vanillic acid profile

Vanillic acid, also known as 4-hydroxy-3-methoxybenzoic acid, is a naturally occurring phenolic compound found in various plants, including vanilla beans, cloves, and blueberries. It is a derivative of benzoic acid with a methoxy group and a hydroxyl group as substituents. Vanillic acid exhibits antioxidant, anti-inflammatory, and antimicrobial properties. It has been shown to protect against oxidative stress and DNA damage. The compound is also being explored for its potential therapeutic applications in conditions such as cancer and neurodegenerative diseases. Vanillic acid is widely studied due to its multifaceted biological activities and its presence in various natural sources. The synthesis of vanillic acid can be achieved through various methods, including chemical synthesis, enzymatic conversion, and microbial fermentation. '

Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	8468
CHEMBL ID	120568
CHEBI ID	30816
SCHEMBL ID	26179
MeSH ID	M0022520

Synonym
benzoic acid, 4-hydroxy-3-methoxy-
protocatechuic acid, 3-methyl ester
wln: qvr dq co1
nsc-3987
acide vanillique
m-anisic acid, 4-hydroxy-
3-methoxy-4-hydroxybenzoic acid
nsc3987
CHEBI:30816 ,
nsc-674322
vnl ,
nsc674322
smr000156289
MLS000574833
vanillic acid
121-34-6
4-hydroxy-3-methoxybenzoic acid
C06672
inchi=1/c8h8o4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9h,1h3,(h,10,11
vanillic acid, >=97%, fg
vanillic acid, 97%
nsc 3987
einecs 204-466-8
p-vanillic acid
brn 2208364
va (van)
nsc 674322
ai3-19542
acid, p-hydroxy-m-methoxy-benzoic
acid, vanillic
acid, 4-hydroxy-3-methoxybenzoic
p-hydroxy-m-methoxy-benzoic acid
p hydroxy m methoxy benzoic acid
4 hydroxy 3 methoxybenzoic acid
3E9555E5-85F5-4FCE-A429-5182E959C6A3
AC-11841
AKOS000113195
CHEMBL120568 ,
4-hydroxy-3-methoxy benzoic acid
BMSE000486
BMSE010205
BMSE000614
FT-0650155
V0017
A804715
NCGC00247610-01
vanilic acid
vanillic acid (m2)
bdbm50337364
4-hydroxyl-3-methoxybenzoic acid
4-hydroxy-3-methoxy-benzoic acid
STL163472
BBL011982
HMS2197E16
4-hydroxy-m-anisic acid
unii-gm8q3jm2y8
gm8q3jm2y8 ,
BP-13246
AM20050239
vanillic acid [mi]
fema no. 3988
droxidopa metabolite (va)
vanillic acid [inci]
m-methoxy-p-hydroxy-benzoic acid
4-hydroxy-3-methoxybenzoic acid [fhfi]
2-methoxy-4-carboxyphenol
S5343
4- hydroxy-3-methoxybenzoic acid
4-hydroxy-3methoxy benzoic acid
SCHEMBL26179
DTXSID6059522 ,
Q-201921
STR02334
HY-N0708
mfcd00002551
vanillic acid, certified reference material, tracecert(r)
vanillic acid, purum, >=97.0% (hplc)
vanillic acid, vetec(tm) reagent grade, 97%
vanillinsaure
vanillicacid
4-hydroxy-3-methoxy-benzoate
protocatechuic acid 3-methyl ester
4-hydroxy-m-anisate
3-methoxy-4-hydroxybenzoate
p-vanillate
SY001450
CS-0009728
Q419672
vanillic acid,(s)
CCG-266343
CK2172
4-hydroxy-3-methoxybenzoicacid
EN300-105765
dtxcid1033668
Z381356666

Excerpt	Reference	Relevance
"Vanillic acid (VA) is a phenolic acid that has previously been attributed with antioxidant, anti-inflammatory, and neuroprotective features."	( Vanillic Acid Improves Stress Resistance and Substantially Extends Life Span in Caenorhabditis elegans. Alavez, S; Brunauer, R; Osorio-Paz, I; Valle-Jiménez, X, 2023)	3.07
"Vanillic acid (VA) is a dietary herbal secondary metabolite with high free radical scavenging activity."	( Vanillic acid abrogates cisplatin-induced ovotoxicity through activating Nrf2 pathway. Alemdar, NT; Aliyazicioglu, Y; Demir, EA; Demir, S; Kucuk, H; Mentese, A; Yulug, E, 2023)	3.07
"Vanillic acid is a dietary phenolic compound reported to exhibit anticancer properties."	( Vanillic Acid Suppresses HIF-1α Expression via Inhibition of mTOR/p70S6K/4E-BP1 and Raf/MEK/ERK Pathways in Human Colon Cancer HCT116 Cells. Gong, J; Yang, S; Zhou, S, 2019)	2.68
"Vanillic acid (VA), is a well-known flavonoid, which possesses various pharmacological activities."	( Vanillic acid attenuates cartilage degeneration by regulating the MAPK and PI3K/AKT/NF-κB pathways. Cheng, H; Chu, X; Huang, X; Ma, X; Mao, Z; Ni, B; Xi, Y; You, H; Zhang, R, 2019)	2.68
"Vanillic acid (VA) is a phenolic acid, and acts as a natural antioxidant in fruits, vegetables and plants. "	( Utilizing a nano-sorbent for the selective solid-phase extraction of vanillic acid prior to its determination by photoluminescence spectroscopy. Abdolmohammad-Zadeh, H; Mahmoudi-Kordi, F; Rahmati, M, 2014)	2.08
"Vanillic acid (1) is a flavoring agent found in edible plants and fruits. "	( Vanillic Acid Inhibits Inflammatory Pain by Inhibiting Neutrophil Recruitment, Oxidative Stress, Cytokine Production, and NFκB Activation in Mice. Baracat, MM; Calixto-Campos, C; Carvalho, TT; Casagrande, R; Fattori, V; Georgetti, SR; Hohmann, MS; Manchope, MF; Pinho-Ribeiro, FA; Verri, WA; Zarpelon, AC, 2015)	3.3
"Vanillic acid is an oxidized form of vanillin produced during the conversion of vanillin to ferulic acid and has free radical scavenging, antioxidant and anti-inflammatory properties. "	( Effect of vanillic acid on ischemia-reperfusion of isolated rat heart: Hemodynamic parameters and infarct size assays. Badavi, M; Dianat, M; Hamzavi, GR; Samarbaf-zadeh, A, 2015)	2.26
"Vanillic acid (VA) is a phenolic compound used widely in the food industry as a flavoring, preservative, and food additive."	( Different responses of vanillic acid, a phenolic compound, in HTC cells: cytotoxicity, antiproliferative activity, and protection from DNA-induced damage. Almeida, IV; Cavalcante, FM; Vicentini, VE, 2016)	1.47
"Vanillic acid is a stronger antioxidant than vanillin, in terms of free radical scavenging activity, reducing power and inhibition of lipid peroxidation."	( Antioxidative characteristics and inhibition of alpha-melanocyte-stimulating hormone-stimulated melanogenesis of vanillin and vanillic acid from Origanum vulgare. Chou, TH; Ding, HY; Hung, WJ; Liang, CH, 2010)	1.29
"Vanillic acid is a benzoic acid derivative that is used as a flavoring agent. "	( Vanillic acid inhibits inflammatory mediators by suppressing NF-κB in lipopolysaccharide-stimulated mouse peritoneal macrophages. Hong, SH; Jeon, YD; Kim, DS; Kim, MC; Kim, SJ; Lee, HS; Park, SJ; Um, JY, 2011)	3.25
"Vanillic acid is a break-down product of adrenalin found in milk, but before its concentration in milk can be used as an indicator/parameter of heat stress in dairy cows, more about the pharmacodynamics of adrenaline in the milk has to be known."	( Parameters for the determination and evaluation of heat stress in dairy cattle in South Africa. Du Preez, JH, 2000)	1.03

Excerpt	Reference	Relevance
"Vanillic acid has been shown to block pro-inflammatory cytokines and suppress inflammatory cascades."	( Regulatory Mechanisms of Vanillic Acid in Cardiovascular Diseases: A Review. Abdolghaffari, AH; Atkin, SL; Lashgari, NA; Momtaz, S; Roudsari, NM; Sahebkar, A, 2023)	1.93
"Vanillic acid (VA) has shown antioxidant and anti-inflammatory activities in different cell types, but its biological effects in the context of early embryo development have not yet been clarified. "	( Attenuation of Oxidative Stress and Regulation of AKT Signaling by Vanillic Acid during Bovine Pre-Implantation Embryo Development. El-Sheikh, M; Joo, MD; Kong, IK; Mesalam, A; Mesalam, AA; Sidrat, T, 2023)	2.59
"Vanillic acid and vanillin have been accepted as the biochemical precursors of guaiacol in fruit juices."	( Precursors and metabolic pathway for guaiacol production by Alicyclobacillus acidoterrestris. Cai, R; Guo, C; Liu, B; Liu, L; Wang, Y; Wang, Z; Yuan, Y; Yue, T, 2015)	1.14
"Vanillic acid has been investigated for its inhibitory effect on Naja naja, Daboia russellii, and Trimeresurus malabaricus venom 5'-nucleotidase activity. "	( Vanillic acid as a novel specific inhibitor of snake venom 5'-nucleotidase: a pharmacological tool in evaluating the role of the enzyme in snake envenomation. D'Souza, CJ; Dhananjaya, BL; Nataraju, A; Raghavendra Gowda, CD; Sharath, BK, 2009)	3.24

Excerpt	Reference	Relevance
"Vanillic acid treatment brought the above parameters towards near normal level."	( Vanillic acid prevents the deregulation of lipid metabolism, endothelin 1 and up regulation of endothelial nitric oxide synthase in nitric oxide deficient hypertensive rats. Kumar, S; Prahalathan, P; Raja, B; Saravanakumar, M, 2014)	2.57
"Vanillic acid pretreated isoproterenol-induced rats positively altered all the above-mentioned biochemical parameters."	( Preventive effects of vanillic acid on lipids, bax, bcl-2 and myocardial infarct size on isoproterenol-induced myocardial infarcted rats: a biochemical and in vitro study. Dhanasekar, K; Prince, PS; Rajakumar, S, 2011)	1.41
"Treatment with vanillic acid resulted in a significant decrease in levels of thymic stromal lymphopoietin and pro-inflammatory cytokines compared to phorbol 12-myristate 13-acetate and calcium ionophore A23187 (PMACI)-treated HMC-1 cells."	( Anti-allergic inflammatory effect of vanillic acid through regulating thymic stromal lymphopoietin secretion from activated mast cells. Jeong, HJ; Jin, MH; Kim, HM; Kim, HY; Kim, MH; Nam, SY; Roh, SS, 2018)	1.09
"Pretreatment with vanillic acid (5 mg/kg and 10 mg/kg body weight) to isoproterenol induced rats showed significant effects on all the biochemical and molecular parameters evaluated."	( Vanillic acid prevents altered ion pumps, ions, inhibits Fas-receptor and caspase mediated apoptosis-signaling pathway and cardiomyocyte death in myocardial infarcted rats. Dhanasekar, K; Rajakumar, S; Stanely Mainzen Prince, P, 2015)	2.18
"Pretreatment with vanillic acid showed significant protective effects on cardiac troponins, lipid peroxidation, antioxidant system, electrocardiogram and expressions of interleukin-1β, interleukin-6 and tumor necrosis factor-α gene in the heart of isoproterenol induced cardiotoxic rats."	( Protective effects of vanillic acid on electrocardiogram, lipid peroxidation, antioxidants, proinflammatory markers and histopathology in isoproterenol induced cardiotoxic rats. Dhanasekar, K; Rajakumar, S; Stanely Mainzen Prince, P, 2011)	1.01

Excerpt	Reference	Relevance
"Cadmium (Cd), an industrial and environmental pollutant, is toxic to several tissues, most notably causing hepatotoxicity on acute administration and nephrotoxicity following chronic exposure."	( Therapeutic efficacy of Picroliv in chronic cadmium toxicity. Khandelwal, S; Yadav, N, 2009)	0.35
" The histopathological examination on toxic models revealed centrizonal necrosis and fatty changes."	( Hepatoprotective activity of picroliv, curcumin and ellagic acid compared to silymarin on paracetamol induced liver toxicity in mice. Girish, C; Jayanthi, S; Koner, BC; Pradhan, SC; Rajesh, B; Ramachandra Rao, K, 2009)	0.35
" VA and VC supplementation attenuated the toxic effects of DEHP on the testicular functions, morphology, and semen characterization of the experimental adult male Wistar rats."	( Vanillic acid and vitamin C attenuated di-2-ethylhexyl phthalate-induced testicular toxicity in adult male rats. Adedotun, OA; Adejayi, J; Gbotolorun, SC; Iteire, K; Ogunlade, B, 2022)	2.16

Excerpt	Reference	Relevance
"Nonanoyl vanillylamide (nonivamide NVA) was compared with trans-8-methyl-N-vanillyl-nonenamide (capsaicin, CAP) with regard to their pharmacokinetic properties, their potency in stimulating primary afferent neurons and depleting them of substance P and somatostatin in rats."	( Comparison of nonivamide and capsaicin with regard to their pharmacokinetics and effects on sensory neurons. Donnerer, J; Lembeck, F; Skofitsch, G, 1984)	0.27
"A sensitive, simple, and accurate method for the determination and pharmacokinetic study of vanillic acid in rat plasma was developed using reverse-phase HPLC with UV detection after oral administration of the traditional Chinese medicine preparation of the Di-Gu-Pi decoction."	( Reverse-phase HPLC determination and pharmacokinetic study of vanillic acid in the plasma of rats treated with the traditional Chinese medicinal preparation Di-Gu-Pi decoction. Bi, K; Chen, X; Jia, Y; Li, K, 2004)	0.78
" The method was successfully applied to pharmacokinetic study of all three aromatic acids and one monoterpene in rat plasma."	( UHPLC-MS simultaneous determination and pharmacokinetic study of three aromatic acids and one monoterpene in rat plasma after oral administration of Shaofu Zhuyu decoction. Cui, W; Duan, JA; Guo, J; Hua, Y; Liu, P; Shang, E; Su, S; Tang, Y, 2013)	0.39
" The plasma pharmacokinetic parameters at the three doses were as follows: t(1/2), (86."	( Pharmacokinetics and tissue distributions of veratric acid after intravenous administration in rats. Liu, C; Liu, LJ; Peng, YS; Wang, RF; Yang, X; Zhao, C, 2015)	0.42
" This study was carried out for comparing the pharmacokinetic profile of these three major bioactive components in rats after oral administration of Typhae Pollen-Trogopterus Feces (TP-TF) drug pair before and after compatibility."	( Comparative Pharmacokinetics of three major bioactive components in rats after oral administration of Typhae Pollen-Trogopterus Feces drug pair before and after compatibility. Duan, JA; Guo, J; Huang, X; Qian, D; Shang, E; Su, S; Tang, Y; Xue, P; Zeng, H, 2016)	0.43
"20 h); for p-coumaric acid, it had similar pharmacokinetic characteristics with vanillic acid."	( Comparative Pharmacokinetics of three major bioactive components in rats after oral administration of Typhae Pollen-Trogopterus Feces drug pair before and after compatibility. Duan, JA; Guo, J; Huang, X; Qian, D; Shang, E; Su, S; Tang, Y; Xue, P; Zeng, H, 2016)	0.66
" Therefore, this study was designed to check metabolic (in vitro and in vivo) profile along with pharmacokinetic profile of picroside I and II."	( In vitro - In vivo metabolism and pharmacokinetics of picroside I and II using LC-ESI-MS method. Anandjiwala, S; Nivsarkar, M; Padh, H; Upadhyay, D, 2016)	0.43
" The pharmacokinetic results indicated that the six components in TGPR could be quickly absorbed and slowly eliminated and their bioavailability were less than 12."	( Pharmacokinetics, tissue distribution and excretion of six bioactive components from total glucosides picrorhizae rhizoma, as simultaneous determined by a UHPLC-MS/MS method. Cai, N; Cao, N; He, Y; Song, Z; Wang, Q; Wu, J; Xiao, X; Yang, X; Zou, S, 2023)	0.91

Excerpt	Reference	Relevance
"The effect of Picroliv treatment on the carcinogenic response and, hepatic and renal antioxidant enzymes of rats administered with 1,2-dimethylhydrazine hydrochloride (DMH) was studied in male Sprague-Dawley rats."	( Modulation of carcinogenic response and antioxidant enzymes of rats administered with 1,2-dimethylhydrazine by Picroliv. Kuttan, R; Rajeshkumar, NV, 2003)	0.32
" We therefore examined the possibility of minimizing these effects by applying miltefosine in lower doses in combination with picrloviv, an immunomodulator against Leishmania donovani in hamsters (Mesocricetus auratus)."	( Efficacy of picroliv in combination with miltefosine, an orally effective antileishmanial drug against experimental visceral leishmaniasis. Gupta, S; Ramesh, SC; Srivastava, VM, 2005)	0.33
" To combat this situation, leishmanicidal efficacy of already marketed standard antifungal drug, fluconazole under the approach of "therapeutic switching" in combination with standard antileishmanial drug, miltefosine, and a potent immunomodulator agent, picroliv, were evaluated in hamsters infected with Leishmania donovani."	( Antileishmanial efficacy of fluconazole and miltefosine in combination with an immunomodulator--picroliv. Gupta, S; Sane, SA; Shakya, N, 2011)	0.37
"An automated online solid-phase extraction with restricted-access material combined with high-performance liquid chromatography and tandem mass spectrometry was developed and validated for the simultaneous quantification of vanillin and its vanillic acid metabolite in human plasma."	( Online restricted-access material combined with high-performance liquid chromatography and tandem mass spectrometry for the simultaneous determination of vanillin and its vanillic acid metabolite in human plasma. Li, DQ; Qi, JL; Yang, XL; Zhang, ZQ; Zhou, CH, 2016)	0.81

Excerpt	Reference	Relevance
"Despite the considerable success in predicting the steady-state dermal absorption rates of chemical compounds from large reservoirs applied to skin, correspondingly little progress has been made in predicting the absorption rate and extent for small doses of topically applied compounds."	( Kinetics of finite dose absorption through skin 1. Vanillylnonanamide. Kasting, GB, 2001)	0.31
"The purpose of this study was to investigate biomarkers of the bioavailability and metabolism of hydroxycinnamate derivatives through the determination of the pharmacokinetics of their urinary elimination and identification of the metabolites excreted."	( Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Hahn, U; Kuhnle, G; Rechner, AR; Rice-Evans, CA; Spencer, JP, 2001)	0.31
" However, the role of sorption to soil in modifying the bioavailability of components in complex allelochemical mixtures is still obscure."	( Preferential sorption of phenolic phytotoxins to soil: implications for altering the availability of allelochemicals. Bhowmik, PC; Tharayil, N; Xing, B, 2006)	0.33
" However, poor bioavailability and temperature and light sensitivity can reduce the efficacy of drugs like curcumin."	( Drug development for liver diseases: focus on picroliv, ellagic acid and curcumin. Girish, C; Pradhan, SC, 2008)	0.35
" The aim of the present study was to investigate the effect of bioprocessing of the bran in whole wheat bread on the bioavailability of phenolic acids, the postprandial plasma antioxidant capacity, and ex vivo antiinflammatory properties."	( Bioprocessing of wheat bran in whole wheat bread increases the bioavailability of phenolic acids in men and exerts antiinflammatory effects ex vivo. Aura, AM; Bast, A; Haenen, GR; Havenaar, R; Mateo Anson, N; Mattila, I; Poutanen, K; Selinheimo, E; van den Berg, R, 2011)	0.37
"05) in oral bioavailability of picrosides I and II from different preparations."	( Comparative pharmacokinetic profiles of picrosides I and II from kutkin, Picrorhiza kurroa extract and its formulation in rats. Anandjiwala, S; Dash, RP; Nivsarkar, M; Upadhyay, D, 2013)	0.39
" Treatment is however still problematic given the poor bioavailability of CoQ10."	( Effect of vanillic acid on COQ6 mutants identified in patients with coenzyme Q10 deficiency. Airik, R; Bergdoll, M; Doimo, M; Hildebrandt, F; Navas, P; Pierrel, F; Salviati, L; Santos-Ocaña, C; Trevisson, E, 2014)	0.8
" Previously, we have reported that oral bioavailability of picroside I and II is low."	( In vitro - In vivo metabolism and pharmacokinetics of picroside I and II using LC-ESI-MS method. Anandjiwala, S; Nivsarkar, M; Padh, H; Upadhyay, D, 2016)	0.43
" However, most of phenolics existed as bound form that with low bioavailability in quinoa."	( Release of characteristic phenolics of quinoa based on extrusion technique. Chen, X; Li, X; Shao, Y; Song, J, 2022)	0.72
" Unfortunately, their low bioavailability restricts their potential medical uses, as it limits the concentration of phenolic acids achievable in the organism."	( Conjugation with Phospholipids as a Modification Increasing Anticancer Activity of Phenolic Acids in Metastatic Melanoma-In Vitro and In Silico Studies. Gliszczyńska, A; Palko-Łabuz, A; Poła, A; Skonieczna, M; Środa-Pomianek, K; Wesołowska, O, 2021)	0.62
" Despite this, its rapid degradation in systemic circulations upon administration, lack of tumor specificity, and low bioavailability limits its anticancer potential."	( Combination therapy of vanillic acid and oxaliplatin co-loaded in polysaccharide based functionalized polymeric micelles could offer effective treatment for colon cancer: A hypothesis. Dua, K; Gowthamarajan, K; Gulati, M; Gupta, G; Kaur, J; Kumar Chellappan, D; Kumar, B; Pandey, NK; Singh, SK; Vishwas, S, 2021)	0.93
" Both the drugs possess dissolution rate-limited oral bioavailability leading to poor therapeutic efficacy."	( Polymeric micelles loaded with glyburide and vanillic acid: I. Formulation development, in-vitro characterization and bioavailability studies. Adams, J; Arshad, MF; Awasthi, A; Bettada, VG; Chellappan, DK; Corrie, L; Dua, K; Famta, P; Gowthamarajan, K; Gulati, M; Gupta, G; Hansbro, PM; Kaur, J; Khatik, GL; Madhunapantula, SV; Paudel, KR; Saini, S; Singh, SK, 2022)	0.98
" The pharmacokinetic results indicated that the six components in TGPR could be quickly absorbed and slowly eliminated and their bioavailability were less than 12."	( Pharmacokinetics, tissue distribution and excretion of six bioactive components from total glucosides picrorhizae rhizoma, as simultaneous determined by a UHPLC-MS/MS method. Cai, N; Cao, N; He, Y; Song, Z; Wang, Q; Wu, J; Xiao, X; Yang, X; Zou, S, 2023)	0.91
" Moreover, the number of hydrogen bond acceptors/donors, solubility, polar surface area and bioavailability score of the vanillic acid and three flavonoids were acceptable compared to Lipinski's Rule of Five."	( Antioxidant activity, anti-tyrosinase activity, molecular docking studies, and molecular dynamic simulation of active compounds found in nipa palm vinegar. Chatatikun, M; Chuaijit, S; Klangbud, WK; Mudpan, A; Palachum, W; Pattaranggoon, NC; Pruksaphanrat, S; Sohbenalee, S; Tedasen, A; Yamasaki, K, 2023)	1.12

Excerpt	Relevance	Reference
" Oral dosage (100 mg/kg) of the aldehyde resulted in urinary excretion of most metabolites within 24 h, mainly as glucuronide and/or sulphate conjugates although the acids formed were also excreted free and as their glycine conjugates."	( The metabolism of vanillin and isovanillin in the rat. Scheline, RR; Strand, LP, 1975)	0.25
" It was found that the humic acid treatment dosage was not significant."	( The formation and control of disinfection by-products using chlorine dioxide. Chang, CY; Hsieh, YH; Hsu, SS; Shih, IC; Wang, KH, 2000)	0.31
" Oral administration of veratric acid at the dosage of 40 mg/kg considerably decreased systolic and diastolic blood pressure, lipid peroxidation products; increased plasma nitric oxide levels and showed no toxicity which was measured using hepatic and renal function markers when compared to other doses of veratric acid (20, 80 mg/kg)."	( Veratric acid, a phenolic acid attenuates blood pressure and oxidative stress in L-NAME induced hypertensive rats. Raja, B; Saravanakumar, M, 2011)	0.37
" In contrast to the switch-like behavior of P(Q5), P(V10) shows a linear dose-response curve at intermediate vanillate concentrations, allowing graded gene expression."	( Synthetic vanillate-regulated promoter for graded gene expression in Sphingomonas. Francez-Charlot, A; Kaczmarczyk, A; Vorholt, JA, 2014)	0.4
" Dosage dependent nephrotoxicity is the major problem in cisplatin chemotherapy."	( Nephroprotective effect of vanillic acid against cisplatin induced nephrotoxicity in wistar rats: a biochemical and molecular study. Nishanthi, E; Sharmila, R; Sindhu, G, 2015)	0.71

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
monohydroxybenzoic acid	Any hydroxybenzoic acid having a single phenolic hydroxy substituent on the benzene ring.
methoxybenzoic acid	Any benzoic acid carrying one or more methoxy substituents.
[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
Flavan-3-ol metabolic pathway	0	70

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Beta-lactamase	Escherichia coli K-12	Potency	25.1189	0.0447	17.8581	100.0000	AID485294
huntingtin isoform 2	Homo sapiens (human)	Potency	3.9811	0.0006	18.4198	1,122.0200	AID1688
DNA polymerase iota isoform a (long)	Homo sapiens (human)	Potency	89.1251	0.0501	27.0736	89.1251	AID588590
[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)
Polyphenol oxidase 2	Agaricus bisporus	IC50 (µMol)	100.0000	0.0340	3.9871	10.0000	AID1059453
Pancreatic triacylglycerol lipase	Sus scrofa (pig)	IC50 (µMol)	250.0000	0.0040	1.1024	6.5000	AID577979
Anthrax toxin receptor 2	Homo sapiens (human)	IC50 (µMol)	300.0000	0.3000	0.4535	0.6070	AID725981
Xanthine dehydrogenase/oxidase	Bos taurus (cattle)	IC50 (µMol)	8.5000	0.0030	3.1015	9.8000	AID1800197
Enoyl-acyl-carrier protein reductase	Plasmodium falciparum (malaria parasite P. falciparum)	IC50 (µMol)	920.0000	0.0660	1.5499	10.0000	AID638541
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
nucleobase-containing compound metabolic process	Thiopurine S-methyltransferase	Homo sapiens (human)
xenobiotic metabolic process	Thiopurine S-methyltransferase	Homo sapiens (human)
methylation	Thiopurine S-methyltransferase	Homo sapiens (human)
xenobiotic catabolic process	Thiopurine S-methyltransferase	Homo sapiens (human)
xanthine catabolic process	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
protein binding	Thiopurine S-methyltransferase	Homo sapiens (human)
thiopurine S-methyltransferase activity	Thiopurine S-methyltransferase	Homo sapiens (human)
S-adenosyl-L-methionine binding	Thiopurine S-methyltransferase	Homo sapiens (human)
protein binding	Anthrax toxin receptor 2	Homo sapiens (human)
metal ion binding	Anthrax toxin receptor 2	Homo sapiens (human)
transmembrane signaling receptor activity	Anthrax toxin receptor 2	Homo sapiens (human)
xanthine dehydrogenase activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
xanthine oxidase activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
iron ion binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
molybdenum ion binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
protein homodimerization activity	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
molybdopterin cofactor binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
flavin adenine dinucleotide binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
2 iron, 2 sulfur cluster binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
FAD binding	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytosol	Thiopurine S-methyltransferase	Homo sapiens (human)
extracellular region	Anthrax toxin receptor 2	Homo sapiens (human)
endoplasmic reticulum membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
endosome membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
cell surface	Anthrax toxin receptor 2	Homo sapiens (human)
extracellular space	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
peroxisome	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
xanthine dehydrogenase complex	Xanthine dehydrogenase/oxidase	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
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
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.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
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.
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.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1083163	Antifungal activity against Botryosphaeria dothidea OGE14 assessed as growth inhibition measured after 1 to 10 days relative to control	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1293751	Antiproliferative activity against human HT-29 cells assessed as growth inhibition after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Two novel phenanthraquinones with anti-cancer activity isolated from Bletilla striata.
AID703914	Binding affinity to quail lipocalin Q83 assessed as second molecule binding at 2:1 compound:protein ratio by isothermal colorimetric analysis	2012	Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17	Toward rational fragment-based lead design without 3D structures.
AID462342	Toxicity in mouse B16-4A5 cells assessed as inhibition of cell proliferation at 30 uM in presence of 1 mM theophylline after 72 hrs by WST8 dye reduction assay	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID355822	Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 30 uM relative to control	2003	Journal of natural products, May, Volume: 66, Issue:5	Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID380234	Cytotoxicity against human Raji cells assessed as cell viability at 1000 molar ratio after 48 hrs	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID465832	Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of D-galactosamine-induced cytotoxicity at 10 uM after 1 hrs by MTT assay relative to control treated before D-galactosamine challenge	2010	Journal of natural products, Feb-26, Volume: 73, Issue:2	Hepatoprotective constituents from the roots and stems of Erycibe hainanesis.
AID485526	Anticancer activity against human Hs683 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID703917	Binding affinity to quail lipocalin Q83	2012	Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17	Toward rational fragment-based lead design without 3D structures.
AID1891161	Inhibition of alpha-glycosidase (unknown origin) using pre-mix of compound and enzyme for 10 mins and then followed by maltose substrate addition and further incubated for 10 mins by microplate reader analysis	2022	Bioorganic & medicinal chemistry letters, 06-01, Volume: 65	Polyphenolic compounds: Synthesis, assessment of antimicrobial effect and enzymes inhibition against important medicinal enzymes with computational details.
AID380233	Inhibition of 12-O-tetradecanoylphorbol-13-acetate induced EBV-early antigen activation in human Raji cells at 10 molar ratio relative to control	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID696879	Inhibition of tyrosinase using L-dihydroxyphenylalanine as substrate preincubated for 30 mins measured after 7 mins by spectrophotometric analysis	2012	Journal of natural products, Nov-26, Volume: 75, Issue:11	Tyrosinase inhibitors from the wood of Artocarpus heterophyllus.
AID380230	Inhibition of 12-O-tetradecanoylphorbol-13-acetate induced EBV-early antigen activation in human Raji cells at 1000 molar ratio relative to control	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID462333	Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 30 uM after 72 hrs	2010	Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6	Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells.
AID485525	Anticancer activity against human LoVo cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID607600	Induction of human U373 cell death assessed as morphological changes at MTT assay-related IC50 after 72 hrs by quantitative video microscopy	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1083160	Antifungal activity against Neofusicoccum luteum CBS110299 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID638541	Inhibition of Plasmodium falciparum enoyl-ACP reductase assessed as oxidation of NADH to NAD+ after 10 mins by spectrophotometric analysis	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Methylenebissantin: a rare methylene-bridged bisflavonoid from Dodonaea viscosa which inhibits Plasmodium falciparum enoyl-ACP reductase.
AID1070421	Inhibition of NF-kappaB activity in TNF-alpha stimulated human HEK-293/NF-kB-luc cells incubated for 30 mins prior to TNF-alpha challenge for 4 hrs by luciferase reporter gene assay	2014	Journal of natural products, Mar-28, Volume: 77, Issue:3	NF-κB inhibitors from Eurycoma longifolia.
AID1293750	Antiproliferative activity against human MCF7 cells assessed as growth inhibition after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Two novel phenanthraquinones with anti-cancer activity isolated from Bletilla striata.
AID642415	Estrogenic activity at ERalpha in human MVLN cells at 20 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID1372697	Inhibition of mushroom tyrosinase using tyrosine as substrate pretreated for 5 mins followed by substrate addition measured after 20 mins by ELISA	2018	Bioorganic & medicinal chemistry, 01-15, Volume: 26, Issue:2	Characterization of tyrosinase inhibitory constituents from the aerial parts of Humulus japonicus using LC-MS/MS coupled online assay.
AID405575	Antitubercular activity against Mycobacterium tuberculosis H37Rv after 2 weeks by agar dilution method	2008	Journal of natural products, Jun, Volume: 71, Issue:6	Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica.
AID293934	Inhibition of pieris rapae Phenoloxidase	2007	Bioorganic & medicinal chemistry, Mar-01, Volume: 15, Issue:5	3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.
AID213093	Inhibition of purified human kidney thiopurine methyltransferase (TPMT)	1986	Journal of medicinal chemistry, Mar, Volume: 29, Issue:3	Thiopurine methyltransferase: structure-activity relationships for benzoic acid inhibitors and thiophenol substrates.
AID1059453	Inhibition of mushroom tyrosinase using L-tyrosine as substrate preincubated for 10 mins followed by enzyme addition measured after 20 mins by microplate reader analysis	2013	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24	Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition.
AID591308	Anticancer activity against human A549 cells by SRB assay	2011	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8	Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID388743	Antioxidant activity assessed as DPPH radical scavenging activity after 20 mins	2008	Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23	Inhibition of aldose reductase from cataracted eye lenses by finger millet (Eleusine coracana) polyphenols.
AID1102544	Inhibition of tyrosinase activity in Oryza sativa Indica (rice) bran using L-tyrosine as substrate at 0.5 umol/ml after 60 min by spectrophotometric analysis	2003	Journal of agricultural and food chemistry, Nov-19, Volume: 51, Issue:24	Tyrosinase inhibitor from black rice bran.
AID1083157	Antifungal activity against Lasiodiplodia theobromae CBS116460 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID485528	Anticancer activity against human U373 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID1293752	Antiproliferative activity against human HUVEC cells assessed as growth inhibition after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Two novel phenanthraquinones with anti-cancer activity isolated from Bletilla striata.
AID278000	Antitubercular activity against Mycobacterium tuberculosis 90-221387	2007	Journal of natural products, Feb, Volume: 70, Issue:2	Antitubercular dihydroagarofuranoid sesquiterpenes from the roots of Microtropis fokienensis.
AID1083161	Antifungal activity against Neofusicoccum parvum PER20 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID383183	Inhibition of Saccharomyces sp. alpha-glucosidase	2008	Journal of natural products, May, Volume: 71, Issue:5	alpha-Glucosidase inhibitory activity of triterpenoids from Cichorium intybus.
AID1083154	Antifungal activity against Diplodia seriata BoF98-1 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID607593	Cytotoxicity against human U373 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID355820	Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 3 uM relative to control	2003	Journal of natural products, May, Volume: 66, Issue:5	Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID647625	Antioxidant activity assessed as trolox equivalent of ABTS radical scavenging activity relative to control	2012	European journal of medicinal chemistry, Apr, Volume: 50	New losartan-hydrocaffeic acid hybrids as antihypertensive-antioxidant dual drugs: Ester, amide and amine linkers.
AID1063365	Hepatoprotective activity against D-galactosamine-induced toxicity in rat WB-F344 cells assessed as cell survival at 10 uM preincubated for 1 hr followed by D-galactosamine challenge measured after 24 hrs by MTT assay relative to normal cell	2014	Journal of natural products, Jan-24, Volume: 77, Issue:1	Chemical constituents from Inonotus obliquus and their biological activities.
AID1368908	Cytotoxicity against human A2780 cells assessed as reduction in cell viability at 5 to 100 uM incubated for 24 hrs by MTT assay	2018	Bioorganic & medicinal chemistry letters, 01-15, Volume: 28, Issue:2	(-)-9'-O-(α-l-Rhamnopyranosyl)lyoniresinol from Lespedeza cuneata suppresses ovarian cancer cell proliferation through induction of apoptosis.
AID1891162	Inhibition of alpha-glycosidase (unknown origin) using pre-mix of compound and maltose substrate for 10 mins and then followed by enzyme addition and further incubated for 10 mins by microplate reader analysis	2022	Bioorganic & medicinal chemistry letters, 06-01, Volume: 65	Polyphenolic compounds: Synthesis, assessment of antimicrobial effect and enzymes inhibition against important medicinal enzymes with computational details.
AID591307	Anticancer activity against human SKOV3 cells by SRB assay	2011	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8	Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID380235	Cytotoxicity against human Raji cells assessed as cell viability at 500 molar ratio after 48 hrs	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID333180	Inhibition of beta-hexosaminidase in anti-DNP IgE sensitized rat RBL2H3 cells at 100 uM after 10 mins	2004	Journal of natural products, Sep, Volume: 67, Issue:9	Structures of new beta-carboline-type alkaloids with antiallergic effects from Stellaria dichotoma(1,2).
AID1083149	Nematotoxic activity against freshly hatched Meloidogyne incognita J2 (root-knot nematode) isolated from tomato roots assessed as induction of nematode paralysis measured 24 hr after immersion in compound test solutions	2012	Journal of agricultural and food chemistry, Nov-28, Volume: 60, Issue:47	Nematotoxic phenolic compounds from Melia azedarach against Meloidogyne incognita.
AID380236	Cytotoxicity against human Raji cells assessed as cell viability at 100 molar ratio after 48 hrs	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID485524	Anticancer activity against human A549 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID1172897	Antioxidant activity assessed as DPPH scavenging activity at 5 to 20 uM after 15 mins by UV-visible spectrophotometry	2014	Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23	Synthesis and characterization of norbelladine, a precursor of Amaryllidaceae alkaloid, as an anti-inflammatory/anti-COX compound.
AID607596	Cytotoxicity against human PC3 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID607594	Cytotoxicity against human OE21 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID385427	Inhibition of soybean 15-lipoxygenase	2008	Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8	Inhibition of 15-lipoxygenase-catalysed oxygenation of arachidonic acid by substituted benzoic acids.
AID485519	Anticancer activity against mouse B16F10 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID607598	Cytotoxicity against human LoVo cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1063364	Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of D-galactosamine-induced toxicity at 10 uM preincubated for 1 hr followed by D-galactosamine challenge measured after 24 hrs by MTT assay relative to control	2014	Journal of natural products, Jan-24, Volume: 77, Issue:1	Chemical constituents from Inonotus obliquus and their biological activities.
AID485521	Anticancer activity against human OE21 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID1083155	Antifungal activity against Diplodia seriata BoF99-1 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID380231	Inhibition of 12-O-tetradecanoylphorbol-13-acetate induced EBV-early antigen activation in human Raji cells at 500 molar ratio relative to control	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID1309213	Drug level in RBL2H3 cells treated with butyl vanillate assessed as esterase-mediated compound formation	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Structure-activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells.
AID380232	Inhibition of 12-O-tetradecanoylphorbol-13-acetate induced EBV-early antigen activation in human Raji cells at 100 molar ratio relative to control	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID1309207	Anti-allergic activity in RBL2H3 cells assessed as inhibition of anti-DNP-IgE-induced degranulation at 100 to 1000 uM incubated for 20 mins followed by DNP-labeled human serum albumin addition measured after 1 hr by beta-hexosaminidase release assay	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Structure-activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells.
AID492140	Antioxidant activity assessed as formazan formation induced absorbance changes at 25 ppm at 570 nm at 37 degC for 6 hrs by MTT assay	2010	Journal of natural products, Jul-23, Volume: 73, Issue:7	An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.
AID309363	Antiinflammatory activity in CD1 mouse assessed as inhibition of croton oil-induced ear oedema at 0.3 umol/cm^2 after 6 hrs	2007	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 17, Issue:20	Synthesis and anti-inflammatory activity of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives.
AID447578	Inhibition of HDAC in human Hela cells nuclear extracts assessed as residual activity at 500 uM by fluorimetric assay	2009	Bioorganic & medicinal chemistry, Jul-15, Volume: 17, Issue:14	Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.
AID639826	Inhibition of human recombinant aldose reductase using D-glyceraldehyde as substrate at 15 uM preincubated for 10 mins before substrate addition measured for every 10 secs for 50 mins by spectrophotometry	2012	Bioorganic & medicinal chemistry, Feb-01, Volume: 20, Issue:3	Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase.
AID1424230	Electrochemical behaviour of the compound assessed as peak potential using disposable screen-printed carbon electrodes	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID1293753	Antiproliferative activity against human A549 cells assessed as growth inhibition after 48 hrs by MTT assay	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Two novel phenanthraquinones with anti-cancer activity isolated from Bletilla striata.
AID485529	Chemical stability after 7 days by HPLC	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID555340	Effect on growth in Staphylococcus aureus MN8 at 0.50 % after 24 hrs (Rvb = 100%)	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID485523	Anticancer activity against human MCF7 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID591309	Anticancer activity against human SK-MEL-2 cells by SRB assay	2011	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8	Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID725981	Inhibition of CMG2 (40 to 217) C175A and R40C double mutant (unknown origin) interaction to full length PA E733C mutant expressed in Escherichia coli by FRET assay	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose inhibits angiogenesis via inhibition of capillary morphogenesis gene 2.
AID1083162	Antifungal activity against Neofusicoccum parvum Bp0014 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1090826	Antifeedant activity against Hylobius abietis (pine weevil ) in compound pre-treated Scots pine twig at 50 mM measured after 24 hr by two-choice laboratory bioassay	2007	Journal of agricultural and food chemistry, Nov-14, Volume: 55, Issue:23	Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach.
AID485520	Anticancer activity against human OE33 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID555341	Effect on growth in Staphylococcus aureus MN8 at 0.10 % after 24 hrs (Rvb = 100%)	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID577979	Inhibition of pig pancreatic lipase assessed as p-NPB hydrolysis by ELISA	2011	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 21, Issue:5	Enhancement of pancreatic lipase inhibitory activity of curcumin by radiolytic transformation.
AID1083156	Antifungal activity against Diplodia seriata LAT28 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID485522	Anticancer activity against human PC3 cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID555372	Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 0.50 % after 24 hrs relative to control	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID355821	Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 10 uM relative to control	2003	Journal of natural products, May, Volume: 66, Issue:5	Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID1309209	Drug level in RBL2H3 cells treated with ferulic acid	2016	Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15	Structure-activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells.
AID380237	Cytotoxicity against human Raji cells assessed as cell viability at 10 molar ratio after 48 hrs	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens.
AID703916	Binding affinity to quail lipocalin Q83 by 1H-15N HSQC-based NMR analysis	2012	Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17	Toward rational fragment-based lead design without 3D structures.
AID1083158	Antifungal activity against Diplodia seriata PLU03 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1192870	Antiinflammatory activity in mouse RAW264.7 cells assessed as decrease in LPS-induced NO production after 24 hrs by Griess assay	2015	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 25, Issue:5	Constituents of the stem barks of Ailanthus altissima and their potential to inhibit LPS-induced nitric oxide production.
AID338336	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of collagen-induced platelet aggregation at 0.25 mg/ml pretreated 2 mins before collagen challenge
AID1083159	Antifungal activity against Diplodia mutila BRA08 assessed as growth inhibition measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1424231	Antioxidant activity assessed as DPPH free radical scavenging activity	2017	European journal of medicinal chemistry, Jun-16, Volume: 133	Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.
AID338335	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation at 0.25 mg/ml pretreated 2 mins before arachidonic acid challenge
AID1233697	Antioxidant activity assessed as AAPH radical scavenging activity by measuring Trolox equivalents after 90 mins by fluorescein probe based ORAC assay	2015	European journal of medicinal chemistry, Jul-15, Volume: 100	1,5-Diarylpyrazole and vanillin hybrids: Synthesis, biological activity and DFT studies.
AID703915	Binding affinity to quail lipocalin Q83 assessed as first molecule binding at 2:1 compound:protein ratio by isothermal colorimetric analysis	2012	Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17	Toward rational fragment-based lead design without 3D structures.
AID1083171	Antifungal activity against Togninia minima SO21 assessed as susceptibility at 500 uM measured after 1 to 10 days	2012	Journal of agricultural and food chemistry, Dec-05, Volume: 60, Issue:48	Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
AID1233693	Antioxidant activity assessed as DPPH radical scavenging activity	2015	European journal of medicinal chemistry, Jul-15, Volume: 100	1,5-Diarylpyrazole and vanillin hybrids: Synthesis, biological activity and DFT studies.
AID1059454	Antioxidant activity assessed as trolox equivalent of APPH-induced peroxyl radical scavenging activity at 5 to 20 uM measured every 1 min for 120 mins by ORAC fluorescence assay	2013	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24	Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition.
AID485527	Anticancer activity against human T98G cells after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID1698073	Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cells assessed as increase in cell viability after 24 hrs by EZ-Cytox assay
AID338339	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation at 1 mg/ml pretreated 2 mins before ADP challenge
AID591310	Anticancer activity against human XF498 cells by SRB assay	2011	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8	Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
AID607601	Cytotoxicity against human U373 cells assessed as growth inhibition at MTT assay-related IC50 by quantitative video microscopy relative to control	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID607595	Cytotoxicity against human A549 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1059449	Inhibition of mushroom tyrosinase using L-tyrosine as substrate at 100 uM preincubated for 10 mins followed by enzyme addition measured after 20 mins by microplate reader analysis relative to control	2013	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24	Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition.
AID338333	Antiplatelet activity against rat platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation at 0.5 mg/ml pretreated 2 mins before arachidonic acid challenge
AID355823	Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 100 uM relative to control	2003	Journal of natural products, May, Volume: 66, Issue:5	Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID607597	Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14	Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID642414	Estrogenic activity at ERalpha in human MVLN cells at 100 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID555373	Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 0.10 % after 24 hrs relative to control	2009	Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5	Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.
AID355819	Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 1 uM relative to control	2003	Journal of natural products, May, Volume: 66, Issue:5	Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID1800198	Alpha-Glucosidase Assay from Article 10.1111/cbdd.12205: \\Antioxidant, a-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).\\	2014	Chemical biology & drug design, Jan, Volume: 83, Issue:1	Antioxidant, α-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).
AID1803326	α-glucosidase Inhibitory Activity Assay from Article 10.3109/14756366.2012.719503: \\Structure-activity relationships of bergenin derivatives effect on a-glucosidase inhibition.\\	2013	Journal of enzyme inhibition and medicinal chemistry, Dec, Volume: 28, Issue:6	Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition.
AID1800197	Xanthine Oxidase Activity from Article 10.1111/cbdd.12205: \\Antioxidant, a-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).\\	2014	Chemical biology & drug design, Jan, Volume: 83, Issue:1	Antioxidant, α-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.).
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).	2014	Journal of biomolecular screening, Jul, Volume: 19, Issue:6	A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	137 (15.19)	18.7374
1990's	102 (11.31)	18.2507
2000's	214 (23.73)	29.6817
2010's	332 (36.81)	24.3611
2020's	117 (12.97)	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	7 (0.76%)	5.53%
Reviews	11 (1.19%)	6.00%
Case Studies	1 (0.11%)	4.05%
Observational	0 (0.00%)	0.25%
Other	907 (97.95%)	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
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	2.13	1	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	2.45	2	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
tartronic acid hydroxymalonic acid : A dicarboxylic acid that is malonic acid substituted by a hydroxy group at position 2.	1.97	1	0	dicarboxylic acid; dicarboxylic fatty acid	plant metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	13.35	90	1	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
dihydro-3-coumaric acid dihydro-3-coumaric acid: intermediate in biosynthesis of dihydrophenanthrenes from phenylalanine. 3-(3-hydroxyphenyl)propanoic acid : A monocarboxylic acid that is propionic acid carrying a 3-hydroxyphenyl substituent at C-3.	2.01	1	0	monocarboxylic acid	Escherichia coli metabolite; human xenobiotic metabolite
3-hydroxybenzaldehyde [no description available]	2.03	1	0	hydroxybenzaldehyde
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.	2.52	2	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzaldehyde [no description available]	4.05	14	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.67	3	0	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	6.49	56	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
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.	3.44	7	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.71	3	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]	2	1	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	3.21	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.	1.98	1	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.05	1	0	aminobenzoic acid	human metabolite; mouse metabolite
benzaldehyde [no description available]	3.21	5	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]	1.98	1	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.	4.39	20	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.	2.51	2	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.03	1	0	amino-acid betaine; glycine derivative	fundamental metabolite
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.	2.52	2	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.	2.46	2	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	1.97	1	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]	3.44	7	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).	2.83	3	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	4.1	4	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	1.96	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.04	1	0	coumarins	fluorescent dye; human metabolite; plant metabolite
cuminaldehyde cuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.	2.49	2	0	benzaldehydes	insecticide; plant metabolite; volatile oil component
4-vinylguaiacol 2-methoxy-4-vinylphenol: a germination inhibitor; also an odorant in green tea; structure in first source. 2-methoxy-4-vinylphenol : A member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group.	3.3	6	0	phenols	flavouring agent; pheromone; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	5.2	15	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.	2.05	1	0	methylcatechol	bacterial xenobiotic metabolite
digallic acid digallic acid: structure given in first source	2.08	1	0	benzoate ester; gallate ester
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	2.69	3	0	benzenetriol; phenolic donor	algal metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	13.49	103	1	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	2.36	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	2.03	1	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
4-aminophenol 4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.	2.15	1	0	aminophenol	allergen; metabolite
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.11	1	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
3-chlorobenzoic acid [no description available]	2.38	2	0	monochlorobenzoic acid	drug metabolite
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	4.63	26	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	2.47	2	0	N-acylglycine	human blood serum metabolite; uremic toxin
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	2.07	1	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental 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.	7.9	4	0	catechols; dihydroxyphenylacetic acid	human 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.	2.13	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna 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.	2.11	1	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	8.8	11	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
glycine [no description available]	2.6	1	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.	1.98	1	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
carbonic acid Carbonic Acid: Carbonic acid (H2C03). The hypothetical acid of carbon dioxide and water. It exists only in the form of its salts (carbonates), acid salts (hydrogen carbonates), amines (carbamic acid), and acid chlorides (carbonyl chloride). (From Grant & Hackh's Chemical Dictionary, 5th ed)	2.41	1	0	carbon oxoacid; chalcocarbonic acid	mouse metabolite
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	2.03	1	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.07	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.	2.77	3	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	7.5	2	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
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.	2.15	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	1.95	1	0	diatomic iodine	nutrient
dihydroxyphenylalanine Dihydroxyphenylalanine: A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.. dopa : A hydroxyphenylalanine carrying hydroxy substituents at positions 3 and 4 of the benzene ring.	3.44	2	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	2.41	1	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.44	2	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse 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.	9.11	15	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	1.95	1	0	inositol phosphate
croton oil [no description available]	2	1	0	N-acyl-hexosamine
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.1	1	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.	2.17	1	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.	3.88	13	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.	3.13	5	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
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)	2.88	3	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	2.03	1	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.65	3	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant 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.	8.32	6	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
phenol [no description available]	3.17	5	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.	2.02	1	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	2.97	4	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.	2.84	3	0	benzenedicarboxylic acid	human xenobiotic metabolite
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.4	2	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	2.17	1	0	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
pyridoxal [no description available]	1.97	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	7.57	2	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	2.05	1	0	benzenetriol; phenolic donor	plant metabolite
quinolinic acid Quinolinic Acid: A metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS.. pyridinedicarboxylic acid : Any member of the class of pyridines carrying two carboxy groups.. quinolinic acid : A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan.	7.41	1	0	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
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.	2.98	4	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
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.	7.15	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.47	2	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	3.58	2	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.	2.06	1	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).	7.03	99	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
catechin [no description available]	2.07	1	0	hydroxyflavan
2,3-dichloro-alpha-methylbenzylamine 2,3-dichloro-alpha-methylbenzylamine: inhibitor of phenethanolamine N-methyltransferase; RN given refers to parent cpd without isomeric designation; structure	2	1	0
vanilmandelic acid Vanilmandelic Acid: A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.. vanillylmandelic acid : An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.	8.46	8	0	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	2.05	1	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
mandelic acid SAMMA: mandelic acid condensation polymer	7.37	2	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
1,2-dimethylhydrazine 1,2-Dimethylhydrazine: A DNA alkylating agent that has been shown to be a potent carcinogen and is widely used to induce colon tumors in experimental animals.. 1,2-dimethylhydrazine : A member of the class of hydrazines that is hydrazine in which one of the hydrogens attached to each nitrogen is replaced by a methyl group. A powerful DNA alkylating agent and carcinogen, it is used to induce colon cancer in laboratory rats and mice.	7.31	1	0	hydrazines	alkylating agent; carcinogenic agent
2,4,5-trichlorophenoxyacetic acid 2,4,5-Trichlorophenoxyacetic Acid: An herbicide with strong irritant properties. Use of this compound on rice fields, orchards, sugarcane, rangeland, and other noncrop sites was terminated by the EPA in 1985. (From Merck Index, 11th ed). (2,4,5-trichlorophenoxy)acetic acid : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2, 4 and 5 are substituted by chlorines.	2	1	0	chlorophenoxyacetic acid; trichlorobenzene	defoliant; phenoxy herbicide; synthetic auxin
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	2.68	3	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
beta-resorcylic acid beta-resorcylic acid: RN given refers to parent cpd; structure	2.74	3	0
3-aminobenzamide [no description available]	1.98	1	0	benzamides; substituted aniline	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
3-methoxytyramine 3-methoxytyramine: RN given refers to parent cpd. 3-methoxytyramine : A monomethoxybenzene that is dopamine in which the hydroxy group at position 3 is replaced by a methoxy group. It is a metabolite of the neurotransmitter dopamine and considered a potential biomarker of pheochromocytomas and paragangliomas.	1.99	1	0	monomethoxybenzene; phenols; phenylethylamine; primary amino compound	biomarker; human blood serum metabolite; human urinary metabolite
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.	2	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	3.91	13	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
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.	8.06	5	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
7,8-dihydroxyflavone 7,8-dihydroxyflavone : A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's.	2.05	1	0	dihydroxyflavone	antidepressant; antineoplastic agent; antioxidant; plant metabolite; tropomyosin-related kinase B receptor agonist
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.05	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	2.41	1	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	3.25	6	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
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	1.96	1	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	3.56	8	0	acetophenones; aromatic ketone; methyl ketone	antirheumatic drug; EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	2.06	1	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
baclofen [no description available]	2.05	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
bay-k-8644 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-(trifluoromethyl)phenyl)-, Methyl ester: A dihydropyridine derivative, which, in contrast to NIFEDIPINE, functions as a calcium channel agonist. The compound facilitates Ca2+ influx through partially activated voltage-dependent Ca2+ channels, thereby causing vasoconstrictor and positive inotropic effects. It is used primarily as a research tool.. Bay-K-8644 : A racemate comprising equimolar amounts of (R)- and (S)-Bay-K-8644. methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate : A pentasubstituted dihydropyridine carrying methoxycarbonyl, 2-(trifluoromethyl)phenyl and nitro substituents at positions 3, 4 and 5 respectively as well as two methyl substituents at positions 2 and 6.	2.07	1	0	(trifluoromethyl)benzenes; C-nitro compound; dihydropyridine; methyl ester
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	1.93	1	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.	7.69	2	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
berberine [no description available]	2.04	1	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one: from maize extracts; structure given in first source. DIMBOA : A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.	2.03	1	0	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite
caffeine [no description available]	2.1	1	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
camphor, (+-)-isomer [no description available]	1.93	1	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.	2.17	1	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
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.04	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
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.	1.98	1	0	clonidine; imidazoline
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.	3.25	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
nonivamide nonivamide: has effect on sensory neurons. nonivamide : A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.	4.55	25	0	capsaicinoid; phenols	lachrymator
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.	2.41	2	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
dicamba Dicamba: A chlorinated organic herbicide.. dicamba : A methoxybenzoic acid that is O-methylsalicylic acid substituted by chloro groups at positions 3 and 6.	2	1	0	dichlorobenzene; methoxybenzoic acid	agrochemical; environmental contaminant; herbicide; synthetic auxin; xenobiotic
dichlorophen Dichlorophen: Nontoxic laxative vermicide effective for taenia infestation. It tends to produce colic and nausea. It is also used as a veterinary fungicide, anthelmintic, and antiprotozoan. (From Merck, 11th ed.)	2.08	1	0	bridged diphenyl fungicide; diarylmethane
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.	2.03	1	0	pentacarboxylic acid	copper chelator
disulfiram [no description available]	2.02	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.05	1	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	2.06	1	0	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	2.17	1	0
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.	2.06	1	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.1	1	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
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.	4.38	6	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	7.59	2	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	2.39	2	0	methoxybenzenes
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.	2.07	1	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
heptaminol Heptaminol: An amino alcohol that has been used as a myocardial stimulant and vasodilator and to relieve bronchospasm. Its most common therapeutic use is in orthostatic hypotension. The mechanism of heptaminol's therapeutic actions is not well understood although it has been suggested to affect catecholamine release or calcium metabolism.	1.95	1	0	tertiary alcohol
hexachlorophene Hexachlorophene: A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797). hexachlorophene : An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in soaps and creams for the treatment of various skin disorders. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union.	2.05	1	0	bridged diphenyl fungicide; polyphenol; trichlorobenzene	acaricide; antibacterial agent; antifungal agrochemical; antiseptic drug
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	2.97	4	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	2.74	3	0	indolyl alcohol	antineoplastic agent; plant metabolite
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.03	1	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
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).	7.17	1	0	carbohydrazide	antitubercular agent; drug allergen
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.	2.68	3	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
juglone juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.	2.03	1	0	hydroxy-1,4-naphthoquinone	geroprotector; herbicide; reactive oxygen species generator
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.	2.06	1	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
kojic acid [no description available]	8.48	7	0	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	2.07	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
mebeverine mebeverine: RN given refers to parent cpd; structure	2.42	2	0	methoxybenzoic acid
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.06	1	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
n-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide: structure given in first source. NS-398 : A C-nitro compound that is N-methylsulfonyl-4-nitroaniline bearing an additional cyclohexyloxy substituent at position 2.	2.1	1	0	aromatic ether; C-nitro compound; sulfonamide	antineoplastic agent; cyclooxygenase 2 inhibitor
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.37	2	0	phenylethanolamines; tyramines	neurotransmitter
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	1.97	1	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.05	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	1.93	1	0	barbiturates	GABAA receptor agonist
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2.05	1	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	1.93	1	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
piperazine [no description available]	2.06	1	0	azacycloalkane; piperazines; saturated organic heteromonocyclic parent	anthelminthic drug
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	2.03	1	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2	1	0	diarylmethane
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.	2.37	2	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	2.41	2	0	trihydroxybenzoic acid
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.	2.38	2	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.05	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
4-phenylbutyric acid, sodium salt sodium phenylbutyrate : The organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders.	2.05	1	0	organic sodium salt	EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector; neuroprotective agent; orphan drug; prodrug
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.46	2	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.05	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulfobromophthalein Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination.	1.95	1	0	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye
2-thiosalicylic acid 2-thiosalicylic acid: a degradation product of thimerosal; RN given refers to parent cpd. thiosalicylic acid : A sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid.	1.96	1	0	sulfanylbenzoic acid	antipyretic; non-narcotic analgesic
triclosan [no description available]	2.46	2	0	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic
tyramine [no description available]	2.41	2	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
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.	7.07	1	0	mitomycin	alkylating agent; antineoplastic agent
phentolamine Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.	1.94	1	0	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
dichloroisoproterenol dichloroisoproterenol: was heading 1968-94; was DICHLORISOPROTERENOL 1963-76; DCI was see DICHLOROISOPROTERENOL 1975-94; use ISOPROTERENOL to search DICHLOROISOPROTERENOL 1968-94 & DICHLORISOPROTERENOL 1966-67	1.94	1	0
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.05	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	2.03	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
pentolinium tartrate Pentolinium Tartrate: A nicotinic antagonist that has been used as a ganglionic blocking agent in hypertension.. pentolinium tartrate : The bitartrate salt of pentolinium.	1.97	1	0	tartrate salt	antihypertensive agent
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.	1.95	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
dimethylphenylpiperazinium iodide Dimethylphenylpiperazinium Iodide: A selective nicotinic cholinergic agonist used as a research tool. DMPP activates nicotinic receptors in autonomic ganglia but has little effect at the neuromuscular junction.	2.07	1	0	N-arylpiperazine; organic iodide salt; piperazinium salt; quaternary ammonium salt	nicotinic acetylcholine receptor agonist
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	7.38	2	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	7.46	2	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.9	4	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.64	3	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	1.97	1	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.74	3	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2	1	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.11	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	2.02	1	0	tetrachlorophenol	xenobiotic metabolite
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.	2.03	1	0	benzoxazole	allelochemical; phytoalexin
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.42	2	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.48	2	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	3.34	6	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	3.08	5	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	1.97	1	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
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.	7.41	1	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
4-nitrobenzoic acid 4-nitrobenzoic acid: RN given refers to parent cpd. 4-nitrobenzoic acid : A nitrobenzoic acid having the nitro group at the 4-position.	1.96	1	0	nitrobenzoic acid
aniline [no description available]	2	1	0	anilines; primary arylamine
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.	2	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
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	2.03	1	0	psoralens	plant metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.25	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
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.	2.49	2	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
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.	3.07	5	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.	2	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
4-chlorobenzoic acid 4-chlorobenzoic acid: RN given refers to parent cpd. 4-chlorobenzoic acid : A monochlorobenzoic acid carrying a chloro substituent at position 4.	1.96	1	0	monochlorobenzoic acid	bacterial xenobiotic metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	2.03	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylamine ethylamine : A two-carbon primary aliphatic amine.	1.93	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.	2.11	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.6	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	8.86	11	0
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	2.05	1	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
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.	1.99	1	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
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.	2.08	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
isobutyric acid isobutyric acid: RN given refers to parent cpd. isobutyric acid : A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.	2.05	1	0	branched-chain saturated fatty acid; fatty acid 4:0; methyl-branched fatty acid	Daphnia magna metabolite; plant metabolite; volatile oil component
terpin terpene : A hydrocarbon of biological origin having carbon skeleton formally derived from isoprene [CH2=C(CH3)CH=CH2].	2.05	1	0	p-menthane monoterpenoid
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.	2.03	1	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.13	1	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
lawsone lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.	2.03	1	0
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	7.31	1	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
2-methylanthraquinone 2-methylanthraquinone: form Morinda officinalis How.. 2-methylanthraquinone : An anthraquinone that is 9,10-anthraquinone in which the hydrogen at position 2 is substituted by a methyl group.	2.13	1	0	anthraquinone
2,6-dihydroxyanthraquinone 2,6-dihydroxyanthraquinone: structure given in first source. anthraflavic acid : A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.	2.03	1	0	dihydroxyanthraquinone	antimutagen; plant metabolite
diisobutyl phthalate diisobutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of isobutanol.	2.07	1	0	diester; phthalate ester	plasticiser; PPAR modulator; teratogenic agent
acetopyrrothine acetopyrrothine: structure. thiolutin : A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases.	1.92	1	0	acetamides; dithiolopyrrolone antibiotic	angiogenesis inhibitor; antibacterial agent; antifungal agent; antineoplastic agent; bacterial metabolite; chelator; EC 2.7.7.6 (RNA polymerase) inhibitor; marine metabolite; protein synthesis inhibitor; toxin
2,4,6-trichlorophenol [no description available]	2.02	1	0	trichlorophenol	carcinogenic agent
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.25	1	0	pyrrolidin-2-ones
2-furoic acid 2-furoic acid: RN given refers to parent cpd. furoic acid : A monocarboxylic acid that consists of a furan ring having a single carboxylic acid group on any ring position and derivatives thereof.. 2-furoic acid : A furoic acid having the carboxylic acid group located at position 2.	2.06	1	0	furoic acid	bacterial xenobiotic metabolite; human xenobiotic metabolite; inhibitor; plant metabolite; Saccharomyces cerevisiae metabolite
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.	4.25	4	1	monoterpenoid; phenols	volatile oil component
resacetophenone resacetophenone: structure in first source. 2',4'-dihydroxyacetophenone : A dihydroxyacetophenone that is acetophenone carrying hydroxy substituents at positions 2' and 4'.	2.06	1	0	dihydroxyacetophenone; resorcinols	plant metabolite
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.03	1	0	hydroxybenzaldehyde	nematicide; plant metabolite
veratrole veratrole: structure. dimethoxybenzene : Any methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives.. veratrole : A dimethoxybenzene with the methoxy groups at ortho-positions.	2.43	2	0	dimethoxybenzene	plant metabolite
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.	2.43	2	0	biphenyls; substituted aniline	carcinogenic agent
veratryl alcohol (3,4-dimethoxyphenyl)methanol : A member of the class of benzyl alcohols that is benzyl alcohol in which the hydrogens at positions 3 and 4 of the phenyl group are substituted by methoxy groups.	2.41	2	0	benzyl alcohols; dimethoxybenzene; primary alcohol	fungal metabolite
veratric acid veratric acid: RN given refers to parent cpd; structure. 3,4-dimethoxybenzoic acid : A member of the class of benzoic acids that is benzoic acid substituted by methoxy groups at positions 2 and 3.	11.62	48	1	benzoic acids	allergen; plant metabolite
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.	2.07	1	0	naphthoic acid	mouse metabolite; xenobiotic metabolite
1-phenylpropanol 1-phenylpropanol: structure in first source	2.01	1	0	organic molecular entity
mecoprop mecoprop: RN given refers to cpd without isomeric designation; structure. 2-(4-chloro-2-methylphenoxy)propanoic acid : A monocarboxylic acid that is lactic acid in which the hydroxyl hydrogen is replaced by a 4-chloro-2-methylphenyl group.. mecoprop : A racemate comprising equimolar amounts of (R)- and (S)-mecoprop.	2	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes
fenoprop fenoprop: RN given is for parent cpd; structure	2	1	0	monocarboxylic acid	phenoxy herbicide
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)	5.12	43	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
butylparaben [no description available]	2.13	1	0	organic molecular entity
piperonylic acid piperonylic acid: RN given refers to parent cpd; structure. piperonylic acid : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties.	2.96	4	0	aromatic carboxylic acid; benzodioxoles; monocarboxylic acid	antifungal agent; EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor; plant metabolite; vulnerary
2-methyl-4-chlorophenoxyacetic acid 2-Methyl-4-chlorophenoxyacetic Acid: A powerful herbicide used as a selective weed killer.. (4-chloro-2-methylphenoxy)acetic acid : A chlorophenoxyacetic acid that is (4-chlorophenoxy)acetic acid substituted by a methyl group at position 2.	2	1	0	chlorophenoxyacetic acid; monochlorobenzenes	environmental contaminant; phenoxy herbicide; synthetic auxin
2,4-dihydroxybenzaldehyde 2,4-dihydroxybenzaldehyde : A dihydroxybenzaldehyde that is resorcinol which has been substituted by a formyl group para to one of the hydroxy groups.	2.03	1	0	dihydroxybenzaldehyde
2-toluidine 2-toluidine: RN given refers to parent cpd. o-toluidine : An aminotoluene in which the amino substituent is ortho to the methyl group.	1.96	1	0	aminotoluene	carcinogenic agent
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.	2.07	1	0	butan-4-olide	metabolite; neurotoxin
furfuryl alcohol furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.	2.07	1	0	furans; primary alcohol	Maillard reaction product
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.83	3	0	aldehyde; furans	Maillard reaction product; metabolite
4-tert-butylbenzoic acid 4-tert-butylbenzoic acid: RN given refers to parent cpd	2.71	3	0	alkylbenzene
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.46	2	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	2.1	1	0	nitroarene; nitrobenzenes
3-toluic acid 3-toluic acid: RN given refers to parent cpd; structure	1.96	1	0	methylbenzoic acid	human xenobiotic metabolite
3-aminobenzoic acid 3-aminobenzoic acid: RN given refers to parent cpd. 3-aminobenzoic acid : An aminobenzoic acid carrying an amino group at position 3.	1.98	1	0	aminobenzoic acid
3-hydroxybenzoic acid 3-hydroxybenzoic acid: RN given refers to parent cpd. 3-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc.	2.74	3	0	monohydroxybenzoic acid	bacterial metabolite; plant metabolite
alpha-resorcylic acid alpha-resorcylic acid: RN given refers to parent cpd. 3,5-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 5.	2.44	2	0	dihydroxybenzoic acid; resorcinols	metabolite
methyl gallate methyl gallate: has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum. methyl 3,4,5-trihydroxybenzoate : A gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties.	2.77	3	0	gallate ester	anti-inflammatory agent; antioxidant; plant metabolite
3,5-dinitrobenzoic acid 3,5-dinitrobenzoic acid : A member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 3 and 5 are replaced by nitro groups.	1.96	1	0	benzoic acids; C-nitro compound
methylparaben methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd. methylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.	2.73	3	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.21	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'.	2.07	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.	1.96	1	0	methylbenzoic acid
4-anisic acid 4-methoxybenzoic acid: structure in first source. 4-methoxybenzoic acid : A methoxybenzoic acid substituted with a methoxy group at position C-4.	3.72	10	0	methoxybenzoic acid	plant metabolite
4-vinylpyridine 4-vinylpyridine: reagent for blocking cysteine function in proteins; RN given refers to parent cpd	2.06	1	0
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2	1	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.44	2	0	monomethoxybenzene	plant metabolite
2-vinylpyridine [no description available]	2.06	1	0
4-benzylphenol 4-benzylphenol: metabolite of diphenylmethane; RN given refers to parent cpd	2.05	1	0
anisyl alcohol anisyl alcohol: structure given in first source	2.01	1	0	benzyl alcohols
4-methylbenzenethiol 4-methylbenzenethiol: structure in first source	1.96	1	0
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.	1.96	1	0	aminotoluene
acrolein [no description available]	2.07	1	0	enal	herbicide; human xenobiotic metabolite; toxin
allylamine Allylamine: Possesses an unusual and selective cytotoxicity for VASCULAR SMOOTH MUSCLE cells in dogs and rats. Useful for experiments dealing with arterial injury, myocardial fibrosis or cardiac decompensation.	2.06	1	0	alkylamine
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.01	1	0	alkane
deanol Deanol: An antidepressive agent that has also been used in the treatment of movement disorders. The mechanism of action is not well understood.. N,N-dimethylethanolamine : A tertiary amine that is ethanolamine having two N-methyl substituents.	6.93	1	0	ethanolamines; tertiary amine	curing agent; radical scavenger
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	1.96	1	0	aryl thiol
3-hydroxypyridine 3-hydroxypyridine: RN given refeirs to parent cpd. 3-pyridinol : A monohydroxypyridine that is pyridine in which the hydrogen at position 3 has been replaced by a hydroxy group. It has been detected as a thermal degradation product from the smoke of the burning leaves of Salvia divinorum, a Mexican psychoactive plant.	2.15	1	0	monohydroxypyridine
n-pentanoic acid n-pentanoic acid: RN given refers to unlabeled parent cpd. valeric acid : A straight-chain saturated fatty acid containing five carbon atoms.	2.05	1	0	short-chain fatty acid; straight-chain saturated fatty acid	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.	2.07	1	0	pyrrole; secondary amine
pelargonic acid pelargonic acid: K salt acts as cariostatic agent; RN given refers to parent cpd; structure. nonanoic acid : A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.	2.64	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
undecanoic acid undecanoic acid : A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.. undecanoate : A medium-chain fatty acid anion that is the conjugate base of undecanoic acid; used in tandem with testosterone cation in the treatment of male hypogonadism. Major species at pH 7.3.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antifungal agent; human metabolite
behenic acid behenic acid: RN given refers to parent cpd; structure. docosanoic acid : A straight-chain, C22, long-chain saturated fatty acid.	2.45	2	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.41	1	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
3,4,5-trimethoxybenzoic acid 3,4,5-trimethoxybenzoic acid: RN given refers to parent cpd; structure. 3,4,5-trimethoxybenzoic acid : A benzoic acid derivative carrying 3-, 4- and 5-methoxy substituents.	1.98	1	0	benzoic acids; methoxybenzenes	human urinary metabolite; human xenobiotic metabolite; plant metabolite
maltol maltol: found in bark of young larch trees; isolated from Passiflora incarnata; possesses depressant properties in mice; potentiates hexobarbital-induced narcosis & inhibits spontaneous motor activity; structure	2.97	4	0	4-pyranones	metabolite
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.34	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
scoparone scoparone: structure. scoparone : A member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities.	2.04	1	0	aromatic ether; coumarins	anti-allergic agent; anti-inflammatory agent; antihypertensive agent; antilipemic drug; immunosuppressive agent; plant metabolite
veratraldehyde [no description available]	2.66	3	0	benzaldehydes; dimethoxybenzene	antifungal agent
dichlorprop dichlorprop: RN given refers to parent cpd without isomeric designation; structure. 2-(2,4-dichlorophenoxy)propanoic acid : An aromatic ether that is 2-hydroxypropanoic acid in which the hydroxy group at position 2 has been converted to its 2,4-dichlorophenyl ether.. dichlorprop : A racemate comprising equimolar amounts of (R)- and (S)-dichlorprop. It is widely used as a herbicide for killing annual and broad leaf weeds. Only the R-enantiomer has herbicidal activity; the S-enantiomer is inactive.	2	1	0	aromatic ether; dichlorobenzene; monocarboxylic acid
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	2.05	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
ethyl vanillin ethyl vanillin : A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.	3.1	5	0	aromatic ether; benzaldehydes; phenols	antioxidant; flavouring agent
3-nitrobenzoic acid 3-nitrobenzoic acid: RN given refers to parent cpd	1.96	1	0
methyl 4-anisate methyl 4-anisate: volatile biomarker of Mycobacterium tuberculosis; structure in first source. methyl p-anisate : A benzoate ester obtained by the formal condensation of the carboxy group of 4-methoxybenzoic acid with methanol.	2.03	1	0	benzoate ester; monomethoxybenzene
syringaldehyde syringaldehyde: isolated from nonfermented fiber fractions of oat hulls and cottonseed hulls. syringaldehyde : A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.	3.56	8	0	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant metabolite
2-Methoxybenzaldehyde [no description available]	2.03	1	0	carbonyl compound
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.46	2	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
2-aminothiophenol 2-aminothiophenol: RN given refers to parent cpd; structure. 2-aminothiophenol : An aryl thiol that is thiophenol substituted at position 2 by an amino group.	1.96	1	0	aryl thiol; substituted aniline	plant metabolite
carzenide [no description available]	1.96	1	0	sulfonamide
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	3.07	4	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nitrilotriacetic acid Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)	2.02	1	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	3.18	5	0	dihydroxybenzaldehyde
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	3.44	7	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	2.07	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	2.07	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
2-vanillin ortho-vanillin : A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.	2.36	2	0	benzaldehydes; guaiacols	antimutagen; plant metabolite
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.	2	1	0	monomethoxybenzene; phenols
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	3.25	1	0	methoxybenzenes; phenols	metabolite
potassium cyanide [no description available]	1.97	1	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
methohexital Methohexital: An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia.. methohexital : A barbiturate, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by allyl and 1-methylpent-2-ynyl groups.	1.97	1	0	acetylenic compound; barbiturates	drug allergen; intravenous anaesthetic
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.	10.95	23	1	catechin	antioxidant; plant metabolite
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.	2.03	1	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.41	2	0	diazine; pyrazines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	2.79	3	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
gamma-resorcylic acid [no description available]	2.04	1	0	dihydroxybenzoic acid	metabolite
ethamivan ethamivan: minor descriptor (65-72); major descriptor (73-86); on-line search BENZAMIDES (66-86); INDEX MEDICUS search BENZAMIDES (65-72); ETHAMIVAN (73-86). etamivan : Phenol substituted at C-2 and C-4 by a methoxy group and an N,N-diethylaminocarbonyl group respectively. A respiratory stimulant drug related to nikethamide, it has now fallen largely into disuse.	6.93	1	0	methoxybenzenes; phenols
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.	1.97	1	0	pyrrolizidine alkaloid
phenylbenzoquinone phenylbenzoquinone: RN given refers to parent cpd	2.41	2	0
pipradrol pipradrol: was heading 1963-94; PIPRADOL was see PIPRADROL 1978-94; use PIPERIDINES to search PIPRADROL 1966-94	6.93	1	0	diarylmethane
glycyrrhetinic acid [no description available]	2	1	0	cyclic terpene ketone; hydroxy monocarboxylic acid; pentacyclic triterpenoid	immunomodulator; plant metabolite
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.03	1	0	bile acid glycine conjugate	human metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	2.15	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
chrysophanic acid chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.	2.46	2	0	dihydroxyanthraquinone	anti-inflammatory agent; antiviral agent; plant metabolite
indole-3-carbaldehyde indole-3-carbaldehyde: metabolite of tryptophan; structure. indole-3-carbaldehyde : A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group.	2.96	4	0	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
topanol 354 Topanol 354: structure	3.25	1	0	methoxybenzenes; phenols
3,5-dimethylbenzoic acid 3,5-dimethylbenzoic acid : A dimethylbenzoic acid in which the two methyl groups are located at positions 3 and 5.	1.96	1	0	dimethylbenzoic acid
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	3.17	5	0	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent
phloretic acid phloretic acid: structure. N-hydroxysuccinimide ester : An ester of N-hydroxysuccinimide.. phloretic acid : A hydroxy monocarboxylic acid consisting of propionic acid having a 4-hydroxyphenyl group at the 3-position.	2.49	2	0	hydroxy monocarboxylic acid	plant metabolite
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.05	1	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
margaric acid margaric acid: RN given refers to unlabeled parent cpd. heptadecanoic acid : A C17 saturated fatty acid and trace component of fats in ruminants.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; mammalian metabolite
arachidic acid icosanoic acid : A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
oleanolic acid [no description available]	3.04	4	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.69	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
physcione physcione: structure. physcion : A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It has been widely isolated and characterised from both terrestrial and marine sources.	2.13	1	0	dihydroxyanthraquinone	anti-inflammatory agent; antibacterial agent; antifungal agent; antineoplastic agent; apoptosis inducer; hepatoprotective agent; metabolite
angelicin angelicin: used as tranquillizer; sedative; or anticonvulsant; structure	2.03	1	0	furanocoumarin
2,4,6-trimethylphenol [no description available]	3.25	1	0	hydroxytoluene
cellobiose beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.	2	1	0	cellobiose	epitope
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	6.69	68	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
herniarin herniarin: methoxy analog of umbelliferone; structure. herniarin : A member of the class of coumarins that is coumarin substituted by a methoxy group at position 7.	2.47	2	0	coumarins	fluorochrome
6-methoxybenzoxazolinone 6-methoxybenzoxazolinone: plant derivative which stimulates reproduction in Microtus montanus. 6-methoxy-2-benzoxazolinone : A 2-benzoxazolinone that is substituted by a methoxy group at position 6.	2.03	1	0	aromatic ether; benzoxazole	antibacterial agent; anticonvulsant; antifungal agent; muscle relaxant; plant metabolite
methoxyhydroxyphenylglycol Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.	2.9	4	0	methoxybenzenes; phenols
cumic acid cumic acid : A member of the class of benzoic acids that is cumene substituted by at least one carboxy group.. p-cumic acid : A cumic acid that consists of benzoic acid substituted by an isopropyl group at position 4.	2.03	1	0	cumic acid	plant metabolite
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	7.6	1	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
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.	3.77	10	0	dialdehyde	biomarker
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
2-propenylurea [no description available]	2.06	1	0
lignoceric acid lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.	2.74	3	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia tenebrosa metabolite; human metabolite; plant metabolite; volatile oil component
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	2.05	1	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
2-hydroxybutyric acid 2-hydroxybutyric acid: RN given refers to cpd without isomeric designation. hydroxybutyric acid : Any compound comprising a butyric acid core carrying at least one hydroxy substituent.. 2-hydroxybutyric acid : A hydroxybutyric acid having a single hydroxyl group located at position 2; urinary secretion of 2-hydroxybutyric acid is increased with alcohol ingestion or vigorous physical exercise and is associated with lactic acidosis and ketoacidosis in humans and diabetes in animals.	2.05	1	0	2-hydroxy monocarboxylic acid; hydroxybutyric acid	algal metabolite; human metabolite
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	2.76	3	0	flavonols; monohydroxyflavone
2-methoxybenzoic acid O-methylsalicylic acid : A methoxybenzoic acid that is the methyl ether of salicylic acid.	1.98	1	0	methoxybenzoic acid	flavouring agent; non-steroidal anti-inflammatory drug
3-methoxybenzoic acid [no description available]	4.08	15	0	methoxybenzoic acid	flavouring agent; human urinary metabolite
3-methoxybenzaldehyde 3-methoxybenzaldehyde : A member of the class of benzaldehydes in which the hydrogen at position 3 of benzaldehyde has been replaced by a methoxy group.	2.03	1	0	benzaldehydes; monomethoxybenzene	Brassica napus metabolite
ethane sulfonate [no description available]	1.99	1	0	alkanesulfonic acid
dansyl chloride dansyl chloride: RN given refers to unlabeled cpd	2.17	1	0	aminonaphthalene; sulfonic acid derivative
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.25	1	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
2,6-dichloro-4-nitrophenol [no description available]	2.08	1	0
5-methyl-2-furfural 5-methyl-2-furfural: RN given refers to cpd with locants as specified	2.07	1	0	aldehyde; furans	EC 2.2.1.6 (acetolactate synthase) inhibitor; flavouring agent; human metabolite; Maillard reaction product
3-hydroxybenzeneacetic acid 3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.	2.31	1	0	monocarboxylic acid; phenols	human xenobiotic metabolite
isovanillin isovanillin: inhibits aldehyde oxidase. isovanillin : A member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase.	2.75	3	0	benzaldehydes; monomethoxybenzene; phenols	animal metabolite; antidiarrhoeal drug; antifungal agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; HIV protease inhibitor; plant metabolite
Berberine chloride (TN) [no description available]	2.07	1	0	organic molecular entity
4-hydroxyisophthalic acid 4-hydroxyisophthalic acid: structure given in first source	1.94	1	0
tridecanoic acid tridecanoate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of tridecanoic acid.. tridecanoic acid : A C13 straight-chain saturated fatty acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	4.42	21	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
nonadecanoic acid nonadecanoic acid : A C19 straight-chain fatty acid of plant or bacterial origin. An intermediate in the biodegradation of n-icosane, it has been shown to inhibit cancer growth.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	fungal metabolite
ethyl gallate ethyl gallate: used with osmium in procedure for mapping neuronal pathways. ethyl gallate : A gallate ester obtained by the formal condensation of gallic acid with ethanol.	1.98	1	0	gallate ester	plant metabolite
n-methylpyrrolidone 1-methylpyrrolidin-2-one: structure in first source. N-methylpyrrolidin-2-one : A member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group.	2.04	1	0	lactam; N-alkylpyrrolidine; pyrrolidin-2-ones	polar aprotic solvent
3-methoxycatechol 3-methoxycatechol : A member of the class of catechols that is catechol in which a hydrogen that is ortho to one of the hydroxy groups has been replaced by a methoxy group. It displays agonistic activity against G protein-coupled receptor 35 (GPR35).	2.08	1	0	aromatic ether; catechols	G-protein-coupled receptor agonist
pentadecanoic acid pentadecanoic acid: in serum as a marker for intake of milk fat. pentadecanoic acid : A straight-chain saturated fatty acid containing fifteen-carbon atoms.	2.08	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; food component; human blood serum metabolite; plant metabolite
ethambutol Ethambutol: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863). ethambutol : An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.	2.76	3	0	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic
tetramethylpyrazine tetramethylpyrazine: found in Ligusticum chuanxiong. tetramethylpyrazine : A member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).	2.02	1	0	alkaloid; pyrazines	antineoplastic agent; apoptosis inhibitor; bacterial metabolite; neuroprotective agent; platelet aggregation inhibitor; vasodilator agent
dihydroferulic acid dihydroferulic acid: structure in first source. dihydroferulic acid : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.	2.21	1	0	guaiacols; monocarboxylic acid; phenylpropanoid	antioxidant; human xenobiotic metabolite; mouse metabolite; plant metabolite
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.	8.23	6	0	zinc molecular entity
monolaurin monolaurin: RN given refers to cpd with unspecified monolaurin locant. 1-monolauroylglycerol : A 1-monoglyceride with dodecanoyl (lauroyl) as the acyl group.. rac-1-monolauroylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-lauroyl-sn-glycerol and 3-lauroyl-sn-glycerol	2.05	1	0	1-monoglyceride; dodecanoate ester; rac-1-monoacylglycerol
tricarballylic acid tricarballylic acid: RN given refers to parent cpd. tricarballylic acid : A tricarboxylic acid that is glutaric acid in which one of the beta-hydrogens is substituted by a carboxy group.	1.97	1	0	tricarboxylic acid
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.54	8	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
3,5-di-tert-butyl-4-hydroxybenzoic acid [no description available]	2.07	1	0
4-nitrothiophenolate 4-nitrothiophenolate: RN given refers to parent cpd	1.96	1	0
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	2	1	0	organic cation	geroprotector; herbicide
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.05	1	0	hydroquinones	food antioxidant
2,4-diacetylphloroglucinol 2,4-diacetylphloroglucinol: produced by Pseudomonas aurantiaca. 2,4-diacetylphloroglucinol : A benzenetriol that is phloroglucinol in which two of the ring hydrogens are replaced by acetyl groups.	2.06	1	0	aromatic ketone; benzenetriol; diketone; methyl ketone	antifungal agent; bacterial metabolite
heneicosanoic acid henicosanoic acid : A long-chain fatty acid that is henicosane in which one of the methyl groups has been oxidised to give the corresponding carboxylic acid.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid
tricosanoic acid tricosanoic acid : A very long-chain fatty acid that is tricosane in which one of the methyl groups has been oxidised to the corresponding carboxylic acid.	2.05	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia magna metabolite; human metabolite; plant metabolite
acetosyringone acetosyringone: plant inducer which induces expression of VirE & VirG in A. tumefaciens. acetosyringone : A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.45	2	0	acetophenones; dimethoxybenzene; phenols	anti-asthmatic drug; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
o-chlorobenzylidenemalonitrile o-Chlorobenzylidenemalonitrile: A riot control agent which causes temporary irritation of the eyes and the mucosal surface of the respiratory tract. It is a more potent irritant than OMEGA-CHLOROACETOPHENONE, but less incapacitating.	1.96	1	0	organochlorine compound
3,4,5-trimethoxybenzamide [no description available]	2.03	1	0
mannose mannopyranose : The pyranose form of mannose.	2.02	1	0	D-aldohexose; D-mannose; mannopyranose	metabolite
phenoxyacetic acid phenoxyacetic acid : A monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes.	2.15	1	0	aromatic ether; monocarboxylic acid	allergen; Aspergillus metabolite; human xenobiotic metabolite; plant growth retardant
3-o-methylgallic acid 3-O-methylgallic acid: structure in first source. 3-O-methylgallic acid : A member of the class of benzoic acids that is gallic acid in which the phenolic hydroxy group at position 3 is converted into the corresponding methyl ether.	2.42	2	0	benzoic acids; catechols
methyl vanillate methyl vanillate: isolated from Hovenia dulcis. methyl vanillate : A benzoate ester that is the methyl ester of vanillic acid.	3.6	8	0	aromatic ether; benzoate ester; phenols	antioxidant; plant metabolite
metanephrine Metanephrine: Product of epinephrine O-methylation. It is a commonly occurring, pharmacologically and physiologically inactive metabolite of epinephrine.	1.99	1	0	catecholamine
5,6-dihydroxytryptamine 5,6-Dihydroxytryptamine: Tryptamine substituted with two hydroxyl groups in positions 5 and 6. It is a neurotoxic serotonin analog that destroys serotonergic neurons preferentially and is used in neuropharmacologic research.	1.97	1	0
vidarabine adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.	2.06	1	0	beta-D-arabinoside; purine nucleoside	antineoplastic agent; bacterial metabolite; nucleoside antibiotic
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.	3.8	1	1	cycloalkene; p-menthadiene	human metabolite
dimethylpropiothetin dimethylpropiothetin: has antineoplastic activity; RN given refers to hydroxide inner salt. S,S-dimethyl-beta-propiothetin : A sulfonium betaine obtained by deprotonation of the carboxy group of 3-dimethylsulfoniopropionic acid.	2.04	1	0	sulfonium betaine	marine metabolite; osmolyte
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.07	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.49	2	0	chromium group element atom	micronutrient
neptunium Neptunium: A radioactive element of the actinide metals family. It has the atomic symbol Np, and atomic number 93.	2.03	1	0	actinoid atom; f-block element atom
neodymium Neodymium: An element of the rare earth family of metals. It has the atomic symbol Nd, atomic number 60, and atomic weight 144.24, and is used in industrial applications.	2	1	0	f-block element atom; lanthanoid atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.31	1	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.1	1	0	elemental platinum; nickel group element atom; platinum group metal 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.	2.31	1	0	iron group element atom; platinum group metal 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.	2	1	0	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.15	1	0	chromium group element atom	micronutrient
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.	2.44	2	0	cadmium molecular entity; zinc group element atom
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	3.23	6	0	D-galactosamine; primary amino compound	toxin
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	2.01	1	0	metal sulfate	emetic; fertilizer; sensitiser
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.39	2	0	dihydrogen
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)	2.31	1	0	nitrogen oxoacid
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.01	1	0	deuterated compound; water	NMR solvent
fluorosulfonic acid perfluorosulfonic acid: sulfonated tetrafluoroethylene-based fluoropolymer–copolymer	2.41	1	0	sulfur oxoacid	NMR solvent
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.41	2	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
chlorine dioxide chlorine dioxide: equal or superior to chlorine when used as wastewater disinfectant	2	1	0	chlorine dioxide
cadmium chloride Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.	2.73	3	0	cadmium coordination entity
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	1	0	titanium oxides	food colouring
4-chlorophenoxyacetic acid 4-chlorophenoxyacetic acid: RN given refers to parent cpd; structure. (4-chlorophenoxy)acetic acid : A chlorophenoxyacetic acid that is phenoxyacetic acid carrying a chloro substituent at position 4.	2	1	0	chlorophenoxyacetic acid; monochlorobenzenes	phenoxy herbicide
levamisole Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.	3.8	1	1	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator
cromolyn sodium Cromolyn Sodium: A chromone complex that acts by inhibiting the release of chemical mediators from sensitized MAST CELLS. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack.. disodium cromoglycate : An organic sodium salt that is the disodium salt of cromoglycic acid.	2.44	2	0	organic sodium salt	anti-asthmatic drug; drug allergen
ferric nitrilotriacetate ferric nitrilotriacetate: induces diabetes in animals (iron loading)	2.02	1	0	iron chelate	carcinogenic agent; mutagen
fluorides [no description available]	1.96	1	0	halide anion; monoatomic fluorine
1-deoxynojirimycin 1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.	2.46	2	0	2-(hydroxymethyl)piperidine-3,4,5-triol; piperidine alkaloid	anti-HIV agent; anti-obesity agent; bacterial metabolite; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; plant metabolite
zingerone zingerone: pungent principle of ginger; structure. zingerone : A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.	2.08	1	0	methyl ketone; monomethoxybenzene; phenols	anti-inflammatory agent; antiemetic; antioxidant; flavouring agent; fragrance; plant metabolite; radiation protective agent
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.	3.87	12	0	benzenes; phenyl acetates
phenoxyethanol phenoxyethanol: structure. 2-phenoxyethanol : An aromatic ether that is phenol substituted on oxygen by a 2-hydroxyethyl group.	2.05	1	0	aromatic ether; glycol ether; primary alcohol	antiinfective agent; central nervous system depressant
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	2.08	1	0	phenols	fungal xenobiotic metabolite
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.	3.29	6	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
myrcene myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.	2.05	1	0	monoterpene	anabolic agent; anti-inflammatory agent; flavouring agent; fragrance; plant metabolite; volatile oil component
butylated hydroxytoluene 2,6-di-tert-butyl-4-methylphenol : A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.	3.88	3	0	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector
silybin silibinin : A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.	2.05	1	0	aromatic ether; benzodioxine; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; hepatoprotective agent; plant metabolite
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	1.95	1	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
etoposide [no description available]	2.06	1	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	2.89	4	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
ribavirin Rebetron: Rebetron is tradename	2.08	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	3.18	5	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	4.26	5	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
acarbose [no description available]	2.57	2	0	tetrasaccharide derivative	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; geroprotector; hypoglycemic agent
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.	1.99	1	0
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	1.97	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	1.97	1	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
dazoxiben dazoxiben: RN given refers to parent cpd	2.11	1	0
esmolol methyl 3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate : A methyl ester that is methyl 3-(4-hydroxyphenyl)propanoate in which the hydrogen attached to the phenolic hydroxy group is substituted by a 2-hydroxy-3-(isopropylamino)propyl group.. esmolol : A racemate comprising equimolar amounts of (R)- and (S)-esmolol. A cardioselective and short-acting beta1 receptor blocker with rapid onset but lacking intrinsic sympathomimetic and membrane-stabilising properties, it is used as the hydrochloride salt in the management of supraventricular arrhythmias, and for the control of hypertension and tachycardia during surgery. While the S enantiomer possesses all of the heart rate control, both enantiomers contribute to lowering blood pressure.	1.99	1	0	aromatic ether; ethanolamines; methyl ester; secondary alcohol; secondary amino compound
3-iodobenzylguanidine 3-Iodobenzylguanidine: A guanidine analog with specific affinity for tissues of the sympathetic nervous system and related tumors. The radiolabeled forms are used as antineoplastic agents and radioactive imaging agents. (Merck Index, 12th ed) MIBG serves as a neuron-blocking agent which has a strong affinity for, and retention in, the adrenal medulla and also inhibits ADP-ribosyltransferase.	1.99	1	0	organoiodine compound
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.05	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
monoammonium molybdate ammonium molybdate: RN given refers to unspecified ammonium molybdate salt. ammonium molybdate : An ammonium salt composed of ammonium and molybdate ions in a 2:1 ratio.	2.08	1	0	ammonium salt	poison
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	2.01	1	0
vanillyl alcohol vanillyl alcohol: structure. vanillyl alcohol : A monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4.	8.34	6	0	benzyl alcohols; guaiacols	plant metabolite
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	3.66	9	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	5.69	24	0	D-glucopyranose	epitope; mouse metabolite
ursolic acid [no description available]	2.49	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
betulinic acid [no description available]	2.42	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
baicalin [no description available]	2.07	1	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.43	2	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
3-amino-4-hydroxybenzoic acid 3-amino-4-hydroxybenzoic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid carrying an additional amino substitutent at position 3.	2.46	2	0	aminobenzoic acid; monohydroxybenzoic acid
gallocatechol gallocatechol: structure give in first source; RN given for (trans-(+-))-omer; inhibits DNA-dependent DNA & RNA polymerases. (+)-gallocatechin : A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.. gallocatechin : A catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii.	2.02	1	0	gallocatechin	antioxidant; metabolite; radical scavenger
xanthotoxol 8-hydroxyfurocoumarin : A furanocoumarin which bears a hydroxy group at position 8.	1.98	1	0	8-hydroxyfurocoumarin
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose pentagalloylglucose: pentahydroxy gallic acid ester of glucose; a phytogenic antineoplastic agent and antibacterial agent. 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions.	2.08	1	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.05	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
secoisolariciresinol secoisolariciresinol: RN given refers to ((R-(R,R))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.	2.44	2	0	secoisolariciresinol	antidepressant; phytoestrogen; plant metabolite
bergenin bergenin: RN refers to (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-isomer; structure	2.08	1	0	trihydroxybenzoic acid	metabolite
2,4,6-trihydroxybenzoic acid [no description available]	2.1	1	0	hydroxybenzoic acid
guaethol [no description available]	2.08	1	0	aromatic ether; phenols; volatile organic compound	flavouring agent
n-acetylvaline N-acetylvaline: RN given refers to the (DL)-isomer	2.17	1	0	L-valine derivative; N-acetyl-L-amino acid
2-ethoxybenzoic acid [no description available]	1.96	1	0
pinocembrin pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.	2.07	1	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
2,4,6-trihydroxyacetophenone monoacetylphloroglucinol: structure in first source. 2',4',6'-trihydroxyacetophenone : A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides.	2.06	1	0	aromatic ketone; benzenetriol; methyl ketone	MALDI matrix material; plant metabolite
n-acetyltyrosine N-acetyl-L-tyrosine : An N-acetyltyrosine in which the chiral centre has L configuration.	2.05	1	0	N-acetyltyrosine; N-acyl-L-tyrosine	biomarker; EC 2.1.1.4 (acetylserotonin O-methyltransferase) inhibitor; human urinary metabolite
1-triacontanol 1-triacontanol: constituent of Apocynum venetum leaf & Cirsium segetum. triacontan-1-ol : An ultra-long-chain primary fatty alcohol that is triacontane in which one of the terminal methyl hydrogens is replaced by a hydroxy group.	2.15	1	0	fatty alcohol 30:0; ultra-long-chain primary fatty alcohol
2-hydroxy-4-methoxybenzaldehyde 2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)	2.03	1	0	methoxybenzenes; phenols
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	2.17	1	0	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
isoscopoletin isoscopoletin : A hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone.	2.17	1	0	aromatic ether; hydroxycoumarin	plant metabolite
3-methoxysalicylic acid 2-hydroxy-3-methoxybenzoic acid: structure in first source	2.48	2	0	methoxysalicylic acid	metabolite
methyl syringate methyl syringate : A benzoate ester obtained by the formal condensation of carboxy group of syringic acid with methanol.	2.03	1	0	benzoate ester; dimethoxybenzene; phenols	plant metabolite
2,5-dihydroxybenzaldehyde 2,5-dihydroxybenzaldehyde: structure in first source. 2,5-dihydroxybenzaldehyde : A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5.	2.03	1	0	dihydroxybenzaldehyde	human metabolite; mouse metabolite; Penicillium metabolite
vanillylamine vanillylamine: inhibits microsomal enzyme function; RN given refers to parent cpd; structure	2.08	1	0	aralkylamino compound
5-methoxyresorcinol 5-methoxyresorcinol: structure in first source. flamenol : A member of the class of resorcinols that is phloroglucinol in which one of the phenolic hydrogens has been replaced by a methyl group.	1.98	1	0	monomethoxybenzene; resorcinols	Brassica napus metabolite
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	2.76	3	0	catechin; polyphenol	antioxidant
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	2.08	1	0	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
tetrahydropalmatine [no description available]	2.07	1	0	an (S)-7,8,13,14-tetrahydroprotoberberine; berberine alkaloid; organic heterotetracyclic compound	adrenergic agent; dopaminergic antagonist; non-narcotic analgesic
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	2.04	1	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
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.	2.07	1	0	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
indole-2-carboxylic acid [no description available]	2.05	1	0	indolyl carboxylic acid
(-)-catechin (-)-catechin : The (-)-enantiomer of catechin.	2.05	1	0	catechin	metabolite
isoalantolactone isoalantolactone: RN given refers to (3aR-(3aalpha,4aalpha,8abeta,9aalpha))-isomer; structure. isoalantolactone : A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium.	2.07	1	0	eudesmane sesquiterpenoid; sesquiterpene lactone	antifungal agent; apoptosis inducer; plant metabolite
magnoflorine magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.	2.06	1	0	aporphine alkaloid; quaternary ammonium ion	plant metabolite
sakuranetin sakuranetin: major rice phytoalexin; RN given for ((S)-(-))-isomer; structure in first source. sakuranetin : A flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group.	2.04	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; flavonoid phytoalexin; monomethoxyflavanone	antimycobacterial drug; plant metabolite
3,4-dimethoxy-5-hydroxybenzoic acid 3,4-dimethoxy-5-hydroxybenzoic acid: thiopurine methyltransferase inhibitor	1.96	1	0	trihydroxybenzoic acid
3-(3,4-dimethoxyphenyl)propanoic acid 3-(3,4-dimethoxyphenyl)propanoic acid : A monocarboxylic acid that is propanoic acid substituted by a 3,4-dimethoxyphenyl group at position 3.	2.02	1	0	dimethoxybenzene; monocarboxylic acid
2-hydroxy-4-methoxy benzoic acid [no description available]	2.03	1	0	methoxybenzoic acid
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.	2.03	1	0	methoxysalicylic acid	bacterial metabolite; human urinary metabolite
methyl alpha-d-galactopyranoside methyl-galactopyranoside: structure in first source. methyl alpha-D-galactoside : An alpha-D-galactoside having a methyl substituent at the anomeric position.	2.04	1	0	alpha-D-galactoside; methyl D-galactoside; monosaccharide derivative
ethyl protocatechuate ethyl protocatechuate: structure. ethyl 3,4-dihydroxybenzoate : An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.	2.17	1	0	catechols; ethyl ester	antibacterial agent; antioxidant; apoptosis inducer; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; plant metabolite
4'-methoxyflavone 4'-methoxyflavone: from seeds of Psoralea corylifolia (Fabaceae); structure in first source	2.05	1	0	ether; flavonoids
3,5-dihydroxy-4-methoxybenzoic acid 3,5-dihydroxy-4-methoxybenzoic acid: catechol methyltransferase inhibitor; N1 same as NM	1.96	1	0	trihydroxybenzoic acid
methyl 2,4-dihydroxy-3,6-dimethyl benzoate atraric acid: structure in first source; from the stem barks of Newbouldia laevis	2.03	1	0	4-hydroxybenzoate ester
dodecyltetraethylene glycol monoether [no description available]	2.05	1	0	poly(ethylene glycol)
methyl 3-(4-hydroxyphenyl)propionate methyl 3-(4-hydroxyphenyl)propionate: a root-exuded compound responsible for biological nitrification inhibition by sorghum (Sorghum bicolor); structure in first source. methyl 3-(4-hydroxyphenyl)propionate : A methyl ester resulting from the formal condensation of the carboxy group of phloretic acid with methanol. It is a nitrification inhibitor and a plant growth regulator.	2.03	1	0	methyl ester; phenols	nitrification inhibitor; plant growth regulator
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	2.5	2	0	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
biotinamide biotin amide : A monocarboxylic acid amide derived from biotin.	2.07	1	0	biotins; monocarboxylic acid amide	human metabolite
coenzyme a [no description available]	2.03	1	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
mebeverine gamma-oryzanol: present in rice bran is associated with various physiological functions; RN given refers to gamma-oryzanol	2.06	1	0
aucubin [no description available]	2.07	1	0	organic molecular entity	metabolite
friedelin 3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.	2.04	1	0	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
7-ketocholesterol 7-ketocholesterol: inhibits uptake of cholesterol in rabbit aorta. 7-ketocholesterol : A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7.	2.02	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; 7-oxo steroid; cholestanoid	neuroprotective agent
catalpol [no description available]	2.07	1	0	organic molecular entity	metabolite
fosthiazate fosthiazate: structure in first source	2.07	1	0	organic phosphonate; organothiophosphate insecticide; phosphonic ester	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; nematicide
lupenone lupenone: structure in first source	2.03	1	0	triterpenoid	metabolite
uvaol uvaol: from Vauquelinia corymbosa (Rosaceae)	2.08	1	0	triterpenoid	metabolite
pyrimidine dimers Pyrimidine Dimers: Dimers found in DNA chains damaged by ULTRAVIOLET RAYS. They consist of two adjacent PYRIMIDINE NUCLEOTIDES, usually THYMINE nucleotides, in which the pyrimidine residues are covalently joined by a cyclobutane ring. These dimers block DNA REPLICATION.	2.08	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.	2.03	1	0	D-glucuronic acid	algal metabolite
dehydrodivanillin dehydrodivanillin: a lignin-related compound	2.01	1	0
3-methoxybenzamide [no description available]	2.38	2	0
Lup-20(29)-en-28-al, 3beta-hydroxy- [no description available]	2.04	1	0	triterpenoid
syringaresinol [no description available]	2.03	1	0	aromatic ether; furofuran; lignan; polyether; polyphenol	plant metabolite
loliolide loliolide: RN given refers to (6S-cis)-isomer	2.43	2	0	benzofurans	metabolite
p-methoxy-n-methylphenethylamine p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.	2.15	1	0	aromatic ether; secondary amino compound	metabolite
carbidopa, levodopa drug combination [no description available]	2.31	1	0
diacetyldichlorofluorescein diacetyldichlorofluorescein: stable storage form of dichlorofluorescein	2.17	1	0
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	2.82	3	0	proanthocyanidin
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	2.47	2	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	2.04	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
dihydrocapsaicin [no description available]	2.71	3	0	capsaicinoid
proanthocyanidin proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.	2.13	1	0
parthenolide [no description available]	2.1	1	0	germacranolide
exp3174 losartan carboxylic acid: structure given in first source. losartan carboxylic acid : A biphenylyltetrazole that is losartan with the hydroxymethyl group at position 5 on the imidazole ring replaced with a carboxylic acid.	2.07	1	0	biphenylyltetrazole; imidazoles; organochlorine compound	metabolite
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.06	1	0
asiatic acid [no description available]	2.08	1	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
matairesinol matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).	2.06	1	0	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	1.92	1	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
cyasterone [no description available]	2	1	0	14alpha-hydroxy steroid; 20-hydroxy steroid; 21-hydroxy steroid; 2beta-hydroxy steroid; 3beta-hydroxy steroid; 6-oxo steroid; phytoecdysteroid; steroid lactone
aromadedrin aromadedrin: inhibits protein kinase C; the dihydro makes it a flavone rather than a flavonol. (+)-dihydrokaempferol : A tetrahydroxyflavanone having hydroxy groupa at the 3-, 4'-, 5- and 7-positions.	2.71	3	0	4'-hydroxyflavanones; dihydroflavonols; secondary alpha-hydroxy ketone; tetrahydroxyflavanone	metabolite
3-hydroxydiploptene 3-hydroxydiploptene: biosynthesized from squalene or epoxy dihydrosqualene in cell-free system from Methylococcus capsulatus; RN given refers to (3beta)-isomer	2.07	1	0
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).	2.05	1	0	nitrogen oxoacid
cyanidin cyanidin: RN given refers to parent cpd; structure. cyanidin cation : An anthocyanidin cation that is flavylium substituted at positions 3, 3', 4', 5 and 7 by hydroxy groups.	2.11	1	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	2.44	2	0	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
substance p (4-11), pro(4)-trp(7,9)- substance P (4-11), Pro(4)-Trp(7,9)-: RN given refers to (D-Pro,D-Trp)-(L-Met,L-Gln,L-Phe,L-Leu)-isomers; RN for cpd without isomeric designation not in Chemline 7/85; substance P antagonist	1.98	1	0
carbapenems [no description available]	2.25	1	0
aspartame [no description available]	2	1	0	carboxylic acid; dipeptide zwitterion; dipeptide; methyl ester	apoptosis inhibitor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; environmental contaminant; micronutrient; nutraceutical; sweetening agent; xenobiotic
xylose xylopyranose: structure in first source	2.51	2	0	D-xylose
4-amino-3-hydroxybenzoic acid [no description available]	2.03	1	0
4-propylbenzoic acid [no description available]	2.03	1	0	alkylbenzene
phytol [no description available]	2.13	1	0
3,3',4',5,6,7,8-heptamethoxyflavone 3,3',4',5,6,7,8-heptamethoxyflavone: has anti-inflammatory activity; isolated from citrus fruit; exhibit antiadhesive action on platelets	2.1	1	0	ether; flavonoids
5-hydroxy-3',4',6,7-tetramethoxyflavone 5-hydroxy-3',4',6,7-tetramethoxyflavone: isolated from Artemisia argyi	2.01	1	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.	2.17	1	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.	7.76	3	0	oxygen hydride; oxygen radical; reactive oxygen species
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.	2.05	1	0	camphor
malvidin malvidin: RN given refers to parent cpd; coloring agent from flowers of Malvaviscus conzatti. malvidin : An anthocyanidin cation that is delphinidin carrying methyl substituents at positions 3' and 5'.	2.08	1	0	5-hydroxyanthocyanidin	biological pigment; metabolite
isolariciresinol isolariciresinol: RN given refers to ((1-S-(1alpha,2beta,3alpha))-isomer); structure given in first source. (+)-isolariciresinol : A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis.	2.44	2	0	guaiacols; lignan; polyphenol; primary alcohol	plant metabolite
3-hydroxystigmast-5-en-7-one [no description available]	2.04	1	0	steroid
vanillactic acid vanillactic acid: metabolite of catecholamines	2.37	2	0	2-oxo monocarboxylic acid
desmethylnaproxen desmethylnaproxen: RN given refers to cpd without isomeric designation. desmethylnaproxen : A member of the class of naphthols that is naproxen in which the 6-methoxy group has been demethylated.	2.17	1	0
dihydrocitrinone [no description available]	2.05	1	0
tanshinone ii a tashinone IIA: a cardiovascular agent with antineoplastic activity; isolated from Salvia miltiorrhiza; structure in first source	2.07	1	0	abietane diterpenoid
paromomycin Paromomycin: An aminoglycoside antibacterial and antiprotozoal agent produced by species of STREPTOMYCES.. paromomycin : An amino cyclitol glycoside that is the 1-O-(2-amino-2-deoxy-alpha-D-glucopyranoside) and the 3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranoside of 4,6-diamino-2,3-dihydroxycyclohexane (the 1R,2R,3S,4R,6S diastereoisomer). It is obtained from various Streptomyces species. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. It is also used as a therapeutic against visceral leishmaniasis.	2.06	1	0	amino cyclitol glycoside; aminoglycoside antibiotic	anthelminthic drug; antibacterial drug; antiparasitic agent; antiprotozoal drug
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.	2.07	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).	2.53	2	0	amino acid zwitterion; angiotensin II	human metabolite
3-n-butyl-4,5-dihydrophthalide 3-N-butyl-4,5-dihydrophthalide: from seeds of Apium graveolens Linn.; RN given refers to (-)-isomer; structure given in first source	2.07	1	0
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.	1.94	1	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.	6.35	48	0
eurylene eurylene: structure in first source	2.1	1	0
(+)-epicatechin (+)-epicatechin : A catechin that is flavan carrying five hydroxy substituents at positions 3, 3', 4', 5 and 7 (the 2S,3S-stereoisomer).	2.07	1	0	catechin; polyphenol	cyclooxygenase 1 inhibitor; plant metabolite
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.07	1	0	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
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.	2.92	4	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
glycitin glycitin: structure in first source. glycitin : A glycosyloxyisoflavone that is isoflavone substituted by a methoxy group at position 6, a hydroxy group at position 4' and a beta-D-glucopyranosyloxy group at position 7.	2.04	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; methoxyisoflavone; monosaccharide derivative	plant metabolite
finalgon ointment Finalgon ointment: contains vanillylamide of nonylic acid; beta-butoxyethyl ester of nicotinic acid	2.33	2	0
veratrylglycerol-beta-guaiacyl ether veratrylglycerol-beta-guaiacyl ether: structure given in first source. veratrylglycerol beta-guaiacyl ether : A idol that is propane-1,3-diol substituted by a 3,4-dimethoxyphenyl group at position 1 and a 2-methoxyphenoxy group at position 2 respectively.	2.03	1	0	dimethoxybenzene; diol
(-)-gallocatechin gallate (-)-gallocatechin gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of (-)-gallocatechin. A natural product found in found in green tea.	2.05	1	0	catechin; gallate ester; polyphenol	antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human xenobiotic metabolite; plant metabolite
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	2.41	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
sitosterol, (3beta)-isomer Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.	2.73	3	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	2.76	3	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
lanosterol [no description available]	2.48	2	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.74	3	0
lupeol [no description available]	2.04	1	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
methyl 3,4-dihydroxybenzoate [no description available]	2.73	3	0	catechols; methyl ester	antioxidant; neuroprotective agent; plant metabolite
wortmannin [no description available]	2.41	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
a-130a [no description available]	2.06	1	0
lariciresinol lariciresinol: found in human urine. (+)-lariciresinol : A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).	2.96	4	0	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; plant metabolite
amyrin acetate [no description available]	2.05	1	0
3,4-dihydroxyphenylpropionic acid 3,4-dihydroxyphenylpropionic acid: metabolite of caffeic acid; RN given refers to parent cpd; structure. 3-(3,4-dihydroxyphenyl)propanoic acid : A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity.	2.76	3	0	(dihydroxyphenyl)propanoic acid	antioxidant; human xenobiotic metabolite
4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en 4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en: RN given for (3R-(3alpha,3abeta,4beta,8aalpha))-isomer; a natural benzyl ester of a carotyl type azulene sesquiterpenoid; structure in first source	2.47	2	0
jatrorrhizine chloride [no description available]	2.07	1	0
(2S,3R)-dihydrodehydrodiconiferyl alcohol [no description available]	2.06	1	0	1-benzofurans; guaiacols; guaiacyl lignin; primary alcohol
norbelladine norbelladine: common metabolic intermediate. norbelladine : A phenethylamine alkaloid that is tyramine in which one of the amino hydrogens has been replaced by a 3,4-dihydroxybenzyl group.	2.1	1	0	catechols; phenethylamine alkaloid; polyphenol; secondary amino compound	plant metabolite
permanganate [no description available]	1.94	1	0	manganese oxoacid
s-adenosylhomocysteine S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.	2.05	1	0	adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide	cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite
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	1	0
bradykinin [no description available]	2.88	4	0	oligopeptide	human blood serum metabolite; vasodilator agent
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	3.33	6	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	2.05	1	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
3,4-dihydroxyphenyllactic acid 3,4-dihydroxyphenyllactic acid: from S. miltiorhiza Bge; dilates coronary artery; RN given refers to parent cpd without isomeric designation	2.52	2	0	2-hydroxy monocarboxylic acid; catechols
scopolin [no description available]	2.13	1	0	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.49	2	0	taxifolin	metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.05	1	0	tartaric acid	Escherichia coli metabolite
cholesteryl glucoside cholesteryl glucoside: RN given refers to cpd without isomeric designation	2.05	1	0	monosaccharide derivative; sterol 3-beta-D-glucoside
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	2.49	2	0	3'-hydroxyflavanones; tetrahydroxyflavanone
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	2.47	2	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; 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.	2.03	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
silychristin silychristin : A flavonolignan isolated from Silybum marianum and has been shown to exhibit inhibitory activities against lipoxygenase and prostaglandin synthetase.	2.05	1	0	1-benzofurans; aromatic ether; flavonolignan; polyphenol; secondary alpha-hydroxy ketone	lipoxygenase inhibitor; metabolite; prostaglandin antagonist; radical scavenger
peonidin peonidin: a COX-2 inhibitor with protein kinase inhibitory and phytogenic antineoplastic activities; RN given for chloride salt. peonidin : An anthocyanidin cation that is flavylium bearing four hydroxy substituents at positions 3, 4', 5 and 7 as well as a methoxy substituent at position 3'.	2.25	1	0	5-hydroxyanthocyanidin	antineoplastic agent; antioxidant; apoptosis inducer; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.03	1	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
tecomine tecomine: RN given refers to (4R-(4alpha,7beta,7abeta))-isomer; Merck and Negwer have numbers for tecomin, a different cpd; structure	2.13	1	0	piperidines
ononin [no description available]	2.07	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones 7-O-beta-D-glucoside; monosaccharide derivative	plant metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	3.19	5	0
syringaresinol (+)-syringaresinol : The (7alpha,7'alpha,8alpha,8'alpha)-stereoisomer of syringaresinol.	2.11	1	0	syringaresinol	antineoplastic agent
petunidin-3-glucoside [no description available]	2.25	1	0	anthocyanin cation; aromatic ether; beta-D-glucoside	antioxidant; metabolite
malvidin-3-glucoside malvidin 3-O-beta-D-glucoside : An anthocyanin cation consisting of malvidin having a beta-D-glucosyl residue attached at the 3-hydroxy position.	2.08	1	0	anthocyanin cation; aromatic ether; beta-D-glucoside	metabolite
isoshinanolone isoshinanolone: from crude extracts; structure in first source	2.03	1	0	tetralins
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.1	1	0	cyclodextrin
acarbose [no description available]	2.1	1	0	amino cyclitol; glycoside
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	4.5	22	0	cinnamic acid	plant metabolite
ergosterol [no description available]	2.03	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.05	1	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
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.	1.97	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
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	2.21	1	0	cyclodextrin
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	3.19	5	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	3.02	4	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
palmitoleic acid hexadecenoate : A long-chain unsaturated fatty acid anion that is the conjugate base of hexadecenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.17	1	0	hexadec-9-enoic acid	algal metabolite; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; human blood serum metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	2.41	1	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	10.63	121	2	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
lycopene [no description available]	2.05	1	0	acyclic carotene	antioxidant; plant metabolite
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	2.42	2	0
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	1.96	1	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	3.67	9	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	2.13	1	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; 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)	1.94	1	0
potassium acetate Potassium Acetate: A potassium salt used to replenish ELECTROLYTES, for restoration of WATER-ELECTROLYTE BALANCE, as well as a urinary and systemic alkalizer, which can be administered orally or by intravenous infusion. Formerly, it was used in DIURETICS and EXPECTORANTS.. potassium acetate : A potassium salt comprising equal numbers of potassium and acetate ions	2.03	1	0	potassium salt	food acidity regulator
sodium benzoate Sodium Benzoate: The sodium salt of BENZOIC ACID. It is used as an antifungal preservative in pharmaceutical preparations and foods. It may also be used as a test for liver function.. sodium benzoate : An organic sodium salt resulting from the replacement of the proton from the carboxy group of benzoic acid by a sodium ion.	2.21	1	0	organic sodium salt	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
methyl indole-3-carboxylate methyl indole-3-carboxylate : The methyl ester of indole-3-carboxylic acid.	2.17	1	0	indoles; methyl ester	metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	2.07	1	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
2-hydroxycinnamic acid trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.	3.25	1	0	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	3.59	2	0	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	8.64	47	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	2.72	3	0	anethole	flavouring agent
geraniol [no description available]	2.05	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	7.34	82	0
ethyl cinnamate ethyl cinnamate: a pine weevil antifeedant; structure in first source	2.03	1	0	alkyl cinnamate; ethyl ester
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	7.67	17	1	sinapic acid	MALDI matrix material; plant metabolite
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	3.97	13	0	isomethyleugenol
beta-ionone beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.	2.05	1	0	ionone	antioxidant; fragrance
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	2.42	2	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	3.04	4	0	stilbene
isoliquiritigenin [no description available]	2.47	2	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
Methylenedioxycinnamic acid [no description available]	2.05	1	0	hydroxycinnamic acid
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.	2.41	2	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
isopropyl thiogalactoside Isopropyl Thiogalactoside: A non-metabolizable galactose analog that induces expression of the LAC OPERON.. isopropyl beta-D-thiogalactopyranoside : An S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.	2.52	2	0	S-glycosyl compound
nsc 4347 NSC 4347: structure in first source	2.07	1	0
sesquiterpenes [no description available]	2.77	3	0
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.07	1	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
dehydrovomifoliol dehydrovomifoliol: isolated from Litsea sessilis; structure in first source. (6S)-dehydrovomifoliol : A dehydrovomifoliol that has S-configuration at the chiral centre.. dehydrovomifoliol : A fenchane monoterpenoid that is substituted by methyl groups at positions 3, 5, and 5, and by both a hydroxy group and a 3-oxobut-1-en-1-yl group at position 4.	2.17	1	0	dehydrovomifoliol	plant metabolite
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	12.78	50	1	caffeic acid	geroprotector; mouse metabolite
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	2.13	1	0	alkyl caffeate ester; methyl ester
isoferulic acid isoferulic acid: isomer of ferulic acid; structure. isoferulic acid : A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.	2.74	3	0	ferulic acids	antioxidant; biomarker; metabolite
phenylalanine methyl ester phenylalanine methyl ester: RN given refers to (L)-isomer. methyl L-phenylalaninate : An alpha-amino acid ester that is the methyl ester of L-phenylalanine.	2.03	1	0	alpha-amino acid ester; L-phenylalanine derivative
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	7.9	4	0	isoeugenol	plant metabolite
2-methoxy-4-prop-1-enylphenyl acetate 2-methoxy-4-prop-1-enylphenyl acetate: structure in first source. isoeugenol acetate : A phenylpropanoid that is the acetate ester of trans-isoeugenol.	2	1	0	monomethoxybenzene; phenyl acetates; phenylpropanoid
flunarizine Flunarizine: Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity. It is effective in the prophylaxis of migraine, occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy.	1.99	1	0	diarylmethane
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.	4.66	8	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
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	4.55	25	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	4.38	6	0	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
allylthiourea [no description available]	2.06	1	0	thioureas	metabolite
aurapten aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.	2.06	1	0	coumarins; monoterpenoid	antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; dopaminergic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; gamma-secretase modulator; gastrointestinal drug; hepatoprotective agent; matrix metalloproteinase inhibitor; neuroprotective agent; plant metabolite; PPARalpha agonist; vulnerary
caryophyllene oxide caryophyllene oxide: has butyrylcholinesterase inhibitory activity; structure in first source. epoxide : Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.	2.11	1	0	epoxide	metabolite
umbelliprenin umbelliprenin: RN given refers to cpd with unspecified isomeric designation	2.06	1	0	terpene lactone
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	7.88	30	2	cinnamate ester; tannin	food component; plant metabolite
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.06	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
D-fructopyranose [no description available]	2.82	3	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.67	3	0	thiocarboxamide	hepatotoxic agent
1,6-anhydro-beta-glucopyranose 1,6-anhydro-beta-glucopyranose: RN given refers to (beta-D)-isomer. levoglucosan : A anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose.	2.02	1	0	anhydrohexose	Arabidopsis thaliana metabolite; biomarker; human metabolite
capsazepine capsazepine: modified capsaicin molecule; a capsaicin receptor antagonist. capsazepine : A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.	2	1	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
n(6)-(1-iminoethyl)lysine N(6)-acetimidoyl-L-lysine : An L-lysine derivative that is L-lysine in which one of the hydrogens attached to N(6) is substituted by an acetimidoyl group	2.11	1	0	L-lysine derivative; non-proteinogenic L-alpha-amino acid
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	2.03	1	0	bile acid taurine conjugate	human metabolite
nadp [no description available]	2.93	4	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)	3.69	9	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.	10.26	15	0
2-(allylthio)pyrazine 2-(allylthio)pyrazine: structure given in first source	2	1	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.	2.02	1	0	alkali metal atom
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	2.06	1	0	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
quinine [no description available]	3.8	1	1	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
3-methoxy-4-hydroxyphenylglycol sulfate 3-methoxy-4-hydroxyphenylglycol sulfate: RN given refers to cpd with unspecified locant for sulfate moiety	2.17	1	0	alcohol; phenols
glyceryl nonivamide N-(4-O-glycerol-3-methoxybenzyl)nonivamide: structure given in first source	1.98	1	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	4	13	0
eugenyl-beta-d-glucopyranoside [no description available]	2.17	1	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.03	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	8.01	4	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.	2.17	1	0	organic sodium salt	detergent; protein denaturant
flavan-3-ol flavan-3-ol: structure in first source	2.17	1	0	hydroxyflavonoid
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.44	2	0
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.1	1	0	long-chain fatty acid
myelin basic protein Myelin Basic Protein: An abundant cytosolic protein that plays a critical role in the structure of multilamellar myelin. Myelin basic protein binds to the cytosolic sides of myelin cell membranes and causes a tight adhesion between opposing cell membranes.	1.99	1	0
sodium butyrate [no description available]	2.05	1	0	organic sodium salt	EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
quercetin [no description available]	6.35	34	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	2.41	2	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.48	2	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
biochanin a [no description available]	2.45	2	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
formononetin [no description available]	2.73	3	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
vitexin [no description available]	3.06	4	0	C-glycosyl compound; trihydroxyflavone	antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite; platelet aggregation inhibitor
acacetin 5,7-dihydroxy-4'-methoxyflavone : A monomethoxyflavone that is the 4'-methyl ether derivative of apigenin.	2.76	3	0	dihydroxyflavone; monomethoxyflavone	anticonvulsant; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	10	11	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	4.88	7	1	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
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.	3.32	6	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
quercitrin [no description available]	2.47	2	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
scopoletin [no description available]	8.3	6	0	hydroxycoumarin	plant growth regulator; plant metabolite
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2.97	4	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	2.51	2	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
maleoylacetic acid maleoylacetic acid: RN given refers to (Z)-isomer. maleylacetic acid : A 4-oxohex-2-enedioic acid with a Z-configuration.. 4-oxohex-2-enedioate : An oxo dicarboxylate that is the conjugate base of 4-oxohex-2-enedioic acid.. maleylacetate : A 4-oxohex-2-enedioate that is the conjugate base of maleylacetic acid.	1.98	1	0	4-oxohex-2-enedioic acid	bacterial xenobiotic metabolite
sinapyl alcohol sinapyl alcohol: has anti-inflammatory and antinociceptive properties; structure in first source. trans-sinapyl alcohol : Sinapyl alcohol in which the configuration of the propenyl double bond is E. It is one of the main monolignols.. sinapyl alcohol : A primary alcohol, being cinnamyl alcohol hydroxylated at C-4 and methoxylated at C-3 and -5.	2.06	1	0	sinapyl alcohol	monolignol
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	3.16	5	0	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
feruloyltyramine feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer	2.5	2	0	tyramines	metabolite
chrysoeriol chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.	2.07	1	0	monomethoxyflavone; trihydroxyflavone	antineoplastic agent; antioxidant; metabolite
stigmasterol stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.	2.97	4	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
sinapaldehyde sinapyl aldehyde: structure in first source. (E)-sinapaldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.06	1	0	cinnamaldehydes; dimethoxybenzene; phenols	antifungal agent; plant metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	2.07	1	0	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	5.45	18	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
3-methylkaempferol 3-methylkaempferol: structure in first source. 3-methoxyapigenin : A trihydroxyflavone that is apigenin substituted by a methoxy group at position 3.	2.07	1	0	monomethoxyflavone; trihydroxyflavone	plant metabolite
kaempferol [no description available]	4.08	14	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.58	2	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
genistein [no description available]	4.08	4	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
erucic acid [no description available]	2.05	1	0	docosenoic acid
nervonic acid (15Z)-tetracosenoic acid : A tetracosenoic acid having a cis-double bond at position 15.	2.05	1	0	tetracosenoic acid
genistin genistin: glycoside of soy bean isoflavone, gentistein	2.45	2	0	7-hydroxyisoflavones 7-O-beta-D-glucoside
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	2.04	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.45	2	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
costunolide [no description available]	2.07	1	0	germacranolide; heterobicyclic compound	anthelminthic drug; antiinfective agent; antineoplastic agent; antiparasitic agent; antiviral drug; metabolite
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	2.42	2	0	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
baicalein [no description available]	2.07	1	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	2.05	1	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
fisetin [no description available]	2.05	1	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
hispidulin hispidulin : A monomethoxyflavone that is scutellarein methylated at position 6.	8.31	1	0	monomethoxyflavone; trihydroxyflavone	anti-inflammatory agent; anticonvulsant; antineoplastic agent; antioxidant; apoptosis inducer; plant metabolite
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	2.07	1	0	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	2.86	3	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
morin morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria). morin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.	2.05	1	0	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent
myricetin [no description available]	2.08	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
orientin orientin: structure given in first source; RN given refers to the (D-glucopyranosyl)-isomer. orientin : A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.	2.58	2	0	3'-hydroxyflavonoid; C-glycosyl compound; tetrahydroxyflavone	antioxidant; metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	2.48	2	0	monomethoxyflavone; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; metabolite
santin santin: from Tanacetum microphyllum; structure given in first source. santin : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 3, 6 and 4' and hydroxy groups at positions 5 and 7 respectively.	2.07	1	0	dihydroxyflavone; trimethoxyflavone	plant metabolite
tricin tricin: from Spartina cynosuroides and other plants; structure	2.15	1	0	3'-methoxyflavones; dimethoxyflavone; trihydroxyflavone	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.48	2	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
daidzein [no description available]	2.95	4	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
polydatin trans-piceid : A stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue.	2.07	1	0	beta-D-glucoside; monosaccharide derivative; polyphenol; stilbenoid	anti-arrhythmia drug; antioxidant; geroprotector; hepatoprotective agent; metabolite; nephroprotective agent; potassium channel modulator
pterostilbene [no description available]	2.07	1	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
epsilon-viniferin epsilon-viniferin: stilbene dimer; isolated from the Oriental medicinal plant Vitis coignetiae; structure given in first source. (-)-trans-epsilon-viniferin : A stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol.	2.07	1	0	1-benzofurans; polyphenol; stilbenoid	metabolite
diferulic acid diferulic acid: structure of 8-5'-diferulic acid in first source	2.11	1	0
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.61	2	0	rosmarinic acid	geroprotector; plant metabolite
salvianolic acid a salvianolic acid A: a nootropic depside from Salvia miltiorrhizia	2.6	1	0	stilbenoid
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	3.86	3	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
prunetin prunetin: reduces herpes virus-1 plaque formation. prunetin : A hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group.	2.07	1	0	7-methoxyisoflavones; hydroxyisoflavone	anti-inflammatory agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor; metabolite
ellagic acid [no description available]	8.43	7	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	7.1	1	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.05	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	2.52	2	0	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
tranilast tranilast: antiallergic drug; potent inhibitor of homologous passive cutaneous anaphylaxis. tranilast : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.	2.02	1	0	amidobenzoic acid; cinnamamides; dimethoxybenzene; secondary carboxamide	anti-allergic agent; anti-asthmatic drug; antineoplastic agent; aryl hydrocarbon receptor agonist; calcium channel blocker; hepatoprotective agent; nephroprotective agent
ketotifen fumarate ketotifen fumarate : An organoammonium salt consisting of equimolar amounts of ketotifen(1+) and fumarate(1-) ions. A blocker of histamine H1 receptors with a stabilising action on mast cells, it is a non-bronchodilator anti-asthmatic drug.	2.02	1	0	organoammonium salt	anti-asthmatic drug; H1-receptor antagonist
ubiquinone 6 [no description available]	2.48	2	0	ubiquinones	Saccharomyces cerevisiae metabolite
ergosta-7,22-dien-3-ol, (3beta,5alpha,6alpha,22e)-isomer 5alpha-ergosta-7,22-dien-3beta-ol : A 3beta-sterol consisting of an ergostane skeleton with double bonds at 7- and 22-positions.	2.1	1	0	3beta-sterol	anti-HSV-1 agent; antifungal agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; metabolite
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	2.06	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
deamino arginine vasopressin Deamino Arginine Vasopressin: A synthetic analog of the pituitary hormone, ARGININE VASOPRESSIN. Its action is mediated by the VASOPRESSIN receptor V2. It has prolonged antidiuretic activity, but little pressor effects. It also modulates levels of circulating FACTOR VIII and VON WILLEBRAND FACTOR.	1.97	1	0	heterodetic cyclic peptide	diagnostic agent; renal agent; vasopressin receptor agonist
olvanil [no description available]	2.69	3	0	methoxybenzenes; phenols
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	2.21	1	0	1-O-acyl-sn-glycero-3-phosphocholine
casticin casticin: from fruit of Vitex rotundifolia; structure in second source. casticin : A tetramethoxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6, 7 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii.	2.21	1	0	dihydroxyflavone; tetramethoxyflavone	apoptosis inducer; plant metabolite
bisdemethoxycurcumin curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.	2.05	1	0	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
syringin syringin: a phenylpropanoid glycoside; see also eleutherosides & lyoniside for eleutheroside A: 474-58-8. syringin : A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	2.15	1	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
linarin linarin: flavone glycoside isolated from leaves of Linaria japonica MIQ	2	1	0
ethyl caffeate (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.	2.13	1	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
glycitein glycitein : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.	2.04	1	0	7-hydroxyisoflavone; methoxyisoflavone	fungal metabolite; phytoestrogen; plant metabolite
isofraxidin isofraxidin: also see fraxidin	2.11	1	0	hydroxycoumarin
ligustilide ligustilide: found in Umbelliferae plants; RN given refers to cpd without isomeric designation; structure in first source	2.07	1	0	butenolide	metabolite
methyl linolenate [no description available]	2.05	1	0	fatty acid methyl ester	insect attractant; plant metabolite
1,3,6-trihydroxy-2-methyl-9,10-anthraquinone 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone: anthraquinone derivative. 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone : A trihydroxyanthraquinone that is 9,10-anthraquinone substituted by hydroxy groups at positions 1, 3 and 6 and a methyl group at position 2. It has been isolated from the roots of Rubia yunnanensis.	2.01	1	0	trihydroxyanthraquinone	plant metabolite
cudraflavone c cudraflavone C: a tyrosinase inhibitor with antimicrobial activity; isolated from Artocarpus integer; structure in first source. cudraflavone C : A tetrahydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 7, 2' and 4' and prenyl groups at positions 3 and 6. Isolated from Morus nigra, it exhibits antibacterial and cytotoxic activities.	2.07	1	0	tetrahydroxyflavone	antibacterial agent; antineoplastic agent; plant metabolite
octadecyl caffeate caffeic acid n-octadecyl ester: isolated from Daphne acutiloba Rehd; structure in first source	2.07	1	0
artemetin [no description available]	2.21	1	0	ether; flavonoids
tiliroside tiliroside: isolated from seeds of Eremocarpus setigerus	2.41	1	0	cinnamate ester; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	plant metabolite
spiraeoside spiraeoside: from flowers of Filipendula ulmaria (L.); structure given in first source. quercetin 4'-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 4'.	2.07	1	0	beta-D-glucoside; flavonols; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; plant metabolite
lacinartin lacinartin: from Zanthoxylum schinifolium; structure in first source	2.06	1	0
5-hydroxy-3,3',4',7-tetramethoxyflavone 5-hydroxy-3,7,3',4'-tetramethoxyflavone: from the rhizome of Kaempferia parviflora; inhibits monocyte adhesion and cellular reactive oxygen species production in human umbilical vein endothelial cells. 5-hydroxy-3,3',4',7-tetramethoxyflavone : A monohydroxyflavone that is 5-hydroxyflavone which is substituted by methoxy groups at positions 3,3',4' and 7.	2.05	1	0	3'-methoxyflavones; monohydroxyflavone; tetramethoxyflavone	plant metabolite
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	2.11	1	0
n-(aminocarbonyl)-2-ethyl-2-butenamide [no description available]	1.93	1	0
muconic acid muconic acid: a metabolite of benzene; reported to be a reliable indicator of occupational exposure to benzene; structure given in first source. trans,trans-muconic acid : The trans,trans-isomer of muconic acid. It is metabolite of benzene in humans and serves as a biomarker of occupational exposure to benzene.. muconic acid : A hexadienedioic acid with unsaturation at positions 2 and 4.	1.98	1	0	muconic acid	biomarker; human xenobiotic metabolite
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.4	2	0	boron group element atom; elemental aluminium; metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.15	1	0	metal atom; pnictogen
n-(4-hydroxy-beta-phenethyl)-4-hydroxycinnamide trans-N-p-coumaroyl tyramine: from the twigs of Celtis chinensis; structure in first source	2.5	2	0	hydroxycinnamic acid	metabolite
2',4'-dihydroxychalcone 2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source	2.06	1	0
aldosterone dehydrodiisoeugenol: an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages; structure in first source	2.03	1	0
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.98	4	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.	2.45	2	0	cysteinium	fundamental metabolite
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.	2.06	1	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	2.84	3	0
bakuchiol bakuchiol: chief component of Psoralea corylifolia Linn; structure	2.03	1	0
bergamottin bergamottin: constituent of bergamot oil; structure given in first source	1.98	1	0	furanocoumarin	metabolite
artepillin c artepillin C: RN refers to (E)-isomer	2.15	1	0
narcissin flavonol narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM))	2.5	2	0	disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; trihydroxyflavone
avicularin avicularin: from Polygonum aviculare L.; RN given refers to L-isomer. avicularin : A quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare.	2.07	1	0	alpha-L-arabinofuranoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
resiniferatoxin resiniferatoxin: phorbol related diterpene ester; potent agonist of vanilloid TRPV1 receptors. resiniferatoxin : A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).	2.43	2	0	carboxylic ester; diterpenoid; enone; monomethoxybenzene; organic heteropentacyclic compound; ortho ester; phenols; tertiary alpha-hydroxy ketone	analgesic; neurotoxin; plant metabolite; TRPV1 agonist
epimedin c epimedin C: structure given in first source; from Epimedium sp.	7.25	1	0	flavonoids; glycoside
quercetin-3'-o-beta-d-glucopyranoside quercetin 3'-O-glucoside: structure in first source	2.21	1	0
4-hydroxycordoin 4-hydroxycordoin: antibacterial and anti-inflammatory from Lonchocarpus neuroscapha Benth. (Fabaceae); structure in first source. 4-hydroxycordoin : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at position 4 and 2' and a (3-methylbut-2-en-1-yl)oxy group at position 4'. It has been isolated from Lonchocarpus neuroscapha.	2.06	1	0	aromatic ether; chalcones; polyphenol	anti-inflammatory agent; antibacterial agent; plant metabolite
derricidin derricidin: from Lonchocarpus sericeus; structure in first source	2.06	1	0	chalcones
bisabolol bisabolol: monocyclic sesquiterpene alcohol with strong bacteriocidal effects, especilly against M. Tuberc.; isolated from seed plant Populus tacamacaha; RN given refers to cpd without isomeric desigation	2.6	1	0
caffeoyl-coenzyme a caffeoyl-coenzyme A: structure given in first source	2	1	0
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.03	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
guaiacylglycerol-beta-guaiacyl ether guaiacylglycerol-beta-guaiacyl ether: structure given in first source. guaiacylglycerol-beta-guaiacyl ether : A glycerol ether in which guaiacyl and guaiacylglycerol subunits are joined by an arylglycerol-beta-aryl (beta-O-4) linkage.	1.96	1	0	glycerol ether
falcarindiol falcarindiol: from leaves of Schefflera digitata (Araliaceae) and in carrots; inhibits germination of spores of most common dermatophyte fungi	2.04	1	0	organic molecular entity	metabolite
columbianadin columbianadin: furanocoumarin isolated from Peucedanum palustre; RN given refers to columbianadin, (S-(Z))-isomer. columbianadin : An alpha,beta-unsaturated carboxylic ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of 2-[(8S)-2-oxo-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-8-yl]propan-2-ol.	2.07	1	0	alpha,beta-unsaturated carboxylic ester; furanocoumarin	anti-inflammatory agent; antineoplastic agent; apoptosis inducer; hepatoprotective agent; plant metabolite; rat metabolite
o-geranylsinapyl alcohol O-geranylsinapyl alcohol: structure given in first source; isolated from the bark of Fagara rhetza, an Indonesian medicinal plant	2.06	1	0
feruloyltyramine, (z)-isomer [no description available]	2.17	1	0	hydroxycinnamic acid
picroside i picroside I: RN given for (1aS-(1aalpha,1bbeta,2beta(E),5abeta,6beta,6aalpha))-isomer; hepatoprotective agent; structure in first source	2.51	2	0
ne 21610 [no description available]	1.99	1	0
alpha-cyperone alpha-cyperone: isolated from the rhizomes of Cyperus rotundus; structure in first source	2.07	1	0
engeletin engeletin: dihydroflavonol glycoside from the leaves of Stelechocarpus cauliflorus; structure in first source	2.04	1	0
4-isopropylbenzaldehyde thiosemicarbazone 4-isopropylbenzaldehyde thiosemicarbazone: structure in first source	2.03	1	0
methyl chlorogenate methyl chlorogenate: from Eriobotrya japonica; structure in first source	2.05	1	0	quinic acid
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.01	1	0	hydroxycinnamic acid
beta-escin [no description available]	4	2	1
3-hydroxy-4-methoxybenzaldehyde thiosemicarbazone 3-hydroxy-4-methoxybenzaldehyde thiosemicarbazone: inhibits cabbage butterfly larvae phenoloxidase; structure in first source	2.03	1	0
bornyl acetate [no description available]	2.11	1	0	acetate ester; monoterpenoid
aminomethyltransferase Aminomethyltransferase: A one-carbon group transferase that transfers lipoamide-linked methylamine groups to tetrahydrofolate (TETRAHYDROFOLATES) to form methylenetetrahydrofolate and AMMONIA. It is one of four components of the glycine decarboxylase complex.	2.15	1	0
beta-sitosterone beta-sitosterone: from Torreya jackii	2.03	1	0
bicyclol bicyclol: an antihepatitis drug, on the metabolism and hepatotoxicity of aflatoxin B1 (AFB1) in rats.	2.48	2	0
capsiate [no description available]	2.45	2	0	carboxylic ester; monomethoxybenzene; phenols	angiogenesis inhibitor; anti-allergic agent; anti-inflammatory agent; antioxidant; capsaicin receptor agonist; hypoglycemic agent; plant metabolite
morachalcone a morachalcone A: tyrosinase inhibitor from the wood of Artocarpus heterophyllus; structure in first source	2.07	1	0	chalcones
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).	3.14	5	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
9-methoxycanthin-6-one 9-methoxycanthin-6-one: from roots of Eurycoma longifolia (Simaroubaceae). 9-methoxycanthin-6-one : An indole alkaloid that is the 9-methoxy derivative of canthin-6-one. Isolated from Eurycoma longifolia and Simaba multiflora, it exhibits cytotoxic activity towards human cancer cell lines.	2.1	1	0	aromatic ether; indole alkaloid; organic heterotetracyclic compound	antineoplastic agent; antiplasmodial drug; metabolite
capsinolol capsinolol: structure given in first source	2.01	1	0
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.	2.37	2	0
kaempferol 7-o-glucoside kaempferol 7-O-glucoside: structure in first source. kaempferol 7-O-beta-D-glucopyranoside : A kaempferol O-glucoside that is kaempferol attached to a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.17	1	0	beta-D-glucoside; flavonols; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
jaeschkeanadiol jaeschkeanadiol: structure in first source	2.07	1	0	sesquiterpenoid
9-hydroxycanthin-6-one 9-hydroxycanthin-6-one: from Eurycoma longifolia Jack (Simaroubaceae), induces penile erection and delays ejaculation. 9-hydroxycanthin-6-one : An indole alkaloid that is canthin-6-one substituted by a hydroxy group at position 9. Isolated from the roots of Eurycoma longifolia, it exhibits antineoplastic activity.	2.1	1	0
teferin teferin: isolated from Ferula hermonis; structure in first source	2.47	2	0
1,4-o-diferuloylsecoisolariciresinol 1,4-O-diferuloylsecoisolariciresinol: inhibits mTOR signaling in cancer cells; structure in first source	2.04	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.	2.07	1	0
isosilybin b [no description available]	2.05	1	0
2-hydroxy-3-methylanthraquinone 2-hydroxy-3-methylanthraquinone: apoptosis-inducing compound from Hedyotis diffusa WILLD; structure in first source	2.1	1	0
ribose ribopyranose : The pyranose form of ribose.	2	1	0	D-ribose; ribopyranose
isosilybin a isosilybin A: has antineoplastic activity; structure in first source	2.05	1	0
nelumal a nelumal A: aromatase inhibitor from Ligularia nelumbifolia; structure in first source	2.06	1	0
murisolin murisolin: structure in first source	2.02	1	0	polyketide
syringaresinol, (1r-(1alpha, 3aalpha,4alpha,6aalpha))-isomer (-)-syringaresinol : The (7beta,7'beta,8beta,8'beta)-stereoisomer of syringaresinol.	2.06	1	0	syringaresinol
2,4,3',5'-tetrahydroxystilbene oleocanthal: newly pressed extra-virgin olive oil contains oleocanthal, acting as a natural anti-inflammatory compound that has a potency and profile strikingly similar to that of ibuprofen; structure in first source. oleocanthal : A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.	2.58	2	0
lyoniresinol lyoniresinol: isoalted from the vine stem of Bauhinia championii; structure in first source. (+)-lyoniresinol : A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.	2.06	1	0	dimethoxybenzene; lignan; polyphenol; primary alcohol; tetralins	antineoplastic agent; metabolite
(+)-dehydrodiconiferyl alcohol (+)-dehydrodiconiferyl alcohol : A dehydrodiconiferyl alcohol that has (2S,3R)-configuration. A natural product isolated from several plant species including Allium sativum and Codonopsis pilosula.	2.05	1	0	dehydrodiconiferyl alcohol	antioxidant; plant metabolite
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.25	1	0
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.08	1	0
trametenolic acid b trametenolic acid B: from Trametes lactinea; structure in first source	2.1	1	0	triterpenoid
grasshopper ketone grasshopper ketone: a phytotoxin isolated from Oryza sativa Awaakamai; structure in first source. grasshopper ketone : A member of the class of allenes that is cyclohexane substituted by 3-oxobut-1-en-1-ylidene, methyl, hydroxy, hydroxy, methyl and methyl groups at positions 1, 2, 2, 4, 6 and 6, respectively (the 2R,3R,4S-stereoisomer). It is isolated from the grasshopper, Romalea microptera.	2.17	1	0
cleomiscosin d cleomiscosin D: from the root bark of Hibiscus syriacus (Malvaceae); structure in first source	2.13	1	0
pedunculoside pedunculoside: from leaves of Ilex chinensis; structure given in first source	2.1	1	0
peonidin 3-glucoside peonidin 3-glucoside: the methylated form of cyanidin 3-glucoside	2.11	1	0
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	3.16	5	0
friedelane friedelane: from leaves of Maytenus aquifolium (Celastraceae); structure in first source. friedelane : A triterpene that is docosahydropicene substituted by 8 methyl groups at positions 2, 2, 4a, 6a, 8a, 9, 12b and 14a.	2.05	1	0	triterpene	metabolite
cyanidin-3-o-beta-glucopyranoside cyanidin-3-O-beta-glucopyranoside: a natural compound distributed in several fruits & vegetables, such as strawberry, rhubarb, cherry, red cabbage, red onion, cranberries, etc.	2.11	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.97	4	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
tannins gallotannin : A class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose).	2.08	1	0	tannin
vitisin a [no description available]	2.07	1	0	benzofurans
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.	4.36	4	1
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	2.75	3	0	glycoside
quercetin [no description available]	2.05	1	0
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.1	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.31	1	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.	2.17	1	0	chlorophyll; methyl ester	cofactor
bis(tri-n-butyltin)oxide bis(tri-n-butyltin)oxide: RN given refers to parent cpd; RN in Chemline for tributylin: 688-73-3	1.99	1	0	inorganic molecular entity
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.69	3	0
pinoresinol pinoresinol: in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol. pinoresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl groups.	7.83	3	0
2-hydroxyursolic acid 2-hydroxyursolic acid: isolated from the stem bark of Physocarpus intermedius; structure in first source	2.08	1	0
oleracein e oleracein E: antioxidant from Portulaca oleracea; structure in first source	2.53	2	0
chitosan [no description available]	3.41	6	0
alpha-pyrone-4,6-dicarboxylic acid alpha-pyrone-4,6-dicarboxylic acid: structure. 2-oxo-2H-pyran-4,6-dicarboxylate : A dicarboxylic acid dianion obtained via deprotonation of both carboxy groups of 2-oxo-2H-pyran-4,6-dicarboxylic acid; major species at pH 7.3.	2.6	1	0	dicarboxylic acid dianion
balanophonin balanophonin: from fruit wall of Cirsium vulgare; structure in first source	2.05	1	0
sodium lactate Sodium Lactate: The sodium salt of racemic or inactive lactic acid. It is a hygroscopic agent used intravenously as a systemic and urinary alkalizer.. sodium lactate : An organic sodium salt having lactate as the counterion.	2.05	1	0	lactate salt; organic sodium salt	food acidity regulator; food preservative
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	2.42	2	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
picrotoxin Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.	6.93	1	0
albiflorin albiflorin: glucoside in peony roots. albiflorin : A monoterpene glycoside with formula C23H28O11, originally isolated from the roots of Paeonia lactiflora.	2.07	1	0	benzoate ester; beta-D-glucoside; bridged compound; gamma-lactone; monoterpene glycoside; secondary alcohol	neuroprotective agent; plant metabolite
catechin [no description available]	2.05	1	0
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	1.93	1	0
mannans [no description available]	2.01	1	0
nitrogenase Nitrogenase: An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.	1.98	1	0
4'-geranyloxyferulic acid 4'-geranyloxyferulic acid: a colon cancer chemopreventive agent isolated from grapefruit skin; structure in first source	2.45	2	0
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	2.07	1	0
feruloyl-coa feruloyl-CoA(4-) : An acyl-CoA(4-) that is the tetraanion of feruloyl-CoA arising from deprotonation of the phosphate and diphosphate OH groups.. trans-feruloyl-CoA(4-) : An acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of 3-trans-feruloyl-CoA. Major structure at pH 7.3.	2	1	0	feruloyl-CoA(4-)
piperidines Piperidines: A family of hexahydropyridines.	2.66	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.	2.13	1	0
mauritianin mauritianin: from Chenopodium quinoa	2.06	1	0
inotodiol inotodiol: structure in first source	2.1	1	0
typhaneoside typhaneoside: isolated from pollen of Typha angustfolia L. (puhuang); structure given in first source	2.49	2	0	flavonoids; glycoside
hydroxocobalamin Hydroxocobalamin: Injectable form of VITAMIN B 12 that has been used therapeutically to treat VITAMIN B 12 DEFICIENCY.	2	1	0
peoniflorin [no description available]	2.07	1	0
eurycomanone [no description available]	2.1	1	0	cyclic ether; delta-lactone; enone; organic heteropentacyclic compound; pentol; quassinoid; secondary alcohol; secondary alpha-hydroxy ketone; tertiary alcohol	antimalarial; antineoplastic agent; metabolite
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.	2.02	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	8.92	12	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening 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.	2.13	1	0
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	1.99	1	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.	5.04	10	1	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.	3.13	5	0	benzenes; hydroxycoumarin; methyl ketone
citrinin Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.	2.05	1	0
ellagitannin ellagitannin: structure; precoxin A/ praecoxin A is a purified ellagitannin. ellagitannin : A form of hydrolysable tannin produced from ellagic acid. Ellagitannins are glucosides which are readily hydrolysed by water to regenerate ellagic acid when the plants are eaten.	3.14	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.08	1	0
nephrin nephrin: gene nephrin is mutated in congenital nephrotic syndrome; amino acid sequence in first source; GenBank F19541; RefSeq NM_019459 (mouse), NM_004646 (human), NM_022628 (rat)	2.13	1	0
peoniflorin peoniflorin: from Radix and of Paeonia suffruticosa	2.48	2	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.	2.7	3	0
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.13	1	0
kutkin kutkin: alcoholic extract of the root and rrhizome of Picrorhiza kurrooa; has heptatoprotective activity; contains picroside I, kutkoside, and a small amount of other minor glycosides of P. kurrooa	7.17	69	0
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.63	2	0
exudates Malaysia: A parliamentary democracy with a constitutional monarch in southeast Asia, consisting of 11 states (West Malaysia) on the Malay Peninsula and two states (East Malaysia) on the island of BORNEO. It is also called the Federation of Malaysia. Its capital is Kuala Lumpur. Before 1963 it was the Union of Malaya. It reorganized in 1948 as the Federation of Malaya, becoming independent from British Malaya in 1957 and becoming Malaysia in 1963 as a federation of Malaya, Sabah, Sarawak, and Singapore (which seceded in 1965). The form Malay- probably derives from the Tamil malay, mountain, with reference to its geography. (From Webster's New Geographical Dictionary, 1988, p715 & Room, Brewer's Dictionary of Names, 1992, p329)	2.44	2	0
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	1.99	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.31	1	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.41	2	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
syringaldazine syringaldazine: used for detection of laccase in sporophores of wood rotting fungi; structure	2.08	1	0
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.	2.94	4	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
5,6,7,8-tetrahydrofolic acid 5,6,7,8-tetrahydrofolic acid: RN given refers to (DL)-isomer	2.91	4	0	tetrahydrofolic acid
salicylaldehyde thiosemicarbazone salicylaldehyde thiosemicarbazone: structure given in first source	2.03	1	0
eye [no description available]	2.37	2	0
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.13	1	0
carbidopa Carbidopa: An inhibitor of DOPA DECARBOXYLASE that prevents conversion of LEVODOPA to dopamine. It is used in PARKINSON DISEASE to reduce peripheral adverse effects of LEVODOPA. It has no anti-parkinson activity by itself.. carbidopa : The hydrate of 3-(3,4-dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa.	2.31	1	0
picroside ii picroside II: RN given for (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6abeta))-isomer; structure in first source	2.51	2	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	7.44	2	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	2.44	2	0
antimony sodium gluconate Antimony Sodium Gluconate: Antimony complex where the metal may exist in either the pentavalent or trivalent states. The pentavalent gluconate is used in leishmaniasis. The trivalent gluconate is most frequently used in schistosomiasis.	1.99	1	0

Condition	Relationship Strength	Studies	Trials
Cancer of Lung [description not available]	3.2	5	0
Papilloma, Squamous Cell [description not available]	2.41	2	0
Cancer of Skin [description not available]	2	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	3.2	5	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.41	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	2	1	0
Innate Inflammatory Response [description not available]	6.76	20	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.	6.76	20	1
Complications of Diabetes Mellitus [description not available]	2.04	1	0
Cataract, Membranous [description not available]	2.04	1	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	2.04	1	0
Endotoxin Shock [description not available]	2.05	1	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	2.05	1	0
B16 Melanoma [description not available]	2.78	3	0
Benign Neoplasms [description not available]	2.43	2	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.	2.43	2	0
Blood Pressure, High [description not available]	3.95	12	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.	8.95	12	0
Angiogenesis, Pathologic [description not available]	2.53	2	0
Plasmodium falciparum Malaria [description not available]	2.1	1	0
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.1	1	0
Alloxan Diabetes [description not available]	2.87	3	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	2.11	1	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	2.11	1	0
Basophilic Leukemia, Acute [description not available]	2.13	1	0
Leukemia, Basophilic, Acute A rare acute myeloid leukemia in which the primary differentiation is to BASOPHILS. It is characterized by an extreme increase of immature basophilic granulated cells in the bone marrow and blood. Mature basophils are usually sparse.	2.13	1	0
Degenerative Diseases, Central Nervous System [description not available]	4.7	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.	4.7	3	0
Cancer of Colon [description not available]	2.31	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.31	1	0
Liver Dysfunction [description not available]	5.08	10	0
Injury, Ischemia-Reperfusion [description not available]	3.16	5	0
Liver Diseases Pathological processes of the LIVER.	5.08	10	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	3.16	5	0
Diabetic Glomerulosclerosis [description not available]	2.41	1	0
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.41	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.62	23	0
Aura [description not available]	2.41	1	0
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	2.41	1	0
Idiopathic Parkinson Disease [description not available]	2.76	2	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	8.68	10	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)	2.76	2	0
Breast Cancer [description not available]	2.41	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.41	1	0
Diabetes Mellitus, Adult-Onset [description not available]	2.96	3	0
Insulin Sensitivity [description not available]	2.59	2	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.	2.96	3	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	7.59	2	0
Sterility, Male [description not available]	2.41	1	0
Rodent Diseases Diseases of rodents of the order RODENTIA. This term includes diseases of Sciuridae (squirrels), Geomyidae (gophers), Heteromyidae (pouched mice), Castoridae (beavers), Cricetidae (rats and mice), Muridae (Old World rats and mice), Erethizontidae (porcupines), and Caviidae (guinea pigs).	2.54	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.	2.41	1	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.	7.76	2	0
Carcinoma, Anaplastic [description not available]	2.59	2	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	7.59	2	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	9.48	4	0
Akinetic-Rigid Variant of Huntington Disease [description not available]	2.41	1	0
Huntington Disease A familial disorder inherited as an autosomal dominant trait and characterized by the onset of progressive CHOREA and DEMENTIA in the fourth or fifth decade of life. Common initial manifestations include paranoia; poor impulse control; DEPRESSION; HALLUCINATIONS; and DELUSIONS. Eventually intellectual impairment; loss of fine motor control; ATHETOSIS; and diffuse chorea involving axial and limb musculature develops, leading to a vegetative state within 10-15 years of disease onset. The juvenile variant has a more fulminant course including SEIZURES; ATAXIA; dementia; and chorea. (From Adams et al., Principles of Neurology, 6th ed, pp1060-4)	2.41	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.71	3	0
Cirrhosis [description not available]	2.6	1	0
Cardiac Failure [description not available]	2.6	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.6	1	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.6	1	0
Autism Spectrum Disorder Wide continuum of associated cognitive and neurobehavioral disorders, including, but not limited to, three core-defining features: impairments in socialization, impairments in verbal and nonverbal communication, and restricted and repetitive patterns of behaviors. (from DSM-V)	2.6	1	0
Autism [description not available]	2.6	1	0
Autistic Disorder A disorder beginning in childhood. It is marked by the presence of markedly abnormal or impaired development in social interaction and communication and a markedly restricted repertoire of activity and interest. Manifestations of the disorder vary greatly depending on the developmental level and chronological age of the individual. (DSM-V)	2.6	1	0
Cardiac Toxicity [description not available]	2.6	1	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.6	1	0
Cirrhosis, Liver [description not available]	2.73	3	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.73	3	0
Adenoma, Prostatic [description not available]	2.6	1	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	7.6	1	0
E coli Infections [description not available]	2.25	1	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.25	1	0
Urinary Tract Infections Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.	2.25	1	0
Atherogenesis [description not available]	2.63	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.	2.63	2	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	2.25	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.	2.25	1	0
Encephalopathy, Toxic [description not available]	2.25	1	0
Cardiac Remodeling, Ventricular [description not available]	2.25	1	0
Arthritis, Degenerative [description not available]	2.63	2	0
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.63	2	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.58	8	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).	2.89	3	0
Infections, Yersinia [description not available]	2.25	1	0
Astrocytosis [description not available]	2.25	1	0
Compensatory Hyperinsulinemia A GLUCOSE-induced HYPERINSULINEMIA, a marker of insulin-resistant state. It is a mechanism to compensate for reduced sensitivity to insulin.	2.58	2	0
Hyperinsulinism A syndrome with excessively high INSULIN levels in the BLOOD. It may cause HYPOGLYCEMIA. Etiology of hyperinsulinism varies, including hypersecretion of a beta cell tumor (INSULINOMA); autoantibodies against insulin (INSULIN ANTIBODIES); defective insulin receptor (INSULIN RESISTANCE); or overuse of exogenous insulin or HYPOGLYCEMIC AGENTS.	2.58	2	0
Age-Related Memory Disorders [description not available]	2.63	2	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	2.63	2	0
Anochlesia [description not available]	2.31	1	0
Muscle Disorders [description not available]	2.31	1	0
Muscular Diseases Acquired, familial, and congenital disorders of SKELETAL MUSCLE and SMOOTH MUSCLE.	2.31	1	0
Cancer of Liver [description not available]	2.31	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.31	1	0
Cerebral Ischemia [description not available]	8.24	5	0
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	3.24	5	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.31	1	0
Fatty Liver, Nonalcoholic [description not available]	3.23	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	8.23	1	0
Malignant Melanoma [description not available]	2.31	1	0
Metastase [description not available]	2.45	2	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.31	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.45	2	0
Carotid Artery Narrowing [description not available]	2.15	1	0
Carotid Stenosis Narrowing or stricture of any part of the CAROTID ARTERIES, most often due to atherosclerotic plaque formation. Ulcerations may form in atherosclerotic plaques and induce THROMBUS formation. Platelet or cholesterol emboli may arise from stenotic carotid lesions and induce a TRANSIENT ISCHEMIC ATTACK; CEREBROVASCULAR ACCIDENT; or temporary blindness (AMAUROSIS FUGAX). (From Adams et al., Principles of Neurology, 6th ed, pp 822-3)	2.15	1	0
Arterial Diseases, Carotid [description not available]	2.17	1	0
Brain Vascular Disorders [description not available]	2.58	2	0
Active Hyperemia [description not available]	2.37	2	0
Carotid Artery Diseases Pathological conditions involving the CAROTID ARTERIES, including the common, internal, and external carotid arteries. ATHEROSCLEROSIS and TRAUMA are relatively frequent causes of carotid artery pathology.	2.17	1	0
Cerebrovascular Disorders A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.	2.58	2	0
Hyperemia The presence of an increased amount of blood in a body part or an organ leading to congestion or engorgement of blood vessels. Hyperemia can be due to increase of blood flow into the area (active or arterial), or due to obstruction of outflow of blood from the area (passive or venous).	7.37	2	0
Koch's Disease [description not available]	2.37	2	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	7.37	2	0
Acute Confusional Senile Dementia [description not available]	2.17	1	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)	2.17	1	0
Disease Resistance The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.	2.17	1	0
Asthma, Bronchial [description not available]	2.46	2	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).	7.46	2	0
Focal Segmental Glomerulosclerosis [description not available]	2.17	1	0
Glomerulosclerosis, Focal Segmental A clinicopathological syndrome or diagnostic term for a type of glomerular injury that has multiple causes, primary or secondary. Clinical features include PROTEINURIA, reduced GLOMERULAR FILTRATION RATE, and EDEMA. Kidney biopsy initially indicates focal segmental glomerular consolidation (hyalinosis) or scarring which can progress to globally sclerotic glomeruli leading to eventual KIDNEY FAILURE.	2.17	1	0
Clinically Isolated CNS Demyelinating Syndrome [description not available]	2.21	1	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.21	1	0
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	2.21	1	0
Cognitive Decline [description not available]	2.17	1	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.17	1	0
Pericementitis [description not available]	2.57	2	0
Alveolar Bone Atrophy [description not available]	2.21	1	0
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	2.57	2	0
Age-Related Osteoporosis [description not available]	2.21	1	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.21	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.21	1	0
Menstruation, Painful [description not available]	2.08	1	0
Dysmenorrhea Painful menstruation.	2.08	1	0
Muscular Weakness [description not available]	2.1	1	0
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.1	1	0
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	2.1	1	0
Muscle Weakness A vague complaint of debility, fatigue, or exhaustion attributable to weakness of various muscles. The weakness can be characterized as subacute or chronic, often progressive, and is a manifestation of many muscle and neuromuscular diseases. (From Wyngaarden et al., Cecil Textbook of Medicine, 19th ed, p2251)	2.1	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.	2.1	1	0
Low Bone Density [description not available]	2.1	1	0
Bone Diseases, Metabolic Diseases that affect the METABOLIC PROCESSES of BONE TISSUE.	2.1	1	0
Apoplexy [description not available]	2.8	3	0
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	2.8	3	0
Lung Injury, Acute [description not available]	2.1	1	0
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	2.1	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.52	2	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	7.52	2	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.03	1	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.44	2	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.11	1	0
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.11	1	0
Cardiovascular Stroke [description not available]	3.02	4	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	3.02	4	0
Cancer of Ovary [description not available]	2.11	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.	2.11	1	0
Anasarca [description not available]	3.14	5	0
Allodynia [description not available]	2.11	1	0
Ache [description not available]	3.38	7	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	3.14	5	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	8.38	7	0
Gingivitis Inflammation of gum tissue (GINGIVA) without loss of connective tissue.	2.13	1	0
Pulmonary Arterial Remodeling [description not available]	2.11	1	0
Injury, Myocardial Reperfusion [description not available]	2.52	2	0
Blood Clot [description not available]	2.11	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.11	1	0
Hyperlipemia [description not available]	3	4	0
Hyperlipidemias Conditions with excess LIPIDS in the blood.	3	4	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	3.51	1	1
Chronic Illness [description not available]	2.13	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.13	1	0
Alopecia Cicatrisata [description not available]	2.13	1	0
Alopecia Absence of hair from areas where it is normally present.	2.13	1	0
Bright Disease A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.	2.13	1	0
Hypersensitivity, Type III [description not available]	2.13	1	0
Glomerulonephritis Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.	7.13	1	0
Chromosome-Defective Micronuclei [description not available]	2.15	1	0
Eczema, Atopic [description not available]	2.13	1	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.13	1	0
Anaphylactic Reaction [description not available]	2.15	1	0
Allergic Reaction [description not available]	2.15	1	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	2.15	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.15	1	0
Infections, Plasmodium [description not available]	3.24	6	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.	3.24	6	0
HbS Disease [description not available]	2.44	2	0
Anemia, Sickle Cell A disease characterized by chronic hemolytic anemia, episodic painful crises, and pathologic involvement of many organs. It is the clinical expression of homozygosity for hemoglobin S.	2.44	2	0
Disease Exacerbation [description not available]	2.04	1	0
Di Guglielmo Disease [description not available]	2.41	2	0
Experimental Leukemia [description not available]	2.04	1	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.41	2	0
Acute Liver Injury, Drug-Induced [description not available]	3.87	12	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.	3.87	12	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.51	8	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	2.42	2	0
Chemical and Drug Induced Liver Injury, Chronic Liver disease lasting six months or more, caused by an adverse effect of a drug or chemical. The adverse effect may be caused by drugs, drug metabolites, chemicals from the environment, or an idiosyncratic response.	2.05	1	0
Black Fever [description not available]	3.27	6	0
Leishmaniasis, Visceral A chronic disease caused by LEISHMANIA DONOVANI and transmitted by the bite of several sandflies of the genera Phlebotomus and Lutzomyia. It is commonly characterized by fever, chills, vomiting, anemia, hepatosplenomegaly, leukopenia, hypergammaglobulinemia, emaciation, and an earth-gray color of the skin. The disease is classified into three main types according to geographic distribution: Indian, Mediterranean (or infantile), and African.	3.27	6	0
Colitis Gravis [description not available]	2.05	1	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.05	1	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.	1.92	1	0
Frigidity [description not available]	2.06	1	0
Sexual Dysfunctions, Psychological Disturbances in sexual desire and the psychophysiologic changes that characterize the sexual response cycle and cause marked distress and interpersonal difficulty. (APA, DSM-IV, 1994)	2.06	1	0
Extravascular Hemolysis [description not available]	2.73	3	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.73	3	0
Elevated Cholesterol [description not available]	2.39	2	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.39	2	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.	2.07	1	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	2.07	1	0
Bleeding [description not available]	2.01	1	0
Hemorrhage Bleeding or escape of blood from a vessel.	2.01	1	0
Experimental Hepatoma [description not available]	2.41	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.01	1	0
Histoplasma capsulatum Infection [description not available]	3.18	6	0
Diseases of Pharynx [description not available]	1.93	1	0
Laryngeal Diseases Pathological processes involving any part of the LARYNX which coordinates many functions such as voice production, breathing, swallowing, and coughing.	1.93	1	0
Histoplasmosis Infection resulting from exposure to the fungus HISTOPLASMA. It is worldwide in distribution and particularly common in the central and eastern states, especially areas around the Ohio and Mississippi River valleys.	3.18	6	0
Dermatoses [description not available]	1.93	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	1.93	1	0
Asystole [description not available]	1.93	1	0
Coccidioides immitis Infection [description not available]	2.84	4	0
Coccidioidomycosis Infection with a fungus of the genus COCCIDIOIDES, endemic to the SOUTHWESTERN UNITED STATES. It is sometimes called valley fever but should not be confused with RIFT VALLEY FEVER. Infection is caused by inhalation of airborne, fungal particles known as arthroconidia, a form of FUNGAL SPORES. A primary form is an acute, benign, self-limited respiratory infection. A secondary form is a virulent, severe, chronic, progressive granulomatous disease with systemic involvement. It can be detected by use of COCCIDIOIDIN.	2.84	4	0
Heart Arrest Cessation of heart beat or MYOCARDIAL CONTRACTION. If it is treated within a few minutes, heart arrest can be reversed in most cases to normal cardiac rhythm and effective circulation.	1.93	1	0
C gattii Infection [description not available]	1.93	1	0
Pachymeningitis [description not available]	1.93	1	0
Cerebral Cryptococcosis [description not available]	1.93	1	0
Cryptococcosis Fungal infection caused by genus CRYPTOCOCCUS.	1.93	1	0
Meningitis Inflammation of the coverings of the brain and/or spinal cord, which consist of the PIA MATER; ARACHNOID; and DURA MATER. Infections (viral, bacterial, and fungal) are the most common causes of this condition, but subarachnoid hemorrhage (HEMORRHAGES, SUBARACHNOID), chemical irritation (chemical MENINGITIS), granulomatous conditions, neoplastic conditions (CARCINOMATOUS MENINGITIS), and other inflammatory conditions may produce this syndrome. (From Joynt, Clinical Neurology, 1994, Ch24, p6)	1.93	1	0
Meningitis, Cryptococcal Meningeal inflammation produced by CRYPTOCOCCUS NEOFORMANS, an encapsulated yeast that tends to infect individuals with ACQUIRED IMMUNODEFICIENCY SYNDROME and other immunocompromised states. The organism enters the body through the respiratory tract, but symptomatic infections are usually limited to the lungs and nervous system. The organism may also produce parenchymal brain lesions (torulomas). Clinically, the course is subacute and may feature HEADACHE; NAUSEA; PHOTOPHOBIA; focal neurologic deficits; SEIZURES; cranial neuropathies; and HYDROCEPHALUS. (From Adams et al., Principles of Neurology, 6th ed, pp721-2)	1.93	1	0
Actinomycetoma [description not available]	1.93	1	0
Mycetoma A chronic progressive subcutaneous infection caused by species of fungi (eumycetoma), or actinomycetes (actinomycetoma). It is characterized by tumefaction, abscesses, and tumor-like granules representing microcolonies of pathogens, such as MADURELLA fungi and bacteria ACTINOMYCETES, with different grain colors.	1.93	1	0
Erythema Redness of the skin produced by congestion of the capillaries. This condition may result from a variety of disease processes.	2.33	2	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.	2.33	2	0
Disease, Pulmonary [description not available]	1.93	1	0
Pleural Diseases Diseases involving the PLEURA.	1.93	1	0
Lung Diseases Pathological processes involving any part of the LUNG.	1.93	1	0
Behavior Disorders [description not available]	2.62	3	0
Amentia [description not available]	2.33	2	0
Psychoses [description not available]	2.33	2	0
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	2.62	3	0
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	2.33	2	0
Psychotic Disorders Disorders in which there is a loss of ego boundaries or a gross impairment in reality testing with delusions or prominent hallucinations. (From DSM-IV, 1994)	2.33	2	0
Diseases, Peripheral Vascular [description not available]	1.93	1	0
Vascular Diseases Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.	1.93	1	0
Peripheral Vascular Diseases Pathological processes involving any one of the BLOOD VESSELS in the vasculature outside the HEART.	1.93	1	0
Bronchitis Inflammation of the large airways in the lung including any part of the BRONCHI, from the PRIMARY BRONCHI to the TERTIARY BRONCHI.	1.93	1	0
Back Ache [description not available]	1.93	1	0
Low Back Ache [description not available]	1.93	1	0
Back Pain Acute or chronic pain located in the posterior regions of the THORAX; LUMBOSACRAL REGION; or the adjacent regions.	1.93	1	0
Low Back Pain Acute or chronic pain in the lumbar or sacral regions, which may be associated with musculo-ligamentous SPRAINS AND STRAINS; INTERVERTEBRAL DISK DISPLACEMENT; and other conditions.	1.93	1	0
Anoxemia [description not available]	2.36	2	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.36	2	0
Absence Seizure [description not available]	1.93	1	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	1.93	1	0
Pheochromocytoma, Extra-Adrenal [description not available]	2.35	2	0
Pheochromocytoma A usually benign, well-encapsulated, lobular, vascular tumor of chromaffin tissue of the ADRENAL MEDULLA or sympathetic paraganglia. The cardinal symptom, reflecting the increased secretion of EPINEPHRINE and NOREPINEPHRINE, is HYPERTENSION, which may be persistent or intermittent. During severe attacks, there may be HEADACHE; SWEATING, palpitation, apprehension, TREMOR; PALLOR or FLUSHING of the face, NAUSEA and VOMITING, pain in the CHEST and ABDOMEN, and paresthesias of the extremities. The incidence of malignancy is as low as 5% but the pathologic distinction between benign and malignant pheochromocytomas is not clear. (Dorland, 27th ed; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1298)	7.35	2	0
Acne [description not available]	1.93	1	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.	1.93	1	0
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	2.02	1	0
Abscess, Amebic, Hepatic [description not available]	2.02	1	0
Bladder Diseases [description not available]	2.94	1	0
Injuries, Spinal Cord [description not available]	2.94	1	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.94	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.03	1	0
Liver Steatosis [description not available]	2.03	1	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.03	1	0
Testicular Diseases Pathological processes of the TESTIS.	2.04	1	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.04	1	0
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.04	1	0
Dystonia An attitude or posture due to the co-contraction of agonists and antagonist muscles in one region of the body. It most often affects the large axial muscles of the trunk and limb girdles. Conditions which feature persistent or recurrent episodes of dystonia as a primary manifestation of disease are referred to as DYSTONIC DISORDERS. (Adams et al., Principles of Neurology, 6th ed, p77)	6.96	1	0
Bile Duct Obstruction [description not available]	2.68	3	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	2.68	3	0
Alcoholic Liver Diseases [description not available]	1.99	1	0
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	1.99	1	0
Recrudescence [description not available]	1.99	1	0
Bone Cancer [description not available]	1.99	1	0
Benign Neoplasms, Brain [description not available]	1.99	1	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	1.99	1	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.	1.99	1	0
Minimally Conscious State [description not available]	1.99	1	0
Brain Dead [description not available]	1.99	1	0
Anoxia, Brain [description not available]	1.99	1	0
Bacterial Infections, Gram-Positive [description not available]	1.99	1	0
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	1.99	1	0
Bone Loss, Osteoclastic [description not available]	1.99	1	0
Bronchospasm [description not available]	1.99	1	0
Bronchial Spasm Spasmodic contraction of the smooth muscle of the bronchi.	1.99	1	0
Exertional Heat Illness [description not available]	2	1	0
Bovine Diseases [description not available]	2	1	0
Sarcoma, Epithelioid [description not available]	2	1	0
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	2	1	0
Neoplasms, Nerve Tissue Neoplasms composed of nerve tissue. This concept does not refer to neoplasms located in the nervous system or its component nerves.	1.95	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	3.27	2	0
Rheumatism [description not available]	3.34	1	1
Rheumatic Diseases Disorders of connective tissue, especially the joints and related structures, characterized by inflammation, degeneration, or metabolic derangement.	3.34	1	1
Blood Pressure, Low [description not available]	1.95	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.	1.95	1	0
Mushroom Poisoning Poisoning from ingestion of mushrooms, primarily from, but not restricted to, toxic varieties.	2.38	2	0
Adjuvant Arthritis [description not available]	1.97	1	0
Ear Infection [description not available]	1.97	1	0
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	1.97	1	0
Liver Diseases, Parasitic Liver diseases caused by infections with PARASITES, such as tapeworms (CESTODA) and flukes (TREMATODA).	1.97	1	0
Hepatitis B Virus Infection [description not available]	1.97	1	0
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	1.97	1	0
Bleb [description not available]	1.96	1	0
Basal Ganglia Diseases Diseases of the BASAL GANGLIA including the PUTAMEN; GLOBUS PALLIDUS; claustrum; AMYGDALA; and CAUDATE NUCLEUS. DYSKINESIAS (most notably involuntary movements and alterations of the rate of movement) represent the primary clinical manifestations of these disorders. Common etiologies include CEREBROVASCULAR DISORDERS; NEURODEGENERATIVE DISEASES; and CRANIOCEREBRAL TRAUMA.	2.86	1	0
Cholera Infantum [description not available]	2.86	1	0
Atherosclerotic Parkinsonism [description not available]	2.86	1	0
Psychoses, Drug [description not available]	2.86	1	0
Long Sleeper Syndrome [description not available]	2.86	1	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	2.86	1	0
Sleep Wake Disorders Abnormal sleep-wake schedule or pattern associated with the CIRCADIAN RHYTHM which affect the length, timing, and/or rigidity of the sleep-wake cycle relative to the day-night cycle.	2.86	1	0

vanillic acid

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Synonyms (95)

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Research Demand Index: 58.71

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