indole profile

ID Source	ID
PubMed CID	798
CHEMBL ID	15844
CHEBI ID	16881
SCHEMBL ID	698
SCHEMBL ID	1921769
SCHEMBL ID	940818
SCHEMBL ID	9559244
MeSH ID	M0096122

Synonym
BIDD:GT0304
wln: t56 bmj
nsc-1964
ketole
nsc1964
1h-indole
benzopyrrole
indol
1-benzazole
1-azaindene
CHEBI:16881 ,
einecs 204-420-7
1-benzo(b)pyrrole
indole (natural)
nsc 1964
ai3-01540
indol [german]
IND ,
indole benzo-pyrrole
inchi=1/c8h7n/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9
ccris 4421
epa pesticide chemical code 025000
2,3-benzopyrole
benzo[b]pyrrole
indole (8ci)
fema no. 2593
1h-indole (9ci)
hsdb 599
caswell no. 498b
120-72-9
indole ,
C00463
2,3-benzopyrrole
indole, >=99%, fg
indole, >=99%
indole, analytical standard
DB04532
indole, 98%
NCGC00167539-01
indole (white flake)
I-0810
I-0800
bdbm50094702
indole, 7
BMSE000097
CHEMBL15844 ,
I0021
AKOS000119629
NCGC00167539-02
NCGC00256348-01
tox21_302937
dtxsid0020737 ,
dtxcid40737
cas-120-72-9
tox21_112536
NCGC00259226-01
tox21_201677
STL163380
BBL011739
8724fjw4m5 ,
unii-8724fjw4m5
BP-10563
FT-0627211
indolum [hpus]
indole [usp-rs]
indole [mi]
indole [hsdb]
indole [fcc]
indole [fhfi]
indolum
185L
S6358
SCHEMBL698
NCGC00167539-03
tox21_112536_1
CG-0501
SCHEMBL1921769
1-h-indole
benzazole
SCHEMBL940818
SCHEMBL9559244
STR01201
1h-benzo[b]pyrrole
mfcd00005607
F2190-0647
CS-W001132
SR-01000944736-1
sr-01000944736
indole, puriss., >=98.5% (gc)
Z57833933
Q319541
HY-W001132
indole 100 microg/ml in acetonitrile
BCP27232
AMY3411
mono-indole
AT36838
82451-55-6
EN300-18285
indole, 3-benzopyrrole, 1-benzazole
indole (usp-rs)

Excerpt	Reference	Relevance
"Indole signaling is an important cross-species communication pathway in the mammalian gut. "	( Dynamics of transcription-translation coordination tune bacterial indole signaling. Ji, H; Wang, T; Wang, TL; Xing, XH; Zhang, C; Zheng, X, 2020)	2.24
"Indole is a microbiota metabolite that exerts anti-inflammatory responses. "	( Indole Alleviates Diet-Induced Hepatic Steatosis and Inflammation in a Manner Involving Myeloid Cell 6-Phosphofructo-2-Kinase/Fructose-2,6-Biphosphatase 3. Alpini, G; Athrey, G; Botchlett, R; Chen, L; Francis, H; Glaser, S; Hu, J; Li, H; Li, Q; Ma, L; Matthews, D; Meng, F; Threadgill, DW; Wu, C; Xiao, X; Zeng, T; Zheng, J; Zhou, J, 2020)	3.44
"Indole is an intercellular signaling molecule that is produced by oral bacteria other than S."	( Biofilm Formation by Streptococcus mutans is Enhanced by Indole via the Quorum Sensing Pathway. Habe, H; Inaba, T; Nomura, N; Obana, N, 2020)	1.52
"Indole is a molecule of considerable biochemical significance, acting as both an interspecies signal molecule and a building block of biological elements. "	( Indole Biodegradation in Acinetobacter sp. Strain O153: Genetic and Biochemical Characterization. Gasparavičiūtė, R; Meškys, R; Sadauskas, M; Vaitekūnas, J, 2017)	3.34
"Indole is a signaling molecule that increases the antibiotic resistance of bacteria, at least in part, through activation of efflux pumps."	( Characterization and regulation of AcrABR, a RND-type multidrug efflux system, in Agrobacterium tumefaciens C58. Dokpikul, T; Khemthong, S; Mongkolsuk, S; Nuonming, P; Sukchawalit, R, 2018)	1.2
"Indole is a typical nitrogen-containing aromatic pollutant in coking wastewater, and it can be used for the microbial production of indigo, one of the oldest dyestuffs. "	( Performance and Microbial Community Analysis of Bioaugmented Activated Sludge System for Indigo Production from Indole. Dai, C; Li, S; Lian, S; Ma, Q; Qu, Y; Zhang, X; Zhou, J, 2019)	2.17
"Indole is a degradation product of tryptophan that functions as a signaling molecule in many bacteria. "	( Indole Inhibits ToxR Regulon Expression in Bina, JE; Bina, XR; Howard, MF, 2019)	3.4
"Indole is an aromatic molecule with diverse signalling roles."	( Indole Pulse Signalling Regulates the Cytoplasmic pH of E. coli in a Memory-Like Manner. Al Nahas, K; Cama, J; Caño-Muñiz, S; Keyser, UF; Summers, DK; Zarkan, A; Zhu, J, 2019)	2.68
"Indole is a versatile pharmacophore, a privileged scaffold and an outstanding heterocyclic compound with wide ranges of pharmacological activities due to different mechanisms of action. "	( Medicinal chemistry of indole derivatives: Current to future therapeutic prospectives. Kumari, A; Singh, RK, 2019)	2.27
"Indole is a universal signal that regulates various bacterial behaviors, such as biofilm formation and antibiotic resistance. "	( Highly active modulators of indole signaling alter pathogenic behaviors in Gram-negative and Gram-positive bacteria. Eguren, K; Melander, C; Minvielle, MJ, 2013)	2.13
"Indole is an organic compound that is widespread in microbial communities inhabiting diverse habitats, like the soil environment and human intestines. "	( Indole: a signaling molecule or a mere metabolic byproduct that alters bacterial physiology at a high concentration? Kim, J; Park, W, 2015)	3.3
"Indole is a characteristic volatile constituent in oolong tea. "	( Formation of Volatile Tea Constituent Indole During the Oolong Tea Manufacturing Process. Dong, F; Du, B; Fu, X; Gui, J; Mei, X; Watanabe, N; Yang, Z; Ye, T; Zeng, L; Zhen, Y; Zhou, Y, 2016)	2.15
"The indole ring system is an essential part of several tubulin inhibitors identified in the recent years."	( Indole molecules as inhibitors of tubulin polymerization: potential new anticancer agents, an update (2013-2015). Beaman, KD; Patil, R; Patil, SA, 2016)	2.36
"As indole nucleus is a central component of many natural and synthetic molecules with extensive biological activity, this review incorporates a variety of such hybrid compounds with indole moiety as one of the active units, where better therapeutic effect has been successfully achieved, by either simultaneous or sequential action of individual functional pharmacore."	( Multi-Target Directed Indole Based Hybrid Molecules in Cancer Therapy : An Up-To-Date Evidence-Based Review. Kamath, PR; Sunil, D, 2017)	1.28
"Indole is an important signal molecule in intra- or interspecies relationships, regulating a variety of bacterial behaviours such as cell aggregation and stress resistance; however, the regulatory mechanism remains an ongoing area of investigation."	( Poly(A) polymerase I participates in the indole regulatory pathway of Pantoea agglomerans YS19. Feng, Y; Jiang, J; Li, Z; Shen, D; Wu, C; Yu, X, 2017)	1.44
"Indole is an intercellular and interkingdom signalling molecule found in diverse ecological niches. "	( Indole-associated predator-prey interactions between the nematode Caenorhabditis elegans and bacteria. Choi, H; Kim, E; Kim, M; Kim, Y; Kim, YG; Lee, J; Lee, JH, 2017)	3.34
"Indole is a bacterial signalling molecule that blocks E. "	( Indole prevents Escherichia coli cell division by modulating membrane potential. Chimerel, C; Field, CM; Keyser, UF; Piñero-Fernandez, S; Summers, DK, 2012)	3.26
"Indole is a signalling molecule, produced by a number of Gram-positive and Gram-negative bacteria both in nature as well as clinical environments. "	( The bacterial signalling molecule indole attenuates the virulence of the fungal pathogen Candida albicans. Go, GW; Kim, Y; Mylonakis, E; Oh, S, 2012)	2.1
"Indole is an important biological signalling molecule produced by many Gram positive and Gram negative bacterial species, including Escherichia coli. "	( The effect of bacterial signal indole on the electrical properties of lipid membranes. Chimerel, C; Keyser, UF; Murray, AJ; Oldewurtel, ER; Summers, DK, 2013)	2.12
"Indole is an interspecies signal that decreases E. "	( Indole is an inter-species biofilm signal mediated by SdiA. Jayaraman, A; Lee, J; Wood, TK, 2007)	3.23
"Indole-diterpenes are a structurally diverse group of secondary metabolites with a common cyclic diterpene backbone derived from geranylgeranyl diphosphate and an indole group derived from indole-3-glycerol phosphate. "	( The genetic basis for indole-diterpene chemical diversity in filamentous fungi. Nicholson, MJ; Parker, EJ; Saikia, S; Scott, B; Young, C, 2008)	2.1

Excerpt	Reference	Relevance
"Indole signalling has been proposed as a potential target for the development of novel virulence inhibitors to control bacterial infections. "	( Indole analogues decreasing the virulence of Vibrio campbellii towards brine shrimp larvae. Defoirdt, T; Yang, Q; Zhang, S, 2022)	3.61
"Indole derivatives have been the focus of many researchers in the study of pharmaceutical compounds for many years. "	( Synthetic strategies, SAR studies, and computer modeling of indole 2 and 3-carboxamides as the strong enzyme inhibitors: a review. Bahmani, A; Chehardoli, G, 2021)	2.31
"Indole and skatole have been associated with the detection of oviposition sites and animal hosts."	( The evolutionarily conserved indolergic receptors of the non-hematophagous elephant mosquito Toxorhynchites amboinensis. Bohbot, JD; Dekel, A; Yakir, E, 2019)	1.53
"Indole has indiscriminate irritating effect on the respiratory tract: Limir is at Limac (77,8 mg/m3)."	( [Toxicological characteristic of indole as a basis for its hygienic regulation]. Gorokhova, LG; Martynova, NA, )	1.13
"Indole has diverse signalling roles, including modulation of biofilm formation, virulence and stress responses. "	( The indole pulse: a new perspective on indole signalling in Escherichia coli. Cama, J; Gaimster, H; Hernández-Ainsa, S; Keyser, UF; Summers, DK, 2014)	2.4
"Indole has received considerable attention because of its remarkable effects on various biological functions of the microbial communities, for example, biofilm formation, motility, virulence, plasmid stability, and antibiotic resistance."	( Indole: a signaling molecule or a mere metabolic byproduct that alters bacterial physiology at a high concentration? Kim, J; Park, W, 2015)	2.58
"Indole has been used as a tractable model to study the hydration structures of biomolecules as well as the interplay of non-covalent interactions within ion-biomolecule-water complexes, which largely determine their structure and dynamics."	( Influence of hydration on ion-biomolecule interactions: M(+)(indole)(H2O)(n) (M = Na, K; n = 3-6). Ke, H; Lisy, JM, 2015)	1.38
"Indole has been proposed to act as an extracellular signal molecule influencing biofilm formation in a range of bacteria. "	( Indole acts as an extracellular cue regulating gene expression in Vibrio cholerae. Bartlett, DH; Beyhan, S; Mueller, RS; Saini, SG; Yildiz, FH, 2009)	3.24
"Indole has many, diverse roles in bacterial signaling. "	( Indole transport across Escherichia coli membranes. Chimerel, C; Keyser, UF; Piñero-Fernandez, S; Summers, DK, 2011)	3.25
"Indole has recently been implicated in cell-cell signaling and biofilm repression through a putative interaction with the LuxR homologue SdiA."	( Characterization of the induction and cellular role of the BaeSR two-component envelope stress response of Escherichia coli. Leblanc, SK; Oates, CW; Raivio, TL, 2011)	1.09
"Five indole compounds have been isolated from bovine pineal tissue and characterized as 5-methoxytryptophol, N-acetyl-5-methoxytryptamine (melatonin), 5-hydroxytryptophol, 5-methoxyindole-3-acetic acid, and 5-hydroxyindole-3-acetic acid. "	( INDOLE COMPOUNDS: ISOLATION FROM PINEAL TISSUE. FARRELL, G; MCISAAC, WM; TABORSKY, RG; TAYLOR, AN, 1965)	2.2

Excerpt	Reference	Relevance
"Indole signaling plays an important role in bacterial pathogenesis. "	( Indole decreases the virulence of the bivalve model pathogens Vibrio tasmaniensis LGP32 and Vibrio crassostreae J2-9. Defoirdt, T; Eggermont, M; Fu, S; Janssen, CR; Yang, Q; Zhang, S, 2022)	3.61
"Indole at lower doses increased PBP and PBF."	( Colonic indole, gut bacteria metabolite of tryptophan, increases portal blood pressure in rats. Huc, T; Konop, M; Onyszkiewicz, M; Podsadni, P; Szczepańska, A; Turło, J; Ufnal, M, 2018)	1.64
"Indole level was lower (P<0.05) in the adipose tissue of T30 than C pigs with intermediate levels in T15."	( Hydrolysable tannin-based diet rich in gallotannins has a minimal impact on pig performance but significantly reduces salivary and bulbourethral gland size. Ampuero-Kragten, S; Bee, G; Čandek-Potokar, M; Litten-Brown, J; Mueller-Harvey, I; Salminen, JP; Silacci, P; Wealleans, AL, 2017)	1.18

Excerpt	Reference	Relevance
"Azaindole-1 treatment resulted in a decreased immunoreactivity for phospho-myosin phosphatase target subunit 1 and proliferating cell nuclear antigen in pulmonary vessels of MCT-injected rats, suggesting an impaired ROCK activity and reduced proliferating cells."	( Therapeutic efficacy of azaindole-1 in experimental pulmonary hypertension. Dahal, BK; Ghofrani, HA; Grimminger, F; Kast, R; Kosanovic, D; Lai, YJ; Pamarthi, PK; Schermuly, RT; Schirok, H; Seeger, W; Stasch, JP; Sydykov, A; Weissmann, N, 2010)	1.17

Excerpt	Reference	Relevance
"Many nitrogen-heterocyclic compounds (NHCs) are toxic and recalcitrant contaminants that need to be degraded by advanced oxidation processes."	( Toxicity change patterns and its mechanism during the degradation of nitrogen-heterocyclic compounds by O(3)/UV. Huang, X; Wang, XM, 2007)	0.34
" It represents a practical and safe cyanation method."	( The palladium-catalyzed cyanation of indole C-H bonds with the combination of NH4HCO3 and DMSO as a safe cyanide source. Chen, F; Chen, J; Cheng, J; Ren, X, 2011)	0.64
"High concentrations of indole are known to be toxic to cells due to perturbations in membrane potential."	( Indole toxicity involves the inhibition of adenosine triphosphate production and protein folding in Pseudomonas putida. Heo, A; Hong, H; Kim, J; Park, W, 2013)	2.14

Excerpt	Reference	Relevance
" Since tetrahydro-β-carbolines and β-carbolines target receptors, ion channels and neuronal membranes which are common to anesthetic agents, we propose a hypothesis that they may pharmacodynamically interact at GABAA receptors, NMDA receptors, voltage-gated Na(+) channels and membrane lipid bilayers to attenuate anesthetics-induced positive allosteric GABAA receptor modulation, NMDA receptor antagonism, ion channel blockade and neuronal membrane modification, thereby affecting anesthetic efficacy."	( Anesthetic effects changeable in habitual drinkers: Mechanistic drug interactions with neuro-active indoleamine-aldehyde condensation products associated with alcoholic beverage consumption. Tsuchiya, H, 2016)	0.65

Excerpt	Reference	Relevance
" Agonistic 5-HT(1A) receptor activity was confirmed in vivo in the ultrasonic vocalization test, and the results suggest that the introduction of the carboxamide residue leads to better bioavailability than the corresponding methyl ether."	( Indolebutylamines as selective 5-HT(1A) agonists. Bartoszyk, GD; Böttcher, H; Greiner, HE; Heinrich, T; Seyfried, CA; Van Amsterdam, C, 2004)	1.77
" Compound 49 also displayed excellent selectivity over a wide panel of MMPs as well as excellent oral bioavailability (F%>90%) in rat n-in-1 PK studies."	( Potent, selective, orally bioavailable inhibitors of tumor necrosis factor-alpha converting enzyme (TACE): discovery of indole, benzofuran, imidazopyridine and pyrazolopyridine P1' substituents. Anand, R; Christ, DD; Covington, MB; Duan, JJ; Liu, RQ; Lu, Z; Newton, RC; Ott, GR; Qian, M; Trzaskos, J; Vaddi, K, 2008)	0.55
" Compound 18c demonstrates in vivo CB1 antagonist efficacy (CB1 agonist induced hypothermia model) and is orally bioavailable in rat."	( Identification and hit-to-lead optimization of a novel class of CB1 antagonists. Baker, J; Cowley, P; Edwards, D; Ho, KK; Jokiel, P; Letourneau, JJ; McAleer, L; Ohlmeyer, MH; Olson, J; Riviello, CM; Swanson, RN; Ward, N; Webb, ML; Yang, J, 2010)	0.36
" Pharmacokinetic data in dog for representative compounds demonstrated moderate oral bioavailability and reasonable half-lives."	( Azaindole N-methyl hydroxamic acids as HIV-1 integrase inhibitors-II. The impact of physicochemical properties on ADME and PK. Butler, SL; Dalvie, D; DeLisle, D; Dress, KR; Hu, Q; Huang, B; Johnson, TW; Kuehler, JE; Kuki, A; Liu, W; Peng, Q; Plewe, MB; Smith, GL; Solowiej, J; Tanis, SP; Tran, KT; Wang, H; Yang, A; Yin, C; Yu, X; Zhang, J; Zhu, H, 2010)	0.98
" The hexahydropyridoindole scaffold represents a valuable lead with a great deal of knowledge on molecular mechanisms of free radical scavenging, on bioavailability and toxicity."	( Substituted pyridoindoles as biological antioxidants: drug design, chemical synthesis, and biological activity. Kovacikova, L; Majekova, M; Stefek, M, 2015)	1.07
" Hydrophobic substitution such as isopropyl at 1-position of the indole moiety without any substitution at 2-position has an essential role for enhancing bioavailability and therefore for high in vivo efficacy."	( Design and synthesis of novel 2-(indol-5-yl)thiazole derivatives as xanthine oxidase inhibitors. Choi, SP; Jung, CK; Jung, SH; Kim, GT; Kim, TH; Lee, JY; Song, JU, 2015)	0.65
" In this review, we discuss the possible influence of carbohydrates, polyphenols, lipids and proteins colonic fermentation on production, bioavailability and biological activity of metabolites linked to the gut-microbiota-brain axis."	( Current evidence linking diet to gut microbiota and brain development and function. Ceppa, F; Mancini, A; Tuohy, K, 2019)	0.51
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51

Excerpt	Relevance	Reference
" Erythrocyte fragility appeared to increase in both groups at 8 hours after dosing and peaked at 16 hours after dosing."	( Acute hemolytic anemia induced by oral administration of indole in ponies. Bayly, WM; Breeze, RG; Counts, DF; Laegreid, WW; Paradis, MR, 1991)	0.53
" Steer 1 was dosed twice resulting in a total of 45 absorption measurements."	( Net absorption of 3-methylindole and indole in cattle after oral administration of L-tryptophan. Breeze, RG; Hammond, AC; Huntington, GB, 1983)	0.57
" The compounds 3-methylindole and indole-3-acetic acid were chosen as representative of indole derivatives in a dose-response study using purified MPO."	( Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid. Brunetti, IL; Faria-Oliveira, OM; Fonseca, LM; Paino, IM; Ximenes, VF, 2005)	2.08
"080 μM), and afforded tumor regression when dosed (200 mpk SC BID) in an EZH2 dependent tumor xenograft model."	( Discovery, design, and synthesis of indole-based EZH2 inhibitors. Albrecht, BK; Audia, JE; Balasubramanian, S; Campbell, R; Cook, AS; Cummings, RT; Dakin, LA; Duplessis, M; Gagnon, A; Gehling, VS; Good, AC; Harmange, JC; Iyer, P; Lee, C; Nasveschuk, CG; Normant, E; Trojer, P; Vaswani, RG; Zhao, F, 2015)	0.69
" Subsequently, we screened their cytotoxicity via CCK-8 assay in HepG2 cells, a human hepatoma cell line and chose compound 4p that showed the lowest dosage of IC50 to study the antitumor activities to HCC."	( Oral administration of indole substituted dipyrido[2,3-d]pyrimidine derivative exhibits anti-tumor activity via inhibiting AKT and ERK1/2 on hepatocellular carcinoma. Cen, L; Gao, X; Li, F; Wen, R; Yan, H; Yao, H; Zhu, S, 2018)	0.79
"Hormesis is a dose-response relationship phenomenon characterized by low-dose stimulation and high-dose inhibition."	( Multiple-species hormetic phenomena induced by indole: A case study on the toxicity of indole to bacteria, algae and human cells. Gong, R; Huang, S; Lin, Z; Pan, Y; Song, J; Sun, H; Zheng, M, 2019)	0.77
" Investigations using rat urine after oral dosing showed that the metabolic pathways of EPT shifted from in vitro hydroxylation of the alkyl amine group to an increased in vivo hydroxylation of the indole ring with several N-dealkyl metabolites."	( Studies on the In Vitro and In Vivo Metabolic Fate of the New Psychoactive Substance N-Ethyl-N-Propyltryptamine for Analytical Purposes. Eckstein, N; Felske, C; Manier, SK; Meyer, MR; Zapp, J, 2021)	0.81

Role	Description
Escherichia coli metabolite	Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
[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
indole	Either of two isomeric forms comprising a benzene ring fused to a pyrrole ring.
polycyclic heteroarene
[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
Metabolism	1496	1108
Biological oxidations	150	276
Phase I - Functionalization of compounds	69	175
Cytochrome P450 - arranged by substrate type	30	110
Miscellaneous substrates	3	15
Tryptophan Metabolism II	6	23
superpathway of phenylalanine, tyrosine and tryptophan biosynthesis	29	25
DIBOA-glucoside biosynthesis	7	13
indigo biosynthesis	0	8
indole degradation to anthranil and anthranilate	0	12
superpathway of benzoxazinoid glucosides biosynthesis	9	20
indican biosynthesis	0	10
L-tryptophan biosynthesis	13	17
L-tryptophan degradation II (via pyruvate)	2	11
superpathway of benzoxazinoid glucosides biosynthesis	10	20
indican biosynthesis	0	11
indigo biosynthesis	0	9
DIBOA-glucoside biosynthesis	8	13
indole degradation to anthranil and anthranilate	0	15
L-tryptophan biosynthesis	20	27
superpathway of aromatic amino acid biosynthesis	21	84
superpathway of chorismate metabolism	56	186
superpathway of L-tryptophan biosynthesis	16	65
superpathway of phenylalanine, tyrosine and tryptophan biosynthesis	13	36
tryptophan biosynthesis	5	17
IAA biosynthesis I	0	25
superpathway of phenylalanine, tyrosine, and tryptophan biosynthesis	0	38
superpathway of tryptophan biosynthesis	0	30
tryptophan degradation II (via pyruvate)	0	8
superpathway of chorismate	5	76
Tryptophan biosynthesis	2	16
IAA biosynthesis I	0	21

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
hypoxia-inducible factor 1 alpha subunit	Homo sapiens (human)	Potency	5.4062	3.1890	29.8841	59.4836	AID1224846
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	3.8582	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
SMAD family member 2	Homo sapiens (human)	Potency	19.1818	0.1737	34.3047	61.8120	AID1346924
SMAD family member 3	Homo sapiens (human)	Potency	19.1818	0.1737	34.3047	61.8120	AID1346924
GLI family zinc finger 3	Homo sapiens (human)	Potency	6.0137	0.0007	14.5928	83.7951	AID1259369
AR protein	Homo sapiens (human)	Potency	14.8500	0.0002	21.2231	8,912.5098	AID1259243
estrogen receptor 2 (ER beta)	Homo sapiens (human)	Potency	40.2299	0.0006	57.9133	22,387.1992	AID1259377; AID1259378
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	12.1961	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
progesterone receptor	Homo sapiens (human)	Potency	6.7475	0.0004	17.9460	75.1148	AID1346795
cytochrome P450 family 3 subfamily A polypeptide 4	Homo sapiens (human)	Potency	33.7858	0.0123	7.9835	43.2770	AID1645841
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	2.6832	0.0002	14.3764	60.0339	AID720692
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	39.7746	0.0030	41.6115	22,387.1992	AID1159552; AID1159553; AID1159555
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	7.4967	0.0008	17.5051	59.3239	AID1159527; AID1159531
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	2.3411	0.0015	30.6073	15,848.9004	AID1224841; AID1224842; AID1224848; AID1224849; AID1259401
pregnane X nuclear receptor	Homo sapiens (human)	Potency	15.1058	0.0054	28.0263	1,258.9301	AID1346982
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	30.1400	0.0002	29.3054	16,493.5996	AID1259244
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	26.9744	0.0007	23.0674	1,258.9301	AID743085; AID743122
thyrotropin-releasing hormone receptor	Homo sapiens (human)	Potency	38.2744	0.1549	17.8702	43.6557	AID1346891
v-jun sarcoma virus 17 oncogene homolog (avian)	Homo sapiens (human)	Potency	2.4148	0.0578	21.1097	61.2679	AID1159526
Histone H2A.x	Cricetulus griseus (Chinese hamster)	Potency	99.1214	0.0391	47.5451	146.8240	AID1224845
potassium voltage-gated channel subfamily H member 2 isoform d	Homo sapiens (human)	Potency	25.1189	0.0178	9.6374	44.6684	AID588834
thyroid hormone receptor beta isoform 2	Rattus norvegicus (Norway rat)	Potency	20.1217	0.0003	23.4451	159.6830	AID743065; AID743067
Voltage-dependent calcium channel gamma-2 subunit	Mus musculus (house mouse)	Potency	30.1400	0.0015	57.7890	15,848.9004	AID1259244
Glutamate receptor 2	Rattus norvegicus (Norway rat)	Potency	30.1400	0.0015	51.7393	15,848.9004	AID1259244
[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)
Carbonic anhydrase 1	Homo sapiens (human)	Ki	27.4000	0.0000	1.3726	10.0000	AID644084
Carbonic anhydrase 2	Homo sapiens (human)	Ki	32.5000	0.0000	0.7236	9.9200	AID644085
Carbonic anhydrase 4	Homo sapiens (human)	Ki	2.3300	0.0002	1.9720	9.9200	AID644086
Carbonic anhydrase 6	Homo sapiens (human)	Ki	3.6300	0.0001	1.4710	9.9200	AID644087
Carbonic anhydrase 3	Bos taurus (cattle)	Ki	17.6000	0.1130	3.8815	9.7100	AID644088
[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)
Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)	EC50 (µMol)	75.2000	0.0003	3.1662	10.0000	AID1682372
Endolysin	Tequatrovirus T4	Kd	290.0000	3.0000	3.0000	3.0000	AID238119
Integrin beta-2	Homo sapiens (human)	Kd	300.0000	0.0200	0.0200	0.0200	AID99593; AID99595
Intercellular adhesion molecule 1	Homo sapiens (human)	Kd	300.0000	0.0200	0.0200	0.0200	AID99593; AID99595
Integrin alpha-L	Homo sapiens (human)	Kd	300.0000	0.0200	0.0200	0.0200	AID99593; AID99595
Adenosine kinase	Homo sapiens (human)	Kd	3,000.0000	0.0130	1.8368	3.4930	AID220591; AID34005
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
monoatomic ion transport	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
intracellular calcium ion homeostasis	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
cell surface receptor signaling pathway	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to cold	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to xenobiotic stimulus	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to organic substance	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to organic cyclic compound	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
sensory perception of pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
calcium-mediated signaling	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
thermoception	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
protein homotetramerization	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
cellular response to hydrogen peroxide	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
calcium ion transmembrane transport	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
cellular response to organic substance	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 1	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 2	Homo sapiens (human)
angiotensin-activated signaling pathway	Carbonic anhydrase 2	Homo sapiens (human)
regulation of monoatomic anion transport	Carbonic anhydrase 2	Homo sapiens (human)
secretion	Carbonic anhydrase 2	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 2	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of dipeptide transmembrane transport	Carbonic anhydrase 2	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 2	Homo sapiens (human)
carbon dioxide transport	Carbonic anhydrase 2	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 2	Homo sapiens (human)
microglial cell activation	Integrin beta-2	Homo sapiens (human)
receptor-mediated endocytosis	Integrin beta-2	Homo sapiens (human)
phagocytosis, engulfment	Integrin beta-2	Homo sapiens (human)
apoptotic process	Integrin beta-2	Homo sapiens (human)
inflammatory response	Integrin beta-2	Homo sapiens (human)
cell adhesion	Integrin beta-2	Homo sapiens (human)
leukocyte cell-cell adhesion	Integrin beta-2	Homo sapiens (human)
cell-matrix adhesion	Integrin beta-2	Homo sapiens (human)
integrin-mediated signaling pathway	Integrin beta-2	Homo sapiens (human)
cell-cell signaling	Integrin beta-2	Homo sapiens (human)
regulation of cell shape	Integrin beta-2	Homo sapiens (human)
neutrophil chemotaxis	Integrin beta-2	Homo sapiens (human)
receptor internalization	Integrin beta-2	Homo sapiens (human)
positive regulation of superoxide anion generation	Integrin beta-2	Homo sapiens (human)
heterotypic cell-cell adhesion	Integrin beta-2	Homo sapiens (human)
endodermal cell differentiation	Integrin beta-2	Homo sapiens (human)
receptor clustering	Integrin beta-2	Homo sapiens (human)
positive regulation of neutrophil degranulation	Integrin beta-2	Homo sapiens (human)
negative regulation of dopamine metabolic process	Integrin beta-2	Homo sapiens (human)
regulation of peptidyl-tyrosine phosphorylation	Integrin beta-2	Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulus	Integrin beta-2	Homo sapiens (human)
positive regulation of protein targeting to membrane	Integrin beta-2	Homo sapiens (human)
amyloid-beta clearance	Integrin beta-2	Homo sapiens (human)
cell-cell adhesion	Integrin beta-2	Homo sapiens (human)
cell-cell adhesion via plasma-membrane adhesion molecules	Integrin beta-2	Homo sapiens (human)
positive regulation of leukocyte adhesion to vascular endothelial cell	Integrin beta-2	Homo sapiens (human)
neutrophil migration	Integrin beta-2	Homo sapiens (human)
positive regulation of prostaglandin-E synthase activity	Integrin beta-2	Homo sapiens (human)
cell adhesion mediated by integrin	Integrin beta-2	Homo sapiens (human)
regulation of leukocyte mediated cytotoxicity	Intercellular adhesion molecule 1	Homo sapiens (human)
T cell activation via T cell receptor contact with antigen bound to MHC molecule on antigen presenting cell	Intercellular adhesion molecule 1	Homo sapiens (human)
T cell antigen processing and presentation	Intercellular adhesion molecule 1	Homo sapiens (human)
positive regulation of cellular extravasation	Intercellular adhesion molecule 1	Homo sapiens (human)
cell adhesion	Intercellular adhesion molecule 1	Homo sapiens (human)
heterophilic cell-cell adhesion via plasma membrane cell adhesion molecules	Intercellular adhesion molecule 1	Homo sapiens (human)
leukocyte cell-cell adhesion	Intercellular adhesion molecule 1	Homo sapiens (human)
membrane to membrane docking	Intercellular adhesion molecule 1	Homo sapiens (human)
cell adhesion mediated by integrin	Intercellular adhesion molecule 1	Homo sapiens (human)
adhesion of symbiont to host	Intercellular adhesion molecule 1	Homo sapiens (human)
symbiont entry into host cell	Intercellular adhesion molecule 1	Homo sapiens (human)
receptor-mediated virion attachment to host cell	Intercellular adhesion molecule 1	Homo sapiens (human)
leukocyte migration	Intercellular adhesion molecule 1	Homo sapiens (human)
establishment of endothelial barrier	Intercellular adhesion molecule 1	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	Intercellular adhesion molecule 1	Homo sapiens (human)
cellular response to glucose stimulus	Intercellular adhesion molecule 1	Homo sapiens (human)
T cell extravasation	Intercellular adhesion molecule 1	Homo sapiens (human)
regulation of ruffle assembly	Intercellular adhesion molecule 1	Homo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway via death domain receptors	Intercellular adhesion molecule 1	Homo sapiens (human)
cellular response to amyloid-beta	Intercellular adhesion molecule 1	Homo sapiens (human)
cellular response to leukemia inhibitory factor	Intercellular adhesion molecule 1	Homo sapiens (human)
negative regulation of endothelial cell apoptotic process	Intercellular adhesion molecule 1	Homo sapiens (human)
regulation of DNA-templated transcription	Trp operon repressor	Escherichia coli K-12
regulation of DNA-templated transcription	Trp operon repressor	Escherichia coli K-12
negative regulation of DNA-templated transcription	Trp operon repressor	Escherichia coli K-12
T cell activation via T cell receptor contact with antigen bound to MHC molecule on antigen presenting cell	Integrin alpha-L	Homo sapiens (human)
phagocytosis	Integrin alpha-L	Homo sapiens (human)
inflammatory response	Integrin alpha-L	Homo sapiens (human)
cell adhesion	Integrin alpha-L	Homo sapiens (human)
heterophilic cell-cell adhesion via plasma membrane cell adhesion molecules	Integrin alpha-L	Homo sapiens (human)
leukocyte cell-cell adhesion	Integrin alpha-L	Homo sapiens (human)
cell-matrix adhesion	Integrin alpha-L	Homo sapiens (human)
signal transduction	Integrin alpha-L	Homo sapiens (human)
integrin-mediated signaling pathway	Integrin alpha-L	Homo sapiens (human)
memory T cell extravasation	Integrin alpha-L	Homo sapiens (human)
receptor clustering	Integrin alpha-L	Homo sapiens (human)
cell-cell adhesion	Integrin alpha-L	Homo sapiens (human)
cell adhesion mediated by integrin	Integrin alpha-L	Homo sapiens (human)
bicarbonate transport	Carbonic anhydrase 4	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 4	Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of bitter taste	Carbonic anhydrase 6	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 6	Homo sapiens (human)
purine ribonucleoside salvage	Adenosine kinase	Homo sapiens (human)
dATP biosynthetic process	Adenosine kinase	Homo sapiens (human)
ribonucleoside monophosphate biosynthetic process	Adenosine kinase	Homo sapiens (human)
GMP salvage	Adenosine kinase	Homo sapiens (human)
AMP salvage	Adenosine kinase	Homo sapiens (human)
dAMP salvage	Adenosine kinase	Homo sapiens (human)
purine nucleobase metabolic process	Adenosine kinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
calcium channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
intracellularly gated calcium channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
identical protein binding	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
temperature-gated cation channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
protein binding	Carbonic anhydrase 1	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 1	Homo sapiens (human)
hydro-lyase activity	Carbonic anhydrase 1	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 2	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
protein binding	Carbonic anhydrase 2	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 2	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
cargo receptor activity	Integrin beta-2	Homo sapiens (human)
amyloid-beta binding	Integrin beta-2	Homo sapiens (human)
complement component C3b binding	Integrin beta-2	Homo sapiens (human)
integrin binding	Integrin beta-2	Homo sapiens (human)
protein binding	Integrin beta-2	Homo sapiens (human)
protein kinase binding	Integrin beta-2	Homo sapiens (human)
ICAM-3 receptor activity	Integrin beta-2	Homo sapiens (human)
heat shock protein binding	Integrin beta-2	Homo sapiens (human)
metal ion binding	Integrin beta-2	Homo sapiens (human)
cell adhesion molecule binding	Integrin beta-2	Homo sapiens (human)
virus receptor activity	Intercellular adhesion molecule 1	Homo sapiens (human)
transmembrane signaling receptor activity	Intercellular adhesion molecule 1	Homo sapiens (human)
integrin binding	Intercellular adhesion molecule 1	Homo sapiens (human)
protein binding	Intercellular adhesion molecule 1	Homo sapiens (human)
signaling receptor activity	Intercellular adhesion molecule 1	Homo sapiens (human)
DNA binding	Trp operon repressor	Escherichia coli K-12
DNA-binding transcription factor activity	Trp operon repressor	Escherichia coli K-12
sequence-specific DNA binding	Trp operon repressor	Escherichia coli K-12
protein binding	Integrin alpha-L	Homo sapiens (human)
ICAM-3 receptor activity	Integrin alpha-L	Homo sapiens (human)
metal ion binding	Integrin alpha-L	Homo sapiens (human)
cell adhesion molecule binding	Integrin alpha-L	Homo sapiens (human)
integrin binding	Integrin alpha-L	Homo sapiens (human)
protein binding	Carbonic anhydrase 4	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 4	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 4	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 6	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 6	Homo sapiens (human)
RNA binding	Adenosine kinase	Homo sapiens (human)
deoxyadenosine kinase activity	Adenosine kinase	Homo sapiens (human)
ATP binding	Adenosine kinase	Homo sapiens (human)
metal ion binding	Adenosine kinase	Homo sapiens (human)
adenosine kinase activity	Adenosine kinase	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 3	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
stereocilium bundle	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
cytosol	Carbonic anhydrase 1	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 1	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
cytosol	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
myelin sheath	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 2	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Integrin beta-2	Homo sapiens (human)
external side of plasma membrane	Integrin beta-2	Homo sapiens (human)
cell surface	Integrin beta-2	Homo sapiens (human)
membrane	Integrin beta-2	Homo sapiens (human)
integrin alphaL-beta2 complex	Integrin beta-2	Homo sapiens (human)
integrin alphaM-beta2 complex	Integrin beta-2	Homo sapiens (human)
integrin alphaX-beta2 complex	Integrin beta-2	Homo sapiens (human)
specific granule membrane	Integrin beta-2	Homo sapiens (human)
plasma membrane raft	Integrin beta-2	Homo sapiens (human)
extracellular exosome	Integrin beta-2	Homo sapiens (human)
tertiary granule membrane	Integrin beta-2	Homo sapiens (human)
ficolin-1-rich granule membrane	Integrin beta-2	Homo sapiens (human)
extracellular vesicle	Integrin beta-2	Homo sapiens (human)
integrin complex	Integrin beta-2	Homo sapiens (human)
receptor complex	Integrin beta-2	Homo sapiens (human)
focal adhesion	Integrin beta-2	Homo sapiens (human)
cell surface	Integrin beta-2	Homo sapiens (human)
immunological synapse	Intercellular adhesion molecule 1	Homo sapiens (human)
extracellular space	Intercellular adhesion molecule 1	Homo sapiens (human)
plasma membrane	Intercellular adhesion molecule 1	Homo sapiens (human)
focal adhesion	Intercellular adhesion molecule 1	Homo sapiens (human)
external side of plasma membrane	Intercellular adhesion molecule 1	Homo sapiens (human)
cell surface	Intercellular adhesion molecule 1	Homo sapiens (human)
membrane	Intercellular adhesion molecule 1	Homo sapiens (human)
membrane raft	Intercellular adhesion molecule 1	Homo sapiens (human)
collagen-containing extracellular matrix	Intercellular adhesion molecule 1	Homo sapiens (human)
extracellular exosome	Intercellular adhesion molecule 1	Homo sapiens (human)
plasma membrane	Intercellular adhesion molecule 1	Homo sapiens (human)
cytoplasm	Trp operon repressor	Escherichia coli K-12
plasma membrane	Glutamate receptor 2	Rattus norvegicus (Norway rat)
plasma membrane	Integrin alpha-L	Homo sapiens (human)
cell surface	Integrin alpha-L	Homo sapiens (human)
membrane	Integrin alpha-L	Homo sapiens (human)
integrin alphaL-beta2 complex	Integrin alpha-L	Homo sapiens (human)
specific granule membrane	Integrin alpha-L	Homo sapiens (human)
extracellular exosome	Integrin alpha-L	Homo sapiens (human)
integrin complex	Integrin alpha-L	Homo sapiens (human)
external side of plasma membrane	Integrin alpha-L	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
rough endoplasmic reticulum	Carbonic anhydrase 4	Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment	Carbonic anhydrase 4	Homo sapiens (human)
Golgi apparatus	Carbonic anhydrase 4	Homo sapiens (human)
trans-Golgi network	Carbonic anhydrase 4	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
external side of plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
cell surface	Carbonic anhydrase 4	Homo sapiens (human)
membrane	Carbonic anhydrase 4	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
transport vesicle membrane	Carbonic anhydrase 4	Homo sapiens (human)
secretory granule membrane	Carbonic anhydrase 4	Homo sapiens (human)
brush border membrane	Carbonic anhydrase 4	Homo sapiens (human)
perinuclear region of cytoplasm	Carbonic anhydrase 4	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 4	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 4	Homo sapiens (human)
extracellular region	Carbonic anhydrase 6	Homo sapiens (human)
extracellular space	Carbonic anhydrase 6	Homo sapiens (human)
cytosol	Carbonic anhydrase 6	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 6	Homo sapiens (human)
extracellular space	Carbonic anhydrase 6	Homo sapiens (human)
nucleoplasm	Adenosine kinase	Homo sapiens (human)
cytosol	Adenosine kinase	Homo sapiens (human)
plasma membrane	Adenosine kinase	Homo sapiens (human)
nucleus	Adenosine kinase	Homo sapiens (human)
cytosol	Adenosine kinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID504749	qHTS profiling for inhibitors of Plasmodium falciparum proliferation	2011	Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043	Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID343398	Octanol-water distribution coefficient, log D at pH 7.4 by shake-flask technique	2008	Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13	Toward prediction of alkane/water partition coefficients.
AID571750	Ratio of EC50 for Hepatitis C virus 796 infected in HuH7 cells to EC50 for Hepatitis C virus 796 harboring NNI P495L mutant site in NS5B infected in HuH7 cells	2008	Antimicrobial agents and chemotherapy, Dec, Volume: 52, Issue:12	1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.
AID475504	Binding affinity to amyloid beta (1 to 42) fibrils by change in fluorescence at 100 uM after 10 mins	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID652685	Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID343680	Hexadecane-water distribution coefficient, log D at pH 7.4 by shake-flask technique	2008	Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13	Toward prediction of alkane/water partition coefficients.
AID1776788	Induction of insulin secretion in rat INS1 cells assessed as increase in PDX-1 expression at 5 uM measured after 24 hrs by western blot assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID571753	Ratio of EC50 for Hepatitis C virus 796 infected in HuH7 cells to EC50 for Hepatitis C virus 796 harboring NNI Y448A mutant site in NS5B infected in HuH7 cells	2008	Antimicrobial agents and chemotherapy, Dec, Volume: 52, Issue:12	1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.
AID1776784	Induction of insulin secretion in rat INS1 cells assessed as increase in phosphorylation of PI3K at 5 uM measured after 24 hrs by western blot assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID1439697	Cytotoxicity against human IN1760 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID1682372	Agonist activity at TRPA1 (unknown origin) by calcium imaging assay	2021	Bioorganic & medicinal chemistry letters, 01-01, Volume: 31	Discovery of natural TRPA1 activators through pharmacophore-based virtual screening and a biological assay.
AID475505	Binding affinity to amyloid beta (1 to 42) oligomers by change in fluorescence at 100 uM after 10 mins	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID1519676	Retention time of compound at pH 7.4 by LC-UV analysis	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID1571459	Antiproliferative activity against human U87MG cells after 72 hrs by sulforhodamine B assay	2018	MedChemComm, Nov-01, Volume: 9, Issue:11	Towards identifying potent new hits for glioblastoma.
AID23714	Partition coefficient (logP)	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography.
AID1092124	Inhibition of immune responses in Spodoptera exigua fifth-instar larvae assessed as inhibition of hemocytic nodulation in response to Escherichia coli challenge by stereomicroscopy	2012	Applied and environmental microbiology, Jun, Volume: 78, Issue:11	Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID1310270	Cytotoxicity against human Hep2 cells after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Aug-08, Volume: 118	Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents.
AID73214	Residual porcine GSK-3-alpha/beta kinase activity with wild-type cytochrome P450 2A6 extract	2004	Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12	Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis.
AID1310269	Cytotoxicity against human HL60 cells after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Aug-08, Volume: 118	Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents.
AID1571463	Antiproliferative activity against human IN1760 cells after 72 hrs by sulforhodamine B assay	2018	MedChemComm, Nov-01, Volume: 9, Issue:11	Towards identifying potent new hits for glioblastoma.
AID1092126	Inhibition of PLA2 in hemocytes of Spodoptera exigua fifth-instar larvae using pyrene-labeled phospholipid substrate by spectrofluorometry	2012	Applied and environmental microbiology, Jun, Volume: 78, Issue:11	Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID1776774	Stimulation of glucose stimulated insulin secretion in rat INS1 cells assessed as glucose stimulation index at 5 uM in presence of glucose measured after 1 hr	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID281482	Inhibition of human intestinal carboxylesterase expressed in sf21 cells up to 100 uM	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID23978	Capacity ratio (log k'w)	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography.
AID288184	Permeability coefficient through artificial membrane in presence of unstirred water layer by PAMPA	2007	Bioorganic & medicinal chemistry, Jun-01, Volume: 15, Issue:11	QSAR study on permeability of hydrophobic compounds with artificial membranes.
AID571752	Ratio of EC50 for Hepatitis C virus 796 infected in HuH7 cells to EC50 for Hepatitis C virus 796 harboring NNI M414Q mutant site in NS5B infected in HuH7 cells	2008	Antimicrobial agents and chemotherapy, Dec, Volume: 52, Issue:12	1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.
AID73213	Residual porcine GSK-3-alpha/beta kinase activity with L240C/N297Q mutant cytochrome P450 2A6 extract	2004	Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12	Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis.
AID1776771	Cytotoxicity against rat INS1 cells assessed as cell viability at 1 to 10 uM measured after 24 hrs by MTT assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID220591	Inhibition of human adenosine kinase	2000	Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25	Design of adenosine kinase inhibitors from the NMR-based screening of fragments.
AID1891831	Lipid-water distribution ratio of the compound	2022	Journal of medicinal chemistry, 05-12, Volume: 65, Issue:9	Development of Azaindole-Based Frameworks as Potential Antiviral Agents and Their Future Perspectives.
AID1776786	Induction of insulin secretion in rat INS1 cells assessed as increase in phosphorylation of AKT at Ser 473 at 5 uM measured after 24 hrs by western blot assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID237685	Lipophilicity determined as logarithm of the partition coefficient in the alkane/water system	2005	Journal of medicinal chemistry, May-05, Volume: 48, Issue:9	Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk).
AID1092125	Inhibition of phenoloxidase activity in hemolymph of Spodoptera exigua fifth-instar larvae using DOPA substrate	2012	Applied and environmental microbiology, Jun, Volume: 78, Issue:11	Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID763542	Antioxidant activity assessed as inhibition of ABTS free radical generation at 17 uM after 20 mins by UV spectrophotometric analysis relative to control	2013	Bioorganic & medicinal chemistry, Aug-01, Volume: 21, Issue:15	Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: synthesis, biological evaluation, and molecular modeling studies.
AID1310272	Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Aug-08, Volume: 118	Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents.
AID644084	Inhibition of human carbonic anhydrase 1 using 4-nitrophenylacetate as substrate after 3 mins using spectrophotometry by Lineweaver-Burk plot analysis	2012	European journal of medicinal chemistry, Mar, Volume: 49	Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI.
AID475508	Inhibition of amyloid beta (1 to 42) aggregation induced by thioflavin after 48 hrs by fluorescence imaging	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID54189	Residual Cyclin-dependent kinase 5-p35nck5a activity with wild-type cytochrome P450 2A6 extract	2004	Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12	Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis.
AID571755	Ratio of EC50 for Hepatitis C virus 796 infected in HuH7 cells to EC50 for Hepatitis C virus 796 harboring NNI C316Y mutant site in NS5B infected in HuH7 cells	2008	Antimicrobial agents and chemotherapy, Dec, Volume: 52, Issue:12	1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.
AID475507	Binding affinity to amyloid beta (1 to 42) oligomers by fluorescence quenching after 30 mins	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID763541	Antioxidant activity assessed as inhibition of ABTS free radical generation at 9 uM after 20 mins by UV spectrophotometric analysis relative to control	2013	Bioorganic & medicinal chemistry, Aug-01, Volume: 21, Issue:15	Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: synthesis, biological evaluation, and molecular modeling studies.
AID281483	Inhibition of human liver CE1 expressed in sf21 cells up to 100 uM	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID281484	Inhibition of rabbit liver carboxylesterase expressed in sf21 cells up to 100 uM	2007	Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8	Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID644085	Inhibition of human carbonic anhydrase 2 using 4-nitrophenylacetate as substrate after 3 mins using spectrophotometry by Lineweaver-Burk plot analysis	2012	European journal of medicinal chemistry, Mar, Volume: 49	Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI.
AID1133966	Antiulcer activity in po dosed albino rat pyloric ligation model assessed as inhibition of gastric secretion administered as single dose 1 to 24 hrs prior to ligation	1977	Journal of medicinal chemistry, Apr, Volume: 20, Issue:4	Experimental antiulcer drugs. 1. Indole-1-alkanamides and pyrrole-1-alkanamides.
AID1571460	Antiproliferative activity against human U251MG cells after 72 hrs by sulforhodamine B assay	2018	MedChemComm, Nov-01, Volume: 9, Issue:11	Towards identifying potent new hits for glioblastoma.
AID1776782	Induction of insulin secretion in rat INS1 cells assessed as increase in phosphorylation of IRS 2 at Ser 731 at 5 uM measured after 24 hrs by western blot assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID1439695	Cytotoxicity against human IN1472 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID1776783	Induction of insulin secretion in rat INS1 cells assessed as increase in IRS-2 expression at 5 uM measured after 24 hrs by western blot assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID288192	Partition coefficient, log P of the compound	2007	Bioorganic & medicinal chemistry, Jun-01, Volume: 15, Issue:11	QSAR study on permeability of hydrophobic compounds with artificial membranes.
AID332912	Antimicrobial activity Propionibacterium acnes ATCC 11827 after 2 days by broth dilution method	1994	Journal of natural products, Jan, Volume: 57, Issue:1	Naturally occurring antiacne agents.
AID1439694	Cytotoxicity against human U251 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID238119	Dissociation constant against T4 lysozyme mutant L99A	2005	Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11	Decoys for docking.
AID19262	Aqueous solubility	2000	Bioorganic & medicinal chemistry letters, Jun-05, Volume: 10, Issue:11	Prediction of drug solubility from Monte Carlo simulations.
AID1571461	Antiproliferative activity against human IN1472 cells after 72 hrs by sulforhodamine B assay	2018	MedChemComm, Nov-01, Volume: 9, Issue:11	Towards identifying potent new hits for glioblastoma.
AID1776773	Stimulation of glucose stimulated insulin secretion in rat INS1 cells assessed as glucose stimulation index at 2.5 uM in presence of glucose measured after 1 hr	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID1891830	Basic dissociation constant, pKa of the compound	2022	Journal of medicinal chemistry, 05-12, Volume: 65, Issue:9	Development of Azaindole-Based Frameworks as Potential Antiviral Agents and Their Future Perspectives.
AID763540	Antioxidant activity assessed as inhibition of ABTS free radical generation at 33 uM after 20 mins by UV spectrophotometric analysis relative to control	2013	Bioorganic & medicinal chemistry, Aug-01, Volume: 21, Issue:15	Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: synthesis, biological evaluation, and molecular modeling studies.
AID23454	Partition coefficient (logP)	1990	Journal of medicinal chemistry, Sep, Volume: 33, Issue:9	Synthesis and in vitro LTD4 antagonist activity of bicyclic and monocyclic cyclopentylurethane and cyclopentylacetamide N-arylsulfonyl amides.
AID571751	Ratio of EC50 for Hepatitis C virus 796 infected in HuH7 cells to EC50 for Hepatitis C virus 796 harboring NNI M423T mutant site in NS5B infected in HuH7 cells	2008	Antimicrobial agents and chemotherapy, Dec, Volume: 52, Issue:12	1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.
AID1439693	Cytotoxicity against human U87 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID571754	Ratio of EC50 for Hepatitis C virus 796 infected in HuH7 cells to EC50 for Hepatitis C virus 796 harboring NNI H95R mutant site in NS5B infected in HuH7 cells	2008	Antimicrobial agents and chemotherapy, Dec, Volume: 52, Issue:12	1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.
AID1064677	Antioxidant activity of the compound assessed as inhibition of ABTS radicals at 33 uM after 20 mins by spectrophotometric analysis	2014	Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3	Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors.
AID236904	Partition coefficient (logP)	2005	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13	Synthesis of selective SRPK-1 inhibitors: novel tricyclic quinoxaline derivatives.
AID203473	Binding constant against bovine serum albumin	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography.
AID1092123	Insecticidal activity against Plutella xylostella (diamondback moth) fourth-instar larvae fed on cabbage leaves soaked in compound solutions measured 48 hr post compound treatment by leaf-dipping method	2012	Applied and environmental microbiology, Jun, Volume: 78, Issue:11	Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID1064674	Antioxidant activity of the compound assessed as inhibition of ABTS radicals after 20 mins by spectrophotometric analysis	2014	Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3	Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors.
AID475506	Binding affinity to amyloid beta (1 to 42) fibrils by fluorescence quenching after 30 mins	2009	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17	A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID1133965	Antiulcer activity in sc dosed albino rat pyloric ligation model assessed as inhibition of gastric secretion administered as single dose 1 to 24 hrs prior to ligation	1977	Journal of medicinal chemistry, Apr, Volume: 20, Issue:4	Experimental antiulcer drugs. 1. Indole-1-alkanamides and pyrrole-1-alkanamides.
AID652686	Cytotoxicity against human SK-N-SH cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID644087	Inhibition of human carbonic anhydrase 6 using 4-nitrophenylacetate as substrate after 3 mins using spectrophotometry by Lineweaver-Burk plot analysis	2012	European journal of medicinal chemistry, Mar, Volume: 49	Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI.
AID652687	Cytotoxicity against human A549 cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID1439696	Cytotoxicity against human IN1528 cells assessed as decrease in cell proliferation after 72 hrs by SRB assay	2017	Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7	Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells.
AID99593	Inhibition of JY-8 cell adhesion via leukocyte function associated antigen 1 (LFA-1) to ICAM-1	2001	Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8	Novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction. 2. Mechanism of inhibition and structure-based improvement of pharmaceutical properties.
AID652688	Cytotoxicity against human MRC5 cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 22, Issue:7	Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity.
AID1776785	Induction of insulin secretion in rat INS1 cells assessed as increase in PI3K expression at 5 uM measured after 24 hrs by western blot assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID1571462	Antiproliferative activity against human IN1528 cells after 72 hrs by sulforhodamine B assay	2018	MedChemComm, Nov-01, Volume: 9, Issue:11	Towards identifying potent new hits for glioblastoma.
AID1682371	Agonist activity at TRPA1 (unknown origin) by calcium imaging assay relative to allyl isothiocyanate	2021	Bioorganic & medicinal chemistry letters, 01-01, Volume: 31	Discovery of natural TRPA1 activators through pharmacophore-based virtual screening and a biological assay.
AID34005	Dissociation constant against adenosine kinase	2004	Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14	Fragment-based drug discovery.
AID1310271	Cytotoxicity against human NCI-H292 cells after 72 hrs by MTT assay	2016	European journal of medicinal chemistry, Aug-08, Volume: 118	Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents.
AID99595	Dissociation constant for Leukocyte function associated antigen 1 (LFA-1)	2004	Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14	Fragment-based drug discovery.
AID1776787	Induction of insulin secretion in rat INS1 cells assessed as increase in AKT expression at 5 uM measured after 24 hrs by western blot assay	2021	Bioorganic & medicinal chemistry letters, 07-01, Volume: 43	Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion.
AID1254103	Binding affinity to rabbit muscle glycogen phosphorylase measured for 0.5 to 4 secs by STD NMR spectrometric analysis	2015	Journal of medicinal chemistry, Nov-12, Volume: 58, Issue:21	Ligand-Orientation Based Fragment Selection in STD NMR Screening.
AID54188	Residual Cyclin-dependent kinase 5-p35nck5a activity with L240C/N297Q mutant cytochrome P450 2A6 extract	2004	Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12	Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis.
AID644086	Inhibition of human carbonic anhydrase 4 using 4-nitrophenylacetate as substrate after 3 mins using spectrophotometry by Lineweaver-Burk plot analysis	2012	European journal of medicinal chemistry, Mar, Volume: 49	Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI.
AID1092122	Potentiation of 1000 ppm Bacillus thuringiensis-induced pathogenicity against Plutella xylostella (diamondback moth) fourth-instar larvae at 10000 ppm measured 48 hr post compound treatment	2012	Applied and environmental microbiology, Jun, Volume: 78, Issue:11	Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID644088	Inhibition of bovine carbonic anhydrase 3 using 4-nitrophenylacetate as substrate after 3 mins using spectrophotometry by Lineweaver-Burk plot analysis	2012	European journal of medicinal chemistry, Mar, Volume: 49	Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI.
AID1519674	Chromatographic hydrophobicity index of compound at 250 uM at pH 7.4 by HPLC analysis	2020	European journal of medicinal chemistry, Jan-01, Volume: 185	Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347094	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425	Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)	2019	The Journal of biological chemistry, 11-15, Volume: 294, Issue:46	Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347098	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347102	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347091	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
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.
AID1347101	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407	qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection	2020	ACS chemical biology, 07-17, Volume: 15, Issue:7	High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347089	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347100	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
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.
AID1347105	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
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.
AID1347107	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424	RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)	2019	The Journal of biological chemistry, 11-15, Volume: 294, Issue:46	Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347090	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1799822	Binding Assay from Article : \\The structural basis for the interaction between L-tryptophan and the Escherichia coli trp aporepressor.\\	1987	The Journal of biological chemistry, Apr-05, Volume: 262, Issue:10	The structural basis for the interaction between L-tryptophan and the Escherichia coli trp aporepressor.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2005	Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11	Decoys for docking.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	484 (25.87)	18.7374
1990's	91 (4.86)	18.2507
2000's	320 (17.10)	29.6817
2010's	766 (40.94)	24.3611
2020's	210 (11.22)	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	8 (0.42%)	5.53%
Reviews	76 (3.97%)	6.00%
Case Studies	5 (0.26%)	4.05%
Observational	0 (0.00%)	0.25%
Other	1,823 (95.35%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	2.41	2	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
ethylene chlorohydrin Ethylene Chlorohydrin: Used as a solvent, in the manufacture of insecticides, and for treating sweet potatoes before planting. May cause nausea, vomiting, pains in head and chest, stupefaction. Irritates mucous membranes and causes kidney and liver degeneration.. chloroethanol : An organochlorine compound that is ethanol substituted by at least one chloro group.	2.03	1	0	chloroethanol	xenobiotic metabolite
3-hydroxyanthranilic acid 3-Hydroxyanthranilic Acid: An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.. 3-hydroxyanthranilic acid : An aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan.. 3-hydroxyanthranilate : A hydroxybenzoate that is the conjugate base of 3-hydroxyanthranilic acid.	2.33	2	0	aminobenzoic acid; monohydroxybenzoic acid	human metabolite; mouse metabolite
3-hydroxybenzaldehyde [no description available]	2.05	1	0	hydroxybenzaldehyde
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.46	2	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.88	4	0	hydroxytryptophan	human metabolite; neurotransmitter
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	1.97	1	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	3.11	5	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	3.21	6	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	2	1	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetoin [no description available]	2.73	3	0	methyl ketone; secondary alpha-hydroxy ketone	metabolite
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	7.69	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]	2.93	4	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.87	11	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.	5.4	20	0	aminobenzoic acid	human metabolite; mouse metabolite
beta-alanine [no description available]	2	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzaldehyde [no description available]	7.96	4	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]	4.26	18	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	2.9	4	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.	2.43	2	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.48	2	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	3.16	5	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.	7.92	4	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
cadaverine [no description available]	2.42	2	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	2.93	4	0	amino-acid anion
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	7.71	3	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
catechol [no description available]	7.9	4	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	5.24	16	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chloroacetic acid chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.	2.02	1	0	chlorocarboxylic acid; haloacetic acid	alkylating agent; herbicide
choline [no description available]	7.46	2	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.35	2	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.	4.91	8	1	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	1.93	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	3.94	12	0	coumarins	fluorescent dye; human metabolite; plant metabolite
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.	2.31	1	0	phenols	flavouring agent; pheromone; plant metabolite
2-cresol 2-cresol: RN given refers to parent cpd. o-cresol : A cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene.	2.75	3	0	cresol	human xenobiotic metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	3.91	12	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.	2.31	1	0	methylcatechol	bacterial xenobiotic metabolite
3-cresol 3-cresol: RN given refers to parent cpd. m-cresol : A cresol with the methyl substituent at position 3. It is a minor urinary metabolite of toluene.	2.02	1	0	cresol	human xenobiotic metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	7.43	2	0	alkane	xenobiotic
1,2-dihydroxy-1,2-dihydronaphthalene 1,2-dihydroxy-1,2-dihydronaphthalene: naphthalene metabolite; RN given refers to cpd without isomeric designation. 1,2-dihydronaphthalene-1,2-diol : A member of the class of naphthalenediols that is 1,2-dihydronaphthalene substituted by hydroxy groups at positions 1 and 2 respectively.	1.99	1	0	dihydronaphthalenes; naphthalenediols	bacterial xenobiotic metabolite; mouse metabolite
2,3-diaminopropionic acid 3-aminoalanine : A diamino acid that is alanine in which one of the hydrogens of the methyl group is replaced by an amino group.	2	1	0	alanine derivative; amino acid zwitterion; beta-amino acid; diamino acid; non-proteinogenic alpha-amino acid	Escherichia coli metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.78	3	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	2.05	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
indoleacetamide indoleacetamide: article does not mention position of acetamide group; amide of indole-3-acetic acid (IAA), the natural auxin found in plants. indole-3-acetamide : A member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA).	2.69	2	0	indoles; monocarboxylic acid amide; N-acylammonia	bacterial metabolite; fungal metabolite; plant metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	7.03	10	2	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.47	2	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
n(1)-methylnicotinamide N(1)-methylnicotinamide: RN given refers to parent cpd. 1-methylnicotinamide : A pyridinium ion comprising nicotinamide having a methyl group at the 1-position. It is a metabolite of nicotinamide which was initially considered to be biologically inactive but has emerged as an anti-thrombotic and anti-inflammatory agent.	2.11	1	0	pyridinium ion	algal metabolite; anti-inflammatory agent; human urinary metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	2.78	3	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.	2.42	2	0	N-acylglycine	human blood serum metabolite; uremic toxin
2-aminoadipic acid 2-Aminoadipic Acid: A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-METHYL-D-ASPARTATE; (NMDA).. 2-aminoadipic acid : An alpha-amino acid that is adipic acid bearing a single amino substituent at position 2. An intermediate in the formation of lysine.	2.21	1	0	amino dicarboxylic acid; dicarboxylic fatty acid; non-proteinogenic alpha-amino acid	Caenorhabditis elegans metabolite; mammalian metabolite
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2	1	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
1-aminocyclopropane-1-carboxylic acid 1-aminocyclopropanecarboxylic acid : A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position.	2.02	1	0	amino acid zwitterion; monocarboxylic acid; non-proteinogenic alpha-amino acid	ethylene releasers; plant 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.	1.98	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
dibenzofuran Dibenzofurans: Compounds that include the structure of dibenzofuran.. dibenzofurans : Any organic heterotricyclic compound based on a dibenzofuran skeleton and its substituted derivatives thereof.. dibenzofuran : A mancude organic heterotricyclic parent that consists of a furan ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	2	1	0	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
cytosine [no description available]	7.67	3	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
alanine [no description available]	2	1	0	alpha-amino acid; amino acid zwitterion	fundamental metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.67	3	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
3,3-dimethylallyl pyrophosphate 3,3-dimethylallyl pyrophosphate: isomeric with isopentenyl pyrophosphate. prenyl diphosphate : A prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol.	3.03	4	0	prenol phosphate	epitope; Escherichia coli metabolite; mouse metabolite; phosphoantigen
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	3.28	6	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	7.33	2	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
hexachlorocyclohexane Lindane: An organochlorine insecticide made up of greater than 99% gamma-Hexachlorocyclohexane. It has been used as a pediculicide and scabicide, and shown to cause cancer.. beta-hexachlorocyclohexane : The beta-isomer of hexachlorocyclohexane.	2	1	0	chlorocyclohexane
glycine [no description available]	7.88	4	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.85	4	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alpha-glycerophosphoric acid [no description available]	2.39	2	0	glycerol monophosphate	algal metabolite; human metabolite
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	6.93	1	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
glyoxylic acid glyoxylic acid: RN given refers to parent cpd. glyoxylic acid : A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.	2.06	1	0	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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)	2.02	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.	2.52	2	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	3.03	5	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	4.56	24	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	3.01	4	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.54	2	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	4.04	14	0	imidazole
indole-3-acetaldehyde indoleacetaldehyde : An aldehyde that is acetaldehyde substituted by an indolyl group.. indol-3-ylacetaldehyde : An indoleacetaldehyde that is acetaldehyde in which one of the methyl hydrogens are replaced by a indol-3-yl group. It is an intermediate metabolite in the metabolism of tryptophan.	2.37	2	0	indoleacetaldehyde	bacterial metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	4.85	35	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
indol-3-yl pyruvic acid 3-(indol-3-yl)pyruvic acid : A 2-oxo monocarboxylic acid that is pyruvic acid substituted by a 1H-indol-3-yl group at position 3. It has been found in Lycopersicon esculentum	2.05	1	0	2-oxo monocarboxylic acid; indol-3-yl carboxylic acid	plant metabolite; Saccharomyces cerevisiae metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.52	2	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.	2.34	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.	5.43	11	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	2.08	1	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
methylmercaptan methylmercaptan: intermediate in the manufacturing of jet fuels, pesticides, fungicides, plastics, synthesis of methionine; odor may cause nausea; narcotic in high concentrations; depresses urea biosynthesis; RN given refers to parent cpd; structure	2.03	1	0	alkanethiol	human metabolite; Saccharomyces cerevisiae 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.	2.21	1	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.	3.26	6	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	3.64	2	0	cyclitol; hexol
melatonin [no description available]	4.45	22	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
acetanilide acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.	2.42	2	0	acetamides; anilide	analgesic
naphthalene [no description available]	4.01	14	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
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.	2.94	4	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.	2.67	3	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.64	3	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.	2.92	4	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)	3.22	6	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
n,n-dimethylaniline N,N-dimethylaniline: RN given refers to parent cpd; structure. dimethylaniline : A methylaniline carrying at least two methyl groups.. N,N-dimethylaniline : A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.	2.02	1	0	dimethylaniline; tertiary amine
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	1.98	1	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
hydroxide ion [no description available]	2.05	1	0	oxygen hydride	mouse metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	1.92	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.44	2	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.5	2	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
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	2.72	3	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	6	35	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetaldehyde [no description available]	2.8	3	0	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	7.46	2	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
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	7.41	1	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	2.17	1	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
porphobilinogen [no description available]	2.06	1	0	aralkylamino compound; dicarboxylic acid; pyrroles	Escherichia coli metabolite; metabolite; mouse metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	1.97	1	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.9	4	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	9.3	4	1	saturated fatty acid; short-chain fatty acid	antifungal drug
pteridines [no description available]	2	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
purine 1H-purine : The 1H-tautomer of purine.. 3H-purine : The 3H-tautomer of purine.. 9H-purine : The 9H-tautomer of purine.. 7H-purine : The 7H-tautomer of purine.	1.94	1	0	purine
putrescine [no description available]	2.69	3	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	2.57	2	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	4.15	16	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	4.88	6	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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).	7.33	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.	7.08	1	0	benzenetriol; phenolic donor	plant metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.71	3	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	8.28	6	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine metabolite
thiosulfates Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.	1.94	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.34	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
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.	2.43	2	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
thiophane [no description available]	2.02	1	0	saturated organic heteromonocyclic parent; tetrahydrothiophenes
thymine [no description available]	2.03	1	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	3.63	9	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
trimethyloxamine trimethyloxamine: used in manufacture of quaternary ammonium cpds; insect attractant; warming agent for gas; oxidant; structure. trimethylamine N-oxide : A tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine.	3.23	1	0	tertiary amine oxide	Escherichia coli metabolite; metabolite; osmolyte
trimethylamine [no description available]	2.46	2	0	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
tryptamine [no description available]	4.47	24	0	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.44	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.	2.5	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.	5.33	10	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).	10.16	3	1	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
isopentenyl pyrophosphate isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.	2.05	1	0	prenol phosphate	antigen; antioxidant; epitope; Escherichia coli metabolite; mouse metabolite; phosphoantigen
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	2.42	2	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	1.97	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.21	1	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	2.17	1	0	alkanethiol; primary alcohol	geroprotector
2-nitro-4-carboxyphenyl-n,n-diphenylcarbamate 2-nitro-4-carboxyphenyl-N,N-diphenylcarbamate: inhibits phospholipase C and serine esterases; structure in first source	1.96	1	0
n-methyl-3,4-methylenedioxyamphetamine N-Methyl-3,4-methylenedioxyamphetamine: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.. 3,4-methylenedioxymethamphetamine : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.	2	1	0	amphetamines; benzodioxoles	neurotoxin
phenytoin [no description available]	2.71	3	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	3.06	5	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.	2.03	1	0	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist
8-phenyltheophylline 8-phenyltheophylline: purinergic P1 receptor antagonist	2.02	1	0
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	3.12	1	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
abt 702 [no description available]	3.51	2	0	bipyridines
acebutolol Acebutolol: A cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action.. acebutolol : An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.	2.03	1	0	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	2.93	4	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	3.64	2	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	3.12	1	0	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
n-acetyltryptophan N-acetyltryptophan : An N-acetylamino acid that is the N-acetyl derivative of tryptophan.	2.03	1	0	N-acetyl-amino acid; tryptophan derivative	metabolite
alprenolol Alprenolol: One of the ADRENERGIC BETA-ANTAGONISTS used as an antihypertensive, anti-anginal, and anti-arrhythmic agent.. alprenolol : A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.	2.43	2	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
theophylline [no description available]	3.13	5	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
2-aminothiazole 2-aminothiazole: RN given refers to parent cpd; structure. 1,3-thiazol-2-amine : A primary amino compound that is 1,3-thiazole substituted by an amino group at position 2.	2.08	1	0	1,3-thiazoles; primary amino compound
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	2.04	1	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	2.43	2	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.05	1	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
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.02	1	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.92	4	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
astemizole Astemizole: Antihistamine drug now withdrawn from the market in many countries because of rare but potentially fatal side effects.. astemizole : A piperidine compound having a 2-(4-methoxyphenyl)ethyl group at the 1-position and an N-[(4-fluorobenzyl)benzimidazol-2-yl]amino group at the 4-position.	2.02	1	0	benzimidazoles; piperidines	anti-allergic agent; anticoronaviral agent; H1-receptor antagonist
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	2.02	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
atrazine [no description available]	2.42	2	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	1.97	1	0	azobenzenes
barbital 5,5-diethylbarbituric acid : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).	2.42	2	0	barbiturates	drug allergen
bemegride Bemegride: A CNS stimulant that is used to induce convulsions in experimental animals. It has also been used as a respiratory stimulant and in the treatment of barbiturate overdose.	1.93	1	0	piperidones
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	7.72	3	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.	1.99	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzocaine Benzocaine: A surface anesthetic that acts by preventing transmission of impulses along NERVE FIBERS and at NERVE ENDINGS.. dextran sulfate sodium : An organic sodium salt of dextran sulfate. It induces colitis in mice.. benzocaine : A benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina.	2	1	0	benzoate ester; substituted aniline	allergen; antipruritic drug; sensitiser; topical anaesthetic
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.	1.99	1	0	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite
bay h 4502 bifonazole : A racemate comprising equimolar amounts of R- and S-bifonazole. It is a broad spectrum antifungal drug used for the treatment of fungal skin and nail infections.. 1-[biphenyl-4-yl(phenyl)methyl]imidazole : A member of the class of imidazoles carrying an alpha-(biphenyl-4-yl)benzyl substituent at position 1.	2	1	0	biphenyls; imidazoles
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2.15	1	0
bromazepam Bromazepam: One of the BENZODIAZEPINES that is used in the treatment of ANXIETY DISORDERS.	2	1	0	organic molecular entity
caffeine [no description available]	8.28	6	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.71	3	0	aromatic ether; nitrile; polyether; tertiary amino compound
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.	2.25	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
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.52	2	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	2.31	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	2.03	1	0	quaternary ammonium ion
cetyl alcohol cetyl alcohol: has been used for eczema, skin irritations; RN given refers to parent cpd; structure. hexadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of sixteen carbon atoms.. hexadecan-1-ol : A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1.	1.98	1	0	hexadecanol; long-chain primary fatty alcohol	algal metabolite; flavouring agent; human metabolite; plant metabolite
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.	2.1	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	2.02	1	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	2.42	2	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorzoxazone Chlorzoxazone: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202). chlorzoxazone : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm.	2.05	1	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	1.95	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.46	2	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
cisapride Cisapride: A substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed). cisapride : The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere.	1.99	1	0	benzamides
N-[4-(4-morpholinyl)butyl]-2-benzofurancarboxamide CL82198: a selective inhibitor of MMP13	3.12	1	0	benzofurans
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.03	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.	4.17	16	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
dapi DAPI: RN given refers to parent cpd.	2.31	1	0	indoles	fluorochrome
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	2.94	4	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
nordazepam Nordazepam: An intermediate in the metabolism of DIAZEPAM to OXAZEPAM. It may have actions similar to those of diazepam.. nordazepam : A 1,4-benzodiazepinone having phenyl and chloro substituents at positions 5 and 7 respectively; it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties but is used primarily in the treatment of anxiety.	2.02	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; GABA modulator; human metabolite; sedative
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	2.68	3	0	primary amine
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.42	2	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diazinon Diazinon: A cholinesterase inhibitor that is used as an organothiophosphorus insecticide.. diazinon : A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.	2.03	1	0	organic thiophosphate; pyrimidines	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; nematicide; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.1	1	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	2	1	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
diethyl pyrocarbonate Diethyl Pyrocarbonate: Preservative for wines, soft drinks, and fruit juices and a gentle esterifying agent.. diethyl pyrocarbonate : The diethyl ester of dicarbonic acid.	1.99	1	0	acyclic carboxylic anhydride
3,3'-diindolylmethane 3,3'-diindolylmethane: anti-inflammatory from edible cruciferous vegetables; a cytochrome P-450 antagonist	3.64	2	0	indoles	antineoplastic agent; P450 inhibitor
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	2.02	1	0	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
benzophenone benzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.	2.74	3	0	benzophenones	photosensitizing agent; plant metabolite
diuron Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.	2	1	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
epinastine epinastine: RN given refers parent cpd. epinastine : A benzazepine that is 6,11-dihydro-5H-dibenzo[b,e]azepine in which the azepine ring is fused to the e side of 4,5-dihydro-1H-imidazol-2-amine.	2.02	1	0	benzazepine; guanidines	anti-allergic agent; H1-receptor antagonist; histamine antagonist; ophthalmology drug
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2.98	4	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
ethoxyresorufin ethoxyresorufin: structure	2.05	1	0	phenoxazine
ethoxzolamide Ethoxzolamide: A carbonic anhydrase inhibitor used as diuretic and in glaucoma. It may cause hypokalemia.. ethoxzolamide : A sulfonamide that is 1,3-benzothiazole-2-sulfonamide which is substituted by an ethoxy group at position 6. A carbonic anhydrase inhibitor, it has been used in the treatment of glaucoma, and as a diuretic.	2.07	1	0	aromatic ether; benzothiazoles; sulfonamide	antiglaucoma drug; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
fenbufen fenbufen: structure; RN given refers to parent cpd	2	1	0	4-oxo monocarboxylic acid; biphenyls	non-steroidal anti-inflammatory drug
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.05	1	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
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.	2.47	2	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flumequine flumequine: structure. flumequine : A racemate comprising equimolar amounts of R- and S-flumequine. A broad-spectrum antibiotic, formerly used in veterinary medicine for stock breeding and treatment of aquacultures.. 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid : A member of the class of pyridoquinolines that is 1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline carrying additional carboxy, methyl and fluoro substituents at positions 2, 5 and 9 respectively.	2.02	1	0	3-oxo monocarboxylic acid; organofluorine compound; pyridoquinoline; quinolone antibiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	2.42	2	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	2.42	2	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	2.43	2	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gliclazide Gliclazide: An oral sulfonylurea hypoglycemic agent which stimulates insulin secretion.	2.31	1	0	N-sulfonylurea	hypoglycemic agent; insulin secretagogue; radical scavenger
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.42	2	0	carboxamidine; guanidines; one-carbon compound
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.02	1	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
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.	2.17	1	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	2.41	2	0	barbiturates
beta-thujaplicin beta-thujaplicin: structure. beta-thujaplicin : A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.	1.98	1	0	cyclic ketone; enol; monoterpenoid	antibacterial agent; antifungal agent; antineoplastic agent; antiplasmodial drug; plant metabolite
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2.31	1	0	phenanthridines	fluorochrome; intercalator
hydrochlorothiazide Hydrochlorothiazide: A thiazide diuretic often considered the prototypical member of this class. It reduces the reabsorption of electrolytes from the renal tubules. This results in increased excretion of water and electrolytes, including sodium, potassium, chloride, and magnesium. It is used in the treatment of several disorders including edema, hypertension, diabetes insipidus, and hypoparathyroidism.. hydrochlorothiazide : A benzothiadiazine that is 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted by a chloro group at position 6 and a sulfonamide at 7. It is diuretic used for the treatment of hypertension and congestive heart failure.	2.03	1	0	benzothiadiazine; organochlorine compound; sulfonamide	antihypertensive agent; diuretic; environmental contaminant; xenobiotic
hydroxyzine Hydroxyzine: A histamine H1 receptor antagonist that is effective in the treatment of chronic urticaria, dermatitis, and histamine-mediated pruritus. Unlike its major metabolite CETIRIZINE, it does cause drowsiness. It is also effective as an antiemetic, for relief of anxiety and tension, and as a sedative.. hydroxyzine : A N-alkylpiperazine that is piperzine in which the nitrogens atoms are substituted by 2-(2-hydroxyethoxy)ethyl and (4-chlorophenyl)(phenyl)methyl groups respectively.	2.02	1	0	hydroxyether; monochlorobenzenes; N-alkylpiperazine	anticoronaviral agent; antipruritic drug; anxiolytic drug; dermatologic drug; H1-receptor antagonist
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	3.13	5	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	2.42	2	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
ifenprodil ifenprodil: NMDA receptor antagonist	2.1	1	0	piperidines
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.94	4	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) 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.	8.13	5	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.	9.77	9	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
indoprofen Indoprofen: A drug that has analgesic and anti-inflammatory properties. Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p21). indoprofen : A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.	2	1	0	gamma-lactam; isoindoles; monocarboxylic acid	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
indolepropionic acid indolepropionic acid: structure in third source. 3-(1H-indol-3-yl)propanoic acid : An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.	3.05	5	0	indol-3-yl carboxylic acid	auxin; human metabolite; plant metabolite
iproniazid [no description available]	1.93	1	0	carbohydrazide; pyridines
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	3.47	2	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2.42	2	0	secondary alcohol; secondary fatty alcohol	protic solvent
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	1.97	1	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.	2.05	1	0	hydroxy-1,4-naphthoquinone	geroprotector; herbicide; reactive oxygen species generator
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	7.94	4	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
kojic acid [no description available]	2.05	1	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
kynurenic acid Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.	2.25	1	0	monohydroxyquinoline; quinolinemonocarboxylic acid	G-protein-coupled receptor agonist; human metabolite; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist; Saccharomyces cerevisiae metabolite
labetalol Labetalol: A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.. labetalol : A diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers ((R,S)-labetolol, (S,R)-labetolol, (S,S)-labetalol and (R,R)-labetalol). It is an adrenergic antagonist used to treat high blood pressure.. 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide : A member of the class of benzamides that is benzamide substituted by a hydroxy group at position 2 and by a 1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl group at position 5.	2.03	1	0	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound
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.	1.98	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
loratadine Loratadine: A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.. loratadine : A benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders.	2.02	1	0	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	2	1	0	benzodiazepine
mescaline Mescaline: Hallucinogenic alkaloid isolated from the flowering heads (peyote) of Lophophora (formerly Anhalonium) williamsii, a Mexican cactus used in Indian religious rites and as an experimental psychotomimetic. Among its cellular effects are agonist actions at some types of serotonin receptors. It has no accepted therapeutic uses although it is legal for religious use by members of the Native American Church.. mescaline : A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.	3.03	1	0	methoxybenzenes; phenethylamine alkaloid; primary amino compound	hallucinogen
methoxyamine methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure	2	1	0	organooxygen compound
methyl salicylate methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.	2.05	1	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
metolazone Metolazone: A quinazoline-sulfonamide derived DIURETIC that functions by inhibiting SODIUM CHLORIDE SYMPORTERS.. metolazone : A quinazoline that consists of 1,2,3,4-tetrahydroquinazolin-4-one bearing additional methyl, 2-tolyl, sulfamyl and chloro substituents at positions 2, 3, 6 and 7 respectively. A quinazoline diuretic, with properties similar to thiazide diuretics.	2.02	1	0	organochlorine compound; quinazolines; sulfonamide	antihypertensive agent; diuretic; ion transport inhibitor
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	2.43	2	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
mirtazapine Mirtazapine: A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.	2.04	1	0	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	2.11	1	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.99	1	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
clorgyline Clorgyline: An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE.. clorgyline : An aromatic ether that is the 2,4-dichlorophenyl ether of 3-aminopropan-1-ol in which the nitrogen is substituted by a methyl group and a prop-1-yn-3-yl group. A monoamine oxidase inhibitor, it was formerly used as an antidepressant.	2.25	1	0	aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound	antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor
fenamic acid fenamic acid: has chloride and potassium channel-blocking activity; RN given refers to parent cpd. fenamic acid : An aminobenzoic acid that is the N-phenyl derivative of anthranilic acid. It acts as a parent skeleton for the synthesis of several non-steroidal anti-inflammatory drugs.	2.03	1	0	aminobenzoic acid; secondary amino compound	membrane transport modulator
nalidixic acid [no description available]	1.96	1	0	1,8-naphthyridine derivative; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; DNA synthesis inhibitor
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	2	1	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	2.05	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	2.45	2	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
oxazepam Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.	2.42	2	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
oxprenolol Oxprenolol: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	2.43	2	0	aromatic ether
aminosalicylic acid Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.	3.12	1	0	aminobenzoic acid; phenols	antitubercular agent
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.46	2	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	2.02	1	0	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
4-chlorophenol 4-chlorophenol: used as a root canal irrigant. 4-chlorophenol : A monochlorophenol substituted at the pare position by a chlorine atom.	2.39	2	0	monochlorophenol
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2.17	1	0	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.02	1	0	barbiturates	GABAA receptor agonist
perphenazine Perphenazine: An antipsychotic phenothiazine derivative with actions and uses similar to those of CHLORPROMAZINE.. perphenazine : A phenothiazine derivative in which the phenothiazine tricycle carries a chloro substituent at the 2-position and a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at N-10.	2.42	2	0	N-(2-hydroxyethyl)piperazine; N-alkylpiperazine; organochlorine compound; phenothiazines	antiemetic; dopaminergic antagonist; phenothiazine antipsychotic drug
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2.43	2	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
phenazopyridine Phenazopyridine: A local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.. phenazopyridine : A diaminopyridine that is 2,6-diaminopyridine substituted at position 3 by a phenylazo group. A local anesthetic that has topical analgesic effect on mucosa lining of the urinary tract. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.	2.02	1	0	diaminopyridine; monoazo compound	anticoronaviral agent; carcinogenic agent; local anaesthetic; non-narcotic analgesic
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.42	2	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	2.05	1	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
o-phthalaldehyde o-Phthalaldehyde: A reagent that forms fluorescent conjugation products with primary amines. It is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.. phthalaldehyde : A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.	2.72	3	0	benzaldehydes; dialdehyde	epitope
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	2.43	2	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
piperazine [no description available]	3.14	5	0	azacycloalkane; piperazines; saturated organic heteromonocyclic parent	anthelminthic drug
pirenzepine Pirenzepine: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.	2.03	1	0	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
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.	2.1	1	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
practolol Practolol: A beta-1 adrenergic antagonist that has been used in the emergency treatment of CARDIAC ARRYTHMIAS.. practolol : N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythmias.	2.43	2	0	acetamides; ethanolamines; propanolamine; secondary alcohol; secondary amino compound	anti-arrhythmia drug; beta-adrenergic antagonist
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.	2.66	3	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	2	1	0	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.43	2	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
psilocin psilocin: psilocybine minus the phosphate ester; RN given refers to parent cpd; structure. psilocin : A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms").	1.93	1	0	hydroxyindoles; phenols; tertiary amino compound; tryptamine alkaloid	drug metabolite; fungal metabolite; hallucinogen; human xenobiotic metabolite; serotonergic agonist
pyrilamine Pyrilamine: A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.. mepyramine : An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.	2.44	2	0	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
ranitidine [no description available]	2.03	1	0	aralkylamine
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	1.97	1	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
risperidone Risperidone: A selective blocker of DOPAMINE D2 RECEPTORS and SEROTONIN 5-HT2 RECEPTORS that acts as an atypical antipsychotic agent. It has been shown to improve both positive and negative symptoms in the treatment of SCHIZOPHRENIA.. risperidone : A member of the class of pyridopyrimidines that is 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.	2.04	1	0	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine	alpha-adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; psychotropic drug; second generation antipsychotic; serotonergic antagonist
saccharin Saccharin: Flavoring agent and non-nutritive sweetener.. saccharin : A 1,2-benzisothiazole having a keto-group at the 3-position and two oxo substituents at the 1-position. It is used as an artificial sweetening agent.	6.97	1	0	1,2-benzisothiazole; N-sulfonylcarboxamide	environmental contaminant; sweetening agent; xenobiotic
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	2.93	4	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.17	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
dpi 201-106 DPI 201-106: structure given in first source	1.99	1	0	diarylmethane
secobarbital Secobarbital: A barbiturate that is used as a sedative. Secobarbital is reported to have no anti-anxiety activity.. secobarbital : A member of the class of barbiturates that is barbituric acid in which the hydrogens at position 5 are substituted by prop-2-en-1-yl and pentan-2-yl groups.	2.02	1	0	barbiturates	anaesthesia adjuvant; GABA modulator; sedative
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	2.02	1	0
sulpiride Sulpiride: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed). sulpiride : A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.	2.02	1	0	benzamides; N-alkylpyrrolidine; sulfonamide	antidepressant; antiemetic; antipsychotic agent; dopaminergic antagonist
terfenadine Terfenadine: A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.	2.02	1	0	diarylmethane
tetracaine Tetracaine: A potent local anesthetic of the ester type used for surface and spinal anesthesia.. tetracaine : A benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia.	2.02	1	0	benzoate ester; tertiary amino compound	local anaesthetic
thioridazine Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.	2	1	0	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
ultram 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol : A tertiary alcohol that is cyclohexanol substituted at positions 1 and 2 by 3-methoxyphenyl and dimethylaminomethyl groups respectively.	2.02	1	0	aromatic ether; tertiary alcohol; tertiary amino compound
tranexamic acid Tranexamic Acid: Antifibrinolytic hemostatic used in severe hemorrhage.	2.02	1	0	amino acid
trifluoperazine [no description available]	2.4	2	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	2	1	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.03	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
tyramine [no description available]	7.84	4	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
zinc chloride zinc chloride: RN given refers to parent cpd. zinc dichloride : A compound of zinc and chloride ions in the ratio 1:2. It exists in four crystalline forms, in each of which the Zn(2+) ions are trigonal planar coordinated to four chloride ions.	3.4	1	1	inorganic chloride; zinc molecular entity	astringent; disinfectant; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; Lewis acid
zonisamide Zonisamide: A benzisoxazole and sulfonamide derivative that acts as a CALCIUM CHANNEL blocker. It is used primarily as an adjunctive antiepileptic agent for the treatment of PARTIAL SEIZURES, with or without secondary generalization.. zonisamide : A 1,2-benzoxazole compound having a sulfamoylmethyl substituent at the 3-position.	2.07	1	0	1,2-benzoxazoles; sulfonamide	anticonvulsant; antioxidant; central nervous system drug; protective agent; T-type calcium channel blocker
corticosterone [no description available]	2.71	3	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	2.03	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	2.02	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
lysergic acid diethylamide Lysergic Acid Diethylamide: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.. lysergic acid diethylamide : An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.	4.42	7	0	ergoline alkaloid; monocarboxylic acid amide; organic heterotetracyclic compound	dopamine agonist; hallucinogen; serotonergic agonist
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	3.03	5	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	3.06	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	2.05	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	3.93	12	0	benzimidazole; polycyclic heteroarene
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	6.98	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
aldosterone [no description available]	2.02	1	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	2	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.73	3	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
androsterone [no description available]	4.69	8	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid; C19-steroid	androgen; anticonvulsant; human blood serum metabolite; human metabolite; human urinary metabolite; mouse metabolite; pheromone
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	6.94	1	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
adrenochrome Adrenochrome: Pigment obtained by the oxidation of epinephrine.	3.18	6	0	indoles
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	6.98	1	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
pheniprazine pheniprazine: was heading 1963-94; use HYDRAZINES to search PHENIPRAZINE 1966-94	1.93	1	0	amphetamines
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.	7.4	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	3.38	7	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	4.62	27	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	7.88	4	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.7	3	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	7.41	2	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.7	3	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	3.32	6	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) 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.	2.02	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.	2.02	1	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	2.43	2	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.73	3	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.	2.76	3	0	tetrachlorophenol	xenobiotic metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	3.66	2	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
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.	1.96	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
p-dimethylaminoazobenzene p-Dimethylaminoazobenzene: A reagent used mainly to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens (NTP 85-002, p. 89) published in 1985, this compound may reasonably be anticipated to be a carcinogen. (Merck, 11th ed)	2.05	1	0	azobenzenes
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.	10.87	13	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.	1.93	1	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
n-methyltryptamine N-methyltryptamine: RN given refers to parent cpd	6.93	1	0	tryptamine alkaloid; tryptamines	metabolite
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.	7.46	2	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
4-toluenesulfonic acid 4-toluenesulfonic acid: RN given refers to parent cpd; other RNs in 9th CI Form Index. toluene-4-sulfonic acid : An arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.	2.17	1	0	arenesulfonic acid; toluenes
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.4	2	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
aniline [no description available]	3.65	9	0	anilines; primary arylamine
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	1.96	1	0	nitrosamine	geroprotector; mutagen
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.67	3	0	lactose
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	2.34	2	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.46	2	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	3.77	11	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	2.02	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	4.44	6	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
cytidine [no description available]	7.15	1	0	cytidines	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
n-hexanal [no description available]	2.1	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
strophanthidin Strophanthidin: 3 beta,5,14-Trihydroxy-19-oxo-5 beta-card-20(22)-enolide. The aglycone cardioactive agent isolated from Strophanthus Kombe, S. gratus and other species; it is a very toxic material formerly used as digitalis. Synonyms: Apocymarin; Corchorin; Cynotoxin; Corchorgenin.	1.93	1	0	14beta-hydroxy steroid; 19-oxo steroid; 3beta-hydroxy steroid; 5beta-hydroxy steroid; cardenolides; steroid aldehyde
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	2.01	1	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	2.43	2	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
sodium citrate, anhydrous Sodium Citrate: Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.. sodium citrate : The trisodium salt of citric acid.	2.25	1	0	organic sodium salt	anticoagulant; flavouring agent
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	2.04	1	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
cycloserine Cycloserine: Antibiotic substance produced by Streptomyces garyphalus.. D-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).	7.34	2	0	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist
chlorisondamine Chlorisondamine: A nicotinic antagonist used primarily as a ganglionic blocker in animal research. It has been used as an antihypertensive agent but has been supplanted by more specific drugs in most clinical applications.	1.93	1	0	isoindoles
tubercidin Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.	1.96	1	0	antibiotic antifungal agent; N-glycosylpyrrolopyrimidine; ribonucleoside	antimetabolite; antineoplastic agent; bacterial metabolite
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	1.96	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	2.72	3	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
phenacyl bromide phenacyl bromide: structure. phenacyl bromide : An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.	2.52	2	0	acetophenones; alpha-bromoketone	metabolite
4-toluenesulfonamide 4-toluenesulfonamide: RN given refers to parent cpd. toluene-4-sulfonamide : A sulfonamide that is benzenesulfonamide bearing a methyl group at position 4.	2	1	0	sulfonamide
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.94	4	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.47	2	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	2.42	2	0	chloroethanes	polar solvent
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.52	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
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.13	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	12.09	211	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.7	3	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	7.47	2	0	alkane; gas molecular entity	plant metabolite; refrigerant
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.73	3	0	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	9.42	6	0	alkyne; gas molecular entity; terminal acetylenic compound
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	1.99	1	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	2.04	1	0	boranes; mononuclear parent hydride
ethylamine ethylamine : A two-carbon primary aliphatic amine.	2.42	2	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.	2.76	3	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.06	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	2.07	1	0	cycloalkane; cyclopropanes	inhalation anaesthetic
nitromethane nitromethane: structure. nitromethane : A primary nitroalkane that is methane in which one of the hydrogens is replace by a nitro group. A polar solvent (b.p. 101 degreeC), it is an important starting material in organic synthesis. It is also used as a fuel for rockets and radio-controlled models.	2.42	2	0	primary nitroalkane; volatile organic compound	EC 4.3.1.3 (histidine ammonia-lyase) inhibitor; explosive; NMR chemical shift reference compound; polar aprotic solvent
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	2.42	2	0	tertiary alcohol	human xenobiotic metabolite
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.	2.44	2	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	2.02	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	3	4	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	3.45	2	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
tetraethoxysilane [no description available]	2.05	1	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.	2.73	3	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.	2.11	1	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	2.02	1	0	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
isobutyraldehyde isobutyraldehyde : A member of the class of propanals that is propanal substituted by a methyl group at position 2.	7.11	1	0	2-methyl-branched fatty aldehyde; propanals	Saccharomyces cerevisiae metabolite
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	2.42	2	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	2	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	7.68	3	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	7.1	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
methyl acetate methyl acetate : An acetate ester resulting from the formal condensation of acetic acid with methanol. A low-boiling (57 degreeC) colourless, flammable liquid, it is used as a solvent for many resins and oils.	2.42	2	0	acetate ester; methyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; fragrance; polar aprotic solvent
nitroethane nitroethane : A nitroalkane that is ethane substituted by a nitro group.	7.42	2	0	primary nitroalkane
dichloroacetic acid [no description available]	2.02	1	0	monocarboxylic acid; organochlorine compound	astringent; marine metabolite
alpha-pinene [no description available]	1.98	1	0	pinene	plant metabolite
skatole [no description available]	9.97	64	2	methylindole	human metabolite; mammalian metabolite
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.	2.02	1	0
dichlorodicyanobenzoquinone dichlorodicyanobenzoquinone: request from searcher	2.06	1	0
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	2.03	1	0	anthraquinone
diethyl phthalate diethyl phthalate: structure. diethyl phthalate : The diethyl ester of benzene-1,2-dicarboxylic acid.	2.03	1	0	diester; ethyl ester; phthalate ester	neurotoxin; plasticiser; teratogenic agent
phthalimide phthalimide: RN given refers to parent cpd. phthalimide : A dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3.	2.48	2	0	phthalimides
fluorene [no description available]	7.89	4	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
carbazole carbazole: structure in first source	5	12	0	carbazole
5-bromoisatin [no description available]	2.03	1	0	indoles	anticoronaviral agent
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	2.84	4	0	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist
2,6-dichlorophenol 2,6-dichlorophenol: RN given refers to unlabeled cpd. 2,6-dichlorophenol : A dichlorophenol with the chloro substituents at positions 2 and 6.	2.02	1	0	dichlorophenol
hexamethylbenzene hexamethylbenzene : A methylbenzene that is benzene in which all six hydrogens have been replaced by methyl groups.	2	1	0	methylbenzene
2-tert-butylphenol [no description available]	2.02	1	0	alkylbenzene
2-isopropylphenol 2-isopropylphenol: structure given in first source. 2-isopropylphenol : A member of the class of phenols carrying an isopropyl group at position 2.	2.02	1	0	phenols
2-nitrotoluene nitrotoluene : Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.	2.4	2	0	mononitrotoluene	carcinogenic agent; environmental contaminant
2-nitroaniline [no description available]	2.43	2	0
2-nitrophenol nitrophenol : Any member of the class of phenols or substituted phenols carrying at least 1 nitro group.	2.75	3	0	2-nitrophenols
2,5-dichloronitrobenzene [no description available]	2.03	1	0
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	2.92	4	0	monoterpenoid; phenols	volatile oil component
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	2.43	2	0	naphthol	genotoxin; human xenobiotic metabolite
2-phenylphenol 2-phenylphenol: RN given refers to parent cpd; structure. biphenyl-2-ol : A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.	2.54	2	0	hydroxybiphenyls	antifungal agrochemical; environmental food contaminant
anthrone anthrone: used in colorimetric determination of sugar & animal starch in body fluids; structure. anthrone : A member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9.	2.05	1	0	anthracenone	radical scavenger
aminacrine Aminacrine: A highly fluorescent anti-infective dye used clinically as a topical antiseptic and experimentally as a mutagen, due to its interaction with DNA. It is also used as an intracellular pH indicator.. 9-aminoacridine : An aminoacridine that is acridine in which the hydrogen at position 9 is replaced by an amino group. A fluorescent dyd and topical antiseptic agent, it is used (usually as the hydrochloride salt) in eye drops for the treatment of superficial eye infections.	2.42	2	0	aminoacridines; primary amino compound	acid-base indicator; antiinfective agent; antiseptic drug; fluorescent dye; MALDI matrix material; mutagen
benzohydrol diphenylmethanol : A secondary alcohol that is diphenylmethane which carries a hydroxy group at position 1.	2.17	1	0	benzyl alcohols; secondary alcohol	bacterial xenobiotic metabolite; human urinary metabolite; human xenobiotic metabolite; rat 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.	2.07	1	0	dimethoxybenzene	plant metabolite
decalin decalin: RN given refers to cpd without isomeric designation; don't confuse with decaline which has a nitrogen at the juncture of the two rings;. trans-decalin : The trans-stereoisomer of decalin.. decalin : An ortho-fused bicyclic hydrocarbon that is the decahydro- derivative of naphthalene.	2.04	1	0	ortho-fused bicyclic hydrocarbon	solvent
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	3.16	5	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
1,2,3,4-tetrahydroisoquinoline 1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified	2.15	1	0	isoquinolines
quinoline [no description available]	5.64	23	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
2,3-dimethylindole [no description available]	2.36	2	0
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	5.19	15	0	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
pyronine Pyronine: Xanthene dye used as a bacterial and biological stain. Synonyms: Pyronin; Pyronine G; Pyronine Y. Use also for Pyronine B. which is diethyl-rather than dimethylamino-.. pyronin Y : An organic chloride salt having 6-(dimethylamino)-N,N-dimethyl-3H-xanthen-3-iminium as the cation. Used with methyl green to selectively demonstrate RNA (red) in contrast to DNA (green) with the Unna-Pappenheim method.	2.15	1	0	iminium salt; organic chloride salt	histological dye
phenidone phenidone: photographic developer; RN given refers to parent cpd; structure	2.02	1	0
2,3-dihydroxynaphthalene 2,3-naphthalenediol: structure in first source	2.02	1	0	naphthalenediol
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	3.24	6	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
4-phenylphenol 4-phenylphenol: RN given refers to cpd without isomeric designation. biphenyl-4-ol : A member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.	3.57	2	0	hydroxybiphenyls
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	1.93	1	0	xanthene
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	2	1	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.	1.99	1	0	benzyl alcohols; dimethoxybenzene; primary alcohol	fungal metabolite
methyleugenol methyleugenol: structure	1.98	1	0	phenylpropanoid
methyl benzoate methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.	2.42	2	0	benzoate ester; methyl ester	insect attractant; metabolite
benzanilide [no description available]	3.54	2	0
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.1	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
indene indene: structure in first source. 1H-indene : An ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.	3.12	5	0	indene; ortho-fused bicyclic arene
benzotriazole benzotriazole: inhibitor of atmospheric metal corrosion; also component of motion picture film & Neva brake fluid. benzotriazole : The simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring.	2.41	2	0	benzotriazoles	environmental contaminant; xenobiotic
benzothiophene [no description available]	8.12	5	0	1-benzothiophenes; benzothiophene
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	3.16	5	0	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
2-methylindole 2-methylindole: SKATOLE refers to 3-methylindole; RN given refers to parent cpd; structure. 2-methyl-1H-indole : A methylindole that is 1H-indole substituted by a methyl group at position 2.	7.86	4	0	methylindole
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	2.02	1	0	xylene
2-chloroaniline [no description available]	2.03	1	0
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.	2.02	1	0	aminotoluene	carcinogenic agent
2-bromophenol bromophenol : A halophenol that is any phenol containing one or more covalently bonded bromine atoms.	2.02	1	0	bromophenol	marine metabolite
2-chlorophenol chlorophenol : A halophenol that is any phenol containing one or more covalently bonded chlorine atoms.	2.76	3	0	2-halophenol; monochlorophenol
3,4-dimethylphenol 3,4-dimethylphenol: RN given refers to parent cpd. 3,4-xylenol : A member of the class of phenols that is phenol substituted by methyl groups at positions 3 and 4.	2.02	1	0	phenols
2,5-xylenol 2,5-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 2 and 5.	2.02	1	0	phenols	animal metabolite; volatile oil component
dilactide dilactide: structure given in first source	2.05	1	0	dioxanes
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.46	2	0	butan-4-olide	metabolite; neurotoxin
furfuryl alcohol furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.	2.1	1	0	furans; primary alcohol	Maillard reaction product
benzotrifluoride alpha,alpha,alpha-trifluorotoluene: structure in first source. (trifluoromethyl)benzene : A fluorohydrocarbon that is fluoroform in which the hydrogen is substituted by a phenyl group.	2	1	0	(trifluoromethyl)benzenes; fluorohydrocarbon	environmental contaminant; NMR chemical shift reference compound; solvent
3-trifluoromethylphenol 3-trifluoromethylphenol: structure in first source	1.97	1	0	(trifluoromethyl)benzenes
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	2.42	2	0	phenols	allergen
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	3.26	6	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	3.27	6	0	nitroarene; nitrobenzenes
3-nitroaniline 3-nitroaniline: used as a sole source of nitrogen , carbon and energy	2.74	3	0
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	1.99	1	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	2.41	2	0	botanical anti-fungal agent; carvones	allergen
3-dinitrobenzene dinitrobenzene : Any member of the class of nitrobenzenes that consists of a benzene ring substituted by two nitro groups. A closed class.. 1,3-dinitrobenzene : A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.	2.11	1	0	dinitrobenzene	neurotoxin
gamma-terpinene gamma-terpinene: RN given refers to gamma-terpinene; structure. gamma-terpinene : One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.	2.05	1	0	cyclohexadiene; monoterpene	antioxidant; human xenobiotic metabolite; plant metabolite; volatile oil component
4-nitrotoluene 4-nitrotoluene: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6470. mononitrotoluene : A nitrotoluene bearing a single nitro substituent at any position. A "closed class".. 4-nitrotoluene : A mononitrotoluene that consists of toluene bearing a nitro substituent at the 4-position.	2.02	1	0	mononitrotoluene
4-chloronitrobenzene [no description available]	1.97	1	0	C-nitro compound
4-nitroaniline [no description available]	2.43	2	0	nitroaniline	bacterial xenobiotic metabolite
4-anisic acid 4-methoxybenzoic acid: structure in first source. 4-methoxybenzoic acid : A methoxybenzoic acid substituted with a methoxy group at position C-4.	2.02	1	0	methoxybenzoic acid	plant metabolite
4-(dimethylamino)benzaldehyde p-dimethylaminobenzaldehyde: structure in first source. 4-(dimethylamino)benzaldehyde : A member of the class of benzaldehydes that is benzaldehyde carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.	2.9	4	0	benzaldehydes; substituted aniline; tertiary amino compound	chromogenic compound
4-nitroanisole 4-nitroanisole: dye intermediate; organic synthesis; structure. 4-nitroanisole : A member of the class of 4-nitroanisoles that is anisole in which one the hydrogen meta to the methoxy group is replaced by a nitro group.	1.97	1	0	4-nitroanisoles
benzyl bromide benzyl bromide: structure given in first source. benzyl bromide : A member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine.	2.03	1	0	benzyl bromides	lachrymator
ethylbenzene [no description available]	2.44	2	0	alkylbenzene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.46	2	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.02	1	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
benzonitrile benzonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group.	3.1	5	0	benzenes; nitrile
4-cyanopyridine 4-cyanopyridine: spectroscopic probe for cytochrome P450 BM3	2.04	1	0
methylaniline methylaniline: RN given refers to parent cpd. methylaniline : A substituted aniline carrying one or more methyl groups at unspecified positions.	2.02	1	0	methylaniline; phenylalkylamine; secondary amine
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	3.12	5	0	monomethoxybenzene	plant metabolite
methylphenylsulfide thioanisole : An aryl sulfide that is thiophenol in which the hydrogen of the thiol group has been replaced by a methyl group.	2.72	3	0	aryl sulfide; benzenes
2-ethylpyridine 2-ethylpyridine: RN given refers to compound with locant	2.03	1	0
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	2.05	1	0	quinuclidines; saturated organic heterobicyclic parent
diphenylmethane diphenylmethane : A diarylmethane that is methane substituted by two phenyl groups.	2.01	1	0	diarylmethane
n-propylbenzene n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.	2.02	1	0	alkylbenzene
2-phenylacetamide 2-phenylacetamide: structure. 2-phenylacetamide : A monocarboxylic acid amide that is acetamide substituted by a phenyl group at position 2.	2.01	1	0	monocarboxylic acid amide	mouse metabolite
n-butylbenzene butylbenzene : An alkylbenzene that is benzene substituted by a butyl group at position 1.	2.02	1	0	alkylbenzene
4-anisidine 4-anisidine: RN given refers to parent cpd. p-anisidine : A substituted aniline that is aniline in which the hydrogen para to the amino group has been replaced by a methoxy group. It is used as a reagent for the detection of oxidation products such as aldehydes and ketones in fats and oils.	1.97	1	0	methoxybenzenes; primary amino compound; substituted aniline	genotoxin; reagent
anisyl alcohol anisyl alcohol: structure given in first source	1.97	1	0	benzyl alcohols
methyl acetoacetate methyl acetoacetate: structure	7.11	1	0	oxo carboxylic acid
2,4-dimethylphenol 2,4-dimethylphenol: RN given refers to parent cpd. 2,4-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 2 and 4.	2.43	2	0	aromatic fungicide; phenols	disinfectant; volatile oil component
4-bromoaniline 4-bromoaniline: RN given refers to parent cpd; structure given in Merck Index, 9th ed, #1403	1.97	1	0
4-bromophenol 4-bromophenol : A bromophenol containing only hydroxy and bromo substituents that are para to one another.	2.39	2	0	bromophenol	human urinary metabolite; human xenobiotic metabolite; marine metabolite; mouse metabolite; persistent organic pollutant; rat metabolite
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	2.02	1	0	xylene
4-chloroaniline 4-chloroaniline: RN given refers to parent cpd; structure. 4-chloroaniline : A chloroaniline in which the chloro atom is para to the aniline amino group.	2.92	4	0	chloroaniline; monochlorobenzenes
4-toluidine 4-toluidine: RN given refers to parent cpd. p-toluidine : An aminotoluene in which the amino substituent is para to the methyl group.	2.39	2	0	aminotoluene
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.04	1	0	alkane; gas molecular entity	food propellant; refrigerant
acrolein [no description available]	2.46	2	0	enal	herbicide; human xenobiotic metabolite; toxin
propylamine propylamine : A member of the class of alkylamines that is propane substituted by an amino group at C-1.	2.02	1	0	alkylamines
propionitrile propionitrile: structure. propionitrile : A nitrile that is acrylonitrile in which the carbon-carbon double bond has been reduced to a single bond.	2	1	0	aliphatic nitrile; volatile organic compound	polar aprotic solvent
acrylonitrile [no description available]	7.1	1	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
propargyl alcohol propargyl alcohol: irreversibly inactivates alcohol oxidase; RN given refers to parent cpd. prop-2-yn-1-ol : A terminal acetylenic compound that is prop-2-yne substituted by a hydroxy group at position 1.	2.1	1	0	propynol; terminal acetylenic compound; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.06	1	0	alkane
2-pentanone pentanone : Any ketone that is pentane substituted by an oxo group at unspecified position.	2.02	1	0	methyl ketone; pentanone	plant metabolite
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2.05	1	0	acyclic carboxylic anhydride	metabolite; reagent
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	2.02	1	0	xylene
3-chloroaniline 3-chloroaniline: RN given refers to parent cpd	2.43	2	0
3-chlorophenol 3-chlorophenol : A monochlorophenol carrying the chloro substituent at position 3.	2.69	3	0	monochlorophenol
3,5-xylenol 3,5-xylenol: RN given refers to 3,5-isomer. 3,5-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 3 and 5.	2.02	1	0	phenols	xenobiotic metabolite
bromobenzene [no description available]	2.42	2	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
4-methylpyridine 4-methylpyridine: structure in first source. 4-methylpyridine : A methylpyridine in which the methyl substituent is at position 4.	2.03	1	0	methylpyridine
chlorobenzene [no description available]	2.42	2	0	monochlorobenzenes	solvent
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.13	1	0	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	7.45	2	0	cyclohexanones	human xenobiotic metabolite
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	2.06	1	0	aryl thiol
2-chloropyridine 2-chloropyridine: structure given in first source	2.04	1	0	monochloropyridine
2-aminopyrimidine pyrimidin-2-amine : An aminopyrimidine carrying an amino group at position 2.. aminopyrimidine : A member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives.	2.31	1	0	aminopyrimidine
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.	2.07	1	0	short-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
propyl acetate propyl acetate: affects aggression without affecting motor activity; RN given refers to parent cpd. propyl acetate : An acetate ester obtained by the formal condensation of acetic acid with propanol.	2.02	1	0	acetate ester	fragrance; plant metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.72	3	0	alkane; volatile organic compound	non-polar solvent; refrigerant
n-butylamine n-butylamine: RN given refers to parent cpd. butan-1-amine : A primary aliphatic amine that is butane substituted by an amino group at position 1.	2.02	1	0	primary aliphatic amine
dimethoxymethane dimethoxymethane : An acetal that is the dimethyl acetal derivative of formaldehyde.	2	1	0	acetal; diether
vinyl ether vinyl ether: major descriptor (65-85); on-line search VINYL COMPOUNDS (66-85); Index Medicus search VINYL ETHER (65-85)	2.08	1	0	ether
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.	5.81	28	0	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	2.42	2	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	3.35	6	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	4.84	10	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	7.42	2	0	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	2	1	0	cycloalkene
piperidine [no description available]	7.99	4	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
morpholine [no description available]	2	1	0	morpholines; saturated organic heteromonocyclic parent	NMR chemical shift reference compound
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	2.71	3	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
heptanol Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.	2.4	2	0	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
heptanal heptanal : An n-alkanal resulting from the oxidation of the alcoholic hydroxy group of heptan-1-ol to the corresponding aldehyde. An endogenous aldehyde coming from membrane lipid oxidation, it is found in the blood of lung cancer patients and has been regarded as a potential biomarker of lung cancer.	2.05	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	biomarker
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.01	1	0	alkane	plant metabolite; volatile oil component
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	2.4	2	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
decanaldehyde decanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of capric acid (decanoic acid).	2.15	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	antifungal agent; fragrance; plant metabolite
undecan-1-ol undecan-1-ol : A primary alcohol that is undecane substituted by a hydroxy group at position 1.. undecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eleven carbon atoms.	1.98	1	0	primary alcohol; undecanol	flavouring agent; plant metabolite
dodecanol Dodecanol: A saturated 12-carbon fatty alcohol obtained from coconut oil fatty acids. It has a floral odor and is used in detergents, lubricating oils, and pharmaceuticals. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). dodecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of twelve carbon atoms.. dodecan-1-ol : A primary alcohol that is dodecane in which a hydrogen from one of the methyl groups is replaced by a hydroxy group. It is registered for use in apple and pear orchards as a Lepidopteran pheromone/sex attractant, used to disrupt the mating behaviour of certain moths whose larvae destroy crops.	1.98	1	0	dodecanol; primary alcohol	bacterial metabolite; cosmetic; insect attractant; insecticide; pheromone; plant metabolite
1-tridecanol 1-tridecanol: RN given refers to parent cpd. tridecan-1-ol : A long-chain primary fatty alcohol that is tridecane substituted by a hydroxy group at position 1.. tridecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of thirteen carbon atoms.	1.98	1	0	long-chain primary fatty alcohol; tridecanol	bacterial metabolite; human metabolite; plant metabolite
myristyl alcohol myristyl alcohol: RN given refers to parent cpd. tetradecan-1-ol : A long-chain fatty alcohol that is tetradecane substituted by a hydroxy group at position 1.. tetradecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of fourteen carbon atoms.	1.98	1	0	long-chain primary fatty alcohol; tetradecanol	pheromone; plant metabolite; volatile oil component
stearyl alcohol octadecan-1-ol : A long-chain primary fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of 18 carbon atoms.. octadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eighteen carbon atoms.	1.98	1	0	long-chain primary fatty alcohol; octadecanol	algal metabolite; human metabolite; plant metabolite
2,2,2-trichloroethanol [no description available]	2.03	1	0	chloroethanol	mouse 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.	2.03	1	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
etryptamine etryptamine: RN given refers to cpd without isomeric designation	1.94	1	0	indoles
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	2.13	1	0	4-pyranones	metabolite
chloranil Chloranil: A quinone fungicide used for treatment of seeds and foliage.. tetrachloro-1,4-benzoquinone : A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.	2.05	1	0	1,4-benzoquinones; organochlorine compound	EC 2.7.1.33 (pantothenate kinase) inhibitor; 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.	1.93	1	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
isoquinoline [no description available]	2.73	3	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	7.03	1	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
veratraldehyde [no description available]	2.05	1	0	benzaldehydes; dimethoxybenzene	antifungal agent
2-naphthoxyacetic acid 2-naphthoxyacetic acid: used as plant hormone to promote the growth of roots on clippings, to prevent fruit from falling prematurely; structure	2.31	1	0	naphthyloxyacetic acid
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	2	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
sulfoxide sulfoxide: synergistic insecticide for use with pyrethrum, allethrin, rotenone, ryania, etc.; RN given refers to parent cpd; structure. sulfoxide : An organosulfur compound having the structure R2S=O or R2C=S=O (R =/= H).	7.73	3	0	benzodioxoles
2,4-dichlorophenol 2,4-dichlorophenol: RN given refers to unlabeled parent+ cpd; structure. 2,4-dichlorophenol : A dichlorophenol that is phenol carrying chloro substituents at positions 2 and 4.	2.47	2	0	dichlorophenol
2,4-dinitrotoluene 2,4-dinitrotoluene : A dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.	1.99	1	0	dinitrotoluene
3-nitrobenzoic acid 3-nitrobenzoic acid: RN given refers to parent cpd	2.42	2	0
1,4-naphthoquinone naphthoquinone : A polycyclic aromatic ketone metabolite of naphthalene.. 1,4-naphthoquinone : The parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties.	2.03	1	0	1,4-naphthoquinones
dimethyl phthalate dimethyl phthalate: used as plasticizer in computer mouse; structure	2.03	1	0	diester; methyl ester; phthalate ester
alpha-naphthylphthalamic acid alpha-naphthylphthalamic acid: RN given refers to parent cpd; structure. naptalam : A dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride.	2.31	1	0	carboxylic acid; dicarboxylic acid monoamide; N-(1-naphthyl)carboxamide	herbicide
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	7.37	2	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant metabolite
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.11	1	0	UDP-D-glucose	fundamental metabolite
methyl anthranilate methyl anthranilate : A benzoate ester that is the methyl ester of anthranilic acid.	1.98	1	0	benzoate ester	flavouring agent; metabolite
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	1.97	1	0	naphthylamine	human xenobiotic metabolite
benzil benzil: structure. benzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.	2.04	1	0	alpha-diketone; aromatic ketone
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.	7.54	2	0	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	3.61	9	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
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.	2.37	2	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.96	4	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.	2.44	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
1-nonanol nonanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of nine carbon atoms.. nonan-1-ol : A nonanol that is nonane substituted by a hydroxy group at position 1. It has been isolated as a component of volatile oils from plants like Hordeum vulgare.	1.98	1	0	nonanol; primary alcohol	antifungal agent; flavouring agent; plant metabolite; volatile oil component
pregnenolone [no description available]	2.46	2	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse 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.	2.63	3	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.	2.05	1	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.	2.39	2	0	monomethoxybenzene; phenols
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	2.39	2	0	methoxybenzenes; phenols	metabolite
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.52	2	0	catechin	antioxidant; plant metabolite
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	2.02	1	0	ortho- and peri-fused polycyclic arene
cinnoline cinnoline: structure in first source. cinnoline : An azaarene that is the 1,2-diaza analogue of naphthalene. The parent of the class of cinnolines.	7.36	2	0	azaarene; cinnolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.89	3	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.72	3	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
6-azaindole [no description available]	3.51	1	0
5-azaindole [no description available]	3.51	1	0
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	3.44	7	0	indazole
7-azaindole [no description available]	3.88	3	0	pyrrolopyridine
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	5.05	12	0	1-benzofurans; benzofuran
4-azaindole [no description available]	3.51	1	0
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.	2.42	2	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
indolizine [no description available]	7.04	1	0	indolizines; mancude organic heterobicyclic parent
triethylenediamine triethylenediamine: RN given refers to parent cpd. triethylenediamine : An organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions.	2.06	1	0	bridged compound; diamine; saturated organic heterobicyclic parent; tertiary amino compound	antioxidant; catalyst; reagent
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	3.87	11	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	7.98	4	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	4.54	7	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	5.38	17	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
1,2,4-triazole 1,2,4-triazole: RN given refers to 1H-1,2,4-triazole	7.84	3	0	1,2,4-triazole
pyridazine pyridazine: structure given in first source	7.25	1	0	diazine; pyridazines
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	4.83	9	0	diazine; pyrimidines	Daphnia magna metabolite
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.	3.01	4	0	diazine; pyrazines	Daphnia magna metabolite
cyclooctane [no description available]	2.01	1	0
indopan indopan: RN given refers to parent cpd without isomeric designation. alpha-methyltryptamine : A tryptamine derivative having a methyl substituent at the alpha-position.	2.34	2	0	tryptamines
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2.66	3	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
hydrazine diamine : Any polyamine that contains two amino groups.	3.76	10	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
5-fluorotryptophan 5-fluorotryptophan: RN given refers to cpd with unspecified isomeric designation. 5-fluorotryptophan : A non-proteinogenic alpha-amino acid that is tryptophan in which the hydrogen at position 5 on the indole ring is replaced by a fluoro group.	2.37	2	0	non-proteinogenic alpha-amino acid; organofluorine compound; tryptophan derivative
2-fluoroaniline 2-fluoroaniline: structure given in first source; RN given refers to parent compound. 2-fluoroaniline : A derivative of aniline in which the hydrogen at position 2 has been substituted by fluorine. It is used as a pharmaceutical intermediate	2.02	1	0	fluoroaniline; primary arylamine
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	7.11	1	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite
thymidine monophosphate Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.. dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).	2	1	0	thymidine 5'-monophosphate	fundamental metabolite
4-fluorophenol 4-fluorophenol: structure given in first source. 4-fluorophenol : A fluorophenol that is phenol in which the hydrogen para- to the hydroxy group has been replaced by a fluorine.	1.97	1	0	fluorophenol; monofluorobenzenes
cyanoacetic acid cyanoacetic acid: RN given refers to parent cpd; structure. cyanoacetic acid : A monocarboxylic acid that consists of acetic acid bearing a cyano substituent.	2.07	1	0	monocarboxylic acid
3-fluoroaniline 3-fluoroaniline: structure given in first source. 3-fluoroaniline : A derivative of aniline in which the hydrogen at position 3 has been substituted by fluorine. It is used as a pharmaceutical intermediate.	1.97	1	0	fluoroaniline; primary arylamine
3-fluorophenol 3-fluorophenol: structure in first source	2.39	2	0
trifluoroacetic anhydride [no description available]	2.46	2	0
2-aminopurine 2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).. aminopurine : Any purine having at least one amino substituent.. 2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.	2.11	1	0	2-aminopurines; nucleobase analogue	antimetabolite
4-methylcatechol [no description available]	2.58	2	0	methylcatechol	antioxidant; carcinogenic agent; hapten; human metabolite; plant metabolite
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.6	1	0	imidazolidine-2,4-dione
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	7.72	3	0	monofluorobenzenes	NMR chemical shift reference compound
propadiene [no description available]	2.51	2	0	allenes
methylguanidine Methylguanidine: A product of putrefaction. Poisonous.. methylguanidine : A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a methyl group.	1.97	1	0	guanidines	EC 1.14.13.39 (nitric oxide synthase) inhibitor; metabolite; uremic toxin
2-bromolysergic acid diethylamide 2-bromolysergic acid diethylamide: was heading 1975-94 (see under LYSERGIC ACID DIETHYLAMIDE 1975-90); BROMO-LSD was see 2-BROMOLYSERGIC ACID DIETHYLAMIDE 1975-94; use LYSERGIC ACID DIETHYLAMIDE to search 2-BROMOLYSERGIC ACID DIETHYLAMIDE 1975-94; a serotonin antagonist	1.93	1	0
indirubin [no description available]	3.27	6	0
indigo [no description available]	2.02	1	0	hydroxyindoles
flavanone flavanone: RN given refers to cpd with unspecified isomeric designation; structure in first source. flavanone : The simplest member of the class of flavanones that consists of flavan bearing an oxo substituent at position 4.	2.05	1	0	flavanones
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.	8.65	9	0	heteroarenecarbaldehyde; indole alkaloid; indoles	bacterial metabolite; human xenobiotic metabolite; marine metabolite; plant metabolite
bufotenin Bufotenin: A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.. bufotenin : A tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5.	4.13	5	0	tertiary amine; tryptamine alkaloid	coral metabolite; hallucinogen
thioxanthone thioxanthone: structure in first source	7.45	2	0
1,4-benzodioxan 1,4-benzodioxan: structure in first source	3.51	2	0
methyl red methyl red: RN given refers to parent cpd; structure. methyl red : An azo dye consisting of benzoic acid substituted at position 2 by a 4-[(dimethylamino)phenyl]diazenyl group.	2.05	1	0
benzohydroxamic acid [no description available]	2.03	1	0
indan indan: structure in first source. indane : An ortho-fused bicyclic hydrocarbon consisting of a benzene ring fused to a cyclopentane ring; a high-boiling (176 (o)C) colourless liquid.	2.03	1	0	indanes; ortho-fused bicyclic hydrocarbon
indoline indoline: structure given in first source	4.08	15	0	indoles
coumaran 2,3-dihydrobenzofuran : A member of the class of 1-benzofurans that is the 2,3-dihydroderivative of benzofuran.	1.96	1	0	1-benzofurans	metabolite
isomaltose [no description available]	2.02	1	0
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.	2.07	1	0	hydroxy monocarboxylic acid	plant metabolite
oxetane oxetane: structure. oxetane : A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.	1.96	1	0	oxetanes; saturated organic heteromonocyclic parent
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.04	1	0
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	3.24	5	0	thiazolidine
tetranitromethane [no description available]	2.02	1	0	organonitrogen compound
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	1.98	1	0	abietane diterpenoid; monocarboxylic acid	plant metabolite
psilocybin Psilocybin: The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being psilocin. (From Merck Index, 11th ed). psilocybin : A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional phosphoryloxy substituent at position 4. The major hallucinogenic alkaloid isolated from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms").	2.85	4	0	organic phosphate; tertiary amino compound; tryptamine alkaloid	fungal metabolite; hallucinogen; prodrug; serotonergic agonist
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	3.14	1	0
1,2-naphthoquinone naphthalene-1,2-dione: structure given in first source. 1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.	2.05	1	0	1,2-naphthoquinones	aryl hydrocarbon receptor agonist; carcinogenic agent
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	2.5	2	0	flavones	metabolite; nematicide
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	3.27	6	0	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
2,3-dimethylphenol [no description available]	2.31	1	0
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	2.11	1	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2.11	1	0	organic molecular entity
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.21	1	0	C-nitro compound; imidazoles	antitubercular agent
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	7.46	2	0	benzenes
3-ethylpyridine 3-ethylpyridine: structure given in Merck	2.03	1	0	pyridines
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	2.02	1	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
4-chloroacetanilide 4-chloroacetanilide : Acetamide substituted on nitrogen by a para-chlorophenyl group.	2	1	0	acetamides; monochlorobenzenes
4-iodophenol [no description available]	1.97	1	0	iodophenol
1-chloropropane 1-chloropropane: structure in first source	2	1	0
2,2,4-trimethylpentane 2,2,4-trimethylpentane: nephrotoxic. isooctane : An alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.	2.04	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
maleimide [no description available]	2.05	1	0	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
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.	2.53	2	0	dialdehyde	biomarker
n-butyl nitrite n-butyl nitrite: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1570	2.11	1	0	nitroso compound
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.	2.49	2	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	3.28	6	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
3-nitrophenol [no description available]	2.74	3	0	3-nitrophenols
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.	1.98	1	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
6-methylsalicylic acid 6-methylsalicylic acid: structure. 6-methylsalicylic acid : A monohydroxybenzoic acid that is salicylic acid in which the hydrogen ortho to the carboxylic acid group is substituted by a methyl group.	1.98	1	0	monohydroxybenzoic acid	Penicillium metabolite; plant metabolite
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	2.05	1	0	bis(azo) compound
1-acetylisatin 1-acetylisatin: structure in first source	2.03	1	0	indoledione
lactulose [no description available]	2.02	1	0	glycosylfructose	gastrointestinal drug; laxative
2,3-dichlorophenol dichlorophenol : Any chlorophenol carrying chloro substituents.	2	1	0
2,6-xylenol [no description available]	2.39	2	0	hydroxytoluene
2-methoxybenzoic acid O-methylsalicylic acid : A methoxybenzoic acid that is the methyl ether of salicylic acid.	2.02	1	0	methoxybenzoic acid	flavouring agent; non-steroidal anti-inflammatory drug
terpinolene [no description available]	2.41	2	0	p-menthadiene	insect repellent; plant metabolite; sedative; volatile oil component
diphenylamine Diphenylamine: In humans it may be irritating to mucous membranes. Methemoglobinemia has been produced experimentally. In veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. An indicator in tests for nitrate poisoning.. diphenylamine : An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.	2.03	1	0	aromatic amine; bridged diphenyl fungicide; secondary amino compound	antifungal agrochemical; antioxidant; carotogenesis inhibitor; EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor; ferroptosis inhibitor; radical scavenger
3,5-dichlorophenol 3,5-dichlorophenol : A dichlorophenol in which the two chloro substituents are located at positions 3 and 5.	2.02	1	0	dichlorophenol
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	2.02	1	0
methyl n-butyl ketone Methyl n-Butyl Ketone: An industrial solvent which causes nervous system degeneration. MBK is an acronym often used to refer to it.. hexanone : A ketone that is a hexane carrying an oxo substituent at unspecified position.	2.02	1	0	ketone
allyl acetate allyl acetate: potential fumigant for treating stored grains	2.15	1	0
1,3-cyclohexadiene 1,3-cyclohexadiene: structure given in first source	2.01	1	0	cyclohexadiene
vinyl bromide vinyl bromide: structure	2.08	1	0	bromoalkene; monohaloethene
n-methylhydroxylamine [no description available]	2	1	0
dimethylselenide dimethylselenide: RN given refers to unlabeled cpd. dimethylselenide : An organoselenium compound of two methyl groups covalently bound to a selenium.	2.04	1	0	organoselenium compound	bacterial xenobiotic metabolite; plant metabolite
1-methylcyclopropane 1-methylcyclopropane: do not confuse with MCP cpd (1-methylcyclopropene)	2.01	1	0
1-methylindole 1-methylindole: SKATOLE refers to 3-methylindole; RN given refers to parent cpd; structure. methylindole : Any member of the class of indoles carrying one or more methyl substituents.	2.94	4	0
1,3-indandione 1,3-indandione : A member of the class of indanones that is indane in which the hydrogens at positions 2 and 4 have been replaced by oxo groups.	2.03	1	0	aromatic ketone; beta-diketone; indanones
ferrocin c N-methyl-2-quinolone: structure in first source	2.04	1	0
5-methylisatin 5-methylisatin: structure in first source	2.03	1	0
2-cyanophenol 2-cyanophenol: structure in first source	2.02	1	0	benzenes; nitrile
n,n-dimethylbenzamide [no description available]	2.04	1	0
phenacylamine phenacylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6990	2.02	1	0	aromatic ketone
5-methylindole [no description available]	2.4	2	0
3-nitrobenzonitrile [no description available]	1.97	1	0
3-ethyltoluene [no description available]	2.02	1	0	toluenes
3-ethylphenol [no description available]	1.97	1	0	phenols
4,4'-bisphenol f 4,4'-bisphenol F: RN given refers to parent cpd. bisphenol F : A bisphenol that is methane in which two of the hydrogens have been replaced by 4-hydroxyphenyl groups.	2.05	1	0	bisphenol; diarylmethane	environmental food contaminant; xenoestrogen
4-ethyltoluene [no description available]	2.02	1	0
methyl butyrate [no description available]	2	1	0	fatty acid ester
dimethyl disulfide [no description available]	1.97	1	0	organic disulfide	xenobiotic metabolite
2,5-dimethylfuran 2,5-dimethylfuran: metabolite of n-hexane. 2,5-dimethylfuran : A member of the class of furans that is furan in which the hydrogens at positions 2 and 5 are replaced by methyl groups.	2.13	1	0	furans	antifungal agent; bacterial metabolite; fuel; fumigant; human urinary metabolite; Maillard reaction product; plant metabolite
2-hexanol hexan-2-ol : A hexanol in which the hydroxy group is at position 2.	1.98	1	0	hexanol; secondary alcohol	human metabolite; plant metabolite; semiochemical
2-nonanol 2-nonanol: from purple and yellow passion fruits. nonan-2-ol : A secondary alcohol that is nonane substituted by a hydroxy group at position 2.	1.98	1	0	nonanol; secondary alcohol	bacterial metabolite; flavouring agent; pheromone; plant metabolite; rat metabolite; volatile oil component
n-tetradecane tetradecane : A straight chain alkane consisting of 14 carbon atoms.	2.03	1	0	long-chain alkane	plant metabolite; volatile oil component
pentadecane pentadecane : A straight-chain alkane with 15 carbon atoms. It is a component of volatile oils isolated from plants species like Scandix balansae.	2.06	1	0	long-chain alkane	animal metabolite; plant metabolite; volatile oil component
2-pyrrolecarboxylic acid 2-pyrrolecarboxylic acid: hypocalcemic action; structure. pyrrole-2-carboxylic acid : A pyrrolecarboxylic acid that is 1H-pyrrole carrying a carboxy substituent at position 2.	2.03	1	0	pyrrolecarboxylic acid	plant metabolite
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	4.55	4	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
hadacidin hadacidin: inhibitor of AMP synthesis; RN given refers to parent cpd; structure. hadacidin : A monocarboxylic acid that is N-hydroxyglycine in which the hydrogen attached to the nitrogen is replaced by a formyl group. It was originally isolated from cultures of Penicillium frequentans.	3.12	1	0	aldehyde; monocarboxylic acid; N-hydroxy-alpha-amino-acid	antimicrobial agent; antineoplastic agent; Penicillium metabolite; teratogenic agent
methoxytryptophol [no description available]	1.94	1	0	indoles
4-cyanophenol 4-cyanophenol: reversible monoamine oxidase inhibitor	2.43	2	0	phenols	EC 1.4.3.4 (monoamine oxidase) inhibitor
2-hydroxy-5-nitrobenzyl bromide 2-Hydroxy-5-nitrobenzyl Bromide: A chemical reagent that reacts with and modifies chemically the tryptophan portion of protein molecules. Used for 'active site' enzyme studies and other protein studies. Sometimes referred to as Koshland's reagent.	2.02	1	0
triphenylphosphine oxide triphenylphosphine oxide: used in the extraction, separation & spectrophotometric determination of cadmium & mercury in environmental samples. triphenylphosphane oxide : A phosphine oxide in which the substituents on phosphorus are three phenyl groups.	2.04	1	0	phosphine oxide	NMR chemical shift reference compound
naphthyl acetate naphthyl acetate: do not confuse with naphthaleneacetic acid; acetic acid ester of naphthol	1.93	1	0
2-(2'-hydroxyphenyl)benzoxazole 2-(2'-hydroxyphenyl)benzoxazole: structure in first source. 2-(1,3-benzoxazol-2-yl)phenol : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazole substituted by a 2-hydroxyphenyl group at position 2.	2.17	1	0	1,3-benzoxazoles; phenols	geroprotector
ethyl n-alpha-acetyl-tyrosinate ethyl N-alpha-acetyl-tyrosinate: RN given refers to parent cpd. ethyl N-acetyl-L-tyrosinate : An L-tyrosine derivative that is the ethyl ester of N-acetyltyrosine.	1.96	1	0	acetamides; ethyl ester; L-tyrosine derivative; phenols
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.	2.31	1	0	lactam; N-alkylpyrrolidine; pyrrolidin-2-ones	polar aprotic solvent
4-phenylpyridine [no description available]	2.02	1	0	phenylpyridine
1,2,3,4-tetrahydrocarbazole 1,2,3,4-tetrahydrocarbazole: structure in first source	7.06	1	0
diphenyl sulfoxide diphenyl sulfoxide: electron acceptor for liver aldehyde oxidase	2.44	2	0	sulfoxide
2-phenylindole alpha-phenylindole: RN given refers to parent cpd	7.67	3	0	phenylindole
methidathion methidathion: widely used on citrus, tobacco, alfalfa, cotton, sorghum & several other crops	2.03	1	0	organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
azure a Azure A: RN given refers to chloride. azure A : An organic chloride salt having 3-amino-7-(dimethylamino)phenothiazin-5-ium as the counterion. It is used in making azure eosin stains for blood smear staining.	2.05	1	0
5-methoxyindole 5-methoxyindole: structure in first source	2.91	4	0	indoles
pyrrolnitrin Pyrrolnitrin: 3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole. Antifungal antibiotic isolated from Pseudomonas pyrrocinia. It is effective mainly against Trichophyton, Microsporium, Epidermophyton, and Penicillium.. pyrrolnitrin : A member of the class of pyrroles carrying chloro and 3-chloro-2-nitrophenyl substituents at positions 3 and 4 respectively.	1.99	1	0	alkaloid; C-nitro compound; monochlorobenzenes; pyrroles	antifungal drug; bacterial metabolite
ammonium bicarbonate ammonium bicarbonate: see also record for ammonium carbonate (di-NH4 salt)	2.06	1	0	organooxygen compound
acetylhydrazine acetylhydrazine: metabolite of isoniazid in animals and humans; RN given refers to parent cpd. acetohydrazide : A carbohydrazide that is hydrazine in which one of the hydrogens is replaced by an acetyl group.	2.63	2	0	carbohydrazide; carbohydrazonic acid	drug metabolite
phenylglyoxal [no description available]	2.04	1	0	phenylacetaldehydes
4-acetylpyridine [no description available]	2.04	1	0
methyl phenyl sulfoxide (methylsulfinyl)benzene : A sulfoxide resulting from the formal oxidation of the sulfur atom of thioanisole.	2.44	2	0	benzenes; sulfoxide
1,4-bis(3-indolyl)-2,3-diaza-1,3-butadiene 1,4-bis(3-indolyl)-2,3-diaza-1,3-butadiene: a fluoride probe; structure in first source	2.05	1	0
beta-pinene beta-pinene: alpha-pinene is also available. beta-pinene : An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.	1.98	1	0	pinene	plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.06	1	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
5-methyltryptamine 5-methyltryptamine: RN given refers to parent cpd	1.97	1	0	tryptamines
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.	7.48	2	0	organic cation	geroprotector; herbicide
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.07	1	0	quaternary ammonium ion
5-hydroxyindole [no description available]	3.74	11	0	hydroxyindoles	human metabolite
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	2.25	1	0	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
carsalam carsalam: structure given in first source	2.1	1	0	benzoxazine
decachlorobiphenyl decachlorobiphenyl: structure. decachlorobiphenyl : A polychlorobiphenyl that is biphenyl in which all of the hydrogens are replaced by chlorines.	2	1	0	pentachlorobenzenes; polychlorobiphenyl
n-methylisatin N-methylisatin: structure given in first source	2.03	1	0
gamma-glycidoxypropyltrimethoxysilane 3-glycidyloxypropyltrimethoxysilane: used to immobilize carbonic anhydrase into mesoporous supports; structure in first source	2.05	1	0
pontamine sky blue [no description available]	2.05	1	0
2-(2'-hydroxyphenyl)benzimidazole 2-(2'-hydroxyphenyl)benzimidazole: structure in first source	2.17	1	0
methional [no description available]	2.1	1	0	aliphatic sulfide	prostaglandin antagonist
1-octen-3-ol 1-octen-3-ol: main flavor component of mushrooms; RN given refers to cpd without isomeric designation; bait for insect vectors (tsetse, sandflies, mosquitoes). oct-1-en-3-ol : An alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-1-C-2. It is a major volatile compound present in many mushrooms and fungi.	3.02	4	0	alkenyl alcohol; medium-chain fatty alcohol	antimicrobial agent; fungal metabolite; insect attractant; volatile oil component
2-(2-hydroxyphenyl)benzothiazole 2-(1,3-benzothiazol-2-yl)phenol : A member of the class of benzothiazoles that is 1,3-benzothiazole substituted by a 2-hydroxyphenyl group at position 2.	2.17	1	0	benzothiazoles; phenols	geroprotector
mannose mannopyranose : The pyranose form of mannose.	1.99	1	0	D-aldohexose; D-mannose; mannopyranose	metabolite
5-methoxyindoleacetic acid 5-methoxyindoleacetic acid: serotonin metabolite. 5-methoxyindole-3-acetic acid : A member of the class of indole-3-acetic acids in which the hydrogen at position 5 of indole-3-acetic acid has been replaced by a methoxy group.	1.94	1	0	aromatic ether; indole-3-acetic acids	antibacterial agent; Brassica napus metabolite; carcinogenic agent; human urinary metabolite; marine xenobiotic metabolite; rat metabolite
dimethyl trisulfide [no description available]	3.05	4	0	organic trisulfide
bpmc BPMC: structure. fenobucarb : A carbamate ester obtained by the formal condensation of 2-sec-butylphenol with methylcarbamic acid.	2.03	1	0	carbamate ester	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; environmental contaminant; herbicide; insecticide
salithion salithion: causes irreversible ataxia in chicken, mice & sheep; structure in Pesticide Index, 5th ed, p.202	2.03	1	0	organic thiophosphate
azatadine azatadine: indulian (UD 21;71k) is dimaleate; do not confuse with AZACITIDINE. azatadine : A benzo[5,6]cyclohepta[1,2-b]pyridine having a 1-methylpiperidin-4-ylidene group at the 11-position.	2.02	1	0	benzocycloheptapyridine; tertiary amine	anti-allergic agent; H1-receptor antagonist
2-octanol 2-octanol: RN given refers to cpd without isomeric designation. octan-2-ol : An octanol carrying the hydroxy group at position 2.	1.98	1	0	octanol; secondary alcohol	plant metabolite; volatile oil component
dimethindene Dimethindene: A histamine H1 antagonist. It is used in hypersensitivity reactions, in rhinitis, for pruritus, and in some common cold remedies.	2.02	1	0	indene
olsalazine olsalazine: cpd with 2 salicylate molecules linked together by an azo bond. olsalazine : An azobenzene that consists of two molecules of 4-aminosalicylic acid joined by an azo linkage. A prodrug for mesalazine, an anti-inflammatory drug, it is used (as the disodium salt) in the treatment of inflammatory bowel disease.	2.02	1	0	azobenzenes; dicarboxylic acid	non-steroidal anti-inflammatory drug; prodrug
nsc 520594 [no description available]	1.93	1	0
3-acetylaminofluorene 3-acetylaminofluorene: non-carcinogenic structural isomer of carcinogen N-2-fluorenylacetamide	1.94	1	0
dysprosium Dysprosium: An element of the rare earth family that has the atomic symbol Dy, atomic number 66, and atomic weight 162.50. Dysprosium is a silvery metal used primarily in the form of various salts.	2.11	1	0	f-block element atom; lanthanoid atom
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	3.17	5	0	cobalt group element atom; platinum group metal atom
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	2.49	2	0	elemental mercury; zinc group element atom	neurotoxin
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.	5.06	38	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.	8.17	5	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	7.46	2	0	manganese group element atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	3.79	10	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	7.5	2	0	iron group element atom; platinum group metal atom
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	7.46	2	0	f-block element atom; lanthanoid atom
scandium Scandium: An element of the rare earth family of metals. It has the atomic symbol Sc, atomic number 21, and atomic weight 45.	2.03	1	0	d-block element atom; rare earth metal atom; scandium group element atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	7.45	2	0	copper group element atom; elemental silver	Escherichia coli metabolite
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.	3.15	5	0	titanium group element atom
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	7.15	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	3.69	9	0	copper group element atom; elemental gold
helium Helium: A noble gas with the atomic symbol He, atomic number 2, and atomic weight 4.003. It is a colorless, odorless, tasteless gas that is not combustible and does not support combustion. It was first detected in the sun and is now obtained from natural gas. Medically it is used as a diluent for other gases, being especially useful with oxygen in the treatment of certain cases of respiratory obstruction, and as a vehicle for general anesthetics.	2.11	1	0	monoatomic helium; noble gas atom; s-block element atom	food packaging gas
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	2.11	1	0	d-block element atom; rare earth metal atom; scandium group element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	8.01	4	0	titanium group element atom
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2	1	0	aluminium coordination entity	Lewis acid
titanium tetrachloride titanium tetrachloride: RN given refers to TiCl4	2.44	2	0
stannic chloride [no description available]	2	1	0
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	7.41	2	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	2.51	2	0	iron coordination entity	astringent; Lewis acid
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	2.57	2	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	1.99	1	0	chromium oxoanion; divalent inorganic anion	oxidising agent
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	2.25	1	0	metal sulfate	emetic; fertilizer; sensitiser
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	3.64	9	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	3.2	5	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	7.46	2	0	diatomic chlorine; gas molecular entity	bleaching agent
desmedipham desmedipham: structure. desmedipham : A carbamate ester that is phenylcarbamic acid in which the hydrogen of the hydroxy group has been replaced by a 3-[(ethoxycarbonyl)amino]phenyl group. It is an agrochemical used as a herbicide.	2	1	0	carbamate ester	agrochemical; environmental contaminant; herbicide; xenobiotic
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.41	2	0
poloxalene Poloxalene: A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.. pluronic : A triblock copolymer composed of a central hydrophobic chain of poly(propylene oxide) flanked by two hydrophilic chains of poly(ethylene oxide).	2.05	1	0	epoxide
vasotocin Vasotocin: A nonapeptide that contains the ring of OXYTOCIN and the side chain of ARG-VASOPRESSIN with the latter determining the specific recognition of hormone receptors. Vasotocin is the non-mammalian vasopressin-like hormone or antidiuretic hormone regulating water and salt metabolism.. vasotocin : A heterodetic cyclic peptide that is homologous to oxytocin and vasopressin. It is a pituitary hormone that acts as an endocrine regulator for water balance, osmotic homoeostasis and is involved in social and sexual behavior in non-mammalian vertebrates.	1.97	1	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	7.44	2	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
camphoroquinone camphoroquinone: a natural monoterpene, non-aromatic quinone; structure given in first source. bornane-2,3-dione : A bornane monoterpenoid that is bicyclo[2.2.1]heptane substituted by methyl groups at positions 1, 7 and 7 and oxo groups at positions 2 and 3.	1.97	1	0	bornane monoterpenoid; carbobicyclic compound
dimethonium dimethonium: RN given refers to unlabeled parent cpd	6.93	1	0
rhamnose [no description available]	2.02	1	0	L-rhamnose
sodium bichromate sodium bichromate: RN given refers to di-Na salt	1.99	1	0	inorganic sodium salt
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.	2.45	2	0	titanium oxides	food colouring
3-carene 3-carene: RN given refers to cpd without isomeric designation	1.98	1	0	monoterpene
sodium tungstate(vi) sodium tungstate(VI): inactivates molybdoenzymes in Anabaena; RN given refers to tungstic acid [H2WO4], di-Na salt. sodium tungstate : An inorganic sodium salt having tungstate as the counterion. Combines with hydrogen peroxide for the oxidation of secondary amines to nitrones.	2.06	1	0	inorganic sodium salt	reagent
apazone Apazone: An anti-inflammatory agent used in the treatment of rheumatoid arthritis. It also has uricosuric properties and has been used to treat gout.. apazone : A member of the class of benzotriazines that is 1,2-dihydro-1,2,4-benzotriazine bearing a dimethylamino substitutent at position 3 and a methyl substituent at position 7 and in which the nitrogens at positions 1 and 2 are both acylated by a carboxy group of propylmalonic acid.	2.02	1	0	benzotriazines	non-steroidal anti-inflammatory drug; uricosuric drug
menthone menthone : The trans-stereoisomer of p-menthan-3-one.. (-)-menthone : A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer).	2.43	2	0	menthone
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.76	3	0
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2.25	1	0	selegiline; terminal acetylenic compound	geroprotector
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.41	2	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
fluorides [no description available]	2.94	4	0	halide anion; monoatomic fluorine
acridine half-mustard acridine half-mustard: RN given refers to parent cpd. acridine half-mustard : A member of the class of aminoacridines that is acridine which is substituted by a methoxy group at position 2, chlorine at position 6, and a {3-[(2-chloroethyl)amino]propyl}amino group at position 9.	1.99	1	0	aminoacridines; aromatic ether; organochlorine compound; secondary amino compound	mutagen
2,4-dihydroxy-1,4-benzoxazin-3-one 2,4-dihydroxy-1,4-benzoxazin-3-one: structure in first source. DIBOA : A lactol that consists of 1,4-benzoxazine bearing two hydroxy substituents at positions 2 and 4 as well as a keto group at position 3.	1.99	1	0	benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; herbicide; phytotoxin; plant metabolite
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.	3.41	1	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
geosmin geosmin: earthy smelling cpd from sediment in Lake Biwa; structure. (-)-geosmin : The (-)-stereoisomer of geosmin, having 4S,4aS,8aR configuration.	2.13	1	0	geosmin
iodine [no description available]	3.5	8	0	halide anion; monoatomic iodine	human metabolite
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	4.57	25	0	benzenes; phenyl acetates
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.	2.75	3	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.	2.05	1	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
isopentyl alcohol isopentyl alcohol: RN given refers to unlabeled parent cpd. isoamylol : An primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group.	2.15	1	0	alkyl alcohol; primary alcohol; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite; xenobiotic metabolite
pyrrolidine [no description available]	2.04	1	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.47	2	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
nonanal nonanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism.	2.5	2	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human metabolite; plant metabolite
carbamide peroxide Carbamide Peroxide: A urea peroxide compound that is commonly used in tooth whitening agents; topical anti-infective agents, and earwax remover.. urea hydrogen peroxide : A mixture obtained by combining equimolar amounts of hydrogen peroxide and urea.	2.07	1	0	mixture	disinfectant; oxidising agent; reagent
chloroprene Chloroprene: Toxic, possibly carcinogenic, monomer of neoprene, a synthetic rubber; causes damage to skin, lungs, CNS, kidneys, liver, blood cells and fetuses. Synonym: 2-chlorobutadiene.	2.46	2	0	chloroolefin
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	2	1	0	acetamides; monocarboxylic acid amide	human metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	8.13	5	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
alkenes [no description available]	8.86	11	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.25	1	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
o,o-diisopropyl-s-benzylthiophosphate O,O-diisopropyl-S-benzylthiophosphate: structure. iprobenfos : An organic thiophosphate that is the S-benzyl O,O-diisopropyl ester of phosphorothioic acid. Used as a rice fungicide to control leaf and ear blast, stem rot and sheath blight.	2.03	1	0	organic thiophosphate	antifungal agrochemical; phospholipid biosynthesis inhibitor
adenosine diphosphate ribose Adenosine Diphosphate Ribose: An ester formed between the aldehydic carbon of RIBOSE and the terminal phosphate of ADENOSINE DIPHOSPHATE. It is produced by the hydrolysis of nicotinamide-adenine dinucleotide (NAD) by a variety of enzymes, some of which transfer an ADP-ribosyl group to target proteins.	2.11	1	0	ADP-sugar	Escherichia coli metabolite; mouse metabolite
timolol (S)-timolol (anhydrous) : The (S)-(-) (more active) enantiomer of timolol. A beta-adrenergic antagonist, both the hemihydrate and the maleate salt are used in the mangement of glaucoma, hypertension, angina pectoris and myocardial infarction, and for the prevention of migraine.	2.02	1	0	timolol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist
benthiocarb Saturn: The sixth planet in order from the sun. It is one of the five outer planets of the solar system. Its twelve natural satellites include Phoebe and Titan.	2.03	1	0	monochlorobenzenes; monothiocarbamic ester
7-ethoxycoumarin 7-ethoxycoumarin : A member of the class of coumarins that is umbelliferone in which the hydroxy group at position 7 is replaced by an ethoxy group.	2.05	1	0	aromatic ether; coumarins
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.05	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
substance p [no description available]	1.93	1	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
penbutolol Penbutolol: A nonselective beta-blocker used as an antihypertensive and an antianginal agent.	2.02	1	0	ethanolamines
5-Methoxyisatin [no description available]	2.03	1	0	indoles	anticoronaviral agent
methyldopa Methyldopa: An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.. alpha-methyl-L-dopa : A derivative of L-tyrosine having a methyl group at the alpha-position and an additional hydroxy group at the 3-position on the phenyl ring.	6.93	1	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	alpha-adrenergic agonist; antihypertensive agent; hapten; peripheral nervous system drug; sympatholytic agent
sq-11725 Nadolol: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for MIGRAINE DISORDERS and for tremor.. nadolol : Nadolol is a diastereoisomeric mixture consisting of equimolar amounts of the four possible 2,3-cis-isomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol.	2.03	1	0
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	2.43	2	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	2	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
foscarnet sodium trisodium phosphonoformate : The trisodium salt of phosphonoformic acid. It is used as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.	2.02	1	0	one-carbon compound; organic sodium salt	antiviral drug
indoxyl 3-hydroxyindole: inhibits amyloid fibril formation; structure in first source	8.45	8	0	heteroaryl hydroxy compound; hydroxyindoles
fenoxycarb fenoxycarb: used against mosquitoes (Diptera:Culicidae); structure given in first source. fenoxycarb : A carbamate ester that is the O-ethyl carbamate of 2-(4-phenoxyphenoxy)ethylamine.	2	1	0	aromatic ether; carbamate ester	environmental contaminant; insecticide; juvenile hormone mimic; xenobiotic
cicletanine [no description available]	2.02	1	0	organochlorine compound
temelastine [no description available]	2.02	1	0	pyrimidone
imiquimod Imiquimod: A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.. imiquimod : An imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.	2.58	2	0	imidazoquinoline	antineoplastic agent; interferon inducer
sertindole sertindole : A phenylindole that is 1H-indole which is substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-oxoimidazolidin-1-yl)ethyl group.	6.99	1	0	heteroarylpiperidine; imidazolidinone; organochlorine compound; organofluorine compound; phenylindole	alpha-adrenergic antagonist; H1-receptor antagonist; second generation antipsychotic; serotonergic antagonist
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	7.08	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	1.97	1	0
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.05	1	0	one-carbon compound; perfluoroalkanesulfonic acid
4-ethylguaiacol 4-ethylguaiacol: a constituent of wood creosote; suppresses intestinal smooth muscle contraction	2.31	1	0	methoxybenzenes; phenols
isothiocyanic acid [no description available]	2.31	1	0	hydracid; one-carbon compound
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.7	3	0	D-glucopyranose	epitope; mouse metabolite
n-methylnicotinamide N-methylnicotinamide: structure. N-methylnicotinamide : A pyridinecarboxamide that is nicotinamide in which one of the amide hydrogens is substituted by a methyl group.	6.92	1	0	pyridinecarboxamide	metabolite
norharman norharman: RN given refers to parent cpd. beta-carboline : The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.	2.03	1	0	beta-carbolines; mancude organic heterotricyclic parent	fungal metabolite; marine metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.05	1	0	organic bromide salt	colorimetric reagent; dye
thionine thionine: do not confuse with the thionins which is a class of polypeptides; RN above is for the chloride;. thionine : An organic chloride salt composed of 3,7-diaminophenothiazin-5-ium and chloride ions in a 1:1 ratio. A strongly metachromatic dye, useful for the staining of acid mucopolysaccharides. It is also a common nuclear stain and can be used for the demonstration of Nissl substance in nerve cells of the CNS.	2.31	1	0
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.	2.05	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
phosphoramidic acid phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds	2.25	1	0	phosphoric acid derivative
lissamine rhodamine b lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt	2.17	1	0
neocuproine neocuproine: Spectrophotometric determination of copper and ultramicro blood sugar determinations; structure; RN given refers to parent cpd. neocuproine : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.	2.05	1	0	phenanthrolines	chelator; copper chelator
phenylethane boronic acid [no description available]	6.96	1	0
fenclofenac fenclofenac: RN given refers to parent cpd	2	1	0	aromatic ether
valerophenone [no description available]	2.48	2	0	aromatic ketone	plant metabolite; volatile oil component
lumiflavin lumiflavin : A compound showing yellow-green fluorescence, formed by a photolysis of riboflavin in alkaline solution.	7.39	2	0	flavin
naphthol as naphthol AS: azo dye coupling component implicated in occupational pigmented contact dermatitis; RN given refers to unlabeled parent cpd; structure	1.93	1	0
4-phenylbenzoic acid 4-phenylbenzoic acid: RN given refers to 4-carboxylic cpd	3.12	1	0
1,2,4-trimethoxybenzene 1,2,4-trimethoxybenzene: a volatile organic compound	2.03	1	0	methoxybenzenes
1,7-phenanthroline [no description available]	2.05	1	0	phenanthroline
anthranil 2,1-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,2-oxazole ring across positions 3 and 4.	2.04	1	0	2,1-benzoxazoles; mancude organic heterobicyclic parent
1h-imidazo(4,5-b)pyridine 1H-imidazo(4,5-b)pyridine: structure given in first source. 4-azabenzimidazole : The [4,5-b]-fused isomer of imidazopyridine.	2.21	1	0	imidazopyridine
benzo-1,2,3-thiadiazole [no description available]	2.13	1	0
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	8.94	12	0	1,2,3-triazole
triflic anhydride triflic anhydride: structure in first source	2.06	1	0	organosulfonic anhydride
5-fluoroindole [no description available]	2.01	1	0	fluoroindole
4-trifluoromethylphenol 4-trifluoromethylphenol: metabolite of fluoxetine; structure in first source. 4-(trifluoromethyl)phenol : A member of the class of (trifluoromethyl)benzenes that is p-cresol in which the methyl group is perfluorinated. It is a metabolite of the drug fluoxetine.	2.02	1	0	(trifluoromethyl)benzenes; phenols	drug metabolite; marine xenobiotic metabolite
4-chromanone [no description available]	2.31	1	0	chromones
coumalic acid coumalic acid: RN given for parent cpd	2.31	1	0	pyranone
n-phenylphthalimide N-phenylphthalimide: structure given in first source	2.03	1	0
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2.35	2	0	anthocyanidin chloride
brinzolamide brinzolamide: an antiglaucoma agent	3.41	1	0	sulfonamide; thienothiazine	antiglaucoma drug; EC 4.2.1.1 (carbonic anhydrase) inhibitor
2,3-dimethylhydroquinone 2,3-dimethylhydroquinone: structure in first source	2.17	1	0
4,4'-Dihydroxybenzophenone [no description available]	2.05	1	0	benzophenones
2-phenylimidazole [no description available]	2	1	0
9-methyladenine 9-methyladenine : Adenine substituted with a methyl group at position N-9.	1.96	1	0	methyladenine	metabolite
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	2.78	3	0	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
2,2'-Dihydroxybenzophenone [no description available]	2.05	1	0	benzophenones
4-methoxybenzonitrile 4-methoxybenzonitrile: RN given refers to parent cpd	2.04	1	0
4-ethylcatechol 4-ethylcatechol: structure in first source	2.31	1	0	catechols
2,3,4-trihydroxbenzophenone 2,3,4-trihydroxbenzophenone : A benzenetriol that is benzophenone in which one of the phenyl groups is substituted by hydroxy groups at positions 2, 3, and 4. It is a redox mediator.	2.05	1	0	benzenetriol; hydroxybenzophenone	drug metabolite; EC 1.14.18.1 (tyrosinase) inhibitor; human urinary metabolite; quorum sensing inhibitor; rat metabolite
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	2.05	1	0	catechin; polyphenol	antioxidant
polygodial [no description available]	1.98	1	0	aldehyde
nagilactone c nagilactone C: norditerpene lactone isolated from leaves of Podocarpus; structure	1.98	1	0
xanthydrol [no description available]	6.93	1	0
serpentine (alkaloid) serpentine (alkaloid): do not confuse with mineral serpentine; RN given refers to (19alpha)-isomer; structure	2.02	1	0	carboxylic ester; iminium betaine; indole alkaloid; quinolizines; zwitterion
tosyllysine chloromethyl ketone Tosyllysine Chloromethyl Ketone: An inhibitor of SERINE ENDOPEPTIDASES. Acts as an alkylating agent and is known to interfere with the translation process.	1.96	1	0	sulfonic acid derivative
strychnine n-oxide strychnine N-oxide: structure in first source. strychnine N-oxide : A tertiary amine oxide resulting from the oxidation of the non-acylated nitrogen of strychnine. It is a metabolite of strychnine.	2.13	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound; tertiary amine oxide	plant metabolite
2,6-difluoropyridine [no description available]	2.04	1	0
1,1,1-trifluoro-2,4-pentanedione 1,1,1-trifluoro-2,4-pentanedione: structure in first source	2.08	1	0
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.03	1	0	carbamate ester; oxazolidinone	metabolite
4-hydroxyindole hydroxyindoles : Any member of the class of indoles carrying at least one hydroxy group.	2.49	2	0	hydroxyindoles; phenols
2,2'-bisphenol f 2,2'-bisphenol F: contact allergen; structure given in first source	2.11	1	0	diarylmethane
5-hydroxy-2-oxindole 5-hydroxyoxindole: Monoamine Oxidase Inhibitor; structure in first source	2.04	1	0
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	2.04	1	0
5-aminoindole 5-aminoindole: structure in first source. 1H-indol-5-amine : An indolamine carrying an amino group at position 5.	7.36	2	0	indolamine
1,2-dithiolane 1,2-dithiolane: structure in first source	2.08	1	0	dithiolane
4-nitrophenylglucuronide 4-nitrophenyl beta-D-glucuronide : A beta-D-glucosiduronic acid having a 4-nitrophenyl substituent at the anomeric position.	1.96	1	0	beta-D-glucosiduronic acid; C-nitro compound	chromogenic compound
3-(trimethoxysilyl)propylamine 3-(trimethoxysilyl)propylamine: reagent for making polymers; structure in first source	2.05	1	0
1,2-dibenzoyl-tert-butylhydrazine 1,2-dibenzoyl-tert-butylhydrazine: structure given in first source	2.03	1	0	bisacylhydrazine insecticide
5-bromoindoxyl acetate 5-bromoindoxyl acetate: substrate for non-specific esterase	2.62	3	0
6-chloroindole [no description available]	2.04	1	0	indoles
5-Chloro-1H-indole-2,3-dione [no description available]	2.03	1	0	indoles	anticoronaviral agent
5-iodoisatin 5-iodoisatin: structure in first source	2.03	1	0	indoles	anticoronaviral agent
n-acetyltyrosine, (dl)-isomer N-acetyltyrosine: RN given refers to (L)-isomer. N-acetyltyrosine : An N-acetyl-amino acid that is tyrosine with an amine hydrogen substituted by an acetyl group.	2.03	1	0	N-acetyl-amino acid; phenols; tyrosine derivative	human urinary metabolite
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	3.09	5	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
4-chloroindole [no description available]	2.74	3	0
aucubin [no description available]	1.94	1	0	organic molecular entity	metabolite
4-methylumbelliferyl glucuronide 4-methylumbelliferone beta-D-glucuronide : A beta-D-glucosiduronic acid having a 4-methylumbelliferyl substituent at the anomeric position. A hyaluronan synthesis inhibitor, it is anti-tumourigenic for various malignant tumours.	2.38	2	0	beta-D-glucosiduronic acid; coumarins; monosaccharide derivative	antineoplastic agent; chromogenic compound; hyaluronan synthesis inhibitor
coronatine coronatine: consists of a coronafacic acid joined by an amide bond to coronamic acid by coronafacate ligase; phytotoxin produced by Pseudomonas syringae; RN given refers to (3aS-(3aalpha,4(1R,2R),6beta,7alpha))-isomer;	2.07	1	0	N-acyl-amino acid
tebufenozide tebufenozide: structure given in first source. tebufenozide : A carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by tert-butyl, 3,5-dimethylbenzoyl and 4-ethylbenzoyl groups respectively. It is an insecticide used widely against caterpillars.	2.03	1	0	carbohydrazide	ecdysone agonist; environmental contaminant; xenobiotic
totarol totarol: structure given in first source; isolated from the bark of Podocarpus nagi	1.98	1	0	diterpenoid	metabolite
5-methyltryptophan 5-methyltryptophan: RN given refers to cpd without isomeric designation. 5-methyltryptophan : A tryptophan derivative that is tryptophan substituted by a methyl group at position 5 of the indole ring.	2.34	2	0	non-proteinogenic alpha-amino acid; tryptophan derivative
quebrachamine quebrachamine: an indole alkaloid; isolated from Aspidosperma tree; structure given in first source	1.93	1	0	alkaloid
cularine cularine: isoquinoline alkaloid from Fumariaceae family; structure given in first source	6.93	1	0	alkaloid
n-acetylphenylalanine ethyl ester N-acetylphenylalanine ethyl ester: RN given refers to (L)-isomer	1.96	1	0
n-acetyltryptophanamide [no description available]	2.93	4	0	acetamides; L-tryptophan derivative; primary carboxamide; secondary carboxamide
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.	2.49	2	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.	2.71	3	0	D-glucuronic acid	algal metabolite
6-fluorotryptophan 6-fluorotryptophan: an inhibitor of serotonin synthesis; RN given refers to parent cpd without isomeric designation	2.07	1	0	indolyl carboxylic acid
6-bromoisatin 6-bromoisatin: anticancer compound from Dicathais orbita; structure in first source	2.08	1	0
benzo(b)thiophene-2-carboxylic acid benzo(b)thiophene-2-carboxylic acid: for prevention of osteoporosis; structure given in first source	3.12	1	0
pimprinine pimprinine: structure	2.07	1	0
nitrophenylgalactosides Nitrophenylgalactosides: Includes ortho-, meta-, and para-nitrophenylgalactosides.. 2-nitrophenyl beta-D-galactoside : A beta-D-galactoside having a 2-nitrophenyl substituent at the anomeric position.	2.02	1	0	beta-D-galactoside; C-nitro compound	chromogenic compound
loliolide loliolide: RN given refers to (6S-cis)-isomer	2.31	1	0	benzofurans	metabolite
4-fluorotryptophan 4-fluorotryptophan: RN given refers to cpd without isomeric designation	2.07	1	0
cinchonidine cinchonidine: has antimalarial activity; diastereoisomer of cinchonine with distinct physiochemical properties; RN given refers to parent cpd(8alpha,9R)-isomer. cinchonidine : 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	2.17	1	0	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
bis(i,i-trifluoroacetoxy)iodobenzene phenyliodine(III) bis(trifluoroacetate): structure in first source	2.21	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	3.12	5	0	cobalt group element atom; metal allergen	micronutrient
hydrogen sulfite [no description available]	1.93	1	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	2.84	4	0
1,4-dihydropyridine [no description available]	7.11	1	0
propidium iodide [no description available]	3.12	1	0	organic iodide salt
paxilline paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.	2.46	2	0	diterpene alkaloid; enone; organic heterohexacyclic compound; terpenoid indole alkaloid; tertiary alcohol	anticonvulsant; Aspergillus metabolite; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor; genotoxin; geroprotector; mycotoxin; Penicillium metabolite; potassium channel blocker
methoxyfenozide methoxyfenozide: structure in first source. methoxyfenozide : A carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by 3-methoxy-2-methylbenzoyl, 3,5-dimethylbenzoyl, and tert-butyl groups respectively.	2.03	1	0	carbohydrazide; monomethoxybenzene	environmental contaminant; insecticide; xenobiotic
fumitremorgin a Fumitremorgin A: isolated from fungus Aspergillus fumigatus; structure given in first source; RN given refers to (5R-(5alpha,10alpha,10aalpha,14aalpha,15balpha))-isomer. fumitremorgin A : An organic heterohexacyclic compound that is a mycotoxic indole alkaloid obtained by prenylation of the 10-hydroxy group of verruculogen.	2.11	1	0	aromatic ether; diol; indole alkaloid; organic heterohexacyclic compound; organic peroxide	mycotoxin
tryptoline tryptoline: neurotoxic factor that may be involved in development of Parkinson's disease; enzymatic prep from human brain converts tryptamine to tryptoline; RN given refers to parent cpd; structure	2.17	1	0	beta-carbolines
1-ethyl-2-pyrrolidinylmethyl-alpha-phenylcyclopentylglycolate, 1-ethyl-3-piperidyl-alpha-phenylcyclopentylglycolate drug combination 1-ethyl-2-pyrrolidinylmethyl-alpha-phenylcyclopentylglycolate, 1-ethyl-3-piperidyl-alpha-phenylcyclopentylglycolate drug combination: contains 70% 1-ethyl-2-pyrrolidinylmethyl-alpha-phenylcyclopentylglycolate & 30% 1-ethyl-3-piperidyl-alpha-phenylcyclopentylglycolate	3.03	1	0
polyterephthalic acid anhydride [no description available]	2.15	1	0
5,6-dihydroxyindole [no description available]	2.1	1	0	dihydroxyindole	mouse metabolite
rh-0345 N-4-chlorobenzoyl-N'-benzoyl-N'-tert-butylhydrazine: structure in first source	2.03	1	0	bisacylhydrazine insecticide; monochlorobenzenes
ici 198615 ICI 198615: an LTD4 receptor antagonist; SRS-A antagonist; structure given in first source	1.97	1	0
paliperidone 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one : A member of the class of pyridopyrimidines that is 9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.. paliperidone : A racemate comprising equimolar amounts of (R)- and (S)-paliperidone. Paliperidone is the primary active metabolite of the older antipsychotic risperidone and is used for treatment of schizophrenia.	2.04	1	0	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine; secondary alcohol
duocarmycin sa duocarmycin SA: structure similar to CC-1065 and yatakemycin, composed of a pyrrolo-indole plus an indole; isolated from Streptomyces	2.17	1	0
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.	2.05	1	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
maculosin maculosin: RN refers to (3S-trans)-isomer; isolated from Alternaria alternata; structure given in first source. maculosin : A homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages.	2.07	1	0	dipeptide; homodetic cyclic peptide; phenols; pyrrolopyrazine	metabolite
tryptophan methyl ester tryptophan methyl ester: RN given refers to parent cpd(DL)-isomer	3.06	5	0
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	3.31	6	0	carbene; methanediyl
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.21	1	0	nitrogen oxoacid
gefitinib [no description available]	2.17	1	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
2-nitrophenylgalactoside 2-nitrophenylgalactoside: RN given refers to cpd without isomeric designation	2.02	1	0
5,5'-bis(8-(phenylamino)-1-naphthalenesulfonate) [no description available]	2.05	1	0
dehydroalanine 2-ammonioprop-2-enoate : An amino acid zwitterion resulting from a transfer of a proton from the carboxy group to the amino group of 2-aminoacrylic acid.. 2-aminoacrylic acid : A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.	2.41	1	0	2,3-dehydroamino acid; alpha,beta-unsaturated monocarboxylic acid; amino acid zwitterion; enamine; non-proteinogenic alpha-amino acid	alkylating agent; human metabolite; mouse metabolite
5'-deoxy-5'-(isobutylthio)-3-deazaadenosine 5'-deoxy-5'-(isobutylthio)-3-deazaadenosine: analog of S-adenosylhomocysteine; structure	1.96	1	0
yuehchukene yuehchukene: anti-implantation indole alkaloid from roots of Murraya paniculata; RN given refers to (6alpha,6aalpha,10aalpha)-(+-)-isomer; structure given in first source	6.98	1	0
estrone-3-o-sulfamate estrone-3-O-sulfamate: a steroid sulfatase inhibitor	2.07	1	0
planinin planinin: from Zanthoxylum planispinum; structure given in first source	2.08	1	0	lignan
l 663581 L 663581: structure given in first source; partial agonist at the benzodiazepine receptor	2.04	1	0
4b,5,9b,10-tetrahydroindeno(1,2-b)indole 4b,5,9b,10-tetrahydroindeno(1,2-b)indole: RN refers to (cis)-isomer; structure given in first source	2.05	1	0
safinamide safinamide: short-acting inhibitor of MOA-B; FCE 26743 is (S)-isomer, FCE 28073 is (R)-isomer; structure in first source	2.25	1	0	amino acid amide
xylose xylopyranose: structure in first source	1.97	1	0	D-xylose
bicyclo(3.3.1)nonane bicyclo(3.3.1)nonane: structure in first source	2.06	1	0
sperm motility inhibitor 2 [no description available]	2.46	2	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.99	4	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
benzoyl l-arginine methyl ester benzoyl L-arginine methyl ester: RN given refers to (L-Arg)-isomer	1.96	1	0
prolyl-tyrosine prolyl-tyrosine: structure given in first source. Pro-Tyr : A dipeptide formed from L-proline and L-tyrosine residues.	2.07	1	0	dipeptide	metabolite
hyoscyamine Hyoscyamine: The 3(S)-endo isomer of atropine.. (S)-atropine : An atropine with a 2S-configuration.	1.95	1	0	tropane alkaloid
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.	2.71	3	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
thionium [no description available]	7.06	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.83	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.	2.4	2	0	camphor
indium trichloride indium trichloride: RN given refers to parent cpd	2.05	1	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	2.06	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
allysine L-allysine : An optically active form of allysine having L-configuration.	2.21	1	0	allysine; amino acid zwitterion; aminoadipate semialdehyde; non-proteinogenic L-alpha-amino acid	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chrysamine g chrysamine G: structure given in first source; RN refers to disodium salt	2.05	1	0
zinc hematoporphyrin [no description available]	2.06	1	0
asenapine asenapine : A racemate consisting of equal amounts of (R,R)- and (S,S)-asenapine. Used as its maleate salt for the acute treatment of schizophrenia and acute treatment of manic or mixed episodes associated with bipolar I disorder with or without psychotic features.. (S,S)-asenapine : A 5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole in which both of the stereocentres have S configuration.	2.04	1	0	5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole
homochelidonine homochelidonine: structure in first source	2.25	1	0	benzophenanthridine alkaloid
dihydrocorynantheol dihydrocorynantheol: alkaloid from Mitragyna species; isomer of corynantheidol;	2.03	1	0
org 4428 [no description available]	2.04	1	0
anacardic acid anacardic acid: isolated from Anacardium occidentale; monophenol monooxygenase inhibitor. anacardic acid : A hydroxybenzoic acid that is salicylic acid substituted by a pentadecyl group at position 6. It is a major component of cashew nut shell liquid and exhibits an extensive range of bioactivities.	1.98	1	0	hydroxy monocarboxylic acid; hydroxybenzoic acid	anti-inflammatory agent; antibacterial agent; anticoronaviral agent; apoptosis inducer; EC 2.3.1.48 (histone acetyltransferase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; neuroprotective agent; plant metabolite
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2	1	0
6,6'-dibromoindigo 6,6'-dibromoindigo: structure in first source	2.21	1	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.77	3	0	divalent inorganic anion; phosphite ion
brevianamide f brevianamide F: isolated from the endophyte from Aspergillus fumigatus associated with Melia azedarach L that could be used to develop a natural eco-friendly herbicide.structure in first source. brevianamide F : A pyrrolopyrazine that is hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tryptophan and L-proline).	2.13	1	0	dipeptide; indoles; pyrrolopyrazine	metabolite
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.	2.06	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
chlorite [no description available]	3.4	1	1	chlorine oxoanion; monovalent inorganic anion
chelidonine chelidonine: benzophenanthridine derived from scoulerine from Chelidonium majus; RN given refers to parent cpd (chelidonine, (5bR-(5balpha,6beta,12alpha))-isomer)	2.25	1	0	alkaloid antibiotic; alkaloid fundamental parent; benzophenanthridine alkaloid
roxindole [no description available]	2.02	1	0	indoles	alpha-adrenergic antagonist; serotonergic drug
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.	7.71	3	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.	1.98	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
erythritol [no description available]	2.05	1	0	butane-1,2,3,4-tetrol	antioxidant; human metabolite; plant metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	2.37	2	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
cortisone [no description available]	2.36	2	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
5-Fluoroisatin [no description available]	2.03	1	0	indoles	anticoronaviral agent
uleine uleine: from the bark of Plumeria lancifolia; structure in first source	7.06	1	0
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	5.24	15	0
2-amino-3,3-dimethylbutanoic acid tert-butylglycine : A glycine derivative that is glycine with a tertiary butyl group at position 2.	2.13	1	0	non-proteinogenic alpha-amino acid	metabolite
wortmannin [no description available]	2.15	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
ibogaine Ibogaine: One of several indole alkaloids extracted from Tabernanthe iboga, Baill. It has a complex pharmacological profile, and interacts with multiple systems of neurotransmission. Ibogaine has psychoactive properties and appears to modulate tolerance to opiates.. ibogaine : An organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group.	7.64	3	0
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	3.67	10	0	gamma-lactam; indolinone
2,4-diaminopteridine 2,4-diaminopteridine: structure in first source	2	1	0
indole-3-acetonitrile indole-3-acetonitrile: occurs in edible cruciferous vegetables. indole-3-acetonitrile : A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.	3.31	6	0	indoles; nitrile	auxin; human xenobiotic metabolite; plant hormone; plant metabolite
trimethoprim, sulfamethoxazole drug combination Trimethoprim, Sulfamethoxazole Drug Combination: A drug combination with broad-spectrum antibacterial activity against both gram-positive and gram-negative organisms. It is effective in the treatment of many infections, including PNEUMOCYSTIS PNEUMONIA in AIDS.. co-trimoxazole : A two-component mixture comprising trimethoprim and sulfamethoxazole.	2.05	1	0
harmicine harmicine: structure in first source	2.11	1	0
diazonamide a diazonamide A: structure in first source	2.07	1	0
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	2.11	1	0
permanganate [no description available]	7.41	1	0	manganese oxoacid
mbx 1066 MBX 1066: structure in first source	7.08	1	0
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.15	1	0
raffinose Raffinose: A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal.. raffinose : A trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 1<->2 glycosidic linkages, respectively.	2.02	1	0	raffinose family oligosaccharide; trisaccharide	mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.05	1	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.	1.93	1	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
tryptophanamide tryptophanamide: used as inhibitor of chymotrypsin; RN given refers to cpd with unspecified isomeric designation. L-tryptophanamide : An amino acid amide that is the carboxamide of L-tryptophan.	2.03	1	0	amino acid amide; tryptophan derivative	human metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	2.05	1	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
salicin [no description available]	1.97	1	0	aromatic primary alcohol; aryl beta-D-glucoside; benzyl alcohols	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.05	1	0	taxifolin	metabolite
isomaltulose 6-O-alpha-D-glucopyranosyl-D-fructofuranose : A glycosylfructose that is D-fructofuranose attached to a alpha-D-glucopyranosyl unit at position 6 via a glycosidic linkage. It is found in honey and sugarcane.	2.02	1	0	glycosylfructose	animal metabolite; plant metabolite; sweetening agent
tosylphenylalanyl chloromethyl ketone Tosylphenylalanyl Chloromethyl Ketone: An inhibitor of Serine Endopeptidases. Acts as alkylating agent and is known to interfere with the translation process.. N-tosyl-L-phenylalanyl chloromethyl ketone : The N-tosyl derivative of L-phenylalanyl chloromethyl ketone.	1.96	1	0	alpha-chloroketone; sulfonamide	alkylating agent; serine proteinase inhibitor
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	1.96	1	0	tartaric acid	Escherichia coli metabolite
n'-formylkynurenine N'-formylkynurenine: a photochemical breakdown product of tryptophan in proteins; RN given refers to parent cpd without isomeric designation	2.05	1	0	amino acid zwitterion; N-formylkynurenine; non-proteinogenic amino acid derivative; non-proteinogenic L-alpha-amino acid	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cortodoxone Cortodoxone: 17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.. 11-deoxycortisol : A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.	2.02	1	0	deoxycortisol; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
(+)-limonene (4R)-limonene : An optically active form of limonene having (4R)-configuration.	2.4	2	0	limonene	plant metabolite
fructans (2->6)-beta-D-fructan : A fructan compound consisting of repeating (2->6)-beta-linked fructofuranose units.	2.05	1	0
cellulase Cellulase: An endocellulase with specificity for the hydrolysis of 1,4-beta-glucosidic linkages in CELLULOSE, lichenin, and cereal beta-glucans.. beta-cellotriose : A cellotriose with a beta-configuration at the anomeric position.	2.02	1	0	cellotriose
(+)-delta-cadinene delta-cadinene: has antineoplastic activity; structure in first source. delta-cadinene : A member of the cadinene family of sesquiterpenes in which the double bonds are located at the 4-4a and 7-8 positions, and in which the isopropyl group at position 1 is cis to the hydrogen at the adjacent bridgehead carbon (position 8a).. (+)-delta-cadinene : A member of the cadinene family of sesquiterpenes in which the double bonds are located at the 4-4a and 7-8 positions, and in which the isopropyl group at position 1 is cis to the hydrogen at the adjacent bridgehead carbon (the 1S,8aR-enantiomer).	1.98	1	0	cadinene; delta-cadinene
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.	3.13	5	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	2.31	1	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2.46	2	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	6.98	1	0	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
miglitol [no description available]	3.41	1	0	piperidines
indican [no description available]	11.16	16	0	beta-D-glucoside; exopolysaccharide; indolyl carbohydrate
brucine brucine: was heading 1991-94 (see under STRYCHNINE 1975-90); DIMETHOXYSTRYCHNINE was see BRUCINE 1975-94; use STRYCHNINE to search BRUCINE 1975-94; very toxic alkaloid from Nux vomica similar to strychnine; used as reagent in analytical chemistry; was MH 1991-94	7.1	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.08	1	0
1-alpha-terpineol (S)-(-)-alpha-terpineol : The (S)-enantiomer of alpha-terpineol.	1.98	1	0	alpha-terpineol	plant metabolite
2-c-methylerythritol 4-phosphate 2-C-methylerythritol 4-phosphate: structure in first source	2.05	1	0	tetritol phosphate	Escherichia coli metabolite
ao 128 AO 128: alpha-glucosidase inhibitor; structure given in first source	3.41	1	0	organic molecular entity
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.52	2	0	cyclodextrin
indoleglycerol phosphate indoleglycerol phosphate: inducer of tryptophan synthase. (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate : The (1S,2R)-diastereomer of 1-C-(indol-3-yl)glycerol 3-phosphate.	3.78	11	0	1-C-(indol-3-yl)glycerol 3-phosphate
ergosterol [no description available]	7.1	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
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.	2.08	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
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.	1.99	1	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	1.98	1	0	farnesol	plant metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.05	1	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	3.06	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant 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.	2.74	3	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.1	1	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.44	2	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	2.54	2	0	D-galactopyranuronic acid
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.66	3	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	2	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
gs 4071 GS 4071: The acid form.. oseltamivir acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza.	3.12	1	0	acetate ester; amino acid; cyclohexenecarboxylic acid; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; marine xenobiotic metabolite
imidazolidines [no description available]	2.07	1	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
laminaran laminaran: beta-1,3-glucan	2.13	1	0
4'-azidocytidine 4'-azidocytidine: antiviral; structure in first source	2.04	1	0	N-glycosyl compound
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).	2.01	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
bms-488043 BMS-488043: anti-HIV agent	3.51	1	0
isoxanthohumol isoxanthohumol: structure in first source	2.31	1	0	flavanones
potassium thiocyanate potassium thiocyanate: RN given refers to cpd with MF of K-CHNS. potassium thiocyanate : A potassium salt which is the monopotassium salt of thiocyanic acid.	6.93	1	0	potassium salt
6-hydroxyindole 6-hydroxyindole: structure in first source	7.68	3	0
alpha-asarone asarone: structure in Merck Index, 9th ed, #847. asarone : A phenylpropanoid that is benzene substituted by methoxy groups at positions 1, 2 and 4 and a propen-1-yl group at position 5. It has been isolated from Acorus.. alpha-asarone : The trans-isomer of asarone.	1.98	1	0	asarone	anticonvulsant; GABA modulator
camalexin camalexin : An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group.	2.74	3	0	1,3-thiazoles; indole phytoalexin	metabolite
deformylflustrabromine deformylflustrabromine: has antineoplastic activity; isolated from Flustra folicea; structure in first source	2.08	1	0	tryptamines
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.	2.03	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
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.	2.05	1	0	3-coumaric acid
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.	1.98	1	0	anethole	flavouring agent
geraniol [no description available]	1.98	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	4.53	7	0
benzylideneacetone benzylideneacetone: RN given refers to cpd without isomeric; structure in Merck Index, 9th ed, #1153. trans-benzylideneacetone : The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.. benzylideneacetone : An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ketone, only the trans-isomer is observed.	2.07	1	0	benzylideneacetone	bacterial metabolite; EC 3.1.1.4 (phospholipase A2) inhibitor; flavouring agent; fragrance
chalcone trans-chalcone : The trans-isomer of chalcone.	5.85	6	1	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isosafrole isosafrole: RN given refers to cpd without isomeric designation	1.98	1	0	benzodioxoles
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.	2.25	1	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.	3.9	3	0	stilbene
glucobrassicin glucobrassicin: isolated from Brussels sprouts; structure given in first source. glucobrassicin : An indolylmethylglucosinolic acid that is 1-thio-beta-D-glucopyranose having a 2-(1H-indol-3-yl)-N-(sulfooxy)ethanimidoyl group attached to the anomeric sulfur.	2.73	3	0	indolyl carbohydrate; indolylmethylglucosinolic 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.	2.08	1	0	S-glycosyl compound
sesquiterpenes [no description available]	4.78	9	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.49	2	0	caffeic acid	geroprotector; mouse metabolite
5-(4-chlorophenyl)-4h-1,2,4-triazole-3-thiol 5-(4-chlorophenyl)-4H-1,2,4-triazole-3-thiol: a YUCCA enzyme inhibitor; structure in first source	2.31	1	0	triazoles
2-mercaptobenzimidazole 2-mercaptobenzimidazole: purine synthesis antimetabolite; RN given refers to parent cpd	2.31	1	0
n-acetyltyrosylamide N-acetyltyrosylamide: substrate for lactoperoxidase; RN given refers to (S)-isomer	1.96	1	0
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	2.31	1	0	isoeugenol	plant metabolite
cotinine Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.	6.93	1	0	N-alkylpyrrolidine; pyridines; pyrrolidin-2-ones; pyrrolidine alkaloid	antidepressant; biomarker; human xenobiotic metabolite; plant metabolite
2-(2-methoxyphenyl)-1H-indole [no description available]	2.17	1	0	phenylindole
thiouracil Thiouracil: Occurs in seeds of Brassica and Crucifera species. Thiouracil has been used as antithyroid, coronary vasodilator, and in congestive heart failure although its use has been largely supplanted by other drugs. It is known to cause blood dyscrasias and suspected of terato- and carcinogenesis.. thiouracil : A nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group.	1.93	1	0	nucleobase analogue; thiocarbonyl compound	antithyroid drug; metabolite
methimazole Methimazole: A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.. methimazole : A member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen.	2.17	1	0	1,3-dihydroimidazole-2-thiones	antithyroid drug
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2	1	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2.1	1	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
metiamide Metiamide: A histamine H2 receptor antagonist that is used as an anti-ulcer agent.	1.95	1	0	imidazoles
cinnamonitrile cinnamonitrile: RN given refers to cpd without isomeric designation	2.03	1	0
longifolene longifolene: from plant products; RN given refers to (1S-(1alpha,3abeta,4alpha,8abeta))-isomer; structure given in first source	1.98	1	0	longifolene
1-[(3,4-dichlorophenyl)methyl]indole-2,3-dione [no description available]	2.03	1	0	indoles
digitoxose [no description available]	2.02	1	0
thiobarbituric acid thiobarbituric acid: RN given refers to parent cpd. 2-thiobarbituric acid : A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur.	7.21	1	0	barbiturates	allergen; reagent
thiosemicarbazide thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.	7.13	1	0	hydrazines; thiocarboxamide; thioureas
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.	3.29	5	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	4.72	28	0
D-fructopyranose [no description available]	1.93	1	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	7.08	1	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
aflatoxin b aflatoxin B2: RN given refers to cpd without isomeric designation. aflatoxin B2 : An aflatoxin having a hexahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	2.06	1	0	aflatoxin
ytterbium(iii) triflate [no description available]	2.05	1	0
fumonisin b1 fumonisin B1: isolated from Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting activity; inhibits ceramide synthase. fumonisin B1 : A diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol.	7.11	1	0	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite
nadp [no description available]	3.03	4	0
scandium triflate scandium triflate: structure in first source	2.03	1	0
3,3,3-trifluoroalanine 3,3,3-trifluoroalanine: RN refers to (DL)-isomer; inhibits pyridoxal-5'-phosphate dependent cystathionine beta-lyase	1.98	1	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.82	3	0
Methyl indole-5-carboxylate [no description available]	2.02	1	0	indolyl carboxylic acid
7-hydroxyindole [no description available]	7.02	1	0
trisindoline trisindoline: an antibiotic indole trimer, produced by Vibrio separated from the marine sponge Hyrtios altum; structure given in first source	2.07	1	0
rhyncophylline rhyncophylline: an oxindole; RN given refers to (7beta,16E,20alpha)-isomer	2.03	1	0
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.02	1	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
estrone sulfate estrone sulfate: sulfoconjugated estrone; RN given refers to parent cpd	2.44	2	0	17-oxo steroid; steroid sulfate	human metabolite; mouse metabolite
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.	2.07	1	0	alkali metal atom
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	2.06	1	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
quinine [no description available]	2.82	3	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
brassinin [no description available]	7.08	1	0	dithiocarbamic ester; indole phytoalexin
rasagiline [no description available]	2.25	1	0	indanes; secondary amine; terminal acetylenic compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; neuroprotective agent
dipyrromethene dipyrromethene: structure in first source. dipyrrin : A dipyrrin that consists of pyrrole bearing a pyrrol-2-ylidenemethyl substituent at the 2-position.	7.06	1	0	dipyrrins
phosphonic acid phosphonic acid : A phosphorus oxoacid that consists of a single pentavalent phosphorus covalently bound via single bonds to a single hydrogen and two hydroxy groups and via a double bond to an oxygen. The parent of the class of phosphonic acids.	2.15	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.1	1	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.	2.74	3	0	organic sodium salt	detergent; protein denaturant
homoserine lactone homoserine lactone: a putative signal for starvation in E. coli; structure in first source. homoserinium lactone : The conjugate acid of homoserine lactone; major species at pH 7.3.. homoserine lactone : A butan-4-olide having an amino substituent at the 2-position.	7.46	2	0	ammonium ion derivative; organic cation
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	3.05	5	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	4.09	4	0
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940	2.13	1	0	alkylbenzene; ring assembly
5-Nitroisatin [no description available]	2.03	1	0	indoles	anticoronaviral agent
diclofenac sodium Diclofenac Sodium: The sodium form of DICLOFENAC. It is used for its analgesic and anti-inflammatory properties.. diclofenac sodium : The sodium salt of diclofenac.	2.02	1	0	organic sodium salt
2-mercaptoacetate 2-mercaptoacetate: RN given refers to parent cpd	1.93	1	0	monocarboxylic acid anion
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	2.15	1	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	2.47	2	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	1.97	1	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	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
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.	2.05	1	0	trihydroxyflavone	antineoplastic agent; metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.79	3	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; 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.	2.11	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.88	4	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
kaempferol [no description available]	2.05	1	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.	2.72	3	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	2.03	1	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	2.05	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.58	2	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	3.46	7	0	oxo monocarboxylic acid	jasmonates; plant metabolite
esculin [no description available]	2.67	3	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.43	2	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
caryophyllene (-)-beta-caryophyllene : A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.. beta-caryophyllene : A sesquiterpene with a [7.2.0]-bicyclic structure comprising fused 9- and 4-membered rings, with a trans-ring junction, a trans-double bond between the 4- and 5-positions of the 9-membered ring, a methylidene group at position 9, and methyl groups at positions 3, 11, and 11. The most commonly occurring form is the (1R,9S)-(-)-enantiomer, which is found in many essential oils, particularly clove oil.. cannabinoid : A diverse group of pharmacologically active secondary metabolite characteristic to Cannabis plant as well as produced naturally in the body by humans and animals. Cannabinoids contain oxygen as a part of the heterocyclic ring or in the form of various functional groups. They are subdivided on the basis of their origin.	1.98	1	0	beta-caryophyllene	fragrance; insect attractant; metabolite; non-steroidal anti-inflammatory drug
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	1.98	1	0	alpha-humulene
myricetin [no description available]	2.05	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
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.	2.05	1	0	rosmarinic acid	geroprotector; plant metabolite
ellagic acid [no description available]	2.05	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
ginkgolic acid [no description available]	1.98	1	0	hydroxybenzoic acid
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.	2.07	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
sphingosine 1-phosphate sphingosine 1-phosphate: RN given refers to (R-(R,S-(E)))-isomer; RN for cpd without isomeric designation not available 8/89. sphingosine 1-phosphate : A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1	2.15	1	0	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent
codeine [no description available]	2	1	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
oleyl alcohol oleyl alcohol: structure; RN given refers to cpd without isomeric designation	2.03	1	0	fatty alcohol 18:1; long-chain primary fatty alcohol	metabolite; nonionic surfactant
4-dimethylaminocinnamaldehyde [no description available]	2.37	2	0	cinnamaldehydes
nerolidol (6E)-nerolidol : A nerolidol in which the double bond at position 6 adopts a trans-configuration.	1.98	1	0	nerolidol
dorzolamide dorzolamide: topically effective ocular hypotensive carbonic anhydrase inhibitor; RN refers to mono-HCl (4S-trans)-isomer. dorzolamide : 5,6-Dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide in which hydrogens at the 4 and 6 positions are substituted by ethylamino and methyl groups, respectively (4S, trans-configuration). A carbonic anhydrase inhibitor, it is used as the hydrochloride in ophthalmic solutions to lower increased intraocular pressure in the treatment of open-angle glaucoma and ocular hypertension.	3.41	1	0	sulfonamide; thiophenes	antiglaucoma drug; antihypertensive agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor
N(2)-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide N(2)-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide : A leucine derivative obtained by fpormal condensation of the secondary amino group of 5-({2,3-dichloro-4-[1-methyl-5-(piperidin-4-yl)-1H-pyrazol-3-yl]phenoxy}methyl)-2-furoic acid and the carboxy group of N-amidino-L-leucylglycine	3.12	1	0	D-leucine derivative; dichlorobenzene; furoic acid; glycine derivative; guanidines; pyrazolylpiperidine
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
diferuloylputrescine diferuloylputrescine: structure in first source	2.05	1	0	hydroxycinnamic acid
fluvoxamine Fluvoxamine: A selective serotonin reuptake inhibitor that is used in the treatment of DEPRESSION and a variety of ANXIETY DISORDERS.. fluvoxamine : An oxime O-ether that is benzene substituted by a (1E)-N-(2-aminoethoxy)-5-methoxypentanimidoyl group at position 1 and a trifluoromethyl group at position 4. It is a selective serotonin reuptake inhibitor that is used for the treatment of obsessive-compulsive disorder.	2	1	0	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor
granulatimide granulatimide: minor alkaloids of the Brazilian ascidian Didemnum; structure in first source	2.01	1	0
casein kinase ii Casein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.	2.81	3	0
su 11248 [no description available]	2.25	1	0	monocarboxylic acid amide; pyrroles	angiogenesis inhibitor; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; immunomodulator; neuroprotective agent; vascular endothelial growth factor receptor antagonist
sclareolide sclareolide: has antineoplastic activity; synthesized by oxidation of sclareol; a minor constituent of Arnica angustifolia and Sideritis nutans; structure in first source	7.6	1	0
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	3.61	2	0
hemiasterlin hemiasterlin: structure in first source	2.15	1	0
3-hexenylacetate 3-hexenylacetate: RN refers to (Z)-isomer	2.21	1	0	carboxylic ester
5-oxo-6,8,11,14-eicosatetraenoic acid 5-oxo-6,8,11,14-eicosatetraenoic acid: RN given is for cpd without isomeric designation; an arachidonate metabolite which stimulates neutrophils to mobilize Ca and promotes PMN degranulation responses	7.17	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.46	2	0	boron group element atom; elemental aluminium; metal atom
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	2.05	1	0	boron group element atom
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	2.07	1	0	boron group element atom
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	5.52	16	1	chalcogen; nonmetal atom	macronutrient
piperic acid piperinic acid: from Piper longum; structure in first source. (E,E)-piperic acid : A monocarboxylic acid that is (E)-penta-2,4-dienoic acid substituted by a 1,3-benzodioxol-5-yl group at position 5. It has been isolated from black pepper (Piper nigrum).	2.25	1	0	alpha,beta-unsaturated monocarboxylic acid; benzodioxoles	plant metabolite
3,4',5-trimethoxystilbene 3,4',5-trimethoxystilbene: structure in first source	2.05	1	0
minfiensine minfiensine: structure in first source	2.17	1	0
sinomenine sinomenine: isolated from root of Sinomenium acutum; antirheumatic, antineuralgic	2.31	1	0	morphinane alkaloid
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.03	1	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.64	3	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	7.9	4	0	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.49	2	0	carbon group element atom; metalloid atom; nonmetal atom
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	7.76	3	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
gluconasturtiin gluconasturtiin: hydrolysis yields phenylethyl isothiocyanate; structure in first source. gluconasturtiin : An aralkylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose attached to a 3-phenyl-N-(sulfooxy)propanimidoyl group at the anomeric sulfur.	2.1	1	0	aralkylglucosinolic acid; benzenes
n-linolenoyl-l-glutamine N-linolenoyl-L-glutamine: an elicitor of plant volatiles, by membrane-associated enzyme(s) in Manduca sexta	2.02	1	0
isosungucine isosungucine: isolated from Strychnos icaja; structure in first source	2.13	1	0
mbx 1090 [no description available]	7.08	1	0
metaproterenol 1-methoxy-3-indolylmethylglucosinolate: isolated from Moricandia arvensis (Cruciferae); structure given in first source. neoglucobrassicin : An indolyl carbohydrate that is glucobrassicin methoxy substituted at position 1 of the indole moiety.	2.57	2	0
progoitrin progoitrin: RN given refers to (R)-isomer; structure. epi-progoitrin : The stereoisomer of xi-progoitrin that has S at the carbon bearing the allylic hydroxy group.. progoitrin : The stereoisomer of xi-progoitrin that has R at the carbon bearing the allylic hydroxy group.	2.31	1	0	alkylglucosinolate
sinigrin sinigrin: glucosinate in mustard seeds etc.; RN given refers to parent cpd. sinigrin : An alkenylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose having a 4-[(sulfooxy)imino]but-1-en-4-yl group attached to the anomeric sulfur.	2.31	1	0	alkenylglucosinolic acid
bms 806 BMS 806: prevents entry of HIV into cells by binding HIV envelope protein gp120; no further info available 4/2002	2.05	1	0
guanabenz Guanabenz: An alpha-2 selective adrenergic agonist used as an antihypertensive agent.	2.02	1	0	dichlorobenzene
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.52	2	0	2-trans-abscisic acid
icariside i icariside I: structure in first source	2.31	1	0
gw-5074 [no description available]	7.08	1	0
n-feruloylserotonin N-feruloylserotonin: structure in first source. N-feruloylserotonin : A member of the class of hydroxyindoles that is the N-feruloyl derivative of serotonin.	2.13	1	0	aromatic ether; cinnamamides; hydroxyindoles; phenols; secondary carboxamide	plant metabolite
phenyl-3-methoxy-4-hydroxystyryl ketone phenyl-3-methoxy-4-hydroxystyryl ketone: structure given in first source	2.05	1	0
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	2.66	2	0	chalcogen; nonmetal atom	micronutrient
selenourea [no description available]	3.41	1	0
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	3.14	5	0
pericalline pericalline: alkaloid isolated from Catharanthus trichophyllus roots; active against experimental neoplasm; RN in Chemline for (-)-isomer: 2122-36-3	2.05	1	0
mucidin mucidin: produced by basidiomycete Oudemansiella mucida; strobilurin A produced by wood rot fungus Strobilurus tenacellus;. mucidin : An enoate ester that is the methyl ester of (2E,3Z,5E)-2-(methoxymethylene)-3-methyl-6-phenylhexa-3,5-dienoic acid.	2.11	1	0	enoate ester; enol ether	antifungal agent; fungal metabolite
bis(1,3-dibutylbarbiturate)trimethine oxonol bis(1,3-dibutylbarbiturate)trimethine oxonol: fluorescent probe for membrane potentials	2.07	1	0
bacteriochlorophylls Bacteriochlorophylls: Pyrrole containing pigments found in photosynthetic bacteria.	2.02	1	0
oxepins Oxepins: Compounds based on a 7-membered heterocyclic ring including an oxygen. They can be considered a medium ring ether. A natural source is the MONTANOA plant genus. Some dibenzo-dioxepins, called depsidones, are found in GARCINIA plants.	2.15	1	0
nifuroxime 5-nitro-2-furaldehyde oxime: structure in first source	2.42	2	0
glucoerucin glucoerucin: structure in first source. glucoerucin : A thia-alkylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose having a 5-(methylsulfanyl)-N-(sulfooxy)pentanimidoyl group attached to the anomeric sulfur.	2.31	1	0	organic sulfide; thia-alkylglucosinolic acid
borneol [no description available]	1.98	1	0	borneol
glucoraphanin glucoraphanin: precursor of sulforaphane. glucoraphanin : A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide.	2.96	3	0	sulfoxide; thia-alkylglucosinolic acid
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	2	1	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
sb 334867-a 1-(2-methylbenzoxazol-6-yl)-3-(1,5)naphthyridin-4-yl urea: selective OX1 receptor antagonist	2	1	0	naphthyridine derivative
androst-16-en-3-one androst-16-en-3-one: boar taint steroid; RN given refers to (5alpha)-isomer. 5alpha-androst-16-en-3-one : An androstanoid that is 5alpha-androst-16-ene substituted by an oxo group at position 3. It is a steroid pheromone found in high concentrations in the saliva of male pigs,.	4.16	15	0	3-oxo steroid; androstanoid	mammalian metabolite; pheromone
morphinans Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.	2.31	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
cyclo(glycyltryptophyl) cyclo(glycyltryptophyl): structure in first source	2.03	1	0	indoles	metabolite
staurosporine staurosporinium : Conjugate acid of staurosporine.	2.02	1	0	ammonium ion derivative
glucoiberin glucoiberin: from Iberis amara; structure in first source	2.31	1	0
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	7.11	1	0
cp 91149 CP 91149: inhibits liver glycogen phosphorylase; structure in first source	3.12	1	0
a 286982 A 286982: inhibits the interaction between leukocyte function-associated antigen-1 and intracellular adhesion molecule-1; structure in first source	2	1	0
ym 26734 YM 26734: inhibits group II phospholipase A2; structure given in first source	2.04	1	0
rwj-56110 RWJ-56110: a PAR-1 antagonist; structure in first source	2	1	0
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.87	4	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
2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trien-1-yl]benzoic acid [no description available]	1.98	1	0	hydroxybenzoic acid
cc 1065 CC 1065: from Streptomyces zelensis; structure in second sourc	3.51	1	0
zeolites [no description available]	2.6	1	0
dimethoxycurcumin dimethoxycurcumin: has antineoplsatic activity; structure in first source	2.05	1	0
2-iodophenyl-(1-(1-methylpiperidin-2-ylmethyl)-1h-indol-3-yl)methanone 2-iodophenyl-(1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl)methanone: a CB1 cannabinoid receptor radioligand; structure in first source	2.06	1	0
tacamonine tacamonine: structure in first source	2.03	1	0
wakayin wakayin: from ascidian Clavelina sp.; structure in first source	3.21	1	0
pazopanib pazopanib: a protein kinase inhibitor. pazopanib : A pyrimidine that is 5-(pyrimidin-2-yl}amino-2-methylbenzenesulfonamide substituted at position 4 by a (2,3-dimethylindazol-6-yl)(methyl)amino group. Used as its hydrochloride salt for treatment of kidney cancer.	2.11	1	0	aminopyrimidine; indazoles; sulfonamide	angiogenesis modulating agent; antineoplastic agent; tyrosine kinase inhibitor; vascular endothelial growth factor receptor antagonist
chromafenozide chromafenozide: has partial ecdysone agonist activity; structure in first source	2.03	1	0	bisacylhydrazine insecticide
clavicipitic acid clavicipitic acid: ergot alkaloid from Claviceps fusiformis; structure in first source	2.48	2	0	ergot alkaloid
akuammicine akuammicine: from Strychnos sp;; structure in first source. akuammicine : A monoterpenoid indole alkaloid with formula C20H22N2O2, isolated from several plant species including Alstonia spatulata, Catharanthus roseus and Vinca major.	2.25	1	0	methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound	plant metabolite
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	5.48	10	0
leucascandrolide a leucascandrolide A: structure in first source	2.06	1	0
bis(pyridine)iodonium(i) tetrafluoroborate bis(pyridine)iodonium(I) tetrafluoroborate: an iodinating reagent for peptides	2.03	1	0
olivose olivose: RN given for (D)-isomer	2.02	1	0	hexose
ribose ribopyranose : The pyranose form of ribose.	6.93	1	0	D-ribose; ribopyranose
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	1.99	1	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
macroline macroline: structure in first source	2.05	1	0
bms-585248 [no description available]	3.51	1	0
phenylnitrene [no description available]	2.06	1	0
cyclo(tyrosyl-tyrosyl) cyclo(L-tyrosyl-L-tyrosyl) : A cyclo(tyrosyl-tyrosyl) in which both stereocentres have L-configuration. Synthesized by Mycobacterium tuberculosis.	2.03	1	0	cyclo(tyrosyl-tyrosyl)	metabolite
latonduine a latonduine A: structure in first source	2.41	1	0
pyrazolone pyrazolone: non-steroid antirheumatic agent. pyrazolone : A member of the class of pyrazoles in which one of the carbons of the pyrazole ring is substituted by an oxo group.	2.06	1	0
glyoxamide glyoxamide : The simplest of the class of glyoxamides, with no substitution on nitrogen.	2.07	1	0	glyoxamides
serotobenine serotobenine: isolated from Ouratea turnarea	7.41	1	0
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.06	1	0
vinyl triflate vinyl triflate: structure in first source	7.1	1	0
imidazolone imidazolone: a reaction product of arginine with 3-deoxyglucosone which markedly accumulates in uremic serum; structure in first source	7.17	1	0	organonitrogen heterocyclic compound
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.	2.01	1	0
thienopyridine thienopyridine: patients were treated with thienopyridine after percutaneous coronary intervention; Antiplatelet Agents. thienopyridine : Any organic heterobicyclic compound whose skeleton results from the formal ortho-fusion of any bond of a pyridine with any bond of a thiophene.	2.17	1	0
2-methyltryptophan 2-methyltryptophan: RN given for (L)-isomer. 2-methyl-L-tryptophan : An L-tryptophan derivative in which the hydrogen at position 2 on the indole ring is replaced by a methyl group.	2.15	1	0	amino acid zwitterion; L-tryptophan derivative	bacterial metabolite
verruculogen verruculogen: complex 6-O-methylindole cpd containing 3 nitrogens; induces tremor; tremorigenic metabolite from Penicillium verruculosum isolated from moldy peanuts; decreases GABA levels in CNS; structure. verruculogen : An organic heterohexacyclic compound that is a mycotoxic indole alkaloid isolated from Penicillium and Aspergillus species.	2.11	1	0	aromatic ether; diol; indole alkaloid; organic heterohexacyclic compound; organic peroxide	Aspergillus metabolite; GABA modulator; mycotoxin; Penicillium metabolite; potassium channel blocker
dragmacidin d dragmacidin D: structure in first source	2.06	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	3.54	8	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.83	3	0
melitten Melitten: Basic polypeptide from the venom of the honey bee (Apis mellifera). It contains 26 amino acids, has cytolytic properties, causes contracture of muscle, releases histamine, and disrupts surface tension, probably due to lysis of cell and mitochondrial membranes.	1.97	1	0
nosiheptide nosiheptide: from Streptomyces actuosus; structure	7.15	1	0	polyol
thymalfasin Thymalfasin: A thymus hormone polypeptide found in thymosin fraction 5 (a crude thymus gland extract) but now produced by synthesis. It is used alone or with interferon as an immunomodulator for the treatment of CHRONIC HEPATITIS B and HEPATITIS C. Thymalfasin is also used for the treatment of chemotherapy-induced immunosuppression, and to enhance the efficacy of influenza and hepatitis B vaccines in immunocompromised patients.	2.13	1	0	polypeptide
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	8.06	5	0
cucurbit(8)uril cucurbit(8)uril: a macrocyclic polymer compound comprising 8 GLYCOLURIL units with methylene bridges	2.08	1	0
oligonucleotides [no description available]	2.02	1	0
complestatin complestatin: compound extracted from Streptomyces lavendulae mycelia; on acid hydrolysis yields D-4-hydroxyphenylglycine & D-3,5-dichloro-4-hydroxyphenylglycine & acidic chromophore; inhibits gp120-CD4 binding. isocomplestatin : A heterodetic cyclic peptide which is a atropisomer of complestatin. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity.. chloropeptin II : A heterodetic cyclic peptide consisting of N-acylated trytophan, 3,5-dichloro-4-hydroxyphenylglycine, 4-hydroxyphenylglycine, 3,5-dichloro-4-hydroxyphenylglycyl, tyrosine and 4-hydroxyphenylglycine residues joined in sequence and in which the side-chain of the central 4-hydroxyphenylglycine residue is attached to the side-chain of the tryptophan via a C3-C6 bond and to the side-chain of the tyrosine via an ether bond from C5. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity.	7.46	2	0	cyclic ether; heterodetic cyclic peptide; indoles; organic heterobicyclic compound; organochlorine compound; peptide antibiotic; polyphenol	anti-HIV-1 agent; antimicrobial agent; HIV-1 integrase inhibitor; metabolite
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	6.17	3	2
incretins Incretins: Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially.	2.1	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	7.66	3	0	glycoside
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	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.45	7	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.	2.37	2	0	chlorophyll; methyl ester	cofactor
sphingosine kinase [no description available]	2.15	1	0
calpain Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.	7.1	1	0
aflatrem aflatrem: tremorgenic toxin isolated from Aspergillus flavus; structure	2.02	1	0	organic heterotricyclic compound; organooxygen compound
pyrazolopyridine pyrazolopyridine: act as competitive antagonists of brain adenosine A1 receptors	7.04	1	0
phenyliodonium phenyliodonium: structure in first source	7.02	1	0
volicitin volicitin: an elicitor that triggers emission of volatile from plants	2.41	2	0
tert-butoxide, potassium [no description available]	2.11	1	0
sodium bisulfite sodium bisulfite: has been used externally for parasitic skin diseases and as gastrointestinal antiseptic; structure. sodium hydrogensulfite : An inorganic sodium salt having hydrogensulfite as the counterion.	1.93	1	0	inorganic sodium salt; sulfite salt	allergen; food antioxidant; food colour retention agent; mutagen; reducing agent
methyl orange methyl orange: indictor of pH with strong acids & bases; also used as reagent to form ion pairs with, and thereby isolate, certain compounds from biological material; minor descriptor (75-86); on-line & INDEX MEDICUS search AZO COMPOUNDS (75-86); file maintained to Azo cpds	1.99	1	0
thiostrepton Thiostrepton: One of the CYCLIC PEPTIDES from Streptomyces that is active against gram-positive bacteria. In veterinary medicine, it has been used in mastitis caused by gram-negative organisms and in dermatologic disorders.. thiostrepton : A heterodetic cyclic peptide, in which the cyclisation step involves a formal lactonisation between the carboxy group of a quinaldic acid-based residue and a secondary alcohol. An antibiotic that inhibits bacterial protein synthesis. Also acts as an antitumor agent.	7.15	1	0
methyl jasmonate [no description available]	7.45	2	0
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.	2.38	2	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	3.35	1	0	BODIPY compound
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	1.93	1	0
xiamycin xiamycin: from Streptomyces sp.; structure in first source	2.53	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)	1.96	1	0
plx4032 [no description available]	2.55	2	0	aromatic ketone; difluorobenzene; monochlorobenzenes; pyrrolopyridine; sulfonamide	antineoplastic agent; B-Raf inhibitor
vincorine vincorine: structure in first source	2.08	1	0
triiodothyronine, reverse Triiodothyronine, Reverse: A metabolite of THYROXINE, formed by the peripheral enzymatic monodeiodination of T4 at the 5 position of the inner ring of the iodothyronine nucleus.. 3,3',5'-triiodo-L-thyronine zwitterion : Zwitterionic form of 3,3',5'-triiodo-L-thyronine.	1.98	1	0	3,3',5'-triiodothyronine; amino acid zwitterion
piperidines Piperidines: A family of hexahydropyridines.	4.61	8	0
thymosin Thymosin: Thymosin. A family of heat-stable, polypeptide hormones secreted by the thymus gland. Their biological activities include lymphocytopoiesis, restoration of immunological competence and enhancement of expression of T-cell characteristics and function. They have therapeutic potential in patients having primary or secondary immunodeficiency diseases, cancer or diseases related to aging.	2.13	1	0
streptochlorin streptochlorin: inhibits both NF-kappaB activation and angiogenesis; isolated from marine Streptomyces; structure in first source	7.15	1	0
jwh-210 4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone: a cannabimimetic; structure in first source	2.25	1	0	indolecarboxamide
colistin Colistin: Cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally.. colistin : A multi-component mixture comprising mostly of colistin A (R = Me) and B (R = H), with small amounts of colistin C and other polymyxins, produced by certain strains of Bacillus polymyxa var. colistinus. An antibiotic, it is used as its sulfate salt (for oral or topical use) or as the sodium salt of the N-methylsulfonic acid derivative (the injectable form) in the treatment of severe Gram-negative infections, partiularly those due to Pseudomonas aeruginosa.	1.99	1	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	8.16	5	0
beta-methyltryptophan beta-methyltryptophan: structure in first source	2.13	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.	2.43	2	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.	2.4	2	0
minocycline Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.	2.05	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.	2.74	3	0	monohydroxybenzoate	plant metabolite
piroxicam [no description available]	2.03	1	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
meclan [no description available]	2.05	1	0
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.	9.24	17	0	benzenes; hydroxycoumarin; methyl ketone
rolitetracycline Rolitetracycline: A pyrrolidinylmethyl TETRACYCLINE.. rolitetracycline : A derivative of tetracycline in which the amide function is substituted with a pyrrolidinomethyl group.	2.05	1	0
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	2.11	1	0
communesin a communesin A: structure in first source	7.13	1	0
indenoindole indenoindole: structure given in first source	2.08	1	0
osimertinib osimertinib: an EGFR tyrosine kinase inhibitor. osimertinib : A member of the class of aminopyrimidines that is 4-(1-methylindol-3-yl)pyrimidin-2-amine in which one of the amino hydrogens is replaced by a 2-methoxy-4-[2-(dimethylamino)ethyl](methyl)amino-5-acrylamidophenyl group. Used (as the mesylate salt) for treatment of EGFR T790M mutation positive non-small cell lung cancer.	7.31	1	0	acrylamides; aminopyrimidine; biaryl; indoles; monomethoxybenzene; secondary amino compound; secondary carboxamide; substituted aniline; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	7.65	3	0
mk-8742 elbasvir: inhibits NS5A protein of hepatitis C virus. elbasvir : A complex organic heterotetracyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with grazoprevir (under the brand name Zepatier) for treatment of chronic HCV genotypes 1 or 4 infection in adults.	2.08	1	0	carbamate ester; imidazoles; L-valine derivative; N-acylpyrrolidine; organic heterotetracyclic compound; ring assembly	antiviral drug; hepatitis C virus nonstructural protein 5A inhibitor; hepatoprotective agent
contraceptives, postcoital Contraceptives, Postcoital: Contraceptive substances to be used after COITUS. These agents include high doses of estrogenic drugs; progesterone-receptor blockers; ANTIMETABOLITES; ALKALOIDS, and PROSTAGLANDINS.	1.98	1	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	2.1	1	0
imidacloprid (E)-imidacloprid : The E-isomer of imidacloprid.	2.03	1	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.77	3	0
hyaluronoglucosaminidase Hyaluronoglucosaminidase: An enzyme that catalyzes the random hydrolysis of 1,4-linkages between N-acetyl-beta-D-glucosamine and D-glucuronate residues in hyaluronate. (From Enzyme Nomenclature, 1992) There has been use as ANTINEOPLASTIC AGENTS to limit NEOPLASM METASTASIS.	2.04	1	0
voacamine voacamine: structure	7.21	1	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	1.93	1	0
lysergic acid lysergic acid : An ergoline alkaloid comprising 6-methylergoline having additional unsaturation at the 9,10-position and a carboxy group at the 8-position.	6.92	1	0
monomethylauristatin f monomethylauristatin F: structure in first source	2.25	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	3.1	5	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	2.25	1	0
fischerindole fischerindole: structure in first source	2.47	2	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	2.52	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	7.06	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	3.1	5	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	2.07	1	0	nucleoside triphosphate analogue
5,10-methylenetetrahydrofolic acid 5,10-methylenetetrahydrofolic acid: RN refers to parent cpd(L-Glu)-isomer	3.12	1	0	benzamides; methylenetetrahydrofolic acid
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.	2.44	2	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	2.02	1	0
azure c Azure C: RN given refers to chloride. azure C : An organic chloride salt having 3-amino-7-(methylamino)phenothiazin-5-ium as the counterion.	2.05	1	0
bis(3',5')-cyclic diguanylic acid [no description available]	2.52	2	0	cyclic purine dinucleotide; guanyl ribonucleotide	immunomodulator; signalling molecule
prodigiosin Prodigiosin: 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- 2,2'-bi-1H-pyrrole. A toxic, bright red tripyrrole pigment from Serratia marcescens and others. It has antibacterial, anticoccidial, antimalarial, and antifungal activities, but is used mainly as a biochemical tool.. prodigiosin : A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens.	1.99	1	0
tsitsikammamine a tsitsikammamine A: from sponge Latrunculid; structure in first source	3.21	1	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	2.44	2	0
thrombin aptamer thrombin aptamer: nucleotide sequence given in first source; a synthetic polynucleotide	2.25	1	0
chloropeptin i chloropeptin I: inhibitor of gp120-CD4 binding; isolated from Streptomyces; structure in first source. chloropeptin I : A heterodetic cyclic peptide consisting of N-acylated trytophan, 3,5-dichloro-4-hydroxyphenylglycine, 4-hydroxyphenylglycine, 3,5-dichloro-4-hydroxyphenylglycyl, tyrosine and 4-hydroxyphenylglycine residues joined in sequence and in which the side-chain of the central 4-hydroxyphenylglycine residue is attached to the side-chain of the tryptophan via a C3-C7 bond and to the side-chain of the tyrosine via an ether bond from C5. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity.	2.05	1	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.72	3	0

Condition	Relationship Strength	Studies	Trials
Emesis [description not available]	1.95	1	0
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	1.95	1	0
Acne [description not available]	1.98	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.	1.98	1	0
Hepatitis B Virus Infection [description not available]	7.47	2	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.	7.47	2	0
Degenerative Diseases, Central Nervous System [description not available]	2.08	1	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.	7.08	1	0
Extravascular Hemolysis [description not available]	3.72	10	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	3.72	10	0
Benign Neoplasms, Brain [description not available]	2.61	2	0
Astrocytoma, Grade IV [description not available]	2.88	3	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.61	2	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	2.88	3	0
Congenital Zika Syndrome [description not available]	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	5.72	17	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1	0
Grippe [description not available]	3.64	2	0
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	3.64	2	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.31	6	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.38	2	0
Innate Inflammatory Response [description not available]	4.97	12	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	4.97	12	0
Experimental Neoplasms [description not available]	3.36	7	0
Infections, Plasmodium [description not available]	3.6	2	0
Benign Neoplasms [description not available]	6.8	20	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.	8.6	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.	11.8	20	0
Alveolitis, Fibrosing [description not available]	2.69	2	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	2.69	2	0
Malignant Melanoma [description not available]	2.7	3	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)	2.7	3	0
Experimental Mammary Neoplasms [description not available]	2.72	2	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	8.99	4	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	7.85	3	0
Colorectal Cancer [description not available]	4.2	3	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	4.2	3	0
Cryptosporidium Infection [description not available]	7.98	3	0
Cryptosporidiosis Intestinal infection with organisms of the genus CRYPTOSPORIDIUM. It occurs in both animals and humans. Symptoms include severe DIARRHEA.	2.98	3	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.66	2	0
Pneumonia Infection of the lung often accompanied by inflammation.	2.66	2	0
Diabetic Feet [description not available]	2.25	1	0
Alloxan Diabetes [description not available]	2.49	2	0
Diabetic Foot Common foot problems in persons with DIABETES MELLITUS, caused by any combination of factors such as DIABETIC NEUROPATHIES; PERIPHERAL VASCULAR DISEASES; and INFECTION. With the loss of sensation and poor circulation, injuries and infections often lead to severe foot ulceration, GANGRENE and AMPUTATION.	2.25	1	0
B16 Melanoma [description not available]	2.58	2	0
Age-Related Memory Disorders [description not available]	2.25	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	3.02	4	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.	2.25	1	0
Leishmania Infection [description not available]	2.25	1	0
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	2.25	1	0
Hyperactivity, Motor [description not available]	2.25	1	0
Chronic Kidney Failure [description not available]	4.6	5	1
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	4.6	5	1
Fatty Liver, Nonalcoholic [description not available]	2.25	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.25	1	0
Breast Cancer [description not available]	4.4	7	0
Breast Neoplasms Tumors or cancer of the human BREAST.	4.4	7	0
Diabetes Mellitus, Adult-Onset [description not available]	7.91	6	4
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	7.91	6	4
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.03	5	0
Tuberculosis, Drug-Resistant [description not available]	3.17	1	0
Koch's Disease [description not available]	3.28	2	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	8.28	2	0
Tuberculosis, Multidrug-Resistant Tuberculosis resistant to chemotherapy with two or more ANTITUBERCULAR AGENTS, including at least ISONIAZID and RIFAMPICIN. The problem of resistance is particularly troublesome in tuberculous OPPORTUNISTIC INFECTIONS associated with HIV INFECTIONS. It requires the use of second line drugs which are more toxic than the first line regimens. TB with isolates that have developed further resistance to at least three of the six classes of second line drugs is defined as EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS.	3.17	1	0
Diseases, Metabolic [description not available]	2.25	1	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.25	1	0
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	2.25	1	0
Chronic Illness [description not available]	2.43	2	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).	2.43	2	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	8.47	2	0
Cancer of Pancreas [description not available]	2.5	2	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.5	2	0
Cancer of Kidney [description not available]	2.25	1	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.25	1	0
Cryptogenic Fibrosing Alveolitis [description not available]	2.25	1	0
Idiopathic Pulmonary Fibrosis A common interstitial lung disease of unknown etiology, usually occurring between 50-70 years of age. Clinically, it is characterized by an insidious onset of breathlessness with exertion and a nonproductive cough, leading to progressive DYSPNEA. Pathological features show scant interstitial inflammation, patchy collagen fibrosis, prominent fibroblast proliferation foci, and microscopic honeycomb change.	2.25	1	0
Liver Dysfunction [description not available]	2.31	1	0
Liver Diseases Pathological processes of the LIVER.	2.31	1	0
Plasmodium falciparum Malaria [description not available]	3.69	3	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.	3.69	3	0
Acute Confusional Senile Dementia [description not available]	3.28	5	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	3.28	5	0
Chronic Kidney Diseases [description not available]	4.01	4	0
Disbacteriosis [description not available]	2.63	2	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	4.01	4	0
Anasarca [description not available]	3.28	6	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	3.28	6	0
Friedreich Disease [description not available]	2.38	2	0
Friedreich Ataxia An autosomal recessive disease, usually of childhood onset, characterized pathologically by degeneration of the spinocerebellar tracts, posterior columns, and to a lesser extent the corticospinal tracts. Clinical manifestations include GAIT ATAXIA, pes cavus, speech impairment, lateral curvature of spine, rhythmic head tremor, kyphoscoliosis, congestive heart failure (secondary to a cardiomyopathy), and lower extremity weakness. Most forms of this condition are associated with a mutation in a gene on chromosome 9, at band q13, which codes for the mitochondrial protein frataxin. (From Adams et al., Principles of Neurology, 6th ed, p1081; N Engl J Med 1996 Oct 17;335(16):1169-75) The severity of Friedreich ataxia associated with expansion of GAA repeats in the first intron of the frataxin gene correlates with the number of trinucleotide repeats. (From Durr et al, N Engl J Med 1996 Oct 17;335(16):1169-75)	2.38	2	0
Complications of Diabetes Mellitus [description not available]	3.23	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	3.69	3	0
Cystic Fibrosis of Pancreas [description not available]	2.31	1	0
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	7.31	1	0
Lung Injury, Acute [description not available]	2.91	3	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).	2.91	3	0
Infections, Klebsiella [description not available]	2.7	3	0
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	2.7	3	0
Cancer of Prostate [description not available]	3.02	4	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.02	4	0
Hematologic Malignancies [description not available]	2.15	1	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	2.15	1	0
Bacterial Disease [description not available]	3.45	2	0
Bacterial Infections Infections by bacteria, general or unspecified.	3.45	2	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.	3.97	4	0
African Sleeping Sickness [description not available]	2.17	1	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.17	1	0
Disease Exacerbation [description not available]	4.11	5	0
Cognitive Decline [description not available]	2.59	2	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.59	2	0
Depression, Endogenous [description not available]	3.09	1	0
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	3.09	1	0
Diathesis [description not available]	4.76	4	0
Candida Infection [description not available]	2.17	1	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.17	1	0
Cruveilhier-Baumgarten Syndrome Liver cirrhosis with intrahepatic portal obstruction, HYPERTENSION, and patent UMBILICAL VEINS.	2.17	1	0
Hypertension, Portal Abnormal increase of resistance to blood flow within the hepatic PORTAL SYSTEM, frequently seen in LIVER CIRRHOSIS and conditions with obstruction of the PORTAL VEIN.	2.17	1	0
Atherogenesis [description not available]	2.51	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.	7.51	2	0
Disease, Pulmonary [description not available]	3.32	2	0
Lung Diseases Pathological processes involving any part of the LUNG.	3.32	2	0
Cadaver A dead body, usually a human body.	2.17	1	0
Experimental Hepatoma [description not available]	2.17	1	0
Hepatocellular Carcinoma [description not available]	7.57	2	0
Cancer of Liver [description not available]	2.38	2	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.57	2	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.38	2	0
Edema, Pulmonary [description not available]	3.6	3	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	3.6	3	0
Infections, Chlamydia [description not available]	3.45	2	0
Chlamydia Infections Infections with bacteria of the genus CHLAMYDIA.	3.45	2	0
E coli Infections [description not available]	2.98	4	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	2.98	4	0
Infections, Helicobacter [description not available]	2.21	1	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.21	1	0
Recrudescence [description not available]	2.21	1	0
Clostridioides difficile Infection [description not available]	2.48	2	0
Clostridium Infections Infections with bacteria of the genus CLOSTRIDIUM and closely related CLOSTRIDIOIDES species.	2.48	2	0
Acute Promyelocytic Leukemia [description not available]	2.21	1	0
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	2.21	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.21	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.08	1	0
HIV Coinfection [description not available]	2.08	1	0
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2.08	1	0
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.1	1	0
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	2.1	1	0
Amyloid Deposits [description not available]	3.47	1	1
Ache [description not available]	2.64	3	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.64	3	0
Genital Tract Infections [description not available]	3.01	1	0
Asthma, Bronchial [description not available]	2.1	1	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.1	1	0
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	7.47	2	0
Blood Poisoning [description not available]	2.11	1	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.11	1	0
Central Nervous System Neoplasm [description not available]	3.03	1	0
Central Nervous System Neoplasms Benign and malignant neoplastic processes that arise from or secondarily involve the brain, spinal cord, or meninges.	3.03	1	0
Vibrio cholerae Infection [description not available]	2.66	3	0
Cholera An acute diarrheal disease endemic in India and Southeast Asia whose causative agent is VIBRIO CHOLERAE. This condition can lead to severe dehydration in a matter of hours unless quickly treated.	2.66	3	0
Acute-Phase Reaction An early local inflammatory reaction to insult or injury that consists of fever, an increase in inflammatory humoral factors, and an increased synthesis by hepatocytes of a number of proteins or glycoproteins usually found in the plasma.	2.11	1	0
Kwashiorkor A syndrome produced by severe protein deficiency, characterized by retarded growth, changes in skin and hair pigment, edema, and pathologic changes in the liver, including fatty infiltration, necrosis, and fibrosis. The word is a local name in Gold Coast, Africa, meaning displaced child. Although first reported from Africa, kwashiorkor is now known throughout the world, but mainly in the tropics and subtropics. It is considered to be related to marasmus. (From Dorland, 27th ed)	2.11	1	0
Pellagra A disease due to deficiency of NIACIN, a B-complex vitamin, or its precursor TRYPTOPHAN. It is characterized by scaly DERMATITIS which is often associated with DIARRHEA and DEMENTIA (the three D's).	7.64	3	0
Dermatoses [description not available]	2.37	2	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.37	2	0
Allodynia [description not available]	2.11	1	0
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	2.47	2	0
Uremia A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.	4.03	5	0
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	2.47	2	0
Maggot Infestations [description not available]	2.11	1	0
Cancer of Lung [description not available]	3.18	5	0
Lung Neoplasms Tumors or cancer of the LUNG.	3.18	5	0
Fungal Diseases [description not available]	3.04	1	0
Mycoses Diseases caused by FUNGI.	3.04	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.5	8	0
Carcinoma, Non-Small Cell Lung [description not available]	2.76	3	0
Angiogenesis, Pathologic [description not available]	2.78	3	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.76	3	0
Weight Gain Increase in BODY WEIGHT over existing weight.	3.8	2	1
Enteritis Inflammation of any segment of the SMALL INTESTINE.	2.41	2	0
Adenocarcinoma, Basal Cell [description not available]	2.41	2	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.41	2	0
Blood Pressure, High [description not available]	3.78	4	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.	8.78	4	0
Allergic Encephalomyelitis [description not available]	2.13	1	0
MS (Multiple Sclerosis) [description not available]	2.13	1	0
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	2.13	1	0
Alcohol Abuse [description not available]	2.13	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.13	1	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	2.13	1	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.37	2	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	2.13	1	0
Colitis Gravis [description not available]	2.13	1	0
Colitis, Granulomatous [description not available]	2.13	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.	2.13	1	0
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	2.13	1	0
Nerve Pain [description not available]	2.13	1	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.13	1	0
Carcinoma, Anaplastic [description not available]	2.38	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.	7.38	2	0
Cirrhosis, Liver [description not available]	2.91	4	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.	2.91	4	0
Glial Cell Tumors [description not available]	2.15	1	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	7.15	1	0
Acute Myelogenous Leukemia [description not available]	2.13	1	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.13	1	0
Mouth Diseases Diseases involving the MOUTH.	2.15	1	0
Bladder Cancer [description not available]	7.34	2	0
Invasiveness, Neoplasm [description not available]	1.94	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.34	2	0
Carcinoma, Transitional Cell A malignant neoplasm derived from TRANSITIONAL EPITHELIAL CELLS, occurring chiefly in the URINARY BLADDER; URETERS; or RENAL PELVIS.	1.94	1	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	1.94	1	0
Leukemia L 1210 [description not available]	2.05	1	0
Colonic Inertia Symptom characterized by the passage of stool once a week or less.	2.36	2	0
Symptom Cluster [description not available]	2.74	3	0
Constipation Infrequent or difficult evacuation of FECES. These symptoms are associated with a variety of causes, including low DIETARY FIBER intake, emotional or nervous disturbances, systemic and structural disorders, drug-induced aggravation, and infections.	2.36	2	0
Syndrome A characteristic symptom complex.	2.74	3	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.	7.71	3	0
Autoimmune Diabetes [description not available]	2.05	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.05	1	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2.05	1	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.05	1	0
Halitosis An offensive, foul breath odor resulting from a variety of causes such as poor oral hygiene, dental or oral infections, or the ingestion of certain foods.	3.82	2	1
Escherichia coli Meningitis [description not available]	2.05	1	0
Dementias, Transmissible [description not available]	2.05	1	0
Cronobacter Infections [description not available]	2.05	1	0
Enterobacteriaceae Infections Infections with bacteria of the family ENTEROBACTERIACEAE.	2.05	1	0
Bovine Diseases [description not available]	2.9	4	0
Action Tremor [description not available]	2.05	1	0
Tremor Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.	7.05	1	0
Encephalopathy, Hepatic [description not available]	2.37	2	0
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	7.37	2	0
Enteric Fever [description not available]	1.92	1	0
Typhoid Fever An acute systemic febrile infection caused by SALMONELLA TYPHI, a serotype of SALMONELLA ENTERICA.	1.92	1	0
Infections, Prosthesis-Related [description not available]	2.05	1	0
Pulmonary Hypertension [description not available]	7.05	1	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	2.05	1	0
Hypothermia, Accidental [description not available]	2.05	1	0
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	2.05	1	0
Colitis, Mucous [description not available]	2.06	1	0
Irritable Bowel Syndrome A disorder with chronic or recurrent colonic symptoms without a clearcut etiology. This condition is characterized by chronic or recurrent ABDOMINAL PAIN, bloating, MUCUS in FECES, and an erratic disturbance of DEFECATION.	2.06	1	0
Tick Infestations Infestations with soft-bodied (Argasidae) or hard-bodied (Ixodidae) ticks.	2.06	1	0
Arterial Diseases, Carotid [description not available]	2.06	1	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.	2.06	1	0
Adipocere [description not available]	2.07	1	0
Brain Vascular Disorders [description not available]	2.08	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.	2.08	1	0
Adjuvant Arthritis [description not available]	2.92	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	1.93	1	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	7.87	4	0
Allergic Reaction [description not available]	1.93	1	0
Diseases of Immune System [description not available]	2.33	2	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	1.93	1	0
Immune System Diseases Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.	2.33	2	0
Deficiency, Mental [description not available]	2.62	3	0
BH4 Deficiency [description not available]	3.03	5	0
Intellectual Disability Subnormal intellectual functioning which originates during the developmental period. This has multiple potential etiologies, including genetic defects and perinatal insults. Intelligence quotient (IQ) scores are commonly used to determine whether an individual has an intellectual disability. IQ scores between 70 and 79 are in the borderline range. Scores below 67 are in the disabled range. (from Joynt, Clinical Neurology, 1992, Ch55, p28)	2.62	3	0
Phenylketonurias A group of autosomal recessive disorders marked by a deficiency of the hepatic enzyme PHENYLALANINE HYDROXYLASE or less frequently by reduced activity of DIHYDROPTERIDINE REDUCTASE (i.e., atypical phenylketonuria). Classical phenylketonuria is caused by a severe deficiency of phenylalanine hydroxylase and presents in infancy with developmental delay; SEIZURES; skin HYPOPIGMENTATION; ECZEMA; and demyelination in the central nervous system. (From Adams et al., Principles of Neurology, 6th ed, p952).	3.03	5	0
Agranulocytosis A decrease in the number of GRANULOCYTES; (BASOPHILS; EOSINOPHILS; and NEUTROPHILS).	1.93	1	0
Blood Pressure, Low [description not available]	2.33	2	0
Hypotension Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.	2.33	2	0
Dementia Praecox [description not available]	4.93	15	0
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	4.93	15	0
Hallucination of Body Sensation [description not available]	2.85	4	0
Hallucinations Subjectively experienced sensations in the absence of an appropriate stimulus, but which are regarded by the individual as real. They may be of organic origin or associated with MENTAL DISORDERS.	2.85	4	0
Argentaffinoma [description not available]	6.93	1	0
Carcinoid Tumor A usually small, slow-growing neoplasm composed of islands of rounded, oxyphilic, or spindle-shaped cells of medium size, with moderately small vesicular nuclei, and covered by intact mucosa with a yellow cut surface. The tumor can occur anywhere in the gastrointestinal tract (and in the lungs and other sites); approximately 90% arise in the appendix. It is now established that these tumors are of neuroendocrine origin and derive from a primitive stem cell. (From Stedman, 25th ed & Holland et al., Cancer Medicine, 3d ed, p1182)	1.93	1	0
Leucocythaemia [description not available]	3.19	6	0
Experimental Leukemia [description not available]	2.85	4	0
Granulocytic Leukemia [description not available]	2.62	3	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	3.19	6	0
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2.62	3	0
Porphyria [description not available]	1.93	1	0
Acute Porphyria [description not available]	1.93	1	0
Porphyrias A diverse group of metabolic diseases characterized by errors in the biosynthetic pathway of HEME in the LIVER, the BONE MARROW, or both. They are classified by the deficiency of specific enzymes, the tissue site of enzyme defect, or the clinical features that include neurological (acute) or cutaneous (skin lesions). Porphyrias can be hereditary or acquired as a result of toxicity to the hepatic or erythropoietic marrow tissues.	1.93	1	0
Porphyria, Acute Intermittent An autosomal dominant porphyria that is due to a deficiency of HYDROXYMETHYLBILANE SYNTHASE in the LIVER, the third enzyme in the 8-enzyme biosynthetic pathway of HEME. Clinical features are recurrent and life-threatening neurologic disturbances, ABDOMINAL PAIN, and elevated level of AMINOLEVULINIC ACID and PORPHOBILINOGEN in the urine.	1.93	1	0
Absence Seizure [description not available]	2.62	3	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.	2.62	3	0
Infant Malnutrition Malnutrition, occurring in infants ages 1 month to 24 months, which is due to insufficient intake of food, dietary nutrients, or a pathophysiologic condition which prevents the absorption and utilization of food. Growth and development are markedly affected.	1.93	1	0
Behavior Disorders [description not available]	3.18	6	0
Psychoses [description not available]	2.85	4	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.	3.18	6	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)	2.85	4	0
Adrenal Cancer [description not available]	1.93	1	0
Psychoses, Drug [description not available]	1.93	1	0
Malignant Carcinoid Syndrome A symptom complex associated with CARCINOID TUMOR and characterized by attacks of severe flushing of the skin, diarrheal watery stools, bronchoconstriction, sudden drops in blood pressure, edema, and ascites. The carcinoid tumors are usually located in the gastrointestinal tract and metastasize to the liver. Symptoms are caused by tumor secretion of serotonin, prostaglandins, and other biologically active substances. Cardiac manifestations constitute CARCINOID HEART DISEASE. (Dorland, 27th ed; Stedman, 25th ed)	1.93	1	0
Bacteriuria The presence of bacteria in the urine which is normally bacteria-free. These bacteria are from the URINARY TRACT and are not contaminants of the surrounding tissues. Bacteriuria can be symptomatic or asymptomatic. Significant bacteriuria is an indicator of urinary tract infection.	2.35	2	0
Enlarged Liver [description not available]	1.93	1	0
Neuroses [description not available]	1.93	1	0
Neurotic Disorders Disorders in which the symptoms are distressing to the individual and recognized by him or her as being unacceptable. Social relationships may be greatly affected but usually remain within acceptable limits. The disturbance is relatively enduring or recurrent without treatment.	1.93	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.	1.93	1	0
Amino Acid Transport Disorder, Neutral [description not available]	1.93	1	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	6.93	1	0
Pus [description not available]	6.93	1	0
Abscess Accumulation of purulent material in tissues, organs, or circumscribed spaces, usually associated with signs of infection.	1.93	1	0
Inadequate Sleep [description not available]	2.34	2	0
Childhood Schizophrenia [description not available]	7.34	2	0
Myotonia Prolonged failure of muscle relaxation after contraction. This may occur after voluntary contractions, muscle percussion, or electrical stimulation of the muscle. Myotonia is a characteristic feature of MYOTONIC DISORDERS.	1.94	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.	1.94	1	0
Contracture Prolonged shortening of the muscle or other soft tissue around a joint, preventing movement of the joint.	1.93	1	0
Infectious Diseases [description not available]	1.94	1	0
Hepatitis, Infectious [description not available]	1.94	1	0
Communicable Diseases An illness caused by an infectious agent or its toxins that occurs through the direct or indirect transmission of the infectious agent or its products from an infected individual or via an animal, vector or the inanimate environment to a susceptible animal or human host.	1.94	1	0
Hepatitis INFLAMMATION of the LIVER.	6.94	1	0
Hepatitis A INFLAMMATION of the LIVER in humans caused by a member of the HEPATOVIRUS genus, HUMAN HEPATITIS A VIRUS. It can be transmitted through fecal contamination of food or water.	1.94	1	0
Sarcoma, Epithelioid [description not available]	1.94	1	0
EHS Tumor [description not available]	1.94	1	0
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	1.94	1	0
Orphan Diseases Rare diseases that have not been well studied.	1.94	1	0
Metastase [description not available]	1.94	1	0
Mixed Pineocytoma-Pineoblastoma [description not available]	1.94	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	1.94	1	0
Pinealoma Neoplasms which originate from pineal parenchymal cells that tend to enlarge the gland and be locally invasive. The two major forms are pineocytoma and the more malignant pineoblastoma. Pineocytomas have moderate cellularity and tend to form rosette patterns. Pineoblastomas are highly cellular tumors containing small, poorly differentiated cells. These tumors occasionally seed the neuroaxis or cause obstructive HYDROCEPHALUS or Parinaud's syndrome. GERMINOMA; CARCINOMA, EMBRYONAL; GLIOMA; and other neoplasms may arise in the pineal region with germinoma being the most common pineal region tumor. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, p2064; Adams et al., Principles of Neurology, 6th ed, p670)	6.94	1	0
Starvation Lengthy and continuous deprivation of food. (Stedman, 25th ed)	6.93	1	0
Eosinophilic Granuloma The most benign and common form of Langerhans-cell histiocytosis which involves localized nodular lesions predominantly of the bones but also of the gastric mucosa, small intestine, lungs, or skin, with infiltration by EOSINOPHILS.	1.94	1	0
Vaccinia The cutaneous and occasional systemic reactions associated with vaccination using smallpox (variola) vaccine.	1.93	1	0
Muscle Disorders [description not available]	1.93	1	0
Muscular Diseases Acquired, familial, and congenital disorders of SKELETAL MUSCLE and SMOOTH MUSCLE.	1.93	1	0
Bleeding [description not available]	6.92	1	0
Hemorrhage Bleeding or escape of blood from a vessel.	1.92	1	0
Avian Diseases [description not available]	2.02	1	0
Infections, Spirochaetales [description not available]	2.41	2	0
Pulmonary Consumption [description not available]	1.92	1	0
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	1.92	1	0
Anemia, Hemolytic, Acquired [description not available]	2.64	3	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	1.92	1	0
Anemia, Hemolytic A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).	2.64	3	0
Infections, Vibrio [description not available]	2.02	1	0
Belching [description not available]	2.02	1	0
Ascariasis Infection by nematodes of the genus ASCARIS. Ingestion of infective eggs causes diarrhea and pneumonitis. Its distribution is more prevalent in areas of poor sanitation and where human feces are used for fertilizer.	2.04	1	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	3.08	5	0
Centriacinar Emphysema [description not available]	3.29	2	0
Adenomatoses, Bovine Pulmonary [description not available]	2.37	2	0
Dysentery Acute inflammation of the intestine associated with infectious DIARRHEA of various etiologies, generally acquired by eating contaminated food containing TOXINS, BIOLOGICAL derived from BACTERIA or other microorganisms. Dysentery is characterized initially by watery FECES then by bloody mucoid stools. It is often associated with ABDOMINAL PAIN; FEVER; and DEHYDRATION.	2.37	2	0
Sterility, Female [description not available]	3.28	2	0
Infertility, Female Diminished or absent ability of a female to achieve conception.	3.28	2	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).	1.98	1	0
Focal Segmental Glomerulosclerosis [description not available]	2.9	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.	2.9	1	0
Canine Diseases [description not available]	1.98	1	0
Infections, Pasteurella [description not available]	1.98	1	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	1.98	1	0
Ovine Diseases [description not available]	1.98	1	0
Cat Diseases Diseases of the domestic cat (Felis catus or F. domesticus). This term does not include diseases of the so-called big cats such as CHEETAHS; LIONS; tigers, cougars, panthers, leopards, and other Felidae for which the heading CARNIVORA is used.	1.98	1	0
Caprine Diseases [description not available]	1.98	1	0
Cancer of Colon [description not available]	2.66	3	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.66	3	0
Colonic Diseases Pathological processes in the COLON region of the large intestine (INTESTINE, LARGE).	1.99	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	1	0
Acute Disease Disease having a short and relatively severe course.	2.67	3	0
Bronchitis Inflammation of the large airways in the lung including any part of the BRONCHI, from the PRIMARY BRONCHI to the TERTIARY BRONCHI.	1.98	1	0
Equine Diseases [description not available]	2.38	2	0
Hemoglobinuria The presence of free HEMOGLOBIN in the URINE, indicating hemolysis of ERYTHROCYTES within the vascular system. After saturating the hemoglobin-binding proteins (HAPTOGLOBINS), free hemoglobin begins to appear in the urine.	2.38	2	0
Bacteroides Infections Infections with bacteria of the genus BACTEROIDES.	1.97	1	0
Fusobacterium Infections Infections with bacteria of the genus FUSOBACTERIUM.	1.97	1	0
Sterility, Male [description not available]	2.88	1	0
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	2.88	1	0
Cancer of Rectum [description not available]	1.96	1	0
Colonic Polyps Discrete tissue masses that protrude into the lumen of the COLON. These POLYPS are connected to the wall of the colon either by a stalk, pedunculus, or by a broad base.	1.96	1	0
Rectal Neoplasms Tumors or cancer of the RECTUM.	1.96	1	0

indole

Cross-References

Synonyms (101)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (1)

Drug Classes (2)

Pathways (23)

Protein Targets (37)

Potency Measurements

Inhibition Measurements

Activation Measurements

Biological Processes (91)

Molecular Functions (30)

Ceullar Components (38)

Bioassays (123)

Research

Studies (1,871)

Market Indicators

Research Demand Index: 88.08

Study Types

indole

Cross-References

Synonyms (101)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (1)

Drug Classes (2)

Pathways (23)

Protein Targets (37)

Potency Measurements

Inhibition Measurements

Activation Measurements

Biological Processes (91)

Molecular Functions (30)

Ceullar Components (38)

Bioassays (123)

Research

Studies (1,871)

Market Indicators

Research Demand Index: 88.08

Study Types

Related Drugs (1,331)

Related Conditions (358)