agonist of RECEPTORS, ADRENERGIC ALPHA-2 that is used in veterinary medicine for its analgesic and sedative properties. It is the racemate of DEXMEDETOMIDINE.	6.99	1	0	imidazoles
sertraline Sertraline: A selective serotonin uptake inhibitor that is used in the treatment of depression.. sertraline : A member of the class of tetralins that is tetralin which is substituted at positions 1 and 4 by a methylamino and a 3,4-dichlorophenyl group, respectively (the S,S diastereoisomer). A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as the hydrochloride salt as an antidepressant for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic stress disorder.	2.21	1	0	dichlorobenzene; secondary amino compound; tetralins	antidepressant; serotonin uptake inhibitor
glycine amide glycine amide: RN given refers to parent cpd	2.33	2	0	amino acid amide; glycine derivative
cyclopropylbenzene [no description available]	1.96	1	0
methotrimeprazine Methotrimeprazine: A phenothiazine with pharmacological activity similar to that of both CHLORPROMAZINE and PROMETHAZINE. It has the histamine-antagonist properties of the antihistamines together with CENTRAL NERVOUS SYSTEM effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). methotrimeprazine : A member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively.	2	1	0	phenothiazines; tertiary amine	anticoronaviral agent; cholinergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; non-narcotic analgesic; phenothiazine antipsychotic drug; serotonergic antagonist
alantolactone alantolactone: allergenic sesquiterpene lactone; crystalline mixture of alantolactones from group of sesquiterpenes; structure. alantolactone : A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.	1.93	1	0	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
bathophenanthroline 4,7-diphenyl-1,10-phenanthroline : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two phenyl substituents at positions 4 and 7.	7	1	0	benzenes; phenanthrolines	chelator
4-aminophthalimide 4-aminophthalimide: structure in first source	3.18	1	0
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.	2.1	1	0	cerium molecular entity; metal oxide
2-naphthyl sulfate 2-naphthyl sulfate: RN given refers to parent cpd. 2-naphthyl sulfate : An aryl sulfate that is naphthalene in which the hydrogen at position 2 is replaced by a sulfooxy group.	1.93	1	0	aryl sulfate; naphthalenes
5-phenyl-1-pentyne [no description available]	2.05	1	0
4-nitrophenyl propionate [no description available]	1.95	1	0
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.	1.93	1	0	hexadecanoate ester; wax ester	coral metabolite; cosmetic
5-methoxysalicylic acid 5-methoxysalicylic acid: enhances intestinal absorption of insulin in rats; RN given refers to parent cpd. 5-methoxysalicylic acid : A methoxysalicylic acid that is salicylic acid which is carrying a methoxy group at position 5.	2.21	1	0	methoxysalicylic acid	bacterial metabolite; human urinary metabolite
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.	1.95	1	0	butyrate ester; C-nitro compound
phenyl hippurate [no description available]	1.95	1	0
benzoyltyrosine ethyl ester ethyl N-benzoyl-L-tyrosinate : An L-tyrosine derivative that is the ethyl ester of N-benzoyltyrosine.	1.95	1	0	benzamides; ethyl ester; L-tyrosine derivative; phenols	chromogenic compound
1,4-dioxin 1,4-dioxine : An oxacycle that is 4H-pyran in which the methylene group at position 4 is replaced by an oxygen. Non-aromatic.	2.03	1	0	oxacycle
benzylphosphonic acid [no description available]	2.06	1	0	benzenes
4-hydroxyphenanthrene 4-hydroxyphenanthrene: a metabolite of polycyclic aromatic hydrocarbon	2.21	1	0	phenanthrol
s20098 [no description available]	2.48	2	0	acetamides
3-(trimethoxysilyl)propylamine 3-(trimethoxysilyl)propylamine: reagent for making polymers; structure in first source	2	1	0
5-bromoindoxyl acetate 5-bromoindoxyl acetate: substrate for non-specific esterase	1.93	1	0
coenzyme a [no description available]	2.49	2	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
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.	2.92	4	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.	2.07	1	0	iditol	fungal metabolite
2,2-dimethoxy-2-phenylacetophenone [no description available]	2.02	1	0
5-bromouridine 5-bromouridine : A uridine having a bromo substituent at the 5-position.	2.05	1	0	uridines	mutagen
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
triptycene triptycene: structure in first source	2.04	1	0	anthracenes
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.	2.05	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.	2.04	1	0
n-acetylphenylalanine ethyl ester N-acetylphenylalanine ethyl ester: RN given refers to (L)-isomer	1.95	1	0
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.	8.03	5	0	D-glucuronic acid	algal metabolite
6-fluorotryptophan 6-fluorotryptophan: an inhibitor of serotonin synthesis; RN given refers to parent cpd without isomeric designation	2.01	1	0	indolyl carboxylic acid
allenolic acid allenolic acid: structure in first source	1.93	1	0	naphthols
2,3-naphthalenedicarboxaldehyde 2,3-naphthalenedicarboxaldehyde: used in colorimetric determination of cholesterol; RN from CA Form Index Vol 90; N1 same as NM	3.01	2	0
4-nitrophenyloctanoate [no description available]	1.95	1	0
1,3,4-oxadiazole 1,3,4-oxadiazole: structure in first source	7.1	1	0
tetrathiafulvalene tetrathiafulvalene: used in carbon paste amperometric enzyme electrode for the determination of glucose in flowing systems. tetrathiafulvalene : A member of the class of fulvalenes that is ethene substituted by 1,3-dithiol-2-ylidene groups at positions 1 and 2.	2.05	1	0	fulvalenes; organosulfur heterocyclic compound
combretastatin combretastatin: cytotoxic principle from South African tree COMBRETUM caffrum; structure given in first source; acts at COLCHICINE site of TUBULIN	2.02	1	0
berbine berbine: structure	2.06	1	0	berberine alkaloid; isoquinoline alkaloid fundamental parent; organic heterotetracyclic compound
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.	8.48	7	0	cobalt group element atom; metal allergen	micronutrient
hydrogen sulfite [no description available]	1.93	1	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.06	1	0	oligopeptide
cyfluthrin cyfluthrin: effective against mosquitoes. cyfluthrin : A carboxylic ester obtained by formal condensation between 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (4-fluoro-3-phenoxyphenyl)(hydroxy)acetonitrile.	7.05	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound; organofluorine compound	agrochemical; pyrethroid ester insecticide
laurdan laurdan: RN from CA Index Guide	1.98	1	0
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).	2.64	3	0
(3h)2-carbomethoxy-3-(4-fluorophenyl)tropane (1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester: RN given refers to (1R-(exo,exo))-isomer	2.07	1	0
s-ethyl glutathione [no description available]	2	1	0	oligopeptide
sivelestat sivelestat: inhibitor of neutrophil elastase; structure given in first source	7.15	1	0	N-acylglycine; pivalate ester
prodan prodan: do not confuse with prodan in Chemline, RN 16893-85-9 which is disodium hexafluorosilicate	3.82	3	0	2-acyl-6-dimethylaminonaphthalene
hydroxycotinine hydroxycotinine: metabolite of nicotine; RN given refers to (S)-isomer; structure. trans-3-hydroxycotinine : An N-alkylpyrrolidine that is cotinine substituted at position C-3 by a hydroxy group (the 3R,5S-diastereomer).	2.05	1	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid
naphthalene 1,2-oxide [no description available]	3.59	9	0	arene epoxide
hexachloronaphthalene [no description available]	2.33	2	0
naphthyl sulfate naphthyl sulfate: RN given refers to parent cpd	2.63	3	0
trans-1,2-dihydro-1,2-naphthalenediol trans-1,2-dihydro-1,2-naphthalenediol: structure in first source. (1S,2S)-1,2-dihydronaphthalene-1,2-diol : The (1S,2S)-isomer of trans-1,2-dihydronaphthalene-1,2-diol.	2.43	2	0	trans-1,2-dihydronaphthalene-1,2-diol
aporphine aporphine: RN given refers to parent cpd without isomeric designation. aporphine : An isoquinoline alkaloid that is the N-methyl derivative of 5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline.	2.06	1	0	aporphine alkaloid; isoquinoline alkaloid fundamental parent; tertiary amino compound
protoberberine protoberberine: a benzyltetrahydroisoquinoline derivative that appears as an isoquinoline annelated (adjoined) with a naphthylene; the nitrogen is typically quarternary; nitidine is annelated differently; RN given refers to parent cpd	2.06	1	0
tenax tenax: porous polymer based on 2,6-diphenyl-p-phenylene oxide; used for trapping volatile organic compounds	7.43	2	0
benzyne benzyne: structure in first source. benzyne : 1,2-didehydrobenzene and its derivatives formed by substitution.	2.31	1	0	aryne; benzyne
stannane [no description available]	7.11	1	0	mononuclear parent hydride; tin hydride
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).	2.46	2	0	carbene; methanediyl
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.02	1	0	nitrogen oxoacid
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.	2.72	3	0	fullerene	geroprotector
gefitinib [no description available]	7.5	2	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
angiotensin ii, des-phe(8)- Ile(5)-angiotensin II (1-7) : An angiotensin compound consisting of the linear heptapeptide sequence L-Asp-L-Arg-L-Val-L-Tyr-L-Ile-L-His-L-Pro.	2.08	1	0	amino acid zwitterion; angiotensin	vasodilator agent
dehydroalanine 2-ammonioprop-2-enoate : An amino acid zwitterion resulting from a transfer of a proton from the carboxy group to the amino group of 2-aminoacrylic acid.. 2-aminoacrylic acid : A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.	2.11	1	0	2,3-dehydroamino acid; alpha,beta-unsaturated monocarboxylic acid; amino acid zwitterion; enamine; non-proteinogenic alpha-amino acid	alkylating agent; human metabolite; mouse metabolite
rti-coc 32 RTI-COC 32: structure given in first source; RN given refers to (1R-(exo,exo))-isomer; RN for cpd without isomeric designation not available 4/91	2.07	1	0
xylose xylopyranose: structure in first source	2.17	1	0	D-xylose
sperm motility inhibitor 2 [no description available]	2.46	2	0
allophanic acid urea-1-carboxylic acid : A member of the class of ureas that is urea in which one of the hydrogens has been replaced by a carboxy group.	2.02	1	0	ureas
naphthyl glucuronide naphthyl glucuronide: RN given refers to D-glucosiduronic acid, 1-naphthyl	2.35	2	0
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.	4.27	5	0	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.	8.91	12	0	oxygen hydride; oxygen radical; reactive oxygen species
naphthalenediimide naphthalenediimide: structure in first source	2.99	4	0
pseudonicotine pseudonicotine: structure. (R)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration.	2.02	1	0	3-(1-methylpyrrolidin-2-yl)pyridine
camphora camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.	2	1	0	camphor
sodium percarbonate sodium percarbonate: RN given refers to unspecified Na salt	2.02	1	0
peroxymonosulfate peroxymonosulfate: oxidizing agent in prevention of tooth discoloration; RN given refers to ion(2-)	7.6	1	0	sulfur oxide; sulfur oxoanion
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.72	3	0
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
al 4114 AL 4114: structure given in first source	1.99	1	0
homochelidonine homochelidonine: structure in first source	2.03	1	0	benzophenanthridine alkaloid
terics terics: medicated blocks used for control of cattle bloat; RN given is for teric N; nonylphenol ethoxylate is resistant to environmental breakdown so EPA discourages use	2.06	1	0
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.	2.04	1	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).	2.08	1	0	amino acid zwitterion; angiotensin II	human 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.	2.41	2	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.	4.11	4	0
erlotinib hydrochloride [no description available]	2.08	1	0	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.71	3	0	divalent inorganic anion; phosphite ion
limonin [no description available]	7.03	1	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
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.	7.68	3	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
aphanorphine aphanorphine: isolated from the fresh water blue-green alga; structure in first source	2.15	1	0
prizes acetamiprid: structure in first source. (E)-acetamiprid : The (E)-stereoisomer of acetamiprid.. acetamiprid : A carboxamidine that is acetamidine in which the amino hydrogens are substituted by a (6-chloropyridin-3-yl)methyl and a methyl group while the hydrogen attached to the imino nitrogen is replaced by a cyano group.	2.06	1	0	carboxamidine; monochloropyridine; nitrile	environmental contaminant; neonicotinoid insectide; xenobiotic
deferasirox Deferasirox: A triazole and benzoate derivative that acts as a selective iron chelator. It is used in the management of chronic IRON OVERLOAD due to blood transfusion or non-transfusion dependent THALASSEMIA.. deferasirox : A member of the class of triazoles, deferasirox is 1,2,4-triazole substituted by a 4-carboxyphenyl group at position 1 and by 2-hydroxyphenyl groups at positions 3 and 5. An orally active iron chelator, it is used to manage chronic iron overload in patients receiving long-term blood transfusions.	2.05	1	0	benzoic acids; monocarboxylic acid; phenols; triazoles	iron chelator
santonin Santonin: Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. (From Merck, 11th ed.)	2.33	2	0	botanical anti-fungal agent; santonin	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.	2.01	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
cortisone [no description available]	6.93	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
propargylamine propargylamine: RN given refers to parent cpd; structure	1.98	1	0
2-chlorobiphenyl 2-chlorobiphenyl: RN from Toxlit. 2-chlorobiphenyl : A monochlorobiphenyl carrying a single chloro substituent at position 2.. monochlorobiphenyl : A chlorobiphenyl carrying a single chloro substituent at unspecified position.. chlorobiphenyl : A chloroarene that consists of a biphenyl skeleton substituted by one or more chloro groups.	3.14	5	0	monochlorobiphenyl
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.77	10	0
metribolone Metribolone: A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.. 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one : A synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.	1.96	1	0	17beta-hydroxy steroid; 3-oxo steroid; anabolic androgenic steroid	androgen
diospyrin diospyrin: structure given in first source	2.03	1	0	hydroxy-1,4-naphthoquinone; ring assembly
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	2.08	1	0	gamma-lactam; indolinone
sorbinil sorbinil: aldose reductase inhibitor. sorbinil : An azaspiro compound having a monofluoro-substituted chromane skeleton spiro-linked to an imidazolidinedione ring.	1.99	1	0	azaspiro compound; chromanes; imidazolidinone; organofluorine compound; oxaspiro compound	antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor
erianin Erianin: from Dendrobium chrysotoxum; structure in first source	7.07	1	0
bortezomib [no description available]	2.17	1	0	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	7.03	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.	2.66	3	0
sorbose sorbopyranose : The pyranose form of sorbose.. L-sorbopyranose : The L-stereoisomer of sorbopyranose.	6.93	1	0	L-sorbose; sorbopyranose
fibrin Fibrin: A protein derived from FIBRINOGEN in the presence of THROMBIN, which forms part of the blood clot.	6.93	1	0	peptide
epiglucan epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.	2.1	1	0
laminaran beta-1,3-glucan: component of fungal cell walls; also used as antitumor polysaccharide; unspecified D usually means BETA-GLUCANS; beta-1,3-D-glucan is also available; glucan phosphate is also available; biosynthesis is inhibited by echinocandins (cyclic hexapeptides). laminarin : A polysaccharide composed of beta-(1->3)-linked glucose residues containing sporadic beta-(1->6)-linkages as branch points or inter-residue linkages and 2-3% D-mannitol at some reducing termini.	2.1	1	0
7-dehydrocholesterol [no description available]	2.04	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; cholestanoid; Delta(5),Delta(7)-sterol	human metabolite; mouse metabolite
(+)-limonene (4R)-limonene : An optically active form of limonene having (4R)-configuration.	2	1	0	limonene	plant metabolite
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	1.93	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	2	1	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2.69	3	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
mycothiol mycothiol: a glyco-inositol-cysteine found in MYCOBACTERIUM BOVIS which conjugates exogenous compounds for detoxication; it is a microbe counterpart to eucaryotic GLUTATHIONE; acted on by mycothiol disulfide reductase and mycothiol S-conjugate amidase and MDF dehydrogenase;. mycothiol S-conjugate : Any S-conjugate of mycothiol.. mycothiol : A pseudodisaccharide, 1D-myo-inosityl-alpha-D-glucopyranoside, in which the hydroxy group at the 2-position of the glucose moiety is replaced by an (N-acetyl-L-cysteinyl)amido group.	2.08	1	0
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.	6.93	1	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
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)	4.49	7	0
dioncophylline a dioncophylline A: derived from the tropical vine Triphyophyllum peltatum; structure given in first source. dioncophylline A : An isoquinoline alkaloid that is the biaryl resulting from substitution of the hydrogen at the 7-position of (1R,3R)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol by a 4,5-dimethoxy-2-methylnaphthalen-1-yl group. It is a naphthylisoquinoline alkaloid isolated from the roots and stem barks of Triphyophyllum peltatum and exhibits antifungal, antimalarial, antineoplastic and molluscicidal activites.	2.03	1	0	biaryl; isoquinoline alkaloid; isoquinolines; methoxynaphthalene; methylnaphthalenes; naphthalenes	antifungal agent; antimalarial; metabolite; molluscicide
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.41	7	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.	2.15	1	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	2.25	1	0	cinnamic acid	plant metabolite
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.	2.05	1	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.	6.96	1	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
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	7.51	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).	2.64	3	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
cyanoginosin lr cyanoginosin LR: cyclic heptapeptide from cyanobacterium Microcystis aeruginosa. microcystin-LR : A microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-beta-aspartyl,L-arginyl, 2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-gamma-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. Produced by the cyanobacterium Microcystis aeruginosa, it is the most studied of the microcystins.	2.21	1	0	microcystin	bacterial metabolite; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; environmental contaminant; xenobiotic
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.	4.08	15	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.	2.15	1	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
phenylalaninol phenylalaninol: inhibits intestinal absorption of phenylalanine; RN given refers to cpd with unspecified stereochemistry. L-phenylalaninol : An amino alcohol resulting from the formal reduction of the carboxy group of L-phenylalanine to the corresponding alcohol.	7.08	1	0	amino alcohol; amphetamines; primary alcohol; primary amino compound
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.	2.88	4	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
zeatin Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)	2.08	1	0	zeatin	plant metabolite
imidazolidines [no description available]	1.99	1	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
conidendrin conidendrin: RN given for (3aR-(3aalpha,4alpha,9alpha,9abeta))-isomer; a phenyl-naphthyl-furanolactone	1.93	1	0	lignan	metabolite
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.03	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
potassium permanganate Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)	2.05	1	0
4-nitrophenyl valerate 4-nitrophenyl valerate: structure in first source	1.95	1	0
oxazolidine oxazolidine: structure given in first source	2.02	1	0	oxazolidine
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.	2.95	4	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
calix(4)arene calix(4)arene: a cyclophane consisting of four phenolic units linked by methylene groups; structure in first source	2.01	1	0
4-nitrophenyl hexanoate [no description available]	1.95	1	0
naphthalan naphthalan: oil containing naphthalanic hydrocarbons, nitric & other cpds	1.93	1	0
glycosides [no description available]	9.37	6	0
chalcone trans-chalcone : The trans-isomer of chalcone.	7.36	2	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
1,3,5,7-cyclooctatetraene 1,3,5,7-cyclooctatetraene: structure in first source. [8]annulene : An antiaromatic annulene that is cyclooctane having four double bonds at positions 1, 3, 5 and 7.	2.1	1	0
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	4.89	11	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.	2.02	1	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)	2.52	2	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
3-hydroxybutyryl-coenzyme a 3-hydroxybutyryl-coenzyme A: RN given refers to cpd without isomeric designation. 3-hydroxybutanoyl-CoA : A hydroxybutanoyl-CoA having 3-hydroxybutanoyl as the S-acyl component.	2.15	1	0	3-hydroxyacyl-CoA; hydroxybutanoyl-CoA	mouse metabolite
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	7.36	2	0	diphosphate ion
polidocanol Polidocanol: An alkyl polyglycol ether of LAURYL ALCOHOL, chemically defined as an alcohol ethoxylate having an average alkyl chain of 12–14 carbon atoms, and an ethylene oxide chain of 9 ethylene oxide units. It is used as a detergent, and medically as a local anesthetic, and as a sclerosing agent for the treatment of ESOPHAGEAL AND GASTRIC VARICES and VARICOSE VEINS.. polidocanol : A hydroxypolyether that is nonaethylene glycol in which one of the terminal hydroxy functions is substituted by a lauryl (dodecyl) group.	2.41	2	0	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
dithizone Dithizone: Chelating agent used for heavy metal poisoning and assay. It causes diabetes.	2.08	1	0
sesquiterpenes [no description available]	2.96	4	0
etomidate Etomidate: Imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic.. etomidate : The ethyl ester of 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid. It is an intravenous general anaesthetic with no analgesic activity.	2.59	2	0	ethyl ester; imidazoles	intravenous anaesthetic; sedative
alpha-naphthyl thiourea alpha-naphthyl thiourea: structure	2.33	2	0	naphthalenes
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.	2.72	3	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
dieldrin Dieldrin: An organochlorine insecticide whose use has been cancelled or suspended in the United States. It has been used to control locusts, tropical disease vectors, in termite control by direct soil injection, and non-food seed and plant treatment. (From HSDB). dieldrin : An organochlorine compound resulting from the epoxidation of the double bond of aldrin. It is the active metabolite of the proinsecticde aldrin.	2.01	1	0	epoxide; organochlorine compound; organochlorine insecticide	carcinogenic agent; xenobiotic
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.	8.51	2	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
rhodanine 2-mercaptothiazolinone: metabolite in urine from persons exposed to CS2; structure	2.03	1	0	thiazolidinone
4,6-dimethyldibenzothiophene [no description available]	2.05	1	0
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2	1	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
terbinafine [no description available]	1.98	1	0	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor
isoeugenol [no description available]	2	1	0	isoeugenol
ethylenethiourea Ethylenethiourea: A degradation product of ethylenebis(dithiocarbamate) fungicides. It has been found to be carcinogenic and to cause THYROID hyperplasia.	6.96	1	0	imidazolidines
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.	9.08	15	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	3.27	6	0
D-fructopyranose [no description available]	2.41	2	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
tamoxifen [no description available]	7.72	3	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
1-octyl-3-methylimidazolium hexafluorophosphate 1-octyl-3-methylimidazolium hexafluorophosphate: is a nonaqueous ionic liquid	2.05	1	0
nadp [no description available]	8.58	9	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.46	2	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.	3.48	7	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.	2.4	2	0	alkali metal atom
zineb Zineb: An agricultural fungicide of the dithiocarbamate class. It has relatively low toxicity and there is little evidence of human injury from exposure.. zineb : A polymeric complex of zinc with the ethylene bis(dithiocarbamate) anionic ligand. Formerly used as an agricultural fungicide for the control of downy mildews and rusts, its use is no longer permitted in the US or the EU.	7.02	1	0	dithiocarbamate salt; macromolecule; zinc coordination entity	antifungal agrochemical
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.	3.11	5	0	nitrogen oxide
fremy's salt Fremy's salt: mild reagent for conversion of phenols to quinones; structure	1.97	1	0	aminoxyls; potassium salt
glutaryl-coenzyme a [no description available]	2.15	1	0	glutaryl-CoAs	mouse metabolite
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.	2.71	3	0
pimeloyl-coenzyme a pimeloyl-CoA : An omega carboxyacyl-CoA that is the S-pimeloyl derivative of coenzyme A.	2.15	1	0	omega-carboxyacyl-CoA	metabolite
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.03	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.49	2	0
anthraquinone sulfonate anthraquinone sulfonate: RN given refers to cpd with unspecified acid locant	2.41	2	0
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.	8.53	8	0	organic sodium salt	detergent; protein denaturant
dimethyldithiocarbamate Dimethyldithiocarbamate: A chemical that acts as a dopamine beta-hydroxylase inhibitor. Its salts are agricultural fungicides. It is inferior to diethyldithiocarbamate as a chelating agent.. dimethyldithiocarbamate : A member of the class of dithiocarbamate anions resulting from the removal of the proton from the dithiocarbamic acid moiety of dimethyldithiocarbamic acid. The major species at pH 7.3.	2	1	0	dithiocarbamate anions
4-(4,5-diphenyl-1h-imidazol-2-yl)benzoyl chloride 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoyl chloride: used to derivatize methamphetamines; structure in first source	2.05	1	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	10.85	31	0
3,4-ethylenedioxythiophene 3,4-ethylenedioxythiophene: structure in first source	2.17	1	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.	2.08	1	0	organic cation; xanthene dye	fluorochrome
3-hydroxychromone 3-hydroxychromone: structure in first source	3.18	1	0
diethyl maleate diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	8.24	6	0	ethyl ester; maleate ester	glutathione depleting agent
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.	2.07	1	0	sphing-4-enine	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.	2.41	2	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
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.	2.03	1	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.	2.87	4	0
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.	7	1	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
maleylpyruvate [no description available]	2.95	4	0	4,6-dioxohept-2-enedioic acid; beta-diketone
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	2.04	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
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.	2.5	2	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.	2.04	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
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	1	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.21	1	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	2.21	1	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
alpha-ionone alpha-ionone: RN given refers to cpd without isomeric designation; structure	2	1	0	enone; ionone; methyl ketone
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	2.11	1	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
sphingosine 1-phosphate sphingosine 1-phosphate: RN given refers to (R-(R,S-(E)))-isomer; RN for cpd without isomeric designation not available 8/89. sphingosine 1-phosphate : A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1	2.07	1	0	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent
codeine [no description available]	2.41	2	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
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.	2.04	1	0	phylloquinones; vitamin K	cofactor; human metabolite; plant metabolite
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.63	3	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
mdl 100907 Serotonin 5-HT2 Receptor Antagonists: Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes.	2.08	1	0
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.	2.03	1	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
stiripentol stiripentol: structure	7.37	2	0
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.	2.1	1	0	phosphatidylcholine(1+)
biliverdine [no description available]	2.05	1	0
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	2	1	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	3.16	5	0	carbon group element atom; elemental lead; metal atom	neurotoxin
tin [no description available]	2.13	1	0	carbon group element atom; elemental tin; metal atom	micronutrient
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.	2.01	1	0	alkali metal atom
triphenyltin triphenyltin: triphenyltin derivatives widely used as pesticides; all of first source is triphenyltin cpds	2.01	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	8.34	6	0	boron group element atom; elemental aluminium; metal atom
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).	7.36	2	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.	2.74	3	0	boron group element atom
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.	3.23	6	0	chalcogen; nonmetal atom	macronutrient
musk musk: pure essence from secretion of preputial follicles of Moschus moschiferus L.	2.07	1	0	macrolide
5-deazaflavin [no description available]	7.41	1	0	pyridopyrimidine
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.	1.99	1	0	alkatriene	fluorochrome
bedaquiline bedaquiline: a diarylquinoline Antitubercular Agent. bedaquiline : A quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria.	7.17	1	0	aromatic ether; naphthalenes; organobromine compound; quinolines; tertiary alcohol; tertiary amino compound	antitubercular agent; ATP synthase inhibitor
nitrofurazone Nitrofurazone: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.. nitrofurazone : A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wounds and skin infections.	2.41	2	0
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).	1.98	1	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	3.83	3	0	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.	4.71	9	0	cysteinium	fundamental metabolite
thyronines Thyronines: A group of metabolites derived from THYROXINE and TRIIODOTHYRONINE via the peripheral enzymatic removal of iodines from the thyroxine nucleus. Thyronine is the thyroxine nucleus devoid of its four iodine atoms.. thyronine : A tyrosine derivative where the phenolic hydrogen of tyrosine is substituted by 4-hydroxyphenyl.	2.13	1	0	thyronine
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].	3.13	5	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.	7.68	3	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.	7.72	3	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
crotonyl-coenzyme a crotonoyl-CoA : The (E)-isomer of but-2-enoyl-CoA.	2.15	1	0	but-2-enoyl-CoA
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.	2.1	1	0	2-trans-abscisic acid
phenyldehydroalanine [no description available]	2.11	1	0
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.	3.29	6	0	chalcogen; nonmetal atom	micronutrient
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.	2.05	1	0
octadecylsilane [no description available]	2.03	1	0
clinoptilolite clinoptilolite: clinoptilolite was SY to zeolite (NM); use zeolites (NM) to search through 1993; RN is for cpd with unknown MF	2	1	0
palonosetron Palonosetron: Isoquinoline and quinuclidine derivative that acts as a 5-HT3 RECEPTOR antagonist. It is used in the prevention of nausea and vomiting induced by cytotoxic chemotherapy, and for the prevention of post-operative nausea and vomiting.. palonosetron : An organic heterotricyclic compound that is an antiemetic used (as its hydrochloride salt) in combination with netupitant (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy.	2.06	1	0	azabicycloalkane; delta-lactam; organic heterotricyclic compound	antiemetic; serotonergic antagonist
beta-naphthylalanine [no description available]	1.93	1	0
vitamin a2 vitamin A2: RN given refers to cpd without isomeric designation. all-trans-3,4-didehydroretinol : A retinoid derived from 3,4-desaturation of the beta-ionone ring of all-trans-retinol.	2.04	1	0	retinoid; vitamin A	human xenobiotic metabolite; marine xenobiotic metabolite; mouse metabolite
fumarylpyruvate fumarylpyruvate: structure given in first source	2.72	3	0
valerenic acid valerenic acid: a saturated oplopanone type indene from Valeriana officinalis. valerenic acid : A monocarboxylic acid that is 2-methylprop-2-enoic acid which is substituted at position 3 by a 3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl group. A bicyclic sesquiterpenoid constituent of the essential oil of the Valerian plant.	2.03	1	0	carbobicyclic compound; monocarboxylic acid; sesquiterpenoid	GABA modulator; plant metabolite; sedative; volatile oil component
nifuroxime 5-nitro-2-furaldehyde oxime: structure in first source	2.69	3	0
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.	2.1	1	0
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	7.7	3	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
bornyl acetate [no description available]	2.07	1	0	acetate ester; monoterpenoid
staurosporine staurosporinium : Conjugate acid of staurosporine.	2.25	1	0	ammonium ion derivative
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	2.11	1	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
phoxim phoxim: structure	2.01	1	0
s-(1,2-dicarboxyethyl)glutathione S-(1,2-dicarboxyethyl)glutathione: isolated from calf lens; structure in first source	1.99	1	0
braco-19 BRACO-19: structure in first source	3.16	1	0	acridines; N-alkylpyrrolidine
omacor Omacor: a drug containing the n-3 fatty acids that corrects plasma lipid; antiarrhthymic	2.15	1	0
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	3.33	6	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
secoisolariciresinol diglucoside secoisolariciresinol diglucoside: major precursor of mammalian lignans; structure given in first source; RN given refers to B-D-GLUCO isomer	2.07	1	0
zeolites [no description available]	8.14	5	0
3-iodothyronamine 3-iodothyronamine: a thyroid hormone derivative that may be involved in a fast response signaling pathway; structure in first source	2.13	1	0	aromatic ether
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.	2.74	3	0
2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane 2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane: used in PET and SPECT imaging of dopamine transporters; structure in first source	2.07	1	0
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	2.05	1	0
tolfenpyrad tolfenpyrad: insecticide; structure in first source. tolfenpyrad : An aromatic amide obtained by formal condensation of the carboxy group of 4-chloro-3-ethyl-1-methylpyrazole-5-carboxylic acid with the amino group of 1-[4-(4-methylphenoxy)phenyl]methylamine.	2.48	2	0	aromatic amide; aromatic ether; organochlorine compound; pyrazole insecticide	agrochemical; antifungal agent; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor
di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone [no description available]	2.05	1	0
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	3	4	0
tamandarin b tamandarin B: structure in first source	2.03	1	0
bis(pyridine)iodonium(i) tetrafluoroborate bis(pyridine)iodonium(I) tetrafluoroborate: an iodinating reagent for peptides	2.03	1	0
lysol [no description available]	1.92	1	0	amino alcohol
azinomycin a azinomycin A: from Streptomyces griseofuscus S42227; structure given in first source; (but Biochemistry. 2000 Dec 5;39(48):14968-75 says Azinomycin B = carzinophilin A)	2.02	1	0
ochromycinone ochromycinone: structure in first source	2.02	1	0
alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc Sialyl Lewis X Antigen: A sialylated version of Lewis X antigen expressed on cell surfaces. It is a ligand for SELECTINS.. alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc : A branched amino tetrasaccharide consisting of a sialyl residue, linked (2->3) to a galactosyl residue that in turn is linked (1->4) to a glucosaminyl residue, which is also carrying a fucosyl residue at the 3-position.	1.99	1	0	amino tetrasaccharide; glucosamine oligosaccharide	epitope
ferryl iron [no description available]	2.01	1	0
propyl 4-(2-(4,6-dimethoxypyrimidin-2-yloxy)benzylamino)benzoate propyl 4-(2-(4,6-dimethoxypyrimidin-2-yloxy)benzylamino)benzoate: an herbicide for use on rape crops; structure in first source	2.13	1	0
resorcinarene resorcinarene: structure in first source	2.02	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.	1.93	1	0
azinomycin b azinomycin B: C31H33N3O11; from Streptomyces griseofuscus S42227; structure given in first source	2.02	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	3.54	8	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
morphine sulfate [no description available]	2	1	0	alkaloid sulfate salt
melitten Melitten: Basic polypeptide from the venom of the honey bee (Apis mellifera). It contains 26 amino acids, has cytolytic properties, causes contracture of muscle, releases histamine, and disrupts surface tension, probably due to lysis of cell and mitochondrial membranes.	3.18	1	0
cucurbit(8)uril cucurbit(8)uril: a macrocyclic polymer compound comprising 8 GLYCOLURIL units with methylene bridges	2.76	3	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.	2.31	1	0
oligonucleotides [no description available]	7.73	3	0
complestatin complestatin: compound extracted from Streptomyces lavendulae mycelia; on acid hydrolysis yields D-4-hydroxyphenylglycine & D-3,5-dichloro-4-hydroxyphenylglycine & acidic chromophore; inhibits gp120-CD4 binding. isocomplestatin : A heterodetic cyclic peptide which is a atropisomer of complestatin. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity.. chloropeptin II : A heterodetic cyclic peptide consisting of N-acylated trytophan, 3,5-dichloro-4-hydroxyphenylglycine, 4-hydroxyphenylglycine, 3,5-dichloro-4-hydroxyphenylglycyl, tyrosine and 4-hydroxyphenylglycine residues joined in sequence and in which the side-chain of the central 4-hydroxyphenylglycine residue is attached to the side-chain of the tryptophan via a C3-C6 bond and to the side-chain of the tyrosine via an ether bond from C5. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity.	2.07	1	0	cyclic ether; heterodetic cyclic peptide; indoles; organic heterobicyclic compound; organochlorine compound; peptide antibiotic; polyphenol	anti-HIV-1 agent; antimicrobial agent; HIV-1 integrase inhibitor; metabolite
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	8.44	7	0	glycoside
sodium borate borax: see also sodium borate. borax : A hydrate that is the decahydrate form of disodium tetraborate.	2.17	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.73	3	0	1,2-diacyl-sn-glycero-3-phosphocholine
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.	2.77	3	0	chlorophyll; methyl ester	cofactor
sodium salicylate [no description available]	2.37	2	0	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.	1.96	1	0
1,2-azaborine 1,2-azaborine: structure in first source	7.11	1	0
chitosan [no description available]	7.46	2	0
9-borabicyclononane 9-borabicyclononane: an amino acid protecting group	2.06	1	0
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	2.11	1	0	inorganic sodium salt	bleaching agent; disinfectant
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	1.97	1	0	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	2.6	1	0
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2	1	0	BODIPY compound
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)	2.54	2	0
glycolipids [no description available]	2.44	2	0
piperidines Piperidines: A family of hexahydropyridines.	2.67	3	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.	2.01	1	0
endrin Endrin: An organochlorine compound that was formerly used as an insecticide. Its manufacture and use has been discontinued in the United States. (From Merck Index, 11th ed). endrin : An organochlorine compound resulting from the epoxidation of the double bond of isodrin. It is the endo, endo stereoisomer of dieldrin. It is an insecticide mainly used on field crops such as cotton and grains and has also been used as a rodenticide to control mice and voles. The product is banned in many countries since it is a persistent organic pollutant.	2.41	2	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	7.44	2	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.	4.04	15	0	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.	2.47	2	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.	2.75	3	0
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.	5.93	33	0	monohydroxybenzoate	plant metabolite
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.	4.98	12	0	benzenes; hydroxycoumarin; methyl ketone
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	7.41	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.	2.17	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.	2.05	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.	7.96	4	0
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.1	1	0
pyrethrins [no description available]	2.05	1	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.	2.04	1	0
ferbam ferbam: structure. ferbam : A dithiocarbamate salt that is the iron(III) salt of dimethyldithiocarbamic acid. Formerly used as a fungicide.	7	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	3.24	6	0
angiotensin i Angiotensin I: A decapeptide that is cleaved from precursor angiotensinogen by RENIN. Angiotensin I has limited biological activity. It is converted to angiotensin II, a potent vasoconstrictor, after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME.. angiotensin I : A ten amino acid peptide formed by renin cleavage of angiotensinogen. Angiotensin I has no direct biological function except that high levels can stimulate catecholamine production. It is metabolized to its biologically active byproduct angiotensin II, a potent vasoconstrictor, by angiotensin converting enzyme (ACE) through cleavage of the two terminal amino acids.. angiotensin I dizwitterion : A peptide zwitterion that is the dizwitterionic form of angiotensin I having both carboxy groups deprotonated and the aspartyl amino group and arginine side-chain protonated. It is the major species at pH 7.3.	2.08	1	0	angiotensin; peptide zwitterion	human metabolite; neurotransmitter agent
adrenomedullin Adrenomedullin: A 52-amino acid peptide with multi-functions. It was originally isolated from PHEOCHROMOCYTOMA and ADRENAL MEDULLA but is widely distributed throughout the body including lung and kidney tissues. Besides controlling fluid-electrolyte homeostasis, adrenomedullin is a potent vasodilator and can inhibit pituitary ACTH secretion.	2.13	1	0
gibberellins [no description available]	1.93	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.	1.93	1	0
transforming growth factor alpha Transforming Growth Factor alpha: An EPIDERMAL GROWTH FACTOR related protein that is found in a variety of tissues including EPITHELIUM, and maternal DECIDUA. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form which binds to the EGF RECEPTOR.	1.99	1	0
lysergic acid lysergic acid : An ergoline alkaloid comprising 6-methylergoline having additional unsaturation at the 9,10-position and a carboxy group at the 8-position.	1.93	1	0
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	7.58	2	0
asbestos, amosite Asbestos, Amosite: Asbestos, grunerite. A monoclinic amphibole form of asbestos having long fibers and a high iron content. It is used in insulation. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2	1	0
carboxymethyl-beta-cyclodextrin [no description available]	7.05	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.	2.1	1	0
deoxyguanosine [no description available]	2.99	4	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine monophosphate Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.. guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.	2.08	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	biomarker; Escherichia coli metabolite; metabolite; mouse metabolite
guanine [no description available]	7.71	3	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.	2.04	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	2.07	1	0	nucleoside triphosphate analogue
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.54	2	0
clozapine Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.	2	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic
ganciclovir [no description available]	2.94	4	0	2-aminopurines; oxopurine	antiinfective agent; antiviral drug
olanzapine Olanzapine: A benzodiazepine derivative that binds SEROTONIN RECEPTORS; MUSCARINIC RECEPTORS; HISTAMINE H1 RECEPTORS; ADRENERGIC ALPHA-1 RECEPTORS; and DOPAMINE RECEPTORS. It is an antipsychotic agent used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER; and MAJOR DEPRESSIVE DISORDER; it may also reduce nausea and vomiting in patients undergoing chemotherapy.. olanzapine : A benzodiazepine that is 10H-thieno[2,3-b][1,5]benzodiazepine substituted by a methyl group at position 2 and a 4-methylpiperazin-1-yl group at position 4.	2.06	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine	antiemetic; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; serotonin uptake 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.	2.92	4	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
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.	3.24	5	0	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.	2.06	1	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
angucyclinone angucyclinone: structure in first source	2.02	1	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	3.53	8	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.04	1	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.	10.79	211	1

Condition	Relationship Strength	Studies	Trials
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)	5.54	26	0
(pPNET) Peripheral Primitive Neuroectodermal Tumors [description not available]	2.05	1	0
Neuroectodermal Tumors, Primitive, Peripheral A group of highly cellular primitive round cell neoplasms which occur extracranially in soft tissue and bone and are derived from embryonal neural crest cells. These tumors occur primarily in children and adolescents and share a number of characteristics with EWING SARCOMA.	2.05	1	0
Iron Overload An excessive accumulation of iron in the body due to a greater than normal absorption of iron from the gastrointestinal tract or from parenteral injection. This may arise from idiopathic hemochromatosis, excessive iron intake, chronic alcoholism, certain types of refractory anemia, or transfusional hemosiderosis. (From Churchill's Illustrated Medical Dictionary, 1989)	2.05	1	0
Innate Inflammatory Response [description not available]	4.74	6	1
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.	4.74	6	1
Acute Confusional Senile Dementia [description not available]	3.02	4	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)	3.02	4	0
Idiopathic Parkinson Disease [description not available]	2.15	1	0
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)	2.15	1	0
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.	2.41	1	0
Chemical Dependence [description not available]	4.01	12	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.61	25	0
Substance-Related Disorders Disorders related to substance use or abuse.	4.01	12	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).	2.61	2	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.	8.83	3	0
Benign Neoplasms [description not available]	5.18	19	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.	5.18	19	0
Airflow Obstruction, Chronic [description not available]	2.52	2	0
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	2.52	2	0
Chronic Lung Injury [description not available]	6.45	15	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	6.29	35	0
Anemia, Hemolytic, Acquired [description not available]	6.52	34	0
Bilirubinemia [description not available]	3.08	5	0
Delayed Effects, Prenatal Exposure [description not available]	2.63	2	0
Anemia, Hemolytic A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).	6.52	34	0
Deficiency of Glucose-6-Phosphate Dehydrogenase [description not available]	5.65	13	0
Methemoglobinemia The presence of methemoglobin in the blood, resulting in cyanosis. A small amount of methemoglobin is present in the blood normally, but injury or toxic agents convert a larger proportion of hemoglobin into methemoglobin, which does not function reversibly as an oxygen carrier. Methemoglobinemia may be due to a defect in the enzyme NADH methemoglobin reductase (an autosomal recessive trait) or to an abnormality in hemoglobin M (an autosomal dominant trait). (Dorland, 27th ed)	4.5	9	0
Glucosephosphate Dehydrogenase Deficiency A disease-producing enzyme deficiency subject to many variants, some of which cause a deficiency of GLUCOSE-6-PHOSPHATE DEHYDROGENASE activity in erythrocytes, leading to hemolytic anemia.	5.65	13	0
Acute Disease Disease having a short and relatively severe course.	3.28	6	0
Genome Instability [description not available]	2.25	1	0
Experimental Neoplasms [description not available]	4.87	14	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	3.17	1	0
Acute Myelogenous Leukemia [description not available]	2.25	1	0
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.	2.25	1	0
Infections, Coronavirus [description not available]	2.25	1	0
2019 Novel Coronavirus Disease [description not available]	2.25	1	0
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	2.25	1	0
Coronavirus Infections Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).	2.25	1	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	4.24	19	0
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.25	1	0
Breast Cancer [description not available]	2.81	3	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.81	3	0
Extravascular Hemolysis [description not available]	4.69	11	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.	2.92	4	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	4.69	11	0
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.	4.15	17	0
Lung Injury, Acute [description not available]	3.58	8	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).	3.58	8	0
Respiratory Tract Diseases Diseases involving the RESPIRATORY SYSTEM.	2.75	3	0
Abnormalities, Autosome [description not available]	2.52	2	0
Cryptosporidium Infection [description not available]	2.15	1	0
Caliciviridae Infections Virus diseases caused by CALICIVIRIDAE. They include HEPATITIS E; VESICULAR EXANTHEMA OF SWINE; acute respiratory infections in felines, rabbit hemorrhagic disease, and some cases of gastroenteritis in humans.	2.15	1	0
Cryptosporidiosis Intestinal infection with organisms of the genus CRYPTOSPORIDIUM. It occurs in both animals and humans. Symptoms include severe DIARRHEA.	2.15	1	0
Blood Poisoning [description not available]	2.45	2	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.	7.45	2	0
Amyloid Deposits [description not available]	2.53	2	0
Cancer of Mouth [description not available]	2.21	1	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.21	1	0
Acute Kidney Failure [description not available]	2.44	2	0
Urethritis Inflammation involving the URETHRA. Similar to CYSTITIS, clinical symptoms range from vague discomfort to painful urination (DYSURIA), urethral discharge, or both.	2.21	1	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.	7.44	2	0
Acute Liver Injury, Drug-Induced [description not available]	3.09	5	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.	3.09	5	0
Hypertrophy, Right Ventricular Enlargement of the RIGHT VENTRICLE of the heart. This increase in ventricular mass is often attributed to PULMONARY HYPERTENSION and is a contributor to cardiovascular morbidity and mortality.	2.08	1	0
Neointima The new and thickened layer of scar tissue that forms on a PROSTHESIS, or as a result of vessel injury especially following ANGIOPLASTY or stent placement.	2.08	1	0
Heritable Pulmonary Arterial Hypertension [description not available]	2.08	1	0
Pulmonary Hypertension [description not available]	2.08	1	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	2.08	1	0
Familial Primary Pulmonary Hypertension Familial or idiopathic hypertension in the PULMONARY CIRCULATION which is not secondary to other disease.	2.08	1	0
Asthma, Bronchial [description not available]	2.99	4	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	3.33	6	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).	2.99	4	0
Pneumonia Infection of the lung often accompanied by inflammation.	3.33	6	0
Cataract, Membranous [description not available]	6.57	49	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)	6.57	49	0
Colicky Pain [description not available]	2.08	1	0
Abdominal Pain Sensation of discomfort, distress, or agony in the abdominal region.	2.08	1	0
Alveolitis, Fibrosing [description not available]	4.19	3	1
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.	4.19	3	1
Glue Abuse [description not available]	2.1	1	0
Abnormalities, Multiple Congenital abnormalities that affect more than one organ or body structure.	2.1	1	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	2.4	2	0
Myoglobinuria The presence of MYOGLOBIN in URINE usually as a result of rhabdomyolysis.	2.1	1	0
Sickle Cell Trait The condition of being heterozygous for hemoglobin S.	2.47	2	0
Cirrhosis [description not available]	2.1	1	0
Metaplasia A condition in which there is a change of one adult cell type to another similar adult cell type.	2.1	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.1	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.	2.49	2	0
Glial Cell Tumors [description not available]	2.52	2	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)	7.52	2	0
Benign Neoplasms, Brain [description not available]	2.37	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.	2.37	2	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)	2.11	1	0
Cancer of Prostate [description not available]	2.13	1	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.13	1	0
Cardiac Remodeling, Ventricular [description not available]	2.11	1	0
Cardiovascular Stroke [description not available]	2.11	1	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.11	1	0
Cancer of Lung [description not available]	5.75	14	0
Lung Neoplasms Tumors or cancer of the LUNG.	5.75	14	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.	2.11	1	0
Dyslipidemia [description not available]	2.11	1	0
Diabetes Mellitus, Adult-Onset [description not available]	2.11	1	0
Blood Pressure, High [description not available]	2.11	1	0
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.	2.11	1	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.	2.11	1	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.	2.11	1	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.	2.11	1	0
Infections, Salmonella [description not available]	2.13	1	0
Asymptomatic Conditions [description not available]	3.06	1	0
Weight Reduction [description not available]	2.15	1	0
Weight Loss Decrease in existing BODY WEIGHT.	2.15	1	0
Cancer of Nose [description not available]	2.46	2	0
Carcinoma, Non-Small Cell Lung [description not available]	2.04	1	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.04	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.	3.08	5	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	2.05	1	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	2.05	1	0
Narcosis A state of depressed CENTRAL NERVOUS SYSTEM marked by stupor or insensibility.	2.05	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.	2.05	1	0
Genetic Predisposition [description not available]	2.05	1	0
Emergencies Situations or conditions requiring immediate intervention to avoid serious adverse results.	2.05	1	0
Intestinal Obstruction Any impairment, arrest, or reversal of the normal flow of INTESTINAL CONTENTS toward the ANAL CANAL.	2.05	1	0
African Sleeping Sickness [description not available]	2.05	1	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.05	1	0
Cystic Fibrosis of Pancreas [description not available]	2.46	2	0
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.	7.46	2	0
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.05	1	0
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	2.05	1	0
Adenocarcinoma, Basal Cell [description not available]	2.96	1	0
Adenoma, Basal Cell [description not available]	3.31	2	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.96	1	0
Adenoma A benign epithelial tumor with a glandular organization.	3.31	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	4.52	9	0
Cancer of Skin [description not available]	3.78	4	0
Skin Neoplasms Tumors or cancer of the SKIN.	3.78	4	0
Degenerative Diseases, Central Nervous System [description not available]	2.05	1	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.	2.69	3	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.	2.05	1	0
Icterus [description not available]	3.18	6	0
Jaundice A clinical manifestation of HYPERBILIRUBINEMIA, characterized by the yellowish staining of the SKIN; MUCOUS MEMBRANE; and SCLERA. Clinical jaundice usually is a sign of LIVER dysfunction.	8.18	6	0
Disease, Pulmonary [description not available]	4.88	13	0
Lung Diseases Pathological processes involving any part of the LUNG.	4.88	13	0
Airway Remodeling The structural changes in the number, mass, size and/or composition of the airway tissues.	2.06	1	0
Wounds, Gunshot Disruption of structural continuity of the body as a result of the discharge of firearms.	1.92	1	0
Osteomyelitis INFLAMMATION of the bone as a result of infection. It may be caused by a variety of infectious agents, especially pyogenic (PUS - producing) BACTERIA.	6.92	1	0
Alloxan Diabetes [description not available]	2.89	4	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.47	2	0
Brain Disorders [description not available]	2.06	1	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.	2.06	1	0
Carcinoma, Lewis Lung A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.	2.06	1	0
Cancer of Liver [description not available]	2.64	3	0
B16 Melanoma [description not available]	2.06	1	0
Metastase [description not available]	2.06	1	0
Invasiveness, Neoplasm [description not available]	2.06	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.64	3	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.06	1	0
Nasal Diseases [description not available]	2.06	1	0
Allergic Reaction [description not available]	2.87	4	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.87	4	0
Dental Plaque A film that attaches to teeth, often causing DENTAL CARIES and GINGIVITIS. It is composed of MUCINS, secreted from salivary glands, and microorganisms.	2.06	1	0
Cancer of Colon [description not available]	2.07	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.07	1	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.07	1	0
Cancer of Ovary [description not available]	2.07	1	0
Peritoneal Carcinomatosis [description not available]	2.07	1	0
Ascites, Gelatinous [description not available]	2.07	1	0
Colorectal Cancer [description not available]	2.07	1	0
Appendiceal Cancer [description not available]	2.07	1	0
Blood Loss, Surgical Loss of blood during a surgical procedure.	2.07	1	0
Appendiceal Neoplasms Tumors or cancer of the APPENDIX.	2.07	1	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.	2.07	1	0
Peritoneal Neoplasms Tumors or cancer of the PERITONEUM.	2.07	1	0
Pseudomyxoma Peritonei A peritoneal adenocarcinoma characterized by build-up of MUCUS in the PERITONEAL CAVITY. Mucus secreting cells may attach to the peritoneal lining and continue to secrete mucus. The majority of cases represent tumor spread from a primary low-grade mucinous neoplasm of the APPENDIX (NCI Thesaurus).	2.07	1	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.	2.07	1	0
Blood Pressure, Low [description not available]	2.07	1	0
Hypotension Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.	2.07	1	0
Leukemia, Lymphocytic, T Cell [description not available]	2.08	1	0
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	2.08	1	0
Tracheal Diseases Diseases involving the TRACHEA.	2.42	2	0
Pyrexia [description not available]	3.18	6	0
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	3.18	6	0
Bladder Cancer [description not available]	3.31	7	0
Sarcoma, Epithelioid [description not available]	2.84	4	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	3.31	7	0
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	2.84	4	0
Bovine Diseases [description not available]	2.84	4	0
Keratoderma Blennorrhagicum [description not available]	2.84	4	0
Keratosis Any horny growth such as a wart or callus.	2.84	4	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.35	7	0
Granuloma, Hodgkin [description not available]	3.03	5	0
Leucocythaemia [description not available]	1.93	1	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	3.54	3	0
Erythremia [description not available]	1.93	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.	3.03	5	0
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)	1.93	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.	3.54	3	0
Polycythemia Vera A myeloproliferative disorder of unknown etiology, characterized by abnormal proliferation of all hematopoietic bone marrow elements and an absolute increase in red cell mass and total blood volume, associated frequently with splenomegaly, leukocytosis, and thrombocythemia. Hematopoiesis is also reactive in extramedullary sites (liver and spleen). In time myelofibrosis occurs.	1.93	1	0
Colonic Inertia Symptom characterized by the passage of stool once a week or less.	1.93	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.	1.93	1	0
Cough A sudden, audible expulsion of air from the lungs through a partially closed glottis, preceded by inhalation. It is a protective response that serves to clear the trachea, bronchi, and/or lungs of irritants and secretions, or to prevent aspiration of foreign materials into the lungs.	3.03	5	0
Infections, Plasmodium [description not available]	2.64	3	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	7.64	3	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	6.93	1	0
Dermatoses [description not available]	3.03	5	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	3.03	5	0
Acne [description not available]	3.31	7	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.	3.31	7	0
Contact Dermatitis [description not available]	3.63	10	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.	3.63	10	0
Abdominal Migraine [description not available]	1.93	1	0
Migraine Disorders A class of disabling primary headache disorders, characterized by recurrent unilateral pulsatile headaches. The two major subtypes are common migraine (without aura) and classic migraine (with aura or neurological symptoms). (International Classification of Headache Disorders, 2nd ed. Cephalalgia 2004: suppl 1)	1.93	1	0
Diseases, Occupational [description not available]	3.64	10	0
Symptom Cluster [description not available]	1.93	1	0
Psychophysiologic Disorders A group of disorders characterized by physical symptoms that are affected by emotional factors and involve a single organ system, usually under AUTONOMIC NERVOUS SYSTEM control. (American Psychiatric Glossary, 1988)	1.93	1	0
Syndrome A characteristic symptom complex.	1.93	1	0
Koch's Disease [description not available]	2.33	2	0
Pulmonary Consumption [description not available]	1.93	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.33	2	0
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	1.93	1	0
Brain Inflammation [description not available]	3.54	9	0
Encephalitis, Japanese B [description not available]	3.54	9	0
Encephalitis Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.	3.54	9	0
Encephalitis, Japanese A mosquito-borne encephalitis caused by the Japanese B encephalitis virus (ENCEPHALITIS VIRUS, JAPANESE) occurring throughout Eastern Asia and Australia. The majority of infections occur in children and are subclinical or have features limited to transient fever and gastrointestinal symptoms. Inflammation of the brain, spinal cord, and meninges may occur and lead to transient or permanent neurologic deficits (including a POLIOMYELITIS-like presentation); SEIZURES; COMA; and death. (From Adams et al., Principles of Neurology, 6th ed, p751; Lancet 1998 Apr 11;351(9109):1094-7)	3.54	9	0
Encephalitis, Polio [description not available]	1.93	1	0
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	1.93	1	0
Eye Disorders [description not available]	1.93	1	0
Eye Diseases Diseases affecting the eye.	1.93	1	0
Dermatitis Any inflammation of the skin.	3.72	11	0
Ancylostomiasis Infection of humans or animals with hookworms of the genus ANCYLOSTOMA. Characteristics include anemia, dyspepsia, eosinophilia, and abdominal swelling.	1.93	1	0
Bunostomiasis [description not available]	2.33	2	0
Hookworm Infections Infection of humans or animals with hookworms other than those caused by the genus Ancylostoma or Necator, for which the specific terms ANCYLOSTOMIASIS and NECATORIASIS are available.	2.33	2	0
Hepatocellular Carcinoma [description not available]	1.93	1	0
Experimental Hepatoma [description not available]	1.93	1	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.	1.93	1	0
Liver Dysfunction [description not available]	3.04	5	0
Liver Diseases Pathological processes of the LIVER.	3.04	5	0
Polyarthritis [description not available]	1.93	1	0
Adjuvant Arthritis [description not available]	1.93	1	0
Arthritis Acute or chronic inflammation of JOINTS.	1.93	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.35	2	0
Bronchospasm [description not available]	1.93	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.	1.93	1	0
Muscle Spasm [description not available]	1.93	1	0
Bronchial Diseases Diseases involving the BRONCHI.	3.36	7	0
Bronchial Spasm Spasmodic contraction of the smooth muscle of the bronchi.	1.93	1	0
Spasm An involuntary contraction of a muscle or group of muscles. Spasms may involve SKELETAL MUSCLE or SMOOTH MUSCLE.	1.93	1	0
Hemoptysis Expectoration or spitting of blood originating from any part of the RESPIRATORY TRACT, usually from hemorrhage in the lung parenchyma (PULMONARY ALVEOLI) and the BRONCHIAL ARTERIES.	1.93	1	0
Bordetella pertussis Infection, Respiratory [description not available]	2.62	3	0
Whooping Cough A respiratory infection caused by BORDETELLA PERTUSSIS and characterized by paroxysmal coughing ending in a prolonged crowing intake of breath.	7.62	3	0
Diseases of Immune System [description not available]	2.34	2	0
Essential Polyarteritis [description not available]	1.93	1	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	2.34	2	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	1.93	1	0
Bleeding [description not available]	3.19	6	0
Hemorrhage Bleeding or escape of blood from a vessel.	3.19	6	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.	1.93	1	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	6.93	1	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.	3.44	8	0
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	1.93	1	0
Atherogenesis [description not available]	2.34	2	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.	2.34	2	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.34	2	0
Blood Clot [description not available]	1.93	1	0
Thromboembolism Obstruction of a blood vessel (embolism) by a blood clot (THROMBUS) in the blood stream.	1.93	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	1.93	1	0
Behavior Disorders [description not available]	1.93	1	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.	1.93	1	0
Retinal Diseases Diseases involving the RETINA.	1.93	1	0
Cicatrization The formation of fibrous tissue in the place of normal tissue during the process of WOUND HEALING. It includes scar tissue formation occurring in healing internal organs as well as in the skin after surface injuries.	6.93	1	0
Cicatrix The fibrous tissue that replaces normal tissue during the process of WOUND HEALING.	1.93	1	0
Heavy Metal Poisoning Poisoning that results from chronic or acute ingestion, injection, inhalation, or skin absorption of HEAVY METALS. Acute and chronic exposures can cause ANEMIA; KIDNEY and LIVER damage; PULMONARY EDEMA; MEMORY LOSS and behavioral changes; bone deformities in children; and MISCARRIAGE or PREMATURE LABOR in pregnant women.	1.93	1	0
Complications, Pregnancy [description not available]	2.66	3	0
Carcinoma 256, Walker A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)	1.93	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)	1.93	1	0
Icterus Gravis Neonatorum [description not available]	2.64	3	0
Bilirubin Encephalopathy [description not available]	2.34	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.	2.64	3	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)	2.34	2	0
Infant, Premature, Diseases Diseases that occur in PREMATURE INFANTS.	1.94	1	0
Kahler Disease [description not available]	1.93	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.	1.93	1	0
Palmoplantaris Pustulosis [description not available]	2.36	2	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	7.36	2	0
EHS Tumor [description not available]	2.33	2	0
Diffuse Large B-Cell Lymphoma [description not available]	1.93	1	0
Abdominal Neoplasms New abnormal growth of tissue in the ABDOMEN.	1.93	1	0
Lymphoma, Large B-Cell, Diffuse Malignant lymphoma composed of large B lymphoid cells whose nuclear size can exceed normal macrophage nuclei, or more than twice the size of a normal lymphocyte. The pattern is predominantly diffuse. Most of these lymphomas represent the malignant counterpart of B-lymphocytes at midstage in the process of differentiation.	1.93	1	0
Sebaceous Gland Diseases Diseases of the sebaceous glands such as sebaceous hyperplasia and sebaceous cell carcinoma (SEBACEOUS GLAND NEOPLASMS).	1.93	1	0
Anemia, Hypoplastic [description not available]	1.93	1	0
Anemia, Aplastic A form of anemia in which the bone marrow fails to produce adequate numbers of peripheral blood elements.	1.93	1	0
Dental Pulp Disease [description not available]	1.92	1	0
Gangrene Death and putrefaction of tissue usually due to a loss of blood supply.	6.92	1	0
Dental Pulp Diseases Endodontic diseases of the DENTAL PULP inside the tooth, which is distinguished from PERIAPICAL DISEASES of the tissue surrounding the root.	1.92	1	0
Cyclitis, Heterochromic [description not available]	1.92	1	0
Iridocyclitis Acute or chronic inflammation of the iris and ciliary body characterized by exudates into the anterior chamber, discoloration of the iris, and constricted, sluggish pupil. Symptoms include radiating pain, photophobia, lacrimation, and interference with vision.	1.92	1	0
Cancer of Stomach [description not available]	1.93	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	1.93	1	0
Inhalation Injury, Smoke [description not available]	2.42	2	0
Allergic Contact Dermatitis [description not available]	7.02	1	0
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	2.39	2	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.	2.02	1	0
Sterility, Male [description not available]	2.43	2	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.	2.43	2	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	2.02	1	0
Adenocarcinoma, Alveolar [description not available]	2.02	1	0
Adenocarcinoma, Bronchiolo-Alveolar A carcinoma derived from epithelium of terminal bronchioles, in which the neoplastic tissue extends along the alveolar walls and grows in small masses within the alveoli. Involvement may be uniformly diffuse and massive, or nodular, or lobular. The neoplastic cells are cuboidal or columnar and form papillary structures. Mucin may be demonstrated in some of the cells and in the material in the alveoli, which also includes denuded cells. Metastases in regional lymph nodes, and in even more distant sites, are known to occur, but are infrequent. (From Stedman, 25th ed)	2.02	1	0
Dysarthosis [description not available]	2.03	1	0
Complications, Labor [description not available]	2.03	1	0
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.	2.03	1	0
Agricultural Worker Disease [description not available]	2.03	1	0
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.03	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.	2.03	1	0
Carcinoma, Oat Cell [description not available]	2.03	1	0
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	2.03	1	0
Eczema, Atopic [description not available]	3.42	1	1
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.	3.42	1	1
Pink Eye [description not available]	1.92	1	0
Conjunctivitis INFLAMMATION of the CONJUNCTIVA.	1.92	1	0
Bronchiolitis, Exudative [description not available]	2.04	1	0
Bronchiolitis Obliterans Inflammation of the BRONCHIOLES leading to an obstructive lung disease. Bronchioles are characterized by fibrous granulation tissue with bronchial exudates in the lumens. Clinical features include a nonproductive cough and DYSPNEA.	2.04	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).	2.38	2	0
Adverse Drug Event [description not available]	2.9	1	0
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.	2.9	1	0
Neovascularization, Optic Disc [description not available]	1.98	1	0
Retinal Degeneration A retrogressive pathological change in the retina, focal or generalized, caused by genetic defects, inflammation, trauma, vascular disease, or aging. Degeneration affecting predominantly the macula lutea of the retina is MACULAR DEGENERATION. (Newell, Ophthalmology: Principles and Concepts, 7th ed, p304)	1.98	1	0
Retinal Neovascularization Formation of new blood vessels originating from the retinal veins and extending along the inner (vitreal) surface of the retina.	6.98	1	0
Albinism, Tyrosinase-Negative [description not available]	1.98	1	0
Albinism, Oculocutaneous Heterogeneous group of autosomal recessive disorders comprising at least four recognized types, all having in common varying degrees of hypopigmentation of the skin, hair, and eyes. The two most common are the tyrosinase-positive and tyrosinase-negative types.	1.98	1	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.	1.99	1	0
Acute Brain Injuries [description not available]	1.99	1	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.	1.99	1	0
Anemia, Hemolytic, Hereditary [description not available]	1.99	1	0
Anemia, Hemolytic, Congenital Hemolytic anemia due to various intrinsic defects of the erythrocyte.	1.99	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	1.99	1	0
Xerophthalmia Dryness of the eye surfaces caused by deficiency of tears or conjunctival secretions. It may be associated with vitamin A deficiency, trauma, or any condition in which the eyelids do not close completely.	1.99	1	0
Erythema Multiforme A skin and mucous membrane disease characterized by an eruption of macules, papules, nodules, vesicles, and/or bullae with characteristic bull's-eye lesions usually occurring on the dorsal aspect of the hands and forearms.	6.99	1	0
Recrudescence [description not available]	3.38	1	1
Nail Fungus [description not available]	3.38	1	1
Foot Dermatoses Skin diseases of the foot, general or unspecified.	3.38	1	1
Onychomycosis A fungal infection of the nail, usually caused by DERMATOPHYTES; YEASTS; or nondermatophyte MOLDS.	3.38	1	1
Chronic Kidney Failure [description not available]	2	1	0
Peripheral Nerve Diseases [description not available]	2	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.	2	1	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	2	1	0
Infections, Rhabdoviridae [description not available]	2	1	0
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	2	1	0
Keratitis Inflammation of the cornea.	1.97	1	0
Chromosome Deletion Actual loss of portion of a chromosome.	2.37	2	0
Drop Attack [description not available]	1.97	1	0
Abnormalities, Sex Chromosome [description not available]	1.97	1	0
Syncope A transient loss of consciousness and postural tone caused by diminished blood flow to the brain (i.e., BRAIN ISCHEMIA). Presyncope refers to the sensation of lightheadedness and loss of strength that precedes a syncopal event or accompanies an incomplete syncope. (From Adams et al., Principles of Neurology, 6th ed, pp367-9)	1.97	1	0
Dermatitis, Eczematous [description not available]	1.96	1	0
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	1.96	1	0
Experimental Mammary Neoplasms [description not available]	2.88	1	0
Birth Weight The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.	1.96	1	0

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naphthalene

Cross-References

Synonyms (134)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (6)

Drug Classes (2)

Pathways (4)

Protein Targets (13)

Potency Measurements

Inhibition Measurements

Biological Processes (27)

Molecular Functions (16)

Ceullar Components (5)

Bioassays (122)

Research

Studies (2,530)

Market Indicators

Research Demand Index: 87.60

Study Types

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