phenylethyl alcohol profile

Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2. [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]

Products

ID Source	ID
PubMed CID	6054
CHEMBL ID	448500
CHEBI ID	49000
SCHEMBL ID	1838
MeSH ID	M0016505

Synonym
smr000059156
MLS001066349
AC-18484
EN300-19347
benzylmethanol
2-hydroxyethylbenzene
phenyl ethyl alcohol
fema no. 2858
phenethyl alcohol (natural)
epa pesticide chemical code 001503
nsc 406252
beta-fenylethanol [czech]
beta-phenylethanol
benzylcarbinol
hsdb 5002
fema number 2858
brn 1905732
beta-fenethylalkohol [czech]
1-phenyl-2-ethanol
caswell no. 655c
einecs 200-456-2
ai3-00744
D00192
phenylethyl alcohol (usp)
beta-phenethyl alcohol
beta-hydroxyethylbenzene
benzeneethanol
inchi=1/c8h10o/c9-7-6-8-4-2-1-3-5-8/h1-5,9h,6-7h
2-phenyl-ethanol
.beta.-phenylethyl alcohol
.beta.-pea
nsc406252
nsc-406252
wln: q2r
.beta.-hydroxyethylbenzene
.beta.-phenethyl alcohol
phenylethanol
2-pea
methanol, benzyl-
phenethanol
2-phenethyl alcohol
benzyl carbinol
2-phenylethyl alcohol
phenylethyl, b- alcohol
ethanol, 2-phenyl-
.beta.-phenylethanol
PEL ,
CHEBI:49000 ,
C05853
2-phenylethanol
60-12-8
phenethyl alcohol
phenylethyl alcohol
HY1 ,
phenethyl alcohol, natural, >=99%, fcc, fg
phenethyl alcohol, >=99%, fcc, fg
DB02192
NCGC00166215-01
2-phenylethanol, >=99.0% (gc)
MLS001336026
phenethylalcohol
0DE4CADC-AB8A-4038-BD6F-EBD009885652
HMS2093H05
AKOS000249688
beta-phenylethyl alcohol
beta-pea
BMSE000659
P0084
CHEMBL448500
.beta.-(hydroxyethyl)benzene
A832606
NCGC00166215-02
NCGC00166215-03
carbinol, benzyl
beta phenylethanol
alcohol, phenylethyl
alcohol, phenethyl
2 phenylethanol
4-06-00-03067 (beilstein handbook reference)
unii-ml9lga7468
beta-fenylethanol
beta-fenethylalkohol
ec 200-456-2
phenylethyl alcohol [usp]
ml9lga7468 ,
2-phenylethan-1-ol
tox21_303383
cas-60-12-8
NCGC00257347-01
dtxsid9026342 ,
dtxcid206342
tox21_113544
tox21_201322
NCGC00258874-01
nsc759116
nsc-759116
pharmakon1600-01505398
phenyl ethanol(natural)
1321-27-3
ethanol, phenyl-
bdbm85807
nsc_6054
cas_60-12-8
HMS2233H06
S3703
benzenethanol
STL281950
FT-0673679
FT-0613332
phenylethyl alcohol [usp-rs]
phenethyl alcohol [who-dd]
phenylethyl alcohol [hsdb]
phenethyl alcohol [inci]
phenylethyl alcohol [ii]
(2-hydroxyethyl)benzene
phenylethyl alcohol [usp monograph]
phenethyl alcohol [mi]
phenylethyl alcohol [fhfi]
phenethyl alcohol [fcc]
phenethyl alcohol [mart.]
HMS3374P04
CCG-213419
a-pea
SCHEMBL1838
NCGC00166215-05
tox21_113544_1
betaphenylethyl alcohol
2-phenyl ethanol
2-(2-hydroxyethyl)benzene
benzene-ethanol
2-phenyl-1-ethanol
Q-200318
phenylethyl, beta- alcohol
2-phenethanol
hydroxyethylbenzene
.beta.-p.e.a.
.beta.-fenethylalkohol
.beta.-phenethanol
mellol
.beta.-fenylethanol
AB00698274_05
mfcd00002886
F0001-1575
sr-01000763553
SR-01000763553-2
phenylethyl alcohol, united states pharmacopeia (usp) reference standard
phenylethyl alcohol (ii)
methanol, benzyl
phenethyl alcohol (mart.)
(beta-pea)
beta-(hydroxyethyl)benzene
2-phenylethane-1-ol
phenylethyl alcohol (usp monograph)
phenylethyl alcohol (usp-rs)
fema number 2858.
phenylethyl alcohol, pharmaceutical secondary standard; certified reference material
2-phenylethanol, 99%
2-phenylethanol, usp
phenyl-ethanol
phenylethyl alcohol, usan
phenethyl alcohol, 8ci, ban
benzeneethanol, 9ci
fema 2858
beta -hydroxyethylbenzene
b-hydroxyethylbenzene
benzyl ethyl alcohol
benzyl-methanol
2-phenyiethanol
SBI-0206858.P001
CS-B1821
HY-B1290
Q209463
BBL036905
phenylethyl alcohol;phenethyl alcohol;benzeneethanol
BCP32115
phenylethyl-alcohol
D70868
19601-20-8
2-phenylethanol;2-phenylethyl alcohol;benzeneethanol;phenylethanol
phenethylalcohol-d5
Z104473586

Excerpt	Reference	Relevance
"Phenylethyl alcohol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a primary alcohol."	( Fragrance material review on phenylethyl alcohol. Api, AM; Jones, L; Letizia, CS; Scognamiglio, J, 2012)	1.39

Excerpt	Reference	Relevance
"The active component of the honeybee hive product propolis, caffeic acid phenethyl ester (CAPE), induces a selective growth suppressive and toxic effect toward cloned rat embryo fibroblast cells transformed by adenovirus type 5 (Ad5) or the Ad5 E1A transforming gene versus untransformed cloned rat embryo fibroblast cells (Z-z."	( Growth suppression and toxicity induced by caffeic acid phenethyl ester (CAPE) in type 5 adenovirus-transformed rat embryo cells correlate directly with transformation progression. Fisher, PB; Grunberger, D; Lin, J; Su, ZZ, 1994)	0.29
"3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a toxic metabolite formed by the oxidative deamination of dopamine."	( 3,4-Dihydroxyphenylacetaldehyde potentiates the toxic effects of metabolic stress in PC12 cells. Eisenhofer, G; Harvey-White, J; Kirk, K; Kopin, IJ; Lamensdorf, I; Nechustan, A, 2000)	0.31
" Our results indicated that CAPE acts in the kidney as a potent scavenger of free radicals to prevent the toxic effects of GEN both at the biochemical and histological level."	( Protective role of caffeic acid phenethyl ester (cape) on gentamicin-induced acute renal toxicity in rats. Acet, A; Bay-Karabulut, A; Parlakpinar, H; Polat, A; Tasdemir, S; Ucar, M; Vardi, N, 2005)	0.33
" These findings confirm a key role for glutathione in protecting cells from CsA-induced adverse effects and do not support a direct link between CsA-mediated ROS generation and adverse renal effects."	( Diverse effects of natural antioxidants on cyclosporin cytotoxicity in rat renal tubular cells. Capasso, G; Chiodini, P; Della Ragione, F; Di Gennaro, CI; Galletti, P; Indaco, S; Manna, C; Migliardi, V; Zappia, V, 2005)	0.33
" The protective effects of the tested extracts or isolated compounds were evaluated from their ability to decrease hydrogen peroxide-induced formation of single strand breaks in the nuclear DNA, while the toxic effects were estimated from the increase of DNA damage when the extracts or isolated compounds were incubated directly with the cells."	( DNA protecting and genotoxic effects of olive oil related components in cells exposed to hydrogen peroxide. Agalias, A; Aligiannis, N; Bazios, D; Doulias, PT; Galaris, D; Mitakou, S; Nousis, L, 2005)	0.33
" Caffeic acid phenethyl ester (CAPE), a component of honeybee propolis, protects tissues from reactive oxygene species mediated oxidative stress in ischemia-reperfusion and toxic injuries."	( Lithium-induced renal toxicity in rats: protection by a novel antioxidant caffeic acid phenethyl ester. Akturk, O; Altuntas, I; Oktem, F; Olgar, S; Ozguner, F; Sulak, O; Yilmaz, HR, 2005)	0.33
" Adverse effects of TAM include hepatotoxicity."	( Caffeic acid phenethyl ester protects against tamoxifen-induced hepatotoxicity in rats. Abdel-Naim, AB; Albukhari, AA; El-Beshbishy, HA; Gashlan, HM; Nagy, AA, 2009)	0.35
" However, its widespread use is restricted because it has serious toxic effects on the kidney."	( Protective effect of caffeic acid phenethyl ester on cyclosporine A-induced nephrotoxicity in rats. Aydin, M; Davarci, M; Gökçe, A; Ilhan, S; Oktar, S; Ozkan, OV; Yalçinkaya, FR; Yönden, Z, 2009)	0.35
"Arsenic trioxide (ATO) treatment is a useful therapy against human acute promyelocytic leukemia (APL), however, it concomitantly brings potential adverse consequences including serious side effect, human carcinogenicity and possible development of resistance."	( Cytotoxicity of arsenic trioxide is enhanced by (-)-epigallocatechin-3-gallate via suppression of ferritin in cancer cells. Cheng, IC; Lee, TC; Shue, JJ; Wang, TC, 2011)	0.37
" L-Buthionine-SR-sulfoximine treatment exerted an additive toxic effect on the CP-treated animals."	( In vivo prevention of bladder urotoxicity: purified hydroxytyrosol ameliorates urotoxic effects of cyclophosphamide and buthionine sulfoximine in mice. Cherif, M; Elgaaied, AB; Hamden, K; Hamrita, B; Jaouadi, B; Kouidi, S; Medimegh, I; Messai, Y; Ouerhani, S; Rouissi, K, 2011)	0.37
"Humans are exposed to dietary acrylamide (AA) during their lifetime, it is therefore necessary to investigate the mechanisms associated with AA-induced toxic effects."	( Olive oil hydroxytyrosol reduces toxicity evoked by acrylamide in human Caco-2 cells by preventing oxidative stress. Bravo, L; Goya, L; Martín, MÁ; Ramos, S; Rodríguez-Ramiro, I, 2011)	0.37
"3 mg/kg per day from the use of multiple consumer personal care products containing PEA, a rat dermal no observed adverse effect level of 70 mg/kg per day, and the percentage of dose absorbed in humans, the margin of safety exceeds 2600 concluding that, under normal fragrance use conditions, PEA is not a developmental toxicity hazard for humans."	( The pharmacokinetics of phenylethyl alcohol (PEA): safety evaluation comparisons in rats, rabbits, and humans. Api, AM; Christian, MS; Diener, RM; Hawkins, DR; Politano, VT; Ritacco, G, )	0.44
" There are some studies suggesting oxidative stress-induced toxic changes on liver related to AFB1 toxicity."	( Caffeic acid phenethyl ester modulates aflatoxin B1-induced hepatotoxicity in rats. Akçam, M; Artan, R; Gelen, T; Nazıroğlu, M; Ozdem, S; Yilmaz, A, 2013)	0.39
"Paraquat (PQ), which is used extensively as a potent herbicide throughout the world, is highly toxic in humans."	( Protective effects of caffeic acid phenethyl ester on the dose-dependent acute nephrotoxicity with paraquat in a rat model. Davarci, M; Dorum, BA; Gokce, H; Nacar, A; Rifaioglu, MM; Sefil, F, 2015)	0.42
" Safety measures included discontinuation rate, treatment-emergent adverse events, serious adverse events, and vital signs."	( Long-Term, Open-Label, Safety Study of Edivoxetine 12 to 18 mg Once Daily as Adjunctive Treatment for Patients With Major Depressive Disorder Who Are Partial Responders to Selective Serotonin Reuptake Inhibitor Treatment. Atkinson, S; Ball, SG; Bangs, M; Dubé, S; Goldberger, C; Sparks, J, 2015)	0.42
" The lowest observed adverse effect level (LOAEL) was the 500 mg HT/kg bw/day based on statistically significant reductions in body weight gain and decreased body weight in males."	( Toxicological evaluation of an olive extract, H35: Subchronic toxicity in the rat. Anyangwe, N; Beilstein, P; Edwards, J; Heilman, J; López, J; Tran, N, 2015)	0.42
" HC-HT CSNPs exhibited LD50 > 125 mg/body surface area of active, which is 100-fold higher than the normal human dose of HC."	( Minimization of Local and Systemic Adverse Effects of Topical Glucocorticoids by Nanoencapsulation: In Vivo Safety of Hydrocortisone-Hydroxytyrosol Loaded Chitosan Nanoparticles. Amin, MCIM; Buang, F; Jamil, A; Katas, H; Ng, SF; Siddique, MI; Zulfakar, MH, 2015)	0.42
"In the ethanol group, TAS levels were significantly lower than the other groups and this finding indicates that the toxic effect of ethanol reduces antioxidant levels."	( Protective Effects of Intralipid and Caffeic Acid Phenyl Esther (CAPE) on Neurotoxicity Induced by Ethanol in Rats. Basarslan, SK; Kaplan, I; Korkmaz, M; Osun, A; Ozkan, U; Senol, S, 2017)	0.46
" The safety assessments included the incidence of adverse events, vital signs, electrocardiograms, laboratory tests, percentile changes in weight, height, and body mass index, and Tanner staging."	( Long-Term, Open-Label, Safety Study of Edivoxetine Monotherapy in Children and Adolescents with Attention-Deficit/Hyperactivity Disorder. Ahl, J; Bangs, M; Liu, P; Nery, ESM; Perahia, D, 2017)	0.46
"9%; N = 264) experienced at least one adverse event."	( Long-Term, Open-Label, Safety Study of Edivoxetine Monotherapy in Children and Adolescents with Attention-Deficit/Hyperactivity Disorder. Ahl, J; Bangs, M; Liu, P; Nery, ESM; Perahia, D, 2017)	0.46
"Hydrocortisone (HC), topical glucocorticoid along with hydroxytyrosol (HT), and anti-microbial- and anti-oxidant-loaded chitosan nanoparticles (CSNPs) were prepared in large scale and analyzed for their adverse effects on healthy human skin followed by repeated applications."	( Potential treatment of atopic dermatitis: tolerability and safety of cream containing nanoparticles loaded with hydrocortisone and hydroxytyrosol in human subjects. Jamil, A; Katas, H; Mohd Amin, MCI; Nadeem, SM; Ng, SF; Siddique, MI; Zulfakar, MH, 2019)	0.51
"Cisplatin is a highly effective chemotherapeutic drug that is toxic to the peripheral nervous system."	( Caffeic Acid Phenethyl Ester (CAPE) Protects PC12 Cells from Cisplatin-Induced Neurotoxicity by Activating the NGF-Signaling Pathway. Dos Santos, AC; Dos Santos, NAG; Fernandes, LS; Ferreira, RS; Martins, NM, 2018)	0.48
" Phosphatidyl-hydroxytyrosol administered in a single oral gavage dose of 2000 mg/kg of body weight (bw) resulted in no adverse events or mortality."	( Acute and repeated dose (28 days) oral safety studies of phosphatidyl-hydroxytyrosol. Anadón, A; Ares, I; Casado, V; Martin, D; Martínez, MA; Martínez-Larrañaga, MR; Reglero, G; Torres, C; Vazquez, L, 2018)	0.48
"Toluene is an organic solvent that is toxic to humans."	( Protective effects of caffeic acid phenethyl ester and thymoquinone on toluene induced liver toxicity. Akbas Tosunoglu, E; Bayındır, N; Bulut, H; Esrefoglu, M; Kurbetli, N; Meral, I; Meydan, S; Ozturk, O; Selek, S, 2019)	0.51
"Peripheral sensory neuropathy (PSN) is a well-known side effect of cisplatin characterized by axonal damage."	( Caffeic Acid Phenethyl Ester (CAPE) Protects PC12 Cells Against Cisplatin-Induced Neurotoxicity by Activating the AMPK/SIRT1, MAPK/Erk, and PI3k/Akt Signaling Pathways. Amaral, L; Bernardes, CP; Dos Santos, AC; Dos Santos, NAG; Ferreira, RS; Fontana, ACK; Sisti, FM, 2019)	0.51
"The HT-based product is effective and safe in preventing recurrent candida episodes and improves the quality of life and sexual function of treated women."	( Efficacy and safety of oral administration of a product based on hydroxytyrosol as preventive therapy for recurrent vulvo-vaginal candidosis: a prospective observational pilot study. Di Pinto, A; Luffarelli, P; Oliva, C; Prata, G; Schiavi, MC; Scudo, M; Zullo, MA, 2020)	0.56
" Taken together, data from this work reveal that HT itself possesses toxic effect on HCs mainly thorough AIF-dependent apoptosis, while, it aggravates the ototoxicity-caused by cisplatin via both JNK and AIF pathways related apoptosis."	( Hydroxytyrosol enhances cisplatin-induced ototoxicity: Possible relation to the alteration in the activity of JNK and AIF pathways. Li, J; Man, R; Yang, H; Yang, Q; Yu, X; Zhang, W, 2020)	0.56
" Although this effect occurs with the formation of differently toxic products, the molecular basis of this inhibition is still unclear."	( Structural Features and Toxicity of α-Synuclein Oligomers Grown in the Presence of DOPAC. Acquasaliente, L; Bucciantini, M; Fongaro, B; Leri, M; Palazzi, L; Polverino de Laureto, P; Stefani, M, 2021)	0.62

Excerpt	Reference	Relevance
" The pharmacokinetic analysis indicates a fast and extensive uptake of the molecule by the organs and tissues investigated, with a preferential renal uptake."	( Pharmacokinetics and metabolism of hydroxytyrosol, a natural antioxidant from olive oil. Capasso, G; D'Angelo, S; Galletti, P; Manna, C; Mazzoni, O; Migliardi, V; Morrica, P; Pontoni, G; Zappia, V, 2001)	0.31
"The main pharmacokinetic parameters ofp-tyrosol upon intravenous injection have been experimentally studied in rats."	( [The main pharmacokinetic parameters of p-tyrosol upon intravenous injection in rats]. Cherkashina, IV; Chernysheva, GA; Krysin, AP; Plotnikov, MB; Smol'niakova, VI; Sorokina, IV; Tolstikova, TG, )	0.13
"The main pharmacokinetic parameters of p-tyrosol after single (in 3 doses) and repeated intravenous injection were studied in rats."	( [The main pharmacokinetic parameters of p-tyrosol upon intravenous injection in rats. II. Verification of the pharmacokinetics linearity and evaluation of the possible accumulation]. Cherkashina, IV; Chernysheva, GA; Krysin, AP; Plotnikov, MB; Smol'iakova, VI; Sorokina, IV; Tolstikova, TG, )	0.13
"The pharmacokinetic profiles of caffeic acid phenethyl ester (CAPE) and its catechol-ring fluorinated derivative (FCAPE) were determined in rats after intravenous administration of 5, 10 or 20 mg/kg for CAPE and 20 mg/kg for FCAPE, respectively."	( Pharmacokinetics of caffeic acid phenethyl ester and its catechol-ring fluorinated derivative following intravenous administration to rats. Bowman, PD; Kerwin, SM; Maffucci, JA; Newman, RA; Pade, DS; Pang, J; Stavchansky, S; Wang, X, 2009)	0.35
" In order to have a good understanding of its pharmacokinetic characters, the paper describes the dose-dependent pharmacokinetics of TG in rats after oral and intravenous administration."	( Dose-dependent pharmacokinetics of tyrosol galactoside as an anti-fatigue drug in rats. Deng, Y; Ding, Z; Liu, X; Wang, Q; Wang, Y, 2011)	0.37
" The time to maximum concentration (t(max)) of edivoxetine was ∼2 hours, which was followed by a mono-exponential decline in plasma concentrations with a terminal elimination half-life (t(1/2)) of ∼6 hours."	( Pharmacokinetics and pharmacodynamics of edivoxetine (LY2216684), a norepinephrine reuptake inhibitor, in pediatric patients with attention-deficit/hyperactivity disorder. Allen, AJ; Dean, RA; Jin, L; Kielbasa, W; Lachno, DR; Quinlan, T; Xu, W, 2012)	0.38
" This study investigated its in vivo anticancer efficacy and its pharmacokinetic and metabolic characteristics."	( Antitumor activity of caffeic acid 3,4-dihydroxyphenethyl ester and its pharmacokinetic and metabolic properties. Guo, X; He, Q; Lian, XY; Shen, L; Tong, Y; Wu, G; Ye, X; Yu, S; Zhang, J; Zhang, Z; Zou, L, 2013)	0.39
" Overall, the GLSM of the ratio [impaired : normal] of Cmax was slightly less than or approximately 1 across the hepatic and renal impairment groups."	( The effect of hepatic or renal impairment on the pharmacokinetics of edivoxetine, a selective norepinephrine transporter reuptake inhibitor. Kielbasa, W; Luffer-Atlas, D; Mitchell, MI; Tesfaye, E; Turik, MA, 2013)	0.39
" This method was used to determine the pharmacokinetic profiles of CAPA and CAPE in male Sprague-Dawley rats following intravenous bolus administration of 5, 10 and 20 mg/kg of CAPA and 20 mg/kg of CAPE."	( Development and validation of an LCMS method to determine the pharmacokinetic profiles of caffeic acid phenethyl amide and caffeic acid phenethyl ester in male Sprague-Dawley rats. Bowman, PD; Kerwin, SM; Stavchansky, S; Yang, J, 2014)	0.4
" The tmax is ∼ 2 h post-dose, and the plasma t1/2 is ∼ 4 - 6 h irrespective of the dose."	( A pharmacokinetic evaluation of oral edivoxetine hydrochloride for the treatment of attention deficit-hyperactivity disorder. Brinda, BJ; Markowitz, JS, 2014)	0.4
" The pharmacokinetic and pharmacodynamic profile of these drugs in plasma and cerebrospinal fluid (CSF) was assessed."	( A pharmacokinetic/pharmacodynamic investigation: assessment of edivoxetine and atomoxetine on systemic and central 3,4-dihydroxyphenylglycol, a biochemical marker for norepinephrine transporter inhibition. Kielbasa, W; Pan, A; Pereira, A, 2015)	0.42
" Pharmacokinetic and pharmacodynamic data were obtained from healthy subjects (n = 160) from 5 clinical trials."	( Pharmacodynamics of norepinephrine reuptake inhibition: Modeling the peripheral and central effects of atomoxetine, duloxetine, and edivoxetine on the biomarker 3,4-dihydroxyphenylglycol in humans. Kielbasa, W; Lobo, E, 2015)	0.42
" To understand the pharmacokinetic characteristics of CAPE, the binding interaction between CAPE and human serum albumin (HSA) was investigated in vitro using multiple spectroscopic methods and molecular docking."	( Caffeic acid phenethyl ester exhibiting distinctive binding interaction with human serum albumin implies the pharmacokinetic basis of propolis bioactive components. Hu, F; Li, H; Tan, J; Wang, K; Wu, F; Zhang, C; Zheng, H, 2016)	0.43
" Dermal pharmacokinetic of CSNPs with a size of 228."	( In-vivo dermal pharmacokinetics, efficacy, and safety of skin targeting nanoparticles for corticosteroid treatment of atopic dermatitis. Amin, MC; Jamil, A; Katas, H; Ng, SF; Siddique, MI; Zulfakar, MH, 2016)	0.43
" This review summarizes new findings on PhGs over the past 10 years, concerning the new structures, their bioactivities, including neuroprotective, anti-inflammatory, antioxidant, antibacterial and antivirus, cytotoxic, immunomodulatory, and enzyme inhibitory effects, and pharmacokinetic properties."	( Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics. Xue, Z; Yang, B, 2016)	0.43
" Thus, the pharmacokinetic characteristics in rat and the gut microbial degradation of tyrosol acyl esters (TYr-Es) with fatty acids of C12:0, C18:0, and C18:2 were investigated for the first time."	( Evaluation of Absorption and Plasma Pharmacokinetics of Tyrosol Acyl Esters in Rats. Hu, Y; Liu, X; Qin, L; Shahidi, F; Wang, X; Xie, H; Yin, F; Zhang, J; Zhou, D, 2020)	0.56
" Pharmacokinetic analysis was performed through GC-MS to evaluate how quickly it absorbs and distributes in plasma."	( Metabolite Profiling, Stability Testing, Pharmacokinetics, and In Vivo Pattern Recognition Analysis of Arq-e-Keora: A Traditional Unani Formulation. Ahmad, S; Khan, AA; Parveen, A; Parveen, R; Zahiruddin, S, 2022)	0.72
" Pharmacokinetics data of phenethyl alcohol showed its absorption was rapid, with Tmax occurring within 1 h after oral administration of Arq-e-Keora."	( Metabolite Profiling, Stability Testing, Pharmacokinetics, and In Vivo Pattern Recognition Analysis of Arq-e-Keora: A Traditional Unani Formulation. Ahmad, S; Khan, AA; Parveen, A; Parveen, R; Zahiruddin, S, 2022)	0.72
"As a result, our model could be used for quality, stability, and pharmacokinetic evaluation of various Unani formulations mentioned in Unani Pharmacopoeia of India."	( Metabolite Profiling, Stability Testing, Pharmacokinetics, and In Vivo Pattern Recognition Analysis of Arq-e-Keora: A Traditional Unani Formulation. Ahmad, S; Khan, AA; Parveen, A; Parveen, R; Zahiruddin, S, 2022)	0.72
"This is the first study of pharmacokinetic analysis and metabolite pattern of traditional Unani formulation after its oral administration in Wistar rats."	( Metabolite Profiling, Stability Testing, Pharmacokinetics, and In Vivo Pattern Recognition Analysis of Arq-e-Keora: A Traditional Unani Formulation. Ahmad, S; Khan, AA; Parveen, A; Parveen, R; Zahiruddin, S, 2022)	0.72

Excerpt	Reference	Relevance
" Interestingly, the -N cultivation combined with 2-phenylethanol exposure reduced the Synechocystis protein content by 27% (w/w DW) but significantly increased PHB levels up to 33% (w/w DW), the highest ever reported photoautotrophic cyanobacterial PHB accumulation in a wild-type strain."	( Chemicals Affecting Cyanobacterial Poly(3-hydroxybutyrate) Accumulation: 2-Phenylethanol Treatment Combined with Nitrogen Deprivation Synergistically Enhanced Poly(3-hydroxybutyrate) Storage in Synechocystis sp. PCC6803 and Anabaena sp. TISTR8076. Incharoensakdi, A; Monshupanee, T; Sukkasam, N, 2022)	0.72
" To achieve the reutilization of the condensate, the ozonation combined with ion-exchange method was used."	( Exploring the resourcing technology of condensate using ozonation combined with ion-exchange in ethanol fermentation. Li, Z; Sheng, X; Zhang, J, 2022)	0.72

Excerpt	Reference	Relevance
" Despite its relevant biological effects, no data are available on its bioavailability and metabolism."	( Transport mechanism and metabolism of olive oil hydroxytyrosol in Caco-2 cells. Cucciolla, V; D'Angelo, S; Galletti, P; Maisto, G; Manna, C; Zappia, V, 2000)	0.31
" Bioavailability and metabolism studies of this compound are extremely limited, in part, related to unavailability of radiolabeled compound."	( Synthesis of tritium-labeled hydroxytyrosol, a phenolic compound found in olive Oil. Hayball, PJ; Tan, HW; Tuck, KL, 2000)	0.31
" One of the prerequisites to extrapolate these data to an in vivo situation is the knowledge of their bioavailability in humans."	( Capillary gas chromatography-mass spectrometry quantitative determination of hydroxytyrosol and tyrosol in human urine after olive oil intake. Covas, MI; de la Torre, R; Farré Albaladejo, M; Lamuela Raventós, RM; Menoyo Colomer, E; Miró-Casas, E; Rodriguez, JO, 2001)	0.31
" Oral bioavailability estimates of hydroxytyrosol when administered in an olive oil solution and when dosed as an aqueous solution were 99% and 75%, respectively."	( The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. Freeman, MP; Hayball, PJ; Stretch, GL; Stupans, I; Tuck, KL, 2001)	0.31
"We have recently demonstrated, in humans, the bioavailability of hydroxytyrosol (3,4-dihydroxyphenylethanol; HT), one of the major antioxidant components of virgin olive oil."	( Urinary excretion of olive oil phenols and their metabolites in humans. Caruso, D; Galli, C; Galli, G; Patelli, R; Visioli, F, 2001)	0.31
" We have demonstrated the bioavailability of tyrosol in humans from virgin olive oil in its natural form."	( Bioavailability of tyrosol, an antioxidant phenolic compound present in wine and olive oil, in humans. Covas, MI; De La Torre, R; Farré-Albadalejo, M; Fitó, M; Gimeno, E; Marrugat, J; Miró-Casas, E, 2003)	0.32
" Hydroxytyrosol is well absorbed in the gastrointestinal tract but its bioavailability is poor because an important first past metabolism both in gut and liver, leading to the formation of sulphate and glucuronide conjugates, to the extent that concentrations in body fluids of its free form are almost undetectable."	( Bioavailability of olive oil phenolic compounds in humans. de la Torre, R, 2008)	0.35
" Their bioavailability in humans is poor, and they are found in biological fluids mainly as conjugated metabolites."	( Antioxidant activities of hydroxytyrosol main metabolites do not contribute to beneficial health effects after olive oil ingestion. Covas, MI; de la Torre, R; Farré, M; Fitó, M; Joglar, J; Khymenets, O; Muñoz-Aguayo, D; Pujadas, M; Torres, JL; Touriño, S, 2010)	0.36
" The bioavailability of TG in rats is 27."	( A rapid determination of drug candidate tyrosol galactoside in rat plasma by HPLC and its application to the pharmacokinetics study. Deng, Y; Li, X; Liu, X; Shi, T; Sun, X; Wang, Q; Wang, Y; Zhou, D, 2011)	0.37
" The method has been successfully applied to the pharmacokinetic study and the oral bioavailability was calculated."	( Simultaneous determination of salidroside and its aglycone metabolite p-tyrosol in rat plasma by liquid chromatography-tandem mass spectrometry. Fan, X; Guo, N; Hu, Z; Li, H; Wang, Y; Xu, T; Yu, T; Zhang, D; Zheng, J, 2012)	0.38
" The good bioavailability by the oral route and good historical safety profile makes propolis an ideal adjuvant agent for future immunomodulatory or anticancer regimens."	( The immunomodulatory and anticancer properties of propolis. Chan, GC; Cheung, KW; Sze, DM, 2013)	0.39
" CADPE was quickly hydrolyzed both in mice and in vitro mice plasma, but was much stable in vitro human plasma, suggesting a better bioavailability of CADPE in human than in mice."	( Antitumor activity of caffeic acid 3,4-dihydroxyphenethyl ester and its pharmacokinetic and metabolic properties. Guo, X; He, Q; Lian, XY; Shen, L; Tong, Y; Wu, G; Ye, X; Yu, S; Zhang, J; Zhang, Z; Zou, L, 2013)	0.39
" To quantify the bioavailability and metabolism of oleuropein and hydroxytyrosol when taken as OLE, nine volunteers (five males) aged 42."	( Human absorption and metabolism of oleuropein and hydroxytyrosol ingested as olive (Olea europaea L.) leaf extract. Cutfield, WS; de Bock, M; Derraik, JG; Henderson, HV; Hofman, PL; Thorstensen, EB, 2013)	0.39
" Further studies are needed to determine the bioavailability of these compounds and their possible beneficial health effects when taken by moderate beer consumption."	( Beer and beer compounds: physiological effects on skin health. Becker, T; Chen, W; Qian, F; Ring, J, 2014)	0.4
" Hydroxytyrosol is an orally bioavailable polyphenol, obtained from olives, which inhibits NF-κβ activity and has elicited promising efficacy signals in several inflammatory diseases."	( NF-κβ signaling and chronic inflammatory diseases: exploring the potential of natural products to drive new therapeutic opportunities. Crea, R; Killeen, MJ; Linder, M; Pontoniere, P, 2014)	0.4
" In this review HT bioavailability and pharmacokinetics are presented prior to discussing health beneficial effects."	( Potential role of olive oil phenolic compounds in the prevention of neurodegenerative diseases. de la Torre, R; Dierssen, M; Farré, M; Fitó, M; Rodríguez-Morató, J; Xicota, L, 2015)	0.42
"The notion that (poly)phenols act as direct free radical scavengers is being challenged by mere chemical and biochemical considerations such as bioavailability and intracellular concentrations."	( One-week administration of hydroxytyrosol to humans does not activate Phase II enzymes. Burgos-Ramos, E; Crespo, MC; Espinosa, MI; Herranz, J; Loria Kohen, V; Tomé-Carneiro, J; Visioli, F, )	0.13
" BCS1 classification was leveraged throughout development to assess the risk associated with not conducting relative bioavailability (RBA) studies and avoiding bioequivalence (BE) studies."	( Leveraging BCS in Development: A Case Study. Aburub, A; Fadda, HM; Hoaglund Hyzer, CS; Rodriguez, JO, 2015)	0.42
" However, the bioavailability of the most important of these compounds, hydroxytyrosol (HT), and its transformation into derivatives within the organism after oral intake are still not completely understood, requiring further in vivo research."	( Gender differences in plasma and urine metabolites from Sprague-Dawley rats after oral administration of normal and high doses of hydroxytyrosol, hydroxytyrosol acetate, and DOPAC. Auñón, D; Domínguez-Perles, R; Ferreres, F; Gil-Izquierdo, A, 2017)	0.46
"Plasma and urine levels indicated that although the three compounds are efficiently absorbed in the gastrointestinal tract and show similar metabolism, the bioavailability is strongly dependent on the derivative considered, dosage, and gender."	( Gender differences in plasma and urine metabolites from Sprague-Dawley rats after oral administration of normal and high doses of hydroxytyrosol, hydroxytyrosol acetate, and DOPAC. Auñón, D; Domínguez-Perles, R; Ferreres, F; Gil-Izquierdo, A, 2017)	0.46
" In conclusion, NO2HT, NO2HT-A, and NO2HT-E show high in vitro bioavailability and are extensively metabolized by hepatic cells."	( Evaluation of the Bioavailability and Metabolism of Nitroderivatives of Hydroxytyrosol Using Caco-2 and HepG2 Human Cell Models. Bravo-Clemente, L; Espartero, JL; Gallardo, E; Gonzalez Correa, JA; Mateos, R; Sarria, B, 2016)	0.43
" We performed a crossover, randomized, double-blind study to evaluate HT bioavailability in HT-enriched biscuits (HT-B) versus non-enriched biscuits (C-B), and the effects on oxidative postprandial status."	( Hydroxytyrosol in functional hydroxytyrosol-enriched biscuits is highly bioavailable and decreases oxidised low density lipoprotein levels in humans. Amigo-Benavent, M; Baeza Arévalo, G; Bravo-Clemente, L; Martínez-López, S; Mateos, R; Sarriá, B, 2016)	0.43
" In this regard, information regarding the bioavailability and metabolic disposition of hydroxytyrosol and tyrosol is of most importance to evaluate the impact they may have on human health."	( Metabolic disposition and biological significance of simple phenols of dietary origin: hydroxytyrosol and tyrosol. Boronat, A; de la Torre, R; Farré, M; Fitó, M; Khymenets, O; Kotronoulas, A; Olesti, E; Pastor, A; Pérez-Mañá, C; Pujadas, M; Rodríguez-Morató, J, 2016)	0.43
" In addition, it is suggested that CAPE-NPs can be used to reduce the dosage of CAPE and improve their bioavailability and thus merit further investigation for bioactive packaging film and coating applications."	( Fabrication of Novel Bioactive Cellulose-Based Films Derived from Caffeic Acid Phenethyl Ester-Loaded Nanoparticles via a Rapid Expansion Process: RESOLV. Assatarakul, K; Saelo, S; Sane, A; Suppakul, P, 2016)	0.43
" The bioavailability and bioactivity was evaluated following gavage with HT/PCy in rabbits."	( Olive and grape seed extract prevents post-traumatic osteoarthritis damages and exhibits in vitro anti IL-1β activities before and after oral consumption. Abadie, J; Beck, L; Gauthier, O; Guicheux, J; Hivernaud, V; Houard, X; Krisa, S; Lesoeur, J; Masson, M; Merceron, C; Mével, E; Nourissat, G; Richard, T; Urban, N; Vinatier, C; Wittrant, Y, 2016)	0.43
" Moreover, we also discuss the chemistry, nutritional aspects and bioavailability of hydroxytyrosol."	( Cardioprotective Effects of the Polyphenol Hydroxytyrosol from Olive Oil. Del Mar Bibiloni, M; Pinya, S; Pons, A; Sureda, A; Tejada, S; Tur, JA, 2017)	0.46
" In addition the concentration, metabolism and bioavailability of specific phenolic compounds will be discussed."	( The Health Benefiting Mechanisms of Virgin Olive Oil Phenolic Compounds. Cicerale, S; Parkinson, L, 2016)	0.43
" This study attempted to prepare liposomes containing water-soluble HT to improve the bioavailability and biocompatibility of the target drug."	( Preparation, Characterization, and Antioxidant Activity Evaluation of Liposomes Containing Water-Soluble Hydroxytyrosol from Olive. Li, B; Qin, FGF; Tu, JL; Yuan, JJ, 2017)	0.46
" Bioavailability studies show that the metabolites detected in plasma depend on the model used (animal or human), the HT source (simple molecule or complex precursors) and the dose administered."	( Hydroxytyrosol: Emerging Trends in Potential Therapeutic Applications. de Las Hazas, MCL; Macia, A; Motilva, MJ; Rubio, L, 2018)	0.48
" In this work, Zn and Se bioavailability was increased in chicken meat emulsions that are enriched with Hydroxytyrosol (HXT), a phenolic compound obtained from olive leaf."	( Fe, Zn and Se Bioavailability in Chicken Meat Emulsions Enriched with Minerals, Hydroxytyrosol and Extra Virgin Olive Oil as Measured by Caco-2 Cell Model. Martínez, L; Nieto, G; Ros, G, 2018)	0.48
" Caffeic acid phenethyl ester (CAPE) and piceatannol (PIC) are natural anti-inflammatory compounds; however, poor bioavailability and limited understanding of biomolecular mechanistic limits its clinical use."	( Albumin nano-encapsulation of caffeic acid phenethyl ester and piceatannol potentiated its ability to modulate HIF and NF-kB pathways and improves therapeutic outcome in experimental colitis. Khan, MN; McCarron, PA; Tambuwala, MM; Thompson, P, 2019)	0.51
" These natural antioxidants molecules revealed several beneficial effects on human health, but a low bioavailability and accessibility to targeted site."	( Chemical characterization of liposomes containing nutraceutical compounds: Tyrosol, hydroxytyrosol and oleuropein. Bonechi, C; Consumi, M; Donati, A; Lamponi, S; Leone, G; Magnani, A; Pardini, A; Rossi, C; Rostom, H; Tamasi, G, 2019)	0.51
"Acrylamide and phenolic compounds on both fresh and cooked olives were monitored by HPLC/MS-MS and reversed-phase-HPLC methods along different procedures: elaboration process, high hydrostatic pressure (HHP), cooking treatment and bioavailability evaluation."	( Monitoring of acrylamide and phenolic compounds in table olive after high hydrostatic pressure and cooking treatments. Cabrera-Bañegil, M; Delgado-Adámez, J; Fernández, A; Lodolini, EM; Martín-Vertedor, D; Ramírez, R, 2019)	0.51
" This review summarizes recent findings regarding biological activities, metabolism and bioavailability of the major olive oil phenolic compounds-hydroxytyrosol, tyrosol, oleuropein, oleocanthal and oleacein-the most important being their antiatherogenic, cardioprotective, anticancer, neuroprotective and endocrine effects."	( Hydroxytyrosol, Tyrosol and Derivatives and Their Potential Effects on Human Health. Barbarić, M; Jakobušić Brala, C; Karković Marković, A; Torić, J, 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
" Nevertheless, some knowledge gaps remain on its bioavailability and metabolism; overall concerning to the real rate per cent of absorption and biovailability of dietary hydroxytyrosol and the influence of the dietary food-containing hydroxytyrosol on it."	( Pharmacokinetics and bioavailability of hydroxytyrosol are dependent on the food matrix in humans. Alemán-Jiménez, C; Auñón, D; Campillo-Cano, M; Domínguez-Perles, R; Ferreres, F; Gil-Izquierdo, Á; López-González, I; Medina, S; Prgomet, I; Simonelli-Muñoz, A, 2021)	0.62
"A double-blind study was performed including 20 volunteers who ingested 5 mg of hydroxytyrosol through diverse food matrices, to discover the influence on pharmacokinetics and bioavailability of HT metabolites (hydroxytyrosol acetate, 3,4-dihydroxyphenylacetic acid (DOPAC), tyrosol, and homovanillic alcohol) of the distinct matrices by UHPLC-ESI-QqQ-MS/MS."	( Pharmacokinetics and bioavailability of hydroxytyrosol are dependent on the food matrix in humans. Alemán-Jiménez, C; Auñón, D; Campillo-Cano, M; Domínguez-Perles, R; Ferreres, F; Gil-Izquierdo, Á; López-González, I; Medina, S; Prgomet, I; Simonelli-Muñoz, A, 2021)	0.62
"The metabolic profile of hydroxytyrosol is influenced by the food matrix in which is incorporated, with the oily nature for the final bioavailability being relevant."	( Pharmacokinetics and bioavailability of hydroxytyrosol are dependent on the food matrix in humans. Alemán-Jiménez, C; Auñón, D; Campillo-Cano, M; Domínguez-Perles, R; Ferreres, F; Gil-Izquierdo, Á; López-González, I; Medina, S; Prgomet, I; Simonelli-Muñoz, A, 2021)	0.62
" However, they have low bioavailability due to their low absorption and high metabolism in human liver and small intestine."	( De novo biosynthesis of tyrosol acetate and hydroxytyrosol acetate from glucose in engineered Escherichia coli. Fu, X; Guo, D; Li, X; Pan, H; Sun, Y, 2021)	0.62
"Many studies have shown that caffeic acid phenethyl ester (CAPE) has various functions, such as antioxidant, anti-inflammatory and anticancer activity, but its low bioavailability and stability limit its application."	( Caffeic acid phenethyl ester loaded in a targeted delivery system based on a solid-in-oil-in-water multilayer emulsion: Characterization, stability, and fate of the emulsion during in vivo digestion. Chen, P; Chen, X; Dai, J; Du, Y; Huang, Y; Li, R; Liu, L; Wang, L; Wang, Q; Wang, Z; Wei, X; Yang, X; Zhou, Z, 2022)	0.72
" However, extremely low absorption rate of olive phenolic compounds restricts their bioactivity."	( Hydroxytyrosol oleate: A promising neuroprotective nanocarrier delivery system of oleuropein and derivatives. Brocchini, S; Nardi, M; Procopio, A; Somavarapu, S, 2023)	0.91
" Bioavailability studies with olive oils showed that HT is bioavailable from its free form and from conjugated forms such as oleuropein and its aglycone."	( Oral Bioavailability and Metabolism of Hydroxytyrosol from Food Supplements. Bender, C; Golz, C; Strassmann, S, 2023)	0.91

Excerpt	Relevance	Reference
" For both compounds, the intravenously and orally administered oil-based dosings resulted in significantly greater elimination of the phenolics in urine within 24 h than the oral, aqueous dosing method."	( The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. Freeman, MP; Hayball, PJ; Stretch, GL; Stupans, I; Tuck, KL, 2001)	0.31
" Recently it was shown that hydroxytyrosol and five metabolites were excreted in urine when hydroxytyrosol was dosed intravenously or orally in an olive oil solution to rats."	( Structural characterization of the metabolites of hydroxytyrosol, the principal phenolic component in olive oil, in rats. Hayball, PJ; Stupans, I; Tuck, KL, 2002)	0.31
" Studies of olfaction did not support unusual sensitivity, defined as lower odor thresholds, among MCS subjects; however, a dose-response pattern of symptoms was observed in response to suprathreshold concentrations of phenyl ethyl alcohol."	( Controlled exposures to volatile organic compounds in sensitive groups. Fiedler, N; Kipen, HM, 2001)	0.31
" The results showed that methyl jasmonate and salicylic acid enhanced greatly the accumulation of PeG and echinacoside (Echin), but their optimum elicitation dosage and addition time were different."	( [Effects of methyl jasmonate and salicylic acid on phenylethanoid glycosides synthesis in suspension cultures of Cistanche deserticola]. Chen, YQ; Fu, CX; Jin, ZP; Xu, LS; Xue, XF; Zhao, DX, 2005)	0.33
" More studies are needed to determine the optimal administration route and effective dosage of this compound."	( Effect of caffeic acid phenethyl ester on treatment of experimentally induced methicillin-resistant Staphylococcus epidermidis endophthalmitis in a rabbit model. Adigüzel, U; Arpaci, R; Aslan, G; Cinel, L; Emekdaş, G; Kanik, A; Oz, O; Tamer, L; Vatansever, H; Yildirim, O; Yilmaz, A, )	0.13
" In addition, the dose-response curves of KCl (2."	( The vasorelaxant effect of caffeic acid phenethyl ester on porcine coronary artery ring segments. Chen, J; Chen, Q; Han, M; Long, Y; Tian, XZ; Wang, R, )	0.13
"-administered at a dosage of 10 µmol/kg, it enhanced the recovery of locomotor function and reduced the lesion size while suppressing the expression of the mRNAs for a pro-inflammatory cytokine interleukin-1β and the inflammatory enzymes, inducible nitric oxide synthase and cyclooxygenase-2."	( Caffeic acid phenethyl ester reduces spinal cord injury-evoked locomotor dysfunction. Fukumitsu, H; Furukawa, S; Kasai, M; Soumiya, H, 2011)	0.37
" In this report, it was observed that combined treatment of a low dosage of curcumin (5-10 µM) with a low concentration (0."	( Combined treatment of curcumin and small molecule inhibitors suppresses proliferation of A549 and H1299 human non-small-cell lung cancer cells. Chuu, CP; Kuo, LK; Lin, HP, 2012)	0.38
" We observed that CAPE dosage dependently suppressed the proliferation of LNCaP, DU-145, and PC-3 human prostate cancer cells."	( Caffeic acid phenethyl ester suppresses the proliferation of human prostate cancer cells through inhibition of p70S6K and Akt signaling networks. Chuu, CP; Ciaccio, MF; Hause, RJ; Hiipakka, RA; Jones, RB; Kokontis, JM; Liao, S; Lin, HP, 2012)	0.38
" The PK and PD data inform edivoxetine pharmacology and can be used to develop comprehensive population PK and/or PK-PD models to guide dosing strategies."	( Pharmacokinetics and pharmacodynamics of edivoxetine (LY2216684), a norepinephrine reuptake inhibitor, in pediatric patients with attention-deficit/hyperactivity disorder. Allen, AJ; Dean, RA; Jin, L; Kielbasa, W; Lachno, DR; Quinlan, T; Xu, W, 2012)	0.38
" Absorption, distribution, metabolism, and excretion were compared following topical application of ¹⁴C-labeled PEA to rats, rabbits, and humans (specific activities of dosing solutions: 58-580, 164, and 50 µCi/mL, respectively)."	( The pharmacokinetics of phenylethyl alcohol (PEA): safety evaluation comparisons in rats, rabbits, and humans. Api, AM; Christian, MS; Diener, RM; Hawkins, DR; Politano, VT; Ritacco, G, )	0.44
" Daily dosing of edivoxetine in a larger population of impaired subjects, including those with dual impairment, would aid in establishing edivoxetine tolerability and PK in a clinical practice scenario."	( The effect of hepatic or renal impairment on the pharmacokinetics of edivoxetine, a selective norepinephrine transporter reuptake inhibitor. Kielbasa, W; Luffer-Atlas, D; Mitchell, MI; Tesfaye, E; Turik, MA, 2013)	0.39
" Dose-response and time-dependence studies were carried out."	( Hydroxytyrosol and oleuropein of olive oil inhibit mast cell degranulation induced by immune and non-immune pathways. Fogal, TH; Mariani, ML; Penissi, AB; Persia, FA, 2014)	0.4
"The aims of this study were to determine the efficacy and tolerability of different dosages of, and to identify the best dosage of, tratinterol hydrochloride tablets in the treatment of bronchial asthma."	( Efficacy and tolerability of tratinterol hydrochloride tablets in bronchial asthma: a multicenter, randomized, double-blind, dose-finding clinical trial. Kang, J; Kong, L; Liu, J; Shao, Y; Sun, S; Yuan, Y, 2014)	0.4
" In terms of the primary and secondary end points, the intermediate dosage was most efficacious, followed by the high and low dosages, respectively."	( Efficacy and tolerability of tratinterol hydrochloride tablets in bronchial asthma: a multicenter, randomized, double-blind, dose-finding clinical trial. Kang, J; Kong, L; Liu, J; Shao, Y; Sun, S; Yuan, Y, 2014)	0.4
"In these patients with bronchial asthma, 100 μg/d was the dosage of tratinterol hydrochloride tablets most efficacious in terms of improvement in lung function."	( Efficacy and tolerability of tratinterol hydrochloride tablets in bronchial asthma: a multicenter, randomized, double-blind, dose-finding clinical trial. Kang, J; Kong, L; Liu, J; Shao, Y; Sun, S; Yuan, Y, 2014)	0.4
" The 15% HT formulated extract did not induce micronuclei in rat bone marrow after 4 weeks of dosing up to 561 mg HT/kg/day."	( Investigations into the genotoxic potential of olive extracts. Beilstein, P; Edwards, J; Kirkland, D; Woehrle, T, 2015)	0.42
"Adult outpatients with MDD who were partial responders to SSRI treatment (N = 1249) entered an open-label 8 week flexibly dosed (12-18 mg/day) adjunctive edivoxetine period."	( Edivoxetine compared to placebo as adjunctive therapy to selective serotonin reuptake inhibitors in the prevention of symptom re-emergence in major depressive disorder. Ahl, J; Dellva, MA; Goldberger, C; Greenbaum, M; Oakes, TM; Perahia, DG; Poppe, C; Waterman, K, 2015)	0.42
" This method has the advantages of simple process and operation, less dosage of organic solvent, highly yield and reproducibility, suitable for the simultaneously preparation of tyrosol, crenulatin and salidroside."	( [Simultaneously preparation of grams of high purity tyrosol, crenulatin and salidroside from Rhodiola crenulata]. Li, SP; Luo, X; Wang, XJ; Wang, ZZ; Xiao, W; Zhang, Q; Zhao, YW, 2015)	0.42
"Fluticasone propionate (FLU) and Azelastine hydrochloride (AZE) are co-formulated with phenylethyl alcohol (PEA) and Benzalkonium chloride (BENZ) (as preservatives) in pharmaceutical dosage form for treatment of seasonal allergies."	( Simultaneous determination of Fluticasone propionate and Azelastine hydrochloride in the presence of pharmaceutical dosage form additives. El-Mosallamy, SS; El-Zeany, BA; Hassan, NY; Merey, HA, 2016)	0.66
" With extraction rate of salidroside, tyrosol, crenulatin and gallic acid as indexes, orthogonal test was used to evaluate effect of 4 factors on extracting technology, including concentration of solvent, the dosage of solvent, duration of extraction, and frequency of extraction."	( [Optimization of extraction technology for salidroside, tyrosol, crenulatin and gallic acid in Rhodiolae Crenulatae Radix et Rhizoma with orthogonal test]. Huang, WZ; Luo, X; Wang, XJ; Wang, ZZ; Xiao, W; Zhao, YW, 2015)	0.42
" In addition, it is suggested that CAPE-NPs can be used to reduce the dosage of CAPE and improve their bioavailability and thus merit further investigation for bioactive packaging film and coating applications."	( Fabrication of Novel Bioactive Cellulose-Based Films Derived from Caffeic Acid Phenethyl Ester-Loaded Nanoparticles via a Rapid Expansion Process: RESOLV. Assatarakul, K; Saelo, S; Sane, A; Suppakul, P, 2016)	0.43
" HT was administered at a daily dosage of 45mg for 8 weeks to volunteers with mild hyperlipidemia (n=14)."	( Hydroxytyrosol supplementation increases vitamin C levels in vivo. A human volunteer trial. Fonolla, J; Lopez-Huertas, E, 2017)	0.46
"This was an open-label study of edivoxetine once daily dosing (0."	( Long-Term, Open-Label, Safety Study of Edivoxetine Monotherapy in Children and Adolescents with Attention-Deficit/Hyperactivity Disorder. Ahl, J; Bangs, M; Liu, P; Nery, ESM; Perahia, D, 2017)	0.46
" A dose-response model in combination with a Markov-chain monte-carlo (MCMC) method for Bayesian inference was used to estimate and compare performance in terms of error rates involved in the detection of insect responses to GC peaks visible on an FID detector."	( Increasing Signal-to-Noise Ratio in Gas Chromatography - Electroantennography Using a Deans Switch Effluent Chopper. Baker, TC; Myrick, AJ, 2018)	0.48
" The effects of substrate concentration, temperature, pH, time, and enzyme dosage on the concentration of TF produced are studied using the design of experiments methodology."	( Screening of Commercial Enzymes for Transfructosylation of Tyrosol: Effect of Process Conditions and Reaction Network. Antošová, M; Hollá, V; Karkeszová, K; Mastihuba, V; Polakovič, M, 2019)	0.51
" The increase in the cytotoxicity was dependent on the CAPE dosage (50 vs."	( Caffeic Acid Phenethyl Ester (CAPE) Synergistically Enhances Paclitaxel Activity in Ovarian Cancer Cells. Dzik, R; Kabała-Dzik, A; Kleczka, A, 2023)	0.91

Product Category	Products
Beauty & Personal Care	95
Household Essentials	1

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Acure Resurfacing Glycolic + Unicorn Root Cleanser -- 4 fl oz	Acure	Beauty & Personal Care	glyceryl oleate, decyl glucoside, ethylhexylglycerin, glycerin, glycolic acid, hemp, lactic acid, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Acure Resurfacing Overnight Glycolic Treatment -- 1 fl oz	Acure	Beauty & Personal Care	citric acid, cetyl alcohol, citric acid, tocopherol, ethylhexylglycerin, tocopherol, glyceryl stearate, glycerin, glycolic acid, hemp, lactic acid, glyceryl laurate, phenethyl alcohol	2024-11-29 10:47:42
Acure Seriously Soothing Cleansing Cream -- 4 fl oz	Acure	Beauty & Personal Care	caprylyl glycol, glyceryl oleate, chamomile, calendula, decyl glucoside, ethylhexylglycerin, glycerin, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Acure Ultra Hydrating 12 Hour Facial Moisturizer -- 1 fl oz	Acure	Beauty & Personal Care	orange, geranium, cetearyl alcohol, cetyl alcohol, tocopherol, ethylhexylglycerin, tocopherol, glycerin, glyceryl laurate, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Acure Ultra Hydrating Eye Cream -- 0.5 fl oz	Acure	Beauty & Personal Care	citric acid, cetyl alcohol, citric acid, tocopherol, ethylhexylglycerin, tocopherol, glyceryl stearate, glycerin, glyceryl laurate, phenethyl alcohol	2024-11-29 10:47:42
Acure Ultra Hydrating Green Juice Cleanser -- 4 fl oz	Acure	Beauty & Personal Care	glyceryl oleate, orange, decyl glucoside, ethylhexylglycerin, glycerin, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Alba Botanica Very Emollient Body Lotion Daily Shade SPF 15 -- 32 fl oz	Alba	Beauty & Personal Care	amyl cinnamal, citric acid, allantoin, ascorbic acid, benzoic acid, cetearyl alcohol, cetyl alcohol, citric acid, dehydroacetic acid, panthenol, triethyl citrate, geraniol, glycerin, glycolic acid, dimethicone, lactic acid, limonene, phenoxyethanol, phenethyl alcohol, potassium hydroxide, sodium benzoate	2024-11-29 10:47:42
Andalou Naturals 1000 Roses Daily Shade Facial Lotion SPF 18 -- 2.7 fl oz	Andalou Naturals	Beauty & Personal Care	octisalate, orange, allantoin, chamomile, vitamin C, cetyl alcohol, tocopherol, panthenol, ethylhexylglycerin, tocopherol, dimethicone, octocrylene, phenethyl alcohol, stearic acid, stearyl alcohol	2024-11-29 10:47:42
Andalou Naturals 1000 Roses Soothing Sleep Mask -- 1.7 fl oz	Andalou Naturals	Beauty & Personal Care	butylene glycol, citric acid, citric acid, ethylhexylglycerin, glycerin, phenethyl alcohol, sodium benzoate, squalane	2024-11-29 10:47:42
Andalou Naturals A Path of Light Hand Cream Clementine -- 3.4 fl oz	Andalou Naturals	Beauty & Personal Care	orange, allantoin, cetyl alcohol, tocopherol, ethylhexylglycerin, tocopherol, palmarosa, glyceryl stearate, phenethyl alcohol, stearic acid, stearyl alcohol	2024-11-29 10:47:42
Andalou Naturals A Path of Light Hand Cream Lime Blossom -- 3.4 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Cetyl Alcohol, Tocopherol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid, Stearyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Age Defying Apricot Probiotic Cleansing Milk -- 6 fl oz	Andalou Naturals	Beauty & Personal Care	orange, allantoin, cetyl alcohol, CoQ10, tocopherol, ethylhexylglycerin, tocopherol, vitamin e, glyceryl stearate, glyceryl monolaurate, phenethyl alcohol, resveratrol, ubiquinone	2024-11-29 10:47:42
Andalou Naturals Age Defying Argan Stem Cell Conditioner -- 11.5 fl oz	Andalou Naturals	Beauty & Personal Care	Biotin, Cetyl Alcohol, Cysteine, Panthenol, Ethylhexylglycerin, Glyceryl Stearate, Niacin, Phenethyl Alcohol, Pyridoxine, Riboflavin, Stearyl Alcohol, Thiamine	2024-11-29 10:47:42
Andalou Naturals Age Defying Argan Stem Cell Scalp Intensive -- 2.1 fl oz	Andalou Naturals	Beauty & Personal Care	Biotin, Cysteine, Panthenol, Ethylhexylglycerin, Niacin, Phenethyl Alcohol, Pyridoxine, Riboflavin, Thiamine	2024-11-29 10:47:42
Andalou Naturals Age Defying Deep Wrinkle Dermal Filler -- 0.6 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Vitamin C, Cetyl Alcohol, CoQ10, Tocopherol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Resveratrol, Stearyl Alcohol, Ubiquinone	2024-11-29 10:47:42
Andalou Naturals Age Defying DIY Booster Facial Serum SPF 30 Unscented -- 2 fl oz	Andalou Naturals	Beauty & Personal Care	Cetyl Alcohol, CoQ10, Ethylhexylglycerin, Phenethyl Alcohol, Resveratrol, Stearyl Alcohol, Ubiquinone	2024-11-29 10:47:42
Andalou Naturals Age Defying Fruit Stem Cell Revitalize Serum -- 1.1 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Vitamin C, Kelp, Cetyl Alcohol, CoQ10, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Melatonin, Glyceryl Laurate, Phenethyl Alcohol, Resveratrol, Riboflavin, Stearyl Alcohol, Ubiquinone	2024-11-29 10:47:42
Andalou Naturals Age Defying Goji Peptide Perfecting Cream -- 1.7 oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Vitamin C, Bisabolol, Cetyl Alcohol, CoQ10, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Glyceryl Laurate, Phenethyl Alcohol, Resveratrol, Riboflavin, Stearic Acid, Ubiquinone	2024-11-29 10:47:42
Andalou Naturals Age Defying Toning Refresher Blossom + Leaf -- 6 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Vitamin C, CoQ10, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Phenethyl Alcohol, Resveratrol, Ubiquinone	2024-11-29 10:47:42
Andalou Naturals Age Defying Ultra Sheer Daily Defense Facial Lotion SPF 18 -- 2.7 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Chamomile, Vitamin C, Kelp, Cetyl Alcohol, CoQ10, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Dimethicone, Phenethyl Alcohol, Resveratrol, Stearic Acid, Stearyl Alcohol, Ubiquinone	2024-11-29 10:47:42
Andalou Naturals Brighten & Tighten Hydro Serum Facial Sheet Mask -- 6 fl oz	Andalou Naturals	Beauty & Personal Care	allantoin, vitamin C, bisabolol, tocopherol, ethylhexylglycerin, tocopherol, vitamin E, phenethyl alcohol	2024-11-29 10:47:42
Andalou Naturals Brightening Clementine + C Illuminating Toner -- 6 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Vitamin C, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Palmarosa, Phenethyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Brightening Creamy Cleanser Meyer Lemon + C -- 6 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Vitamin C, Cetyl Alcohol, Cocamidopropyl Betaine, Tocopherol, and, Panthenol, Ethylhexylglycerin, Tocopherol, Phenethyl Alcohol, Sorbitol, Stearic Acid, Stearyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Brightening Luminous Eye Serum -- 0.6 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Chamomile, Vitamin C, Kelp, Caffeine, Cetyl Alcohol, Tocopherol, Ethylhexylglycerin, Tocopherol, Phenethyl Alcohol, Stearyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Brightening Purple Carrot + C Luminous Night Cream -- 1.7 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Vitamin C, Cetyl Alcohol, Tocopherol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Riboflavin, Stearyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Brightening Renewal Cream Brightening Probiotic + C -- 1.7 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Vitamin C, Cetyl Alcohol, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid	2024-11-29 10:47:42
Andalou Naturals Brilliant Shine Conditioner Sunflower and Citrus -- 11.5 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Chamomile, Cetyl Alcohol, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Clear Skin Willow Bark Pure Pore Toner -- 6 fl oz	Andalou Naturals	Beauty & Personal Care	Vitamin C, Camphor, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Phenethyl Alcohol, Salicylic Acid	2024-11-29 10:47:42
Andalou Naturals Color Care 1000 Roses Shampoo -- 11.5 fl oz	Andalou Naturals	Beauty & Personal Care	orange, cocamidopropyl betaine, tocopherol, and, ethylhexylglycerin, tocopherol, phenethyl alcohol, sodium lauroyl sarcosinate	2024-11-29 10:47:42
Andalou Naturals Firming Body Butter Lavender Shea -- 8 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, CoQ10, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid, Stearyl Alcohol, Ubiquinone	2024-11-29 10:47:42
Andalou Naturals Hand Cream Lavender Shea -- 3.4 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Cetyl Alcohol, Tocopherol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid, Stearyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Hyaluronic DMAE Lift & Firm Cream Age Defying -- 1.7 oz	Andalou Naturals	Beauty & Personal Care	orange, allantoin, vitamin C, bisabolol, CoQ10, tocopherol, dimethylaminoethanol, panthenol, ethylhexylglycerin, tocopherol, glyceryl stearate, phenethyl alcohol, resveratrol, riboflavin, ubiquinone	2024-11-29 10:47:42
Andalou Naturals Moisture Rich Conditioner Argan Oil & Shea -- 11.5 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Arginine, Cetyl Alcohol, Tocopherol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Serine, Stearyl Alcohol, Threonine	2024-11-29 10:47:42
Andalou Naturals Nourishing Body Butter Kukui Cocoa -- 8 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid, Stearyl Alcohol	2024-11-29 10:47:42
Andalou Naturals Pure Pore Hydro Serum Facial Sheet Mask -- 0.6 fl oz	Andalou Naturals	Beauty & Personal Care	allantoin, bisabolol, tocopherol, tocopherol, palmarosa, vitamin E, phenethyl alcohol	2024-11-29 10:47:42
Andalou Naturals Refreshing Body Lotion Lavender and Thyme -- 8 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Cetyl Alcohol, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid	2024-11-29 10:47:42
Andalou Naturals Resveratrol Q10 Night Repair Cream -- 1.7 fl oz	Andalou Naturals	Beauty & Personal Care	allantoin, vitamin c, cetyl alcohol, coq10, comfrey, tocopherol, ethylhexylglycerin, tocopherol, glyceryl stearate, phenethyl alcohol, resveratrol, riboflavin, stearyl alcohol, ubiquinone	2024-11-29 10:47:42
Andalou Naturals Soothing Body Lotion 1000 Roses -- 8 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Cetyl Alcohol, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid	2024-11-29 10:47:42
Andalou Naturals Uplifting Body Lotion Citrus Sunflower -- 8 fl oz	Andalou Naturals	Beauty & Personal Care	Allantoin, Cetyl Alcohol, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid	2024-11-29 10:47:42
Andalou Naturals Velvet Soft 1000 Roses Body Butter -- 8 fl oz	Andalou Naturals	Beauty & Personal Care	orange, allantoin, tocopherol, panthenol, ethylhexylglycerin, tocopherol, glyceryl stearate, phenethyl alcohol, stearic acid, stearyl alcohol	2024-11-29 10:47:42
Andalou Naturals Vitalizing Body Lotion Mandarin Vanilla -- 8 fl oz	Andalou Naturals	Beauty & Personal Care	Orange, Allantoin, Cetyl Alcohol, Tocopherol, Panthenol, Ethylhexylglycerin, Tocopherol, Glyceryl Stearate, Phenethyl Alcohol, Stearic Acid	2024-11-29 10:47:42
Avalon Organics Wrinkle Therapy Cleansing Milk -- 8.5 fl oz	Avalon Organics	Beauty & Personal Care	benzyl alcohol, cetearyl alcohol, cetyl alcohol, citronellol, CoQ10, geraniol, glycerin, phenethyl alcohol, potassium hydroxide, ribose, sodium benzoate, sorbitol, stearic acid, ubiquinone	2024-11-29 10:47:42
Avalon Organics Wrinkle Therapy Day Cream -- 1.75 oz	Avalon Organics	Beauty & Personal Care	Cetyl Alcohol, Citral, Citronellol, CoQ10, Geraniol, Glyceryl Stearate, Glycerin, Phenethyl Alcohol, Ribose, Sodium Benzoate, Stearyl Alcohol, Ubiquinone	2024-11-29 10:47:42
Avalon Organics Wrinkle Therapy Facial Serum -- 0.55 fl oz	Avalon Organics	Beauty & Personal Care	cetyl alcohol, citral, citronellol, CoQ10, geraniol, glyceryl stearate, phenethyl alcohol, ribose, sodium benzoate, squalane, ubiquinone	2024-11-29 10:47:42
Avalon Organics Wrinkle Therapy Firming Body Lotion with CoQ10 & Rosehip -- 8 fl oz	Avalon Organics	Beauty & Personal Care	Benzyl Alcohol, Bisabolol, Cetyl Alcohol, Citral, Citronellol, CoQ10, Geraniol, Glycerin, Phenethyl Alcohol, Potassium Hydroxide, Ribose, Sodium Benzoate, Stearic Acid, Stearyl Alcohol, Ubiquinone	2024-11-29 10:47:42
Babe Original Brow Volumizing Brow Filler Dark Brown -- 0.12 oz	Babe Original	Beauty & Personal Care	citric acid, biotin, citric acid, panthenol, glyceryl stearate, glycerin, glyceryl caprylate, phenethyl alcohol, sodium benzoate, titanium dioxide	2024-11-29 10:47:42
Babe Original Brow Volumizing Brow Filler Taupe -- 0.12 oz	Babe Original	Beauty & Personal Care	citric acid, biotin, citric acid, panthenol, glyceryl stearate, glycerin, glyceryl caprylate, phenethyl alcohol, sodium benzoate, titanium dioxide	2024-11-29 10:47:42
Babe Original Densifying Hair Serum -- 1.76 oz	Babe Original	Beauty & Personal Care	caprylyl glycol, butylene glycol, apigenin, arginine, benzoic acid, benzyl alcohol, gluconolactone, biotin, caffeine, tocopherol, dimethyl sulfone, disodium edta, tocopherol, glycerin, glycine, lactic acid, trisodium ethylenediamine disuccinate, oleanolic acid, phenoxyethanol, phenethyl alcohol, propanediol, sodium benzoate, sodium metabisulfite, sorbic acid, xylitol, zinc chloride	2024-11-29 10:47:42
Babo Botanicals Daily Sheer Sunscreen SPF 40 Extra Sensitive For Face -- 1.7 fl oz	Babo Botanicals	Beauty & Personal Care	hydroxyethyl acrylate, and, ethylhexylglycerin, glycerin, triethoxycaprylylsilane, phenethyl alcohol	2024-11-29 10:47:42
Babo Botanicals Smoothing Detangling Conditioner Spray Berry & Primrose -- 8 fl oz	Babo Botanicals	Beauty & Personal Care	isopropyl alcohol, cetearyl alcohol, tocopherol, ethylhexylglycerin, tocopherol, vitamin e, glycerin, phenethyl alcohol	2024-11-29 10:47:42
Clearly Natural Essentials Glycerin Liquid Hand Soap with Vitamin E -- 12 fl oz	Clearly Natural	Household Essentials	tocopherol acetate, vitamin E, vitamin E, glycerine, glycine, oleic acid, phenylethyl alcohol, potassium hydroxide	2024-11-29 10:47:42
Honeybee Gardens Bellissima Volumizing Mascara - Coffee Bean -- 0.13 oz	Honeybee Gardens	Beauty & Personal Care	aminomethyl propanediol, cellulose, cetearyl alcohol, tocopherol, ethylhexylglycerin, tocopherol, hydroxyethylcellulose, phenethyl alcohol, propanediol, stearic acid, undecyl alcohol	2024-11-29 10:47:42
Honeybee Gardens Pressed Mineral Powder Foundation Luminous -- 0.26 oz	Honeybee Gardens	Beauty & Personal Care	tocopherol, ethylhexylglycerin, tocopherol, phenethyl alcohol	2024-11-29 10:47:42
Honeybee Gardens Truly Natural Lipstick Heirloom -- 0.13 oz	Honeybee Gardens	Beauty & Personal Care	phenethyl alcohol, propanediol, titanium dioxide, undecyl alcohol	2024-11-29 10:47:42
Honeybee Gardens Truly Natural Lipstick San Francisco -- 0.13 oz	Honeybee Gardens	Beauty & Personal Care	Phenethyl Alcohol, Propanediol, Titanium Dioxide, Undecyl Alcohol	2024-11-29 10:47:42
Jason Body Wash Pure Relaxing Chamomile & Lotus Blossom -- 30 fl oz	Jason	Beauty & Personal Care	citric acid, allantoin, terpineol, benzyl alcohol, citric acid, panthenol, triethyl citrate, glycerin, phenethyl alcohol, sodium benzoate, stearic acid	2024-11-29 10:47:42
Jason Dandruff Relief 2 in1 Shampoo + Conditioner -- 12 fl oz	Jason	Beauty & Personal Care	glyceryl oleate, orange, citric acid, terpineol, benzylacetate, cetyl alcohol, citric acid, triethyl citrate, glycerin, limonene, linalool, maltodextrin, phenethyl alcohol, sodium cocoyl glutamate, sodium hydroxide, zinc carbonate	2024-11-29 10:47:42
Jason Extra Volumizing Biotin Conditioner -- 8 fl oz	Jason	Beauty & Personal Care	isopropyl alcohol, citric acid, ascorbyl palmitate, linolenic acid, benzyl alcohol, biotin, cetearyl alcohol, cetyl alcohol, citric acid, panthenol, triethyl citrate, glycerin, linoleic acid, maltodextrin, menthol, phenoxyethanol, phenethyl alcohol, stearyl alcohol	2024-11-29 10:47:42
Jason Intense Moisture Conditioner Aloe Vera + Prickly Pear -- 16 fl oz	Jason	Beauty & Personal Care	isopropyl alcohol, phytantriol, citric acid, ascorbyl palmitate, linolenic acid, terpineol, benzyl alcohol, betaine, cetearyl alcohol, cetyl alcohol, citric acid, panthenol, triethyl citrate, glycerin, linoleic acid, phenoxyethanol, phenethyl alcohol, stearyl alcohol	2024-11-29 10:47:42
Jason Purifying Tea Tree Conditioner -- 12 fl oz	Jason	Beauty & Personal Care	isopropyl alcohol, citric acid, linolenic acid, terpineol, benzyl alcohol, cetearyl alcohol, cetyl alcohol, citric acid, tocopherol, panthenol, triethyl citrate, tocopherol, glycerin, linoleic acid, phenethyl alcohol, stearyl alcohol	2024-11-29 10:47:42
Jason Shampoo Jojoba plus Castor Oil Strong & Healthy -- 16 fl oz	Jason	Beauty & Personal Care	citric acid, terpineol, benzyl alcohol, citric acid, panthenol, triethyl citrate, glycerin, maltodextrin, phenoxyethanol, phenethyl alcohol	2024-11-29 10:47:42
Jason Thicken & Restore Biotin + Hyaluronic Acid Shampoo -- 16 fl oz	Jason	Beauty & Personal Care	citric acid, ascorbyl palmitate, benzyl alcohol, biotin, citric acid, panthenol, triethyl citrate, glycerin, linoleic acid, menthol, phenoxyethanol, phenethyl alcohol	2024-11-29 10:47:42
Mad Hippie Blemish Cream -- 0.5 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, glyceryl oleate, astaxanthin, cetyl alcohol, curcumin, ethylhexyl glycerin, fucoxanthin, glyceryl stearate, glycerin, microcrystalline cellulose, isopropyl palmitate, phenethyl alcohol, squalane, stearyl alcohol	2024-11-29 10:47:42
Mad Hippie Corrective Peptide Serum -- 1.02 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, orange, ceramide NP, ethylhexyl glycerin, glycerin, hydroxyethylcellulose, oat, phenethyl alcohol, propanediol, squalane, stearyl alcohol	2024-11-29 10:47:42
Mad Hippie Day-Night Vitamin C and Super A Serum Dual Pack -- 0.5 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, dimethyl isosorbide, acetyl glucosamine, vitamin c, vitamin e, ethylhexyl glycerin, ferulic acid, vitamin e, glycerin, phenethyl alcohol, stearyl alcohol, tocotrienol	2024-11-29 10:47:42
Mad Hippie Face Cream -- 1 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, citric acid, cetearyl alcohol, citric acid, tocopherol, ethylhexylglycerin, tocopherol, glyceryl stearate, glycerin, isopropyl palmitate, phenethyl alcohol, sorbic acid, tocotrienol, ubiquinone	2024-11-29 10:47:42
Mad Hippie Holiday Skin Care Gift Bag -- 1 Set	Mad Hippie	Beauty & Personal Care	caprylyl glycol, orange, allantoin, ascorbyl glucoside, vitamin C, ceramide 3, cetyl alcohol, vitamin E, and, ethylhexyl glycerin, ferulic acid, vitamin E, glyceryl stearate, glycerin, hydroxyethylcellulose, isopropyl palmitate, oat, phenethyl alcohol, propanediol, vitamin B2, squalane, stearic acid, stearyl alcohol, tocotrienol	2024-11-29 10:47:42
Mad Hippie Jelly Cleanser -- 4 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, chamomile, tocopherol, decyl glucoside, ethylhexyl glycerin, tocopherol, phenethyl alcohol, resveratrol	2024-11-29 10:47:42
Mad Hippie Microdermabrasion Facial -- 2.1 oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, orange, cetyl alcohol, ethylhexyl glycerin, glycerin, glycolic acid, lactic acid, mandelic acid, probiotic, myristic acid, phenethyl alcohol, squalane, stearic acid	2024-11-29 10:47:42
Mad Hippie Super Vitamin A Serum -- 1.02 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, dimethyl isosorbide, acetyl glucosamine, ethylhexyl glycerin, glycerin, phenethyl alcohol, stearyl alcohol	2024-11-29 10:47:42
Mad Hippie Triple C Night Cream -- 2.1 oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, allantoin, ascorbyl glucoside, vitamin C, ceramide 3, cetyl alcohol, vitamin E, and, ethylhexyl glycerin, vitamin E, glyceryl stearate, glycerin, isopropyl palmitate, phenethyl alcohol, vitamin B2, squalane, stearic acid, tocotrienol	2024-11-29 10:47:42
Mad Hippie Vitamin C Toning Mist -- 4 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, N-acetyl glucosamine, ethylhexyl glycerin, ferulic acid, glycerin, phenethyl alcohol	2024-11-29 10:47:42
Mineral Fusion Lipstick Cosmopolitan -- 0.13 oz	Mineral Fusion	Beauty & Personal Care	tocopherol, tocopherol, phenethyl alcohol, titanium dioxide	2024-11-29 10:47:42
Mineral Fusion Lipstick Paloma -- 0.13 oz	Mineral Fusion	Beauty & Personal Care	tocopherol, tocopherol, phenethyl alcohol, titanium dioxide	2024-11-29 10:47:42
Mineral Fusion Lipstick Passion Punch -- 0.13 oz	Mineral Fusion	Beauty & Personal Care	tocopherol, tocopherol, phenethyl alcohol, titanium dioxide	2024-11-29 10:47:42
Mineral Fusion Lipstick Peach Bellini -- 0.13 oz	Mineral Fusion	Beauty & Personal Care	tocopherol, tocopherol, phenethyl alcohol, titanium dioxide	2024-11-29 10:47:42
Mineral Fusion Lipstick Plum Prosecco -- 0.13 oz	Mineral Fusion	Beauty & Personal Care	tocopherol, tocopherol, phenethyl alcohol, titanium dioxide	2024-11-29 10:47:42
Mineral Fusion Lipstick Plum Wine -- 0.13 oz	Mineral Fusion	Beauty & Personal Care	tocopherol, tocopherol, phenethyl alcohol, titanium dioxide	2024-11-29 10:47:42
Mineral Fusion Lipstick Rose Sangria -- 0.13 oz	Mineral Fusion	Beauty & Personal Care	tocopherol, tocopherol, phenethyl alcohol, titanium dioxide	2024-11-29 10:47:42
MyChelle Dermaceuticals Ageless Supreme Polypeptide Cream Unscented -- 1.2 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	D-Alpha, Caprylyl Glycol, Orange, Citric Acid, Cetearyl Alcohol, Palm, Citric Acid, Tocopherol, Tocopherol, Glycerin, Trisodium Ethylenediamine Disuccinate, Phenethyl Alcohol, Squalane, Tocotrienols, Totarol	2024-11-29 10:47:42
MyChelle Dermaceuticals Brighten Perfect C Eye Cream -- 0.5 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	D-alpha, caprylyl glycol, orange, citric acid, allantoin, ascorbic acid, cetearyl alcohol, cetyl alcohol, palm, citric acid, tocopherol, tocopherol, palmarosa, sodium gluconate, glyceryl stearate, glycerin, phenethyl alcohol, phytic acid, stearic acid, tocotrienols	2024-11-29 10:47:42
MyChelle Dermaceuticals Hydrate Ultra Hyaluronic Hydrating Serum -- 1 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	caprylyl glycol, geranium, citric acid, allantoin, arginine, D-beta, citric acid, glycerin, trisodium ethylenediamine disuccinate, phenethyl alcohol, squalane	2024-11-29 10:47:42
MyChelle Dermaceuticals Renew Remarkable Retinal Night Cream -- 1.2 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	D-alpha, caprylyl glycol, citric acid, allantoin, ascorbic acid, D-beta, carnosine, casticin, cetearyl alcohol, palm, citric acid, tocopherol, tocopherol, glyceryl stearate, glycerin, trisodium ethylenediamine disuccinate, phenethyl alcohol, retinaldehyde, squalane, stearic acid, tocotrienols, totarol, trehalose	2024-11-29 10:47:42
MyChelle Dermaceuticals Strengthen Creamy Pumpkin Cleanser -- 4.4 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	caprylyl glycol, astaxanthin, behenyl alcohol, glycerin, trisodium ethylenediamine disuccinate, phenethyl alcohol, nutmeg, sugar	2024-11-29 10:47:42
MyChelle Dermaceuticals Strengthen Fruit Enzyme Scrub -- 2.3 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	caprylyl glycol, calendula, panthenol, behenyl alcohol, glycerin, trisodium ethylenediamine disuccinate, phenethyl alcohol, sodium cocoyl glutamate	2024-11-29 10:47:42
MyChelle Dermaceuticals Strengthen Pumpkin Renew Cream -- 1.2 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	D-alpha, caprylyl glycol, orange, astaxanthin, gluconolactone, D-beta, carnosine, cetearyl alcohol, chlorophyll, palm, tocopherol, tocopherol, glyceryl stearate, glycerin, lactic acid, phenyl t-butylnitrone, phenethyl alcohol, nutmeg, sodium benzoate, tocotrienols, totarol	2024-11-29 10:47:42
Sibu Beauty Hydrating Serum Sea Buckthorn -- 1 fl oz	Sibu Beauty	Beauty & Personal Care	betaine, tocopherol, tocopherol, glycerin, phenethyl alcohol, retinyl palmitate	2024-11-29 10:47:42
The Seaweed Bath Co Calm Body Wash - Vetiver Geranium -- 12 fl oz	The Seaweed Bath Co	Beauty & Personal Care	geranium, citric acid, citric acid, cocamidopropyl betaine, decyl glucoside, ethylhexylglycerin, glycerin, phenethyl alcohol	2024-11-29 10:47:42
The Seaweed Bath Co Detox Body Scrub - Orange Cedar -- 6 fl oz	The Seaweed Bath Co	Beauty & Personal Care	carbomer, cocamidopropyl betaine, ethylhexylglycerin, phenethyl alcohol, montmorillonite	2024-11-29 10:47:42
The Seaweed Bath Co Detox Body Scrub - Rosemary Mint -- 1.5 fl oz	The Seaweed Bath Co	Beauty & Personal Care	cocamidopropyl betaine, vitamin e, triethyl citrate, ethylhexylglycerin, vitamin e, glycerin, illite, kaolin, phenethyl alcohol, montmorillonite, sodium hydroxide	2024-11-29 10:47:42
The Seaweed Bath Co Detox Body Scrub - Rosemary Mint -- 6 fl oz	The Seaweed Bath Co	Beauty & Personal Care	carbomer, cocamidopropyl betaine, ethylhexylglycerin, phenethyl alcohol, montmorillonite	2024-11-29 10:47:42
The Seaweed Bath Co Energize Body Wash - Grapefruit Orange -- 12 fl oz	The Seaweed Bath Co	Beauty & Personal Care	orange, ascorbic acid, cocamidopropyl betaine, decyl glucoside, ethylhexylglycerin, glycerin, phenethyl alcohol	2024-11-29 10:47:42
The Seaweed Bath Co Firming Body Cream - Rosemary Mint -- 6 fl oz	The Seaweed Bath Co	Beauty & Personal Care	allantoin, caffeine, carbomer, tocopherol, panthenol, ethylhexylglycerin, tocopherol, glyceryl stearate, phenethyl alcohol, stearic acid, stearyl alcohol	2024-11-29 10:47:42
The Seaweed Bath Co Hydrate Body Cream - Citrus Vanilla -- 6 fl oz	The Seaweed Bath Co	Beauty & Personal Care	orange, allantoin, tocopherol, panthenol, methyl sulfonyl methane, tocopherol, glyceryl stearate, phenethyl alcohol, stearic acid, stearyl alcohol, vanilla	2024-11-29 10:47:42
The Seaweed Bath Co Hydrate Body Cream - Lavender -- 6 fl oz	The Seaweed Bath Co	Beauty & Personal Care	allantoin, tocopherol, panthenol, methyl sulfonyl methane, tocopherol, glyceryl stearate, phenethyl alcohol, stearic acid, stearyl alcohol	2024-11-29 10:47:42
The Seaweed Bath Co Hydrate Body Cream - Unscented -- 6 fl oz	The Seaweed Bath Co	Beauty & Personal Care	tocopherol, panthenol, methyl sulfonyl methane, tocopherol, glyceryl stearate, phenethyl alcohol, stearic acid, stearyl alcohol	2024-11-29 10:47:42

Role	Description
fragrance	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.
Saccharomyces cerevisiae metabolite	Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae).
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Aspergillus metabolite	Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus.
plant growth retardant	null
[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
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.
benzenes	Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
[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
tea aroma glycosidic precursor bioactivation	1	10
L-phenylalanine degradation III	1	12
phenylethanol glycoconjugate biosynthesis	0	6
phenylethyl acetate biosynthesis	1	4
phenylethanol biosynthesis	9	14
tea aroma glycosidic precursor bioactivation	1	16
phenylethanol glycoconjugate biosynthesis	0	7
L-phenylalanine degradation III	12	13
phenylethanol biosynthesis	8	15
phenylalanine degradation	11	12
phenylalanine degradation III	1	12
Ehrlich pathway	0	11

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE	Homo sapiens (human)	Potency	100.0000	0.0032	45.4673	12,589.2998	AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	89.1251	0.0040	23.8416	100.0000	AID485290
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	20.2478	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
GLI family zinc finger 3	Homo sapiens (human)	Potency	59.5083	0.0007	14.5928	83.7951	AID1259369; AID1259392
AR protein	Homo sapiens (human)	Potency	22.6142	0.0002	21.2231	8,912.5098	AID743036; AID743053
progesterone receptor	Homo sapiens (human)	Potency	33.4915	0.0004	17.9460	75.1148	AID1346795
cytochrome P450 family 3 subfamily A polypeptide 4	Homo sapiens (human)	Potency	10.9640	0.0123	7.9835	43.2770	AID1645841
farnesoid X nuclear receptor	Homo sapiens (human)	Potency	16.7842	0.3758	27.4851	61.6524	AID743239
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	0.0982	0.0002	29.3054	16,493.5996	AID743069
cytochrome P450 2D6	Homo sapiens (human)	Potency	24.5454	0.0010	8.3798	61.1304	AID1645840
geminin	Homo sapiens (human)	Potency	0.5623	0.0046	11.3741	33.4983	AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845	Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
AID1090484	Antifungal activity against Colletotrichum camelliae assessed as inhibition of mycelial growth at 500 ug/mL measured after 5 days of cultivation	2006	Journal of agricultural and food chemistry, May-31, Volume: 54, Issue:11	Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea.
AID1101945	Inhibition of intact Triticum aestivum (wheat) seed germination assessed as appearance of distinct rootlets at 500 ppm after 4 days relative to wheat grains RL4137 germination	2002	Journal of agricultural and food chemistry, Oct-23, Volume: 50, Issue:22	Germination and growth inhibitors from wheat (Triticum aestivum L.) husks.
AID1101944	Inhibition of intact Triticum aestivum (wheat) seed germination assessed as appearance of sprouts at 500 ppm after 4 days relative to wheat grains RL4137 germination	2002	Journal of agricultural and food chemistry, Oct-23, Volume: 50, Issue:22	Germination and growth inhibitors from wheat (Triticum aestivum L.) husks.
AID1101946	Growth inhibition of intact Triticum aestivum (wheat) seed assessed as appearance of sprouts at 500 ppm after 4 days relative to wheat grains RL4137 germination	2002	Journal of agricultural and food chemistry, Oct-23, Volume: 50, Issue:22	Germination and growth inhibitors from wheat (Triticum aestivum L.) husks.
AID1090481	Antifungal activity against Colletotrichum camelliae assessed as inhibition of mycelial growth at 2000 ug/mL measured after 5 days of cultivation	2006	Journal of agricultural and food chemistry, May-31, Volume: 54, Issue:11	Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea.
AID1090713	Thrips luring activity against female New Zealand Thrips obscuratus (flower thrips) assessed as ratio of thrips in baited traps to unbaited traps during field trapping study	2007	Journal of agricultural and food chemistry, Jul-25, Volume: 55, Issue:15	4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.
AID346025	Binding affinity to beta cyclodextrin	2009	Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2	Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.
AID1101947	Growth inhibition of intact Triticum aestivum (wheat) seed assessed as appearance of distinct rootlets at 500 ppm after 4 days relative to wheat grains RL4137 germination	2002	Journal of agricultural and food chemistry, Oct-23, Volume: 50, Issue:22	Germination and growth inhibitors from wheat (Triticum aestivum L.) husks.
AID1090712	Thrips luring activity against male New Zealand Thrips obscuratus (flower thrips) assessed as ratio of thrips in baited traps to unbaited traps during field trapping study	2007	Journal of agricultural and food chemistry, Jul-25, Volume: 55, Issue:15	4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.
AID1090482	Antifungal activity against Colletotrichum camelliae assessed as inhibition of mycelial growth at 1500 ug/mL measured after 5 days of cultivation	2006	Journal of agricultural and food chemistry, May-31, Volume: 54, Issue:11	Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea.
AID1102450	Fungitoxicity against Colletotrichum gloeosporioides assessed as mycelial growth inhibition by poisoned food technique	2003	Journal of agricultural and food chemistry, Aug-27, Volume: 51, Issue:18	Quantitative structure-fungitoxicity relationships of some monohydric alcohols.
AID1090711	Thrips luring activity against female Thrips tabaci (onion thrips) assessed as ratio of thrips in baited traps to unbaited traps during field trapping study	2007	Journal of agricultural and food chemistry, Jul-25, Volume: 55, Issue:15	4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.
AID1090483	Antifungal activity against Colletotrichum camelliae assessed as inhibition of mycelial growth at 1000 ug/mL measured after 5 days of cultivation	2006	Journal of agricultural and food chemistry, May-31, Volume: 54, Issue:11	Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea.
AID1090485	Antifungal activity against Colletotrichum camelliae assessed as inhibition of mycelial growth at 100 ug/mL measured after 5 days of cultivation	2006	Journal of agricultural and food chemistry, May-31, Volume: 54, Issue:11	Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea.
AID762933	Antimelanogenic activity in mouse B16F10 cells assessed as inhibition of alpha-MSH-induced melanin production at 1 to 2 uM after 72 hrs by spectrophotometry	2013	Journal of natural products, Aug-23, Volume: 76, Issue:8	Caffeic acid phenethyl ester inhibits alpha-melanocyte stimulating hormone-induced melanin synthesis through suppressing transactivation activity of microphthalmia-associated transcription factor.
AID1090480	Antifungal activity against Colletotrichum camelliae assessed as inhibition of mycelial growth measured after 5 days of cultivation	2006	Journal of agricultural and food chemistry, May-31, Volume: 54, Issue:11	Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea.
AID1745855	NCATS anti-infectives library activity on the primary C. elegans qHTS viability assay	2023	Disease models & mechanisms, 03-01, Volume: 16, Issue:3	In vivo quantitative high-throughput screening for drug discovery and comparative toxicology.
AID1745854	NCATS anti-infectives library activity on HEK293 viability as a counter-qHTS vs the C. elegans viability qHTS	2023	Disease models & mechanisms, 03-01, Volume: 16, Issue:3	In vivo quantitative high-throughput screening for drug discovery and comparative toxicology.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	137 (5.26)	18.7374
1990's	109 (4.18)	18.2507
2000's	662 (25.39)	29.6817
2010's	1288 (49.41)	24.3611
2020's	411 (15.77)	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	63 (2.34%)	5.53%
Reviews	123 (4.56%)	6.00%
Case Studies	2 (0.07%)	4.05%
Observational	4 (0.15%)	0.25%
Other	2,504 (92.88%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Trial	Phase	Enrollment	Study Type	Start Date	Status
Open Label Pilot Study Using Hydroxytyrosol (HT) as a Dietary Supplement in Patients With Mitochondrial Diseases (MDs) [NCT04543968]		12 participants (Anticipated)	Interventional	2022-07-05	Recruiting
Foods Such as Virgin Olive Oil Rich in Phenolic Compounds, and Prebiotic Supplementation: Dietary Strategy to Tackle Sarcopenia in Early Elderly Subjects (FOOP-Sarc) [NCT05485402]		135 participants (Anticipated)	Interventional	2022-09-01	Recruiting
The Effect of Suggestion of Harmful/Beneficial Effects of Odors on Asthma Symptoms [NCT02624362]		48 participants (Anticipated)	Interventional	2015-08-31	Enrolling by invitation
Effects of Punicalagin and Hydroxytyrosol Mixture on Different Inflammatory Markers Related With Cardiovascular Disease: a Crossover Study in Healthy Middle-aged Volunteers [NCT02042742]	Phase 4	76 participants (Actual)	Interventional	2013-04-30	Completed
Long-Term, Open-Label, Safety Study of LY2216684 12 to 18 mg Once Daily as Adjunctive Treatment for Patients With Major Depressive Disorder Who Are Partial Responders to Selective Serotonin Reuptake Inhibitor Treatment [NCT01155661]	Phase 3	608 participants (Actual)	Interventional	2010-10-31	Completed
Hydroxytyrosol and Vitamin E in the Treatment of Children With Biopsy-proven NASH [NCT02842567]	Phase 3	80 participants (Actual)	Interventional	2017-04-01	Completed
Effect of LY2216684 on Heart Rate and Blood Pressure in Healthy Subjects Receiving Oral Doses of Albuterol or Propranolol [NCT01263197]	Phase 1	48 participants (Actual)	Interventional	2010-12-31	Completed
A Study to Investigate the Pharmacodynamic and Pharmacokinetic Interaction of LY2216684 With Alcohol in Healthy Subjects [NCT01380691]	Phase 1	28 participants (Actual)	Interventional	2011-06-30	Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial	Outcome
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Clinical Global Impression - Severity (CGI-S)
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in EuroQol Questionnaire - 5 Dimension (EQ-5D)
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Hospital Anxiety and Depression Scale (HADS) Anxiety Subscale Score
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Hospital Anxiety and Depression Scale (HADS) Depression Subscale Score
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Massachusetts General Hospital Cognitive and Physical Functioning Questionnaire (CPFQ)
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Quality of Life Enjoyment and Satisfaction Questionnaire-Short Form (Q-LES-Q-SF)
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in the Arizona Sexual Experiences (ASEX) Scale
NCT01155661 (22) [back to overview]	Change From Baseline to Week 54 Endpoint in Pulse Rate
NCT01155661 (22) [back to overview]	Percentage of Participants Who Meet Remission Criteria of Depressive Symptoms by Week 8
NCT01155661 (22) [back to overview]	Percentage of Participants Who Meet Response Criteria of Depressive Symptoms by Week 8
NCT01155661 (22) [back to overview]	Percentage of Participants With Discontinuation-Emergent Adverse Events (DEAEs)
NCT01155661 (22) [back to overview]	Probability of Meeting the Remission Criteria for Depressive Symptoms at Week 54 Endpoint
NCT01155661 (22) [back to overview]	Probability of Meeting the Response Criteria for Depressive Symptoms at Week 54 Endpoint
NCT01155661 (22) [back to overview]	The Number of Participants Experiencing Clinically Significant Effects
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Blood Pressure
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Fatigue Associated With Depression (FAsD) Average Score and Subscale Scores
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Montgomery-Asberg Depression Rating Scale (MADRS) Total Score and Individual Items
NCT01155661 (22) [back to overview]	Change From Baseline to 54 Week Endpoint in Sheehan Disability Scale (SDS) Total Score and Subscores
NCT01155661 (22) [back to overview]	Percent of Participants With Suicidal Ideation and Behavior Based on the Columbia-Suicide Severity Rating Scale (C-SSRS)
NCT01155661 (22) [back to overview]	Percentage of Participants Who Reported Resource Utilization (RU) at Baseline and at the Week 54 Endpoint
NCT01155661 (22) [back to overview]	Plasma Concentration of LY2216684
NCT01155661 (22) [back to overview]	The Number of Participants Experiencing Clinically Significant Effects as a Function of CYP2D6 Predicted Phenotype at Week 54 Endpoint
NCT01263197 (3) [back to overview]	Maximum, Minimum and Average Changes in Diastolic Blood Pressure
NCT01263197 (3) [back to overview]	Maximum, Minimum and Average Changes in Heart Rate
NCT01263197 (3) [back to overview]	Maximum, Minimum and Average Changes in Systolic Blood Pressure
NCT01380691 (14) [back to overview]	Change From Baseline to 10 Hours in Continuity of Attention Composite Score
NCT01380691 (14) [back to overview]	Change From Baseline to 10 Hours in Postural Stability
NCT01380691 (14) [back to overview]	Change From Baseline to 10 Hours in Power of Attention Composite Score
NCT01380691 (14) [back to overview]	Change From Baseline to 10 Hours in Self-Rated Alertness
NCT01380691 (14) [back to overview]	Pharmacokinetics: Area Under the Concentration Time Curve From Time Zero to the Last Time Point With a Measurable Concentration (AUC[0-tlast]) of Alcohol
NCT01380691 (14) [back to overview]	Pharmacokinetics: Area Under the Concentration Time Curve Over a Dosing Interval (AUCt) of LY2216684
NCT01380691 (14) [back to overview]	Pharmacokinetics: Observed Cmax of Alcohol
NCT01380691 (14) [back to overview]	Pharmacokinetics: Observed Maximum Plasma Concentration (Cmax) of LY2216684
NCT01380691 (14) [back to overview]	Pharmacokinetics: Observed Time to Maximum Plasma Concentration (Tmax) of LY2216684
NCT01380691 (14) [back to overview]	Pharmacokinetics: Observed Tmax of Alcohol
NCT01380691 (14) [back to overview]	Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Episodic Memory
NCT01380691 (14) [back to overview]	Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Self-Ratings of Calmness and Contentment
NCT01380691 (14) [back to overview]	Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Speed of Retrieval of Information From Memory
NCT01380691 (14) [back to overview]	Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Working Memory

Intervention	units on a scale (Least Squares Mean)
LY2216684 + SSRI	-2.17

Intervention	units on a scale (Least Squares Mean)
LY2216684 + SSRI	23.607

Intervention	units on a scale (Least Squares Mean)
LY2216684 + SSRI	-4.57

Intervention	units on a scale (Least Squares Mean)
LY2216684 + SSRI	-6.32

Intervention	units on a scale (Least Squares Mean)
LY2216684 + SSRI	-8.64

Intervention	units on a scale (Least Squares Mean)
LY2216684 + SSRI	21.56

Intervention	units on a scale (Least Squares Mean)
LY2216684 + SSRI	-2.28

Intervention	beats per minute (bpm) (Least Squares Mean)
LY2216684 + SSRI	7.01

Intervention	percentage of participants (Number)
LY2216684 + SSRI	47.7

Intervention	percentage of participants (Number)
LY2216684 + SSRI	59.2

Intervention	percentage of participants (Number)
LY2216684 + SSRI	20.97

Intervention	Probability of remission (Number)
LY2216684 + SSRI	0.758

Intervention	Probability of response (Number)
LY2216684 + SSRI	0.772

Intervention	participants (Number)
LY2216684 + SSRI	13

Intervention	millimeters of mercury (mm Hg) (Least Squares Mean)
	Sitting Systolic Blood Pressure	Sitting Diastolic Blood Pressure
LY2216684 + SSRI	2.28	2.17

Intervention	units on a scale (Least Squares Mean)
	FAsD Experience Score	FAsD Impact Score	FAsD Average Score
LY2216684 + SSRI	-1.25	-1.37	-1.30

Intervention	units on a scale (Least Squares Mean)
	MADRS Item 1: Apparent Sadness	MADRS Item 2: Reported Sadness	MADRS Item 3: Inner Tension	MADRS Item 4: Reduced Sleep	MADRS Item 5: Reduced Appetite	MADRS Item 6: Concentration Difficulties	MADRS Item 7: Lassitude	MADRS Item 8: Inability to Feel	MADRS Item 9: Pessimistic Thoughts	MADRS Item 10: Suicidal Thoughts	MADRS Total Score
LY2216684 + SSRI	-2.17	-2.38	-1.56	-1.97	-1.08	-1.88	-2.18	-2.22	-1.52	-0.26	-16.97

Intervention	units on a scale (Least Squares Mean)
	SDS Global Functional Impairment(Imp) Score	Work/School Imp Score	Social Life/Leisure Activity Imp Score	Family Life/Home Responsibility Imp Score
LY2216684 + SSRI	-10.71	-3.36	-3.74	-3.61

Intervention	percentage of participants (Number)
	Suicidal Ideation	Suicidal Behavior
LY2216684 + SSRI	11.71	0.17

Intervention	percentage of participants (Number)
	Primary Care Doctor Visits, Baseline	Primary Care Doctor Visits, Week 54	Psychiatrist Visits, Baseline	Psychiatrist Visits, Week 54
LY2216684 + SSRI	62.27	30.18	44.15	4.75

Intervention	nanograms per milliliter (ng/mL) (Mean)
	12 mg dose	18 mg dose
LY2216684 + SSRI	29.6	53.6

Intervention	participants (Number)
	Poor Metabolizer	Non-poor Metabolizer
LY2216684 + SSRI	17	408

Intervention	millimeters of mercury (mm Hg) (Least Squares Mean)
	Day 1 Maximum Change	Day 1 Minimum Change	Day 1 Average Change	Day 3 Maximum Change	Day 3 Minimum Change	Day 3 Average Change	Day 5 Maximum Change	Day 5 Minimum Change	Day 5 Average
Albuterol	10.8	-19.9	-3.27	11.8	-21.5	-3.10	12.8	-21.6	-3.17
LY2216684 (Group 1)	13.4	-17.3	-0.674	13.6	-18.1	-0.537	13.8	-17.0	0.233
LY2216684 (Group 2)	14.9	-17.9	0.481	15.4	-17.8	0.619	13.1	-19.1	-0.631
LY2216684+Albuterol	12.2	-16.2	-0.873	12.7	-18.6	-0.159	14.7	-20.5	-0.140
LY2216684+Propranolol	10.6	-17.6	-1.44	12.5	-18.8	-1.20	13.8	-21.0	-1.80
Propranolol	8.16	-26.7	-7.47	6.87	-26.6	-7.80	6.58	-26.6	-7.33

Intervention	beats per minute (bpm) (Least Squares Mean)
	Day 1 Maximum Change	Day 1 Minimum Change	Day 1 Average Change	Day 3 Maximum Change	Day 3 Minimum Change	Day 3 Average Change	Day 5 Maximum Change	Day 5 Minimum Change	Day 5 Average Change
Albuterol	15.7	-15.2	-0.788	19.7	-16.3	0.102	19.9	-16.3	1.05
LY2216684 (Group 1)	33.4	-9.23	9.33	36.3	-7.05	12.6	40.4	-9.47	14.6
LY2216684 (Group 2)	31.1	-5.81	9.55	37.2	-5.94	14.2	36.9	-5.21	15.0
LY2216684+Albuterol	35.7	-9.03	10.9	37.2	-9.76	14.3	39.3	-7.27	15.7
LY2216684+Propranolol	17.2	-10.4	1.11	27.3	-9.40	6.01	26.3	-9.46	6.25
Propranolol	9.41	-14.8	-3.94	15.2	-16.1	-4.34	14.0	-15.4	-3.65

Intervention	millimeters of mercury (mm Hg) (Least Squares Mean)
	Day 1 Maximum Change	Day 1 Minimum Change	Day 1 Average Change	Day 3 Maximum Change	Day 3 Minimum Change	Day 3 Average Change	Day 5 Maximum Change	Day 5 Minimum Change	Day 5 Average Change
Albuterol	15.2	-20.5	-0.912	15.6	-24.9	-1.87	15.9	-22.1	-2.36
LY2216684 (Group 1)	14.1	-18.0	-0.986	13.5	-19.4	-1.65	13.9	-20.8	-2.07
LY2216684 (Group 2)	17.3	-17.7	1.73	15.3	-18.5	0.289	14.7	-21.1	-1.72
LY2216684+Albuterol	15.8	-15.3	1.69	13.5	-20.6	-1.99	16.2	-18.9	-0.233
LY2216684+Propranolol	10.9	-17.5	-1.35	11.2	-23.3	-3.91	13.1	-21.2	-2.55
Propranolol	9.39	-29.0	-8.50	7.99	-27.2	-8.75	11.1	-24.9	-6.83

Intervention	units on a scale (Least Squares Mean)
LY2216684 + Alcohol	-4.21
Placebo-matching LY2216684 + Alcohol	-1.16
LY2216684 + Placebo-matching Alcohol	-3.31
Placebo-matching LY2216684 + Placebo-matching Alcohol	-1.24

Intervention	1/3 degree of angle of sway (Least Squares Mean)
LY2216684 + Alcohol	0.14
Placebo-matching LY2216684 + Alcohol	-3.51
LY2216684 + Placebo-matching Alcohol	-3.65
Placebo-matching LY2216684 + Placebo-matching Alcohol	5.2

Intervention	minutes (Least Squares Mean)
LY2216684 + Alcohol	67.82
Placebo-matching LY2216684 + Alcohol	52.77
LY2216684 + Placebo-matching Alcohol	20.6
Placebo-matching LY2216684 + Placebo-matching Alcohol	6.78

Intervention	units on a scale (Least Squares Mean)
LY2216684 + Alcohol	3.85
Placebo-matching LY2216684 + Alcohol	-2.37
LY2216684 + Placebo-matching Alcohol	11.88
Placebo-matching LY2216684 + Placebo-matching Alcohol	3.02

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acetylcarnitine Acetylcarnitine: An acetic acid ester of CARNITINE that facilitates movement of ACETYL COA into the matrices of mammalian MITOCHONDRIA during the oxidation of FATTY ACIDS.	2.78	3	0	O-acylcarnitine	human metabolite
alpha-ketoisovalerate alpha-ketoisovalerate: RN given refers to parent cpd. 3-methyl-2-oxobutanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 3-methyl-2-oxobutanoic acid, arising from deprotonation of the carboxy group.. 3-methyl-2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.	2.06	1	0	2-oxo monocarboxylic acid; branched-chain keto acid	human metabolite; Saccharomyces cerevisiae metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.96	4	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
4-hydroxybenzyl alcohol 4-hydroxybenzyl alcohol: the aglycone of gastrodin. p-hydroxybenzyl alcohol : A member of the class of benzyl alcohols that is benzyl alcohol substituted by a hydroxy group at position 4. It has been isolated from Arcangelisia gusanlung.	3.01	4	0	benzyl alcohols; phenols	plant metabolite
4-hydroxybenzaldehyde [no description available]	2.46	2	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	3.11	5	0	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.95	4	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	2.6	1	0	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.48	2	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	7.35	21	2	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.	7.07	24	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
acetoin [no description available]	3.01	4	0	methyl ketone; secondary alpha-hydroxy ketone	metabolite
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	3.49	8	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]	2.73	3	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.	2.06	1	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
benzaldehyde [no description available]	4.69	8	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]	2.47	2	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.	2.46	2	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	9.41	21	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.17	1	0	amino-acid betaine; glycine derivative	fundamental metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.01	1	0	halide anion; monoatomic bromine
butyraldehyde [no description available]	2.25	1	0	butanals	biomarker; Escherichia coli metabolite; mouse metabolite
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	2.78	3	0	butanediol; glycol; secondary alcohol
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.	6.42	22	2	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.41	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	2	1	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.46	2	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.81	3	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
catechol [no description available]	4.39	7	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	3.22	5	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.25	1	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	1.95	1	0	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.	2.43	2	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	3.06	4	0	coumarins	fluorescent dye; human metabolite; plant metabolite
cuminaldehyde cuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.	2.31	1	0	benzaldehydes	insecticide; plant metabolite; volatile oil component
4-vinylguaiacol 2-methoxy-4-vinylphenol: a germination inhibitor; also an odorant in green tea; structure in first source. 2-methoxy-4-vinylphenol : A member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group.	2.98	4	0	phenols	flavouring agent; pheromone; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	3.06	4	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
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.	2.05	1	0	cresol	human xenobiotic metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	2.05	1	0	alkane	xenobiotic
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	5.21	14	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.	2.77	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	5.13	10	1	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
dihydrolipoic acid dihydrolipoic acid: RN given refers to parent cpd without isomeric designation. dihydrolipoic acid : A thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.. dihydrolipoate : The conjugate base of dihydrolipoic acid.	2.08	1	0	thio-fatty acid	antioxidant; human metabolite; neuroprotective agent
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.41	1	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	4.66	8	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
n(g),n(g')-dimethyl-l-arginine N,N-dimethylarginine: asymmetric dimethylarginine; do not confuse with N,N'-dimethylarginine	2.61	2	0	alpha-amino acid
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	2.15	1	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental 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.	2.11	1	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	4.71	29	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.	2.05	1	0	dibenzofurans; mancude organic heterotricyclic parent; polycyclic heteroarene	xenobiotic
creatine [no description available]	2.1	1	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	3.73	9	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	2.53	2	0	alpha-diketone	Escherichia coli metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	3.08	5	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.06	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	2.52	2	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.	3.81	11	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]	1.95	1	0	glycerol monophosphate	algal metabolite; human metabolite
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	2.03	1	0	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
histamine [no description available]	3.31	6	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
homogentisic acid Homogentisic Acid: Dihydroxyphenylacetic acid with hydroxyls at the 2 and 5 positions of the phenyl ring.. homogentisic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions.	2	1	0	dihydroxyphenylacetic acid; hydroquinones	human metabolite; plant metabolite
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	3.66	9	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	3.11	5	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	3.02	4	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
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.	1.95	1	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	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.	4.73	8	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	2.05	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.	3.04	4	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.	3.75	10	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.25	1	0	cyclitol; hexol
melatonin [no description available]	8.6	18	3	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.	2.05	1	0	acetamides; anilide	analgesic
n-methylphenylethanolamine 2-methylamino-1-phenylethanol: structure in first source	2.05	1	0	alkaloid; phenylethanolamines	human metabolite; plant metabolite
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.	2.7	3	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.	2.55	2	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.51	2	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.29	6	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.01	1	0	nitrogen oxoacid
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)	3.83	11	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.	2.05	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.	2.43	2	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-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.	2.05	1	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
phenol [no description available]	5.29	15	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylpyruvic acid phenylpyruvic acid: RN given refers to parent cpd. phenylpyruvate : A 2-oxo monocarboxylic acid anion resulting from deprotonation of the carboxy group of either keto- or enol-phenylpyruvic acid.. keto-phenylpyruvic acid : A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway.	2.45	2	0	2-oxo monocarboxylic acid	chromogenic compound; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; fundamental metabolite
phenylacetaldehyde [no description available]	6.81	18	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.	6.24	17	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
2-hydroxyphenethylamine 2-amino-1-phenylethanol: structure in first source	2.05	1	0	phenylethanolamines	human metabolite
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	3.29	6	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
picolinic acid picolinic acid: iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7206. picolinic acid : A pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan.	2.42	2	0	pyridinemonocarboxylic acid	human metabolite; MALDI matrix material
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.38	2	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.	3.49	8	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	3.13	5	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	5.75	3	2	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.	2.1	1	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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).	2.08	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.76	3	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.07	1	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.	2	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human metabolite
dithionite Dithionite: Dithionite. The dithionous acid ion and its salts.	2.04	1	0	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.	3.19	5	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.21	1	0	sulfur oxoacid	catalyst
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	2.13	1	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	2.6	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymine [no description available]	2.35	2	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.	3.31	6	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	3.48	2	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	3.04	4	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	3.1	5	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).	3.57	8	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	4.04	4	0	xanthine	Saccharomyces cerevisiae metabolite
ibotenic acid Ibotenic Acid: A neurotoxic isoxazole (similar to KAINIC ACID and MUSCIMOL) found in AMANITA mushrooms. It causes motor depression, ataxia, and changes in mood, perceptions and feelings, and is a potent excitatory amino acid agonist.	2.11	1	0	non-proteinogenic alpha-amino acid	neurotoxin
normetanephrine Normetanephrine: A methylated metabolite of norepinephrine that is excreted in the urine and found in certain tissues. It is a marker for tumors.	1.96	1	0	catecholamine
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	2.95	4	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1-aminocyclohexanecarboxylic acid 1-aminocyclohexanecarboxylic acid: RN given refers to parent cpd. 1-amino-1-cyclohexanecarboxylic acid : An alpha-amino acid that is cyclohexanecarboxylic acid substituted by an amino group at position 1.	2.01	1	0	alpha-amino acid
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.	5.11	41	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
pd 173074 [no description available]	2.07	1	0	aromatic amine; biaryl; dimethoxybenzene; pyridopyrimidine; tertiary amino compound; ureas	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; fibroblast growth factor receptor antagonist
amitrole Amitrole: A non-selective post-emergence, translocated herbicide. According to the Seventh Annual Report on Carcinogens (PB95-109781, 1994) this substance may reasonably be anticipated to be a carcinogen. (From Merck Index, 12th ed) It is an irreversible inhibitor of CATALASE, and thus impairs activity of peroxisomes.. amitrole : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	2.02	1	0	aromatic amine; triazoles	carotenoid biosynthesis inhibitor; EC 1.11.1.6 (catalase) inhibitor; herbicide
3-aminobenzamide [no description available]	2.6	1	0	benzamides; substituted aniline	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
3-methoxytyramine 3-methoxytyramine: RN given refers to parent cpd. 3-methoxytyramine : A monomethoxybenzene that is dopamine in which the hydroxy group at position 3 is replaced by a methoxy group. It is a metabolite of the neurotransmitter dopamine and considered a potential biomarker of pheochromocytomas and paragangliomas.	2.4	2	0	monomethoxybenzene; phenols; phenylethylamine; primary amino compound	biomarker; human blood serum metabolite; human urinary metabolite
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2.4	2	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
3-nitropropionic acid 3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.	2.06	1	0	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
pleconaril WIN 63843: structure given in first source	2.6	1	0
4-(2-aminoethyl)benzenesulfonylfluoride [no description available]	2.6	1	0
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	6.22	23	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
phenytoin [no description available]	2.6	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5-hydroxydecanoate 5-hydroxydecanoic acid: Potassium Channel Blocker; RN refers to parent cpd	2.02	1	0	medium-chain fatty acid
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	1.97	1	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.	1.96	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
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	2.75	3	0	monoazo compound
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.	2.7	3	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)	2.6	1	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
acetohexamide Acetohexamide: A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide.. acetohexamide : An N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is replaced by a p-acetylphenylsulfonyl group, while a hydrogen attached to the other nitrogen is replaced by a cyclohexyl group.	2.05	1	0	acetophenones; N-sulfonylurea	hypoglycemic agent; insulin secretagogue
tyrphostin ag 1024 tyrphostin AG 1024: modulates radiosensitivity in human breast cancer cells; also an IGF1 receptor inhibitor	2.07	1	0	alkylbenzene
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.	2.6	1	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
amantadine amant: an antiviral compound consisting of an adamantane derivative chemically linked to a water-solube polyanioic matrix; structure in first source	2.6	1	0	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
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.	2.6	1	0	1,3-thiazoles; primary amino compound
amobarbital Amobarbital: A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565). amobarbital : A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hypnotic properties.	2.05	1	0	barbiturates
amodiaquine Amodiaquine: A 4-aminoquinoline compound with anti-inflammatory properties.. amodiaquine : A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.	2.6	1	0	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.02	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.	3.6	8	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
aurintricarboxylic acid Aurintricarboxylic Acid: A dye which inhibits protein biosynthesis at the initial stages. The ammonium salt (aluminon) is a reagent for the colorimetric estimation of aluminum in water, foods, and tissues.. aurintricarboxylic acid : A member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'.	2.02	1	0	monohydroxybenzoic acid; quinomethanes; tricarboxylic acid	fluorochrome; histological dye; insulin-like growth factor receptor 1 antagonist
azelastine azelastine: azeptin is azelastine hydrochloride; structure; eye drop formulation effective in relieving symptoms of allergic conjunctivitis; do not confuse with 5-loxin which is an extract of Boswellia. azelastine : A phthalazine compound having an oxo substituent at the 1-position, a 1-methylazepan-4-yl group at the 2-position and a 4-chlorobenzyl substituent at the 4-position.	2.13	1	0	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor
baclofen [no description available]	2.6	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
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).	2.05	1	0	barbiturates	drug allergen
bendroflumethiazide Bendroflumethiazide: A thiazide diuretic with actions and uses similar to those of HYDROCHLOROTHIAZIDE. It has been used in the treatment of familial hyperkalemia, hypertension, edema, and urinary tract disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p810). bendroflumethiazide : A sulfonamide consisting of 7-sulfamoyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by a trifluoromethyl group and that at position 3 is substituted by a benzyl group.	2.05	1	0	benzothiadiazine; sulfonamide	antihypertensive agent; diuretic
benserazide Benserazide: An inhibitor of DOPA DECARBOXYLASE that does not enter the central nervous system. It is often given with LEVODOPA in the treatment of parkinsonism to prevent the conversion of levodopa to dopamine in the periphery, thereby increasing the amount that reaches the central nervous system and reducing the required dose. It has no antiparkinson actions when given alone.. benserazide : A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone.	1.96	1	0	carbohydrazide; catechols; primary alcohol; primary amino compound	antiparkinson drug; dopaminergic agent; EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.6	1	0	benzamides
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	2.08	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.	2.05	1	0	benzoate ester; substituted aniline	allergen; antipruritic drug; sensitiser; topical anaesthetic
benzyl benzoate benzyl benzoate: structure; acarosan, a moist powder composed of wetted cellulose and benzyl benzoate, is used on carpets as an acaricide. benzyl benzoate : A benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia.	2.05	1	0	benzoate ester; benzyl ester	acaricide; plant metabolite; scabicide
bepridil Bepridil: A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.. bepridil : A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.	2.01	1	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
berberine [no description available]	2.57	2	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
busulfan [no description available]	2.25	1	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; insect sterilant; teratogenic agent
butamben butamben: structure. butamben : An amino acid ester resulting from the formal condensation of the carboxy group of 4-aminobenzoic acid with the hydroxy group of butan-1-ol. Its local anaesthetic properties have been used for surface anaesthesia of the skin and mucous membranes, and for relief of pain and itching associated with some anorectal disorders.	2.05	1	0	amino acid ester; benzoate ester; primary amino compound; substituted aniline	local anaesthetic
caffeine [no description available]	2.13	1	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
camostat camostat : A benzoate ester resulting from the formal condensation of the carboxy group of 4-guanidinobenzoic acid with the hydroxy group of 2-(dimethylamino)-2-oxoethyl (4-hydroxyphenyl)acetate. It is a potent inhibitor of the human transmembrane protease serine 2 (TMPRSS2) and its mesylate salt is currently under investigation for its effectiveness in COVID-19 patients.	2.6	1	0	benzoate ester; carboxylic ester; diester; guanidines; tertiary carboxamide	anti-inflammatory agent; anticoronaviral agent; antifibrinolytic drug; antihypertensive agent; antineoplastic agent; antiviral agent; serine protease inhibitor
camphor, (+-)-isomer [no description available]	2.93	3	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
candesartan candesartan: a nonpeptide angiotensin II receptor antagonist. candesartan : A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin receptor antagonist used for the treatment of hypertension.	2.6	1	0	benzimidazolecarboxylic acid; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
carprofen carprofen: RN given refers to cpd without isomeric designation. carprofen : Propanoic acid in which one of the methylene hydrogens is substituted by a 6-chloro-9H-carbazol-2-yl group. A non-steroidal anti-inflammatory drug, it is no longer used in human medicine but is still used for treatment of arthritis in elderly dogs.	2.21	1	0	carbazoles; organochlorine compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug; photosensitizing agent
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.38	2	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	2.21	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetyl alcohol cetyl alcohol: has been used for eczema, skin irritations; RN given refers to parent cpd; structure. hexadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of sixteen carbon atoms.. hexadecan-1-ol : A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1.	2.01	1	0	hexadecanol; long-chain primary fatty alcohol	algal metabolite; flavouring agent; human metabolite; plant metabolite
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	2.6	1	0	pyridinium ion
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.17	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chloroxylenol chloroxylenol: topical antiseptic; RN given refers to parent cpd; structure. 4-chloro-3,5-dimethylphenol : A member of the class of phenols that is 3,5-xylenol which is substituted at position 4 by chlorine. It is bactericidal against most Gram-positive bacteria but less effective against Staphylococci and Gram-negative bacteria, and often inactive against Pseudomonas species. It is ineffective against bacterial spores.	2.6	1	0	monochlorobenzenes; phenols	antiseptic drug; disinfectant; molluscicide
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.	2.6	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.55	2	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
cilostazol [no description available]	2.03	1	0	lactam; tetrazoles	anticoagulant; bronchodilator agent; EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor; fibrin modulating drug; neuroprotective agent; platelet aggregation inhibitor; vasodilator agent
eucalyptol [no description available]	6.1	10	1
ciprofibrate [no description available]	2.6	1	0	cyclopropanes; monocarboxylic acid; organochlorine compound	antilipemic drug
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	2.17	1	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clomipramine Clomipramine: A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.. clomipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.	2.6	1	0	dibenzoazepine	anticoronaviral agent; antidepressant; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; serotonergic antagonist; serotonergic drug; serotonin uptake inhibitor
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.47	2	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
danthron danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.	2.6	1	0	dihydroxyanthraquinone	apoptosis inducer; plant metabolite
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	3.4	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
deferiprone Deferiprone: A pyridone derivative and iron chelator that is used in the treatment of IRON OVERLOAD in patients with THALASSEMIA.. deferiprone : A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.	2.6	1	0	4-pyridones	iron chelator; protective agent
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.	2.05	1	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.	2.1	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
diazoxide Diazoxide: A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.. diazoxide : A benzothiadiazine that is the S,S-dioxide of 2H-1,2,4-benzothiadiazine which is substituted at position 3 by a methyl group and at position 7 by chlorine. A peripheral vasodilator, it increases the concentration of glucose in the plasma and inhibits the secretion of insulin by the beta- cells of the pancreas. It is used orally in the management of intractable hypoglycaemia and intravenously in the management of hypertensive emergencies.	2.03	1	0	benzothiadiazine; organochlorine compound; sulfone	antihypertensive agent; beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; diuretic; K-ATP channel agonist; sodium channel blocker; sympathomimetic agent; vasodilator agent
dibenzothiophene dibenzothiophene : A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.	2.05	1	0	dibenzothiophenes; mancude organic heterotricyclic parent	keratolytic drug
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	2.07	1	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
dichlorvos Dichlorvos: An organophosphorus insecticide that inhibits ACETYLCHOLINESTERASE.. dichlorvos : An alkenyl phosphate that is the 2,2-dichloroethenyl ester of dimethyl phosphate.	2.13	1	0	alkenyl phosphate; dialkyl phosphate; organochlorine acaricide; organophosphate insecticide	anthelminthic drug; antibacterial agent; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	2.6	1	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
disulfiram [no description available]	2.43	2	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.6	1	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
doxazosin Doxazosin: A prazosin-related compound that is a selective alpha-1-adrenergic blocker.. doxazosin : A member of the class of quinazolines that is quinazoline substituted by an amino group at position 4, methoxy groups at positions 6 and 7 and a piperazin-1-yl group at position 2 which in turn is substituted by a 2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl group at position 4. An antihypertensive agent, it is used in the treatment of high blood pressure.	2.6	1	0	aromatic amine; benzodioxine; monocarboxylic acid amide; N-acylpiperazine; N-arylpiperazine; quinazolines	alpha-adrenergic antagonist; antihyperplasia drug; antihypertensive agent; antineoplastic agent; vasodilator agent
ebselen ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.	2.6	1	0	benzoselenazole	anti-inflammatory drug; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 3.5.4.1 (cytosine deaminase) inhibitor; EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor; enzyme mimic; ferroptosis inhibitor; genotoxin; hepatoprotective agent; neuroprotective agent; radical scavenger
embelin embelin: from Embelia fruit (Myrsinaceae). embelin : A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease.	3.35	1	0	dihydroxy-1,4-benzoquinones	antimicrobial agent; antineoplastic agent; hepatitis C protease inhibitor; plant metabolite
enoxacin Enoxacin: A broad-spectrum 6-fluoronaphthyridinone antibacterial agent that is structurally related to NALIDIXIC ACID.. enoxacin : A 1,8-naphthyridine derivative that is 1,4-dihydro-1,8-naphthyridine with an ethyl group at the 1 position, a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a piperazin-1-yl group at the 7 position. An antibacterial, it is used in the treatment of urinary-tract infections and gonorrhoea.	2.03	1	0	1,8-naphthyridine derivative; amino acid; fluoroquinolone antibiotic; monocarboxylic acid; N-arylpiperazine; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	3.15	5	0
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	3.52	8	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
etidronate Etidronic Acid: A diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover.. etidronic acid : A 1,1-bis(phosphonic acid) that is (ethane-1,1-diyl)bis(phosphonic acid) having a hydroxy substituent at the 1-position. It inhibits the formation, growth, and dissolution of hydroxyapatite crystals by chemisorption to calcium phosphate surfaces.	2.6	1	0	1,1-bis(phosphonic acid)	antineoplastic agent; bone density conservation agent; chelator
2-hexyloxybenzamide 2-hexyloxybenzamide: structure	2.6	1	0	aromatic ether; benzamides	antifungal agent
brl 42810 [no description available]	2.6	1	0	2-aminopurines; acetate ester	antiviral drug; prodrug
carbonyl cyanide p-trifluoromethoxyphenylhydrazone Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.	1.97	1	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
fenbufen fenbufen: structure; RN given refers to parent cpd	2.05	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	2.15	1	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	1.98	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
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.	3.37	6	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
fludiazepam fludiazepam: RN given refers to parent cpd; structure	2.05	1	0	1,4-benzodiazepinone; organochlorine compound; organofluorine compound	anxiolytic drug
flufenamic acid Flufenamic Acid: An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16). flufenamic acid : An aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders.	2.05	1	0	aromatic amino acid; organofluorine compound	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fluphenazine [no description available]	2.6	1	0	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	4.33	6	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	2.13	1	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.	2.05	1	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	2.08	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
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.	2.05	1	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gabexate Gabexate: A serine proteinase inhibitor used therapeutically in the treatment of pancreatitis, disseminated intravascular coagulation (DIC), and as a regional anticoagulant for hemodialysis. The drug inhibits the hydrolytic effects of thrombin, plasmin, and kallikrein, but not of chymotrypsin and aprotinin.	2.6	1	0	benzoate ester
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.97	4	0
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	3.15	5	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.47	2	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
go 6976 [no description available]	2.05	1	0	indolocarbazole; organic heterohexacyclic compound	EC 2.7.11.13 (protein kinase C) inhibitor
fasudil fasudil: intracellular calcium antagonist; structure in first source. fasudil : An isoquinoline substituted by a (1,4-diazepan-1-yl)sulfonyl group at position 5. It is a Rho-kinase inhibitor and its hydrochloride hydrate form is approved for the treatment of cerebral vasospasm and cerebral ischemia.	2.6	1	0	isoquinolines; N-sulfonyldiazepane	antihypertensive agent; calcium channel blocker; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; geroprotector; neuroprotective agent; nootropic agent; vasodilator agent
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.	2.6	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.	2.6	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.	2.05	1	0	barbiturates
hexylresorcinol [no description available]	2.6	1	0	resorcinols
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.	2.6	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.	3.98	4	0	phenanthridines	fluorochrome; intercalator
hycanthone Hycanthone: Potentially toxic, but effective antischistosomal agent, it is a metabolite of LUCANTHONE.. hycanthone : A thioxanthen-9-one compound having a hydroxymethyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. It was formerly used (particularly as the monomethanesulfonic acid salt) as a schistosomicide for individual or mass treatement of infection with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel.	2.6	1	0	thioxanthenes	mutagen; schistosomicide drug
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.	2.53	2	0	benzothiadiazine; organochlorine compound; sulfonamide	antihypertensive agent; diuretic; environmental contaminant; xenobiotic
hydroxyurea [no description available]	4.2	5	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.84	3	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
phenelzine Phenelzine: One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC.	1.95	1	0	primary amine
ifosfamide [no description available]	2.13	1	0	ifosfamides	alkylating agent; antineoplastic agent; environmental contaminant; immunosuppressive agent; xenobiotic
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	3.65	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
avapro Irbesartan: A spiro compound, biphenyl and tetrazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION, and in the treatment of kidney disease.. irbesartan : A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension.	2.6	1	0	azaspiro compound; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	2.02	1	0	3-isobutyl-1-methylxanthine
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	2.07	1	0	organofluorine compound	inhalation anaesthetic
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2.97	4	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	3.41	7	0	secondary alcohol; secondary fatty alcohol	protic solvent
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	3.13	5	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
itraconazole [no description available]	2.6	1	0	piperazines
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.	2.25	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.	2.05	1	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
kojic acid [no description available]	2.69	2	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
lapachol lapachol : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.	2.52	2	0
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	2.08	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
loperamide Loperamide: One of the long-acting synthetic ANTIDIARRHEALS; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.. loperamide : A synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease.	2.6	1	0	monocarboxylic acid amide; monochlorobenzenes; piperidines; tertiary alcohol	anticoronaviral agent; antidiarrhoeal drug; mu-opioid receptor agonist
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.	2.6	1	0	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	2.6	1	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source	2.98	4	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
4-(dimethylamino)-n-(7-(hydroxyamino)-7-oxoheptyl)benzamide 4-(dimethylamino)-N-(7-(hydroxyamino)-7-oxoheptyl)benzamide: structure in first source. 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]benzamide : A benzamide resulting from the formal condensation of the carboxy group of 4-(dimethylamino)benzoic acid with the amino group of 7-amino-N-hydroxyheptanamide. It is a potent inhibitor of histone deacetylases and induces cell cycle arrest and apoptosis in several human cancer cell lines.	2.6	1	0	benzamides; hydroxamic acid; secondary carboxamide; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
mafenide Mafenide: A sulfonamide that inhibits the enzyme CARBONIC ANHYDRASE and is used as a topical anti-bacterial agent, especially in burn therapy.	2.6	1	0	aromatic amine
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	2.03	1	0	nitrogen mustard; organochlorine compound	alkylating agent
meclofenamic acid Meclofenamic Acid: A non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis.. meclofenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoea (painful periods), osteoarthritis and rheumatoid arthritis.	2.05	1	0	aminobenzoic acid; organochlorine compound; secondary amino compound	analgesic; anticonvulsant; antineoplastic agent; antipyretic; antirheumatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
medazepam Medazepam: A benzodiazepine derivative used in the treatment of anxiety. It has sedative, muscle relaxant, and anticonvulsant properties. One of its metabolites is DIAZEPAM and one of its excretion products is OXAZEPAM.	2.05	1	0	organic molecular entity
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	2.05	1	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.96	4	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
methazolamide Methazolamide: A carbonic anhydrase inhibitor that is used as a diuretic and in the treatment of glaucoma.	2.6	1	0	sulfonamide; thiadiazoles
methocarbamol Methocarbamol: A centrally acting muscle relaxant whose mode of action has not been established. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1206). methocarbamol : A racemate comprising equimolar amounts of (R)- and (S)-methocarbamol. A centrally acting skeletal muscle relaxant, it is used as an adjunct in the short-term symptomatic treatment of painful muscle spasm. The (R)-enantiomer is more active than the (S)-enantiomer.. 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate : A carbamate ester that is glycerol in which one of the primary alcohol groups has been converted to its 2-methoxyphenyl ether while the other has been converted to the corresponding carbamate ester.	2.6	1	0	aromatic ether; carbamate ester; secondary alcohol
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.	3.15	5	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
5-methylfurtrethonium 5-methylfurtrethonium: RN given refers to parent cpd; structure	2.02	1	0	aralkylamine
methyl methanesulfonate [no description available]	2.43	2	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	4.4	1	1	beta-amino acid ester; methyl ester; piperidines
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.	2.6	1	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
entinostat [no description available]	2.6	1	0	benzamides; carbamate ester; primary amino compound; pyridines; substituted aniline	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	2.6	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
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.	2.05	1	0	aminobenzoic acid; secondary amino compound	membrane transport modulator
nabumetone Nabumetone: A butanone non-steroidal anti-inflammatory drug and cyclooxygenase-2 (COX2) inhibitor that is used in the management of pain associated with OSTEOARTHRITIS and RHEUMATOID ARTHRITIS.. nabumetone : A methyl ketone that is 2-butanone in which one of the methyl hydrogens at position 4 is replaced by a 6-methoxy-2-naphthyl group. A prodrug that is converted to the active metabolite, 6-methoxy-2-naphthylacetic acid, following oral administration. It is shown to have a slightly lower risk of gastrointestinal side effects than most other non-steroidal anti-inflammatory drugs.	2.6	1	0	methoxynaphthalene; methyl ketone	cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
nafamostat nafamostat: inhibitor of trypsin, plasmin, pancreatic kallikrein, plasma kallikrein & thrombin; strongly inhibits esterolytic activities of C1r & C1 esterase complement-mediated hemolysis; antineoplastic	2.6	1	0	benzoic acids; guanidines
nalidixic acid [no description available]	3.75	3	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.	2.6	1	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
niclosamide Niclosamide: An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48). niclosamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections.	2.15	1	0	benzamides; C-nitro compound; monochlorobenzenes; salicylanilides; secondary carboxamide	anthelminthic drug; anticoronaviral agent; antiparasitic agent; apoptosis inducer; molluscicide; piscicide; STAT3 inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.43	2	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nimetazepam nimetazepam : A nitrazepam which is substituted at positions 1 by a methyl group. It is used as an anticonvulsant and as a hypnotic for the short-term management of insomnia.	2.05	1	0	1,4-benzodiazepinone; C-nitro compound	anticonvulsant; antispasmodic drug; GABA modulator; sedative
nitrazepam Nitrazepam: A benzodiazepine derivative used as an anticonvulsant and hypnotic.. nitrazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one which is substituted at positions 5 and 7 by phenyl and nitro groups, respectively. It is used as a hypnotic for the short-term management of insomnia and for the treatment of epileptic spasms in infants (West's syndrome).	2.05	1	0	1,4-benzodiazepinone; C-nitro compound	anticonvulsant; antispasmodic drug; drug metabolite; GABA modulator; sedative
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.36	2	0	phenylethanolamines; tyramines	neurotransmitter
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	2.6	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
osalmide osalmide: structure	2.6	1	0	organic molecular entity
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	2.49	2	0	1,3,5-triazines; monocarboxylic acid
oxethazaine [no description available]	2.6	1	0	amino acid amide
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	3.57	8	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
p-fluorophenylalanine p-Fluorophenylalanine: 3-(p-Fluorophenyl)-alanine.. 4-fluorophenylalanine : A phenylalanine derivative in which the hydrogen at position 4 on the benzene ring is replaced by a fluoro group.	2.43	2	0	fluoroamino acid; monofluorobenzenes; non-proteinogenic alpha-amino acid; phenylalanine derivative
palmidrol palmidrol: a cannabinoid receptor-inactive eCB-related molecule used as prophylactic in helping to prevent respiratory viral infection. palmitoyl ethanolamide : An N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid.	3.86	2	0	endocannabinoid; N-(long-chain-acyl)ethanolamine; N-(saturated fatty acyl)ethanolamine	anti-inflammatory drug; anticonvulsant; antihypertensive agent; neuroprotective agent
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	2.6	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.	2.47	2	0	monochlorophenol
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.72	3	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.05	1	0	barbiturates	GABAA receptor agonist
pentoxifylline [no description available]	2.88	3	0	oxopurine
perhexiline Perhexiline: 2-(2,2-Dicyclohexylethyl)piperidine. Coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis.	2.6	1	0	piperidines	cardiovascular 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.	2.6	1	0	diaminopyridine; monoazo compound	anticoronaviral agent; carcinogenic agent; local anaesthetic; non-narcotic analgesic
phenazine [no description available]	2.05	1	0	azaarene; heteranthrene; mancude organic heterotricyclic parent; phenazines; polycyclic heteroarene
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.67	3	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2.5	2	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	2.69	2	0	acyl fluoride	serine proteinase inhibitor
phloretin [no description available]	2.11	1	0	dihydrochalcones	antineoplastic agent; plant metabolite
pimobendan pimobendan: produces arterial & venous dilatation in dogs; structure given in first source	2.6	1	0	benzimidazoles; pyridazinone	cardiotonic drug; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; vasodilator agent
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	2.05	1	0	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
pj-34 PJ34 : A member of the class of phenanthridines that is 5,6-dihydrophenanthridine substituted at positions 2 and 6 by (N,N-dimethylglycyl)amino and oxo groups, respectively. It is a potent inhibitor of poly(ADP-ribose) polymerases PARP1 and PARP2 (IC50 of 110 nM and 86 nM, respectively) and exhibits anti-cancer, cardioprotective and neuroprotective properties.	2.6	1	0	phenanthridines; secondary carboxamide; tertiary amino compound	angiogenesis inhibitor; anti-inflammatory agent; antiatherosclerotic agent; antineoplastic agent; apoptosis inducer; cardioprotective agent; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; neuroprotective agent
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.	2.7	3	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
praziquantel azinox: Russian drug	2.6	1	0	isoquinolines
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	2.07	1	0	diarylmethane
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	2.6	1	0	benzoic acids; sulfonamide	uricosuric drug
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	2.47	2	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
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.	3.22	6	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
procaterol Procaterol: A long-acting beta-2-adrenergic receptor agonist.	3.5	1	1	quinolines
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.	2.6	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
promethazine Promethazine: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.. promethazine : A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.	2.6	1	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	2.03	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.67	3	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	2.43	2	0	trihydroxybenzoic acid
riluzole Riluzole: A glutamate antagonist (RECEPTORS, GLUTAMATE) used as an anticonvulsant (ANTICONVULSANTS) and to prolong the survival of patients with AMYOTROPHIC LATERAL SCLEROSIS.	2.02	1	0	benzothiazoles
rimantadine Rimantadine: An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.	2.6	1	0	alkylamine
ro 31-8220 Ro 31-8220: a protein kinase C inhibitor	2.05	1	0	imidothiocarbamic ester; indoles; maleimides	EC 2.7.11.13 (protein kinase C) inhibitor
rolipram [no description available]	2.6	1	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
aurin aurin: structure	2.02	1	0	diarylmethane
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.	1.95	1	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
salicyl alcohol salicyl alcohol: RN given refers to parent cpd; saligenin is the aglycone of salicin; structure; it is oxidatively metabolized to gentisic acid. salicyl alcohol : A hydroxybenzyl alcohol that is phenol substituted by a hydroxymethyl group at C-2.	2.06	1	0	aromatic primary alcohol; hydroxybenzyl alcohol	human urinary metabolite
scriptaid scriptide: provokes translocation of GLUT4 to increase glucose uptake; structure in first source	2.6	1	0	isoquinolines
sebacic acid sebacic acid : An alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.	2.6	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite; plant metabolite
sevoflurane Sevoflurane: A non-explosive inhalation anesthetic used in the induction and maintenance of general anesthesia. It does not cause respiratory irritation and may also prevent PLATELET AGGREGATION.. sevoflurane : An ether compound having fluoromethyl and 1,1,1,3,3,3-hexafluoroisopropyl as the two alkyl groups.	2.13	1	0	ether; organofluorine compound	central nervous system depressant; inhalation anaesthetic; platelet aggregation inhibitor
sulfadiazine Sulfadiazine: One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.. sulfadiazine : A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.. diazine : The parent structure of the diazines.	2.05	1	0	pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; antiprotozoal drug; coccidiostat; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sodium fluoride [no description available]	2.03	1	0	fluoride salt	mutagen
fenofibrate [no description available]	2.6	1	0	benzochromenone; delta-lactone; naphtho-alpha-pyrone	platelet aggregation inhibitor; Sir2 inhibitor
imatinib [no description available]	2.6	1	0	aromatic amine; benzamides; N-methylpiperazine; pyridines; pyrimidines	antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
streptonigrin [no description available]	3.74	3	0	pyridines; quinolone	antimicrobial agent; antineoplastic agent
sulfadimethoxine Sulfadimethoxine: A sulfanilamide that is used as an anti-infective agent.. sulfadimethoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	2.05	1	0	aromatic ether; pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; drug allergen; environmental contaminant; xenobiotic
sulfamerazine [no description available]	2.05	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen
sulfamonomethoxine Sulfamonomethoxine: Long acting sulfonamide antibacterial agent.	2.05	1	0	benzenes; sulfonamide
sulfanilamide [no description available]	2.05	1	0	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sulfaphenazole Sulfaphenazole: A sulfonilamide anti-infective agent.. sulfaphenazole : A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.	2.05	1	0	primary amino compound; pyrazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial drug; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor; P450 inhibitor
sulfapyridine Sulfapyridine: Antibacterial, potentially toxic, used to treat certain skin diseases.. sulfapyridine : A sulfonamide consisting of pyridine with a 4-aminobenzenesulfonamido group at the 2-position.	2.05	1	0	pyridines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; dermatologic drug; drug allergen; environmental contaminant; xenobiotic
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.	2.01	1	0
sulfisomidine Sulfisomidine: A sulfanilamide antibacterial agent.. sulfisomidine : A sulfonamide consisting of pyrimidine having methyl substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	2.05	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent
sulfisoxazole Sulfisoxazole: A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms.. sulfisoxazole : A sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of gram-negative and gram-positive organisms.	2.05	1	0	isoxazoles; sulfonamide antibiotic; sulfonamide	antibacterial drug; drug allergen
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	3.35	1	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
suprofen Suprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.. suprofen : An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.	2.6	1	0	aromatic ketone; monocarboxylic acid; thiophenes	antirheumatic drug; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
thalidomide Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.	2.6	1	0	phthalimides; piperidones
ticlopidine Ticlopidine: An effective inhibitor of platelet aggregation commonly used in the placement of STENTS in CORONARY ARTERIES.. ticlopidine : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group.	2.6	1	0	monochlorobenzenes; thienopyridine	anticoagulant; fibrin modulating drug; hematologic agent; P2Y12 receptor antagonist; platelet aggregation inhibitor
tilisolol [no description available]	1.98	1	0	isoquinolines
tolnaftate [no description available]	2.05	1	0	monothiocarbamic ester	antifungal drug
triamterene Triamterene: A pteridinetriamine compound that inhibits SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS.. triamterene : Pteridine substituted at positions 2, 4 and 7 with amino groups and at position 6 with a phenyl group. A sodium channel blocker, it is used as a diuretic in the treatment of hypertension and oedema.	2.6	1	0	pteridines	diuretic; sodium channel blocker
trifluoperazine [no description available]	2.6	1	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	2.6	1	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trigonelline trigonelline: in hydra among other organisms; RN given refers to hydroxide inner salt; structure. N-methylnicotinic acid : A pyridinium ion consisting of nicotinic acid having a methyl substituent on the pyridine nitrogen.. N-methylnicotinate : An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.	2.6	1	0	alkaloid; iminium betaine	food component; human urinary metabolite; plant metabolite
trimethobenzamide trimethobenzamide: major descriptor (64-84); on-line search BENZAMIDES (64-84); Index Medicus search TRIMETHOBENZAMIDE (64-84); RN given refers to parent cpd. trimethobenzamide : The amide obtained by formal condensation of 3,4,5-trihydroxybenzoic acid with 4-[2-(N,N-dimethylamino)ethoxy]benzylamine. It is used to prevent nausea and vomitting in humans.	2.6	1	0	benzamides; tertiary amino compound	antiemetic
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.	2.6	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
tyramine [no description available]	5.25	4	1	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
tyrphostin a9 [no description available]	2.6	1	0	alkylbenzene	geroprotector
delavirdine Delavirdine: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.. delavirdine : The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.	2.6	1	0	aminopyridine; indolecarboxamide; N-acylpiperazine; sulfonamide	antiviral drug; HIV-1 reverse transcriptase inhibitor
vesnarinone [no description available]	2.6	1	0	organic molecular entity
hydrocortisone acetate hydrocortisone acetate: RN given refers to cpd without isomeric designation	2.05	1	0	cortisol ester; tertiary alpha-hydroxy ketone
cortisone acetate Cortisone Acetate: The acetate ester of cortisone that is used mainly for replacement therapy in adrenocortical insufficiency and in the treatment of many allergic and inflammatory disorders.	2.05	1	0	corticosteroid hormone
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	2.37	2	0	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	3.03	4	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.	2.48	2	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
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.	3.05	1	0	ergoline alkaloid; monocarboxylic acid amide; organic heterotetracyclic compound	dopamine agonist; hallucinogen; serotonergic agonist
phentolamine Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.	2.35	2	0	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.03	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	3.21	6	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
2-aminophenol [no description available]	2.1	1	0	aminophenol	bacterial metabolite
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	3.31	6	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	2.03	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
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	2.05	1	0	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
prednisolone acetate prednisolone acetate: RN given refers to cpd with locant for acetate group in position 21 & (11 beta)-isomer	2.05	1	0	corticosteroid hormone
cyclobarbital cyclobarbital: was heading 1977-94 (see under BARBITURATES 1977-90); CYCLOBARBITONE, HEXEMAL, & TETRAHYDROPHENOBARBITAL were see CYCLOBARBITAL 1977-94; use BARBITURATES to search CYCLOBARBITAL 1977-94; short to intermediate duration barbiturate used as hypnotic and sedative	2.05	1	0	barbiturates
allobarbital allobarbital: was heading 1976-94 (see under BARBITURATES 1976-90); ALLOBARBITONE, DIALLYLBARBITAL, DIALLYLBARBITURIC ACID, & DIALLYLMAL were see ALLOBARBITAL 1976-94; use BARBITURATES to search ALLOBARBITAL 1976-94; a barbiturate derivative with effects of intermediate duration; at lower doses, it is used as a sedative; at higher doses, it displays hypnotic effects	2.05	1	0	barbiturates
paramethasone Paramethasone: A glucocorticoid with the general properties of corticosteroids. It has been used by mouth in the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than HYDROCORTISONE with supplementary FLUDROCORTISONE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p737)	2.05	1	0	fluorinated steroid
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.25	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	2.74	3	0	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	2.36	2	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
idoxuridine [no description available]	2.6	1	0	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	2.05	1	0	pilocarpine	antiglaucoma drug
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	2.45	2	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.	2.03	1	0	2-halophenol; amino acid zwitterion; iodophenol; iodothyronine	human metabolite; mouse metabolite; thyroid hormone
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2.97	4	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	3.65	9	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
cantharidin Cantharidin: A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.. cantharidin : A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.	2.17	1	0	cyclic dicarboxylic anhydride; monoterpenoid	EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; herbicide
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.	2.17	1	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.	3.26	6	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.	3.09	5	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	1	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	3.06	4	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
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	4.31	4	1	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; 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.	1.94	1	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
chlorobutanol [no description available]	6.94	1	0	tertiary alcohol
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.	5.5	5	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	1.99	1	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.37	2	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.	2.1	1	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	1.95	1	0	uridines	drug metabolite; fundamental metabolite; human metabolite
uridine diphosphate Uridine Diphosphate: A uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.	2.21	1	0	pyrimidine ribonucleoside 5'-diphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
galactose galactopyranose : The pyranose form of galactose.	2.84	3	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	2.77	3	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	3.63	9	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	4.58	8	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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.	6.66	26	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
phlorhizin [no description available]	2.48	2	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
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.	2.04	1	0	arenesulfonic acid; toluenes
zoxazolamine Zoxazolamine: A uricosuric and muscle relaxant. Zoxazolamine acts centrally as a muscle relaxant, but the mechanism of its action is not understood.	2.6	1	0	benzoxazole
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.	2.69	3	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
4-nitrobenzoic acid 4-nitrobenzoic acid: RN given refers to parent cpd. 4-nitrobenzoic acid : A nitrobenzoic acid having the nitro group at the 4-position.	2.05	1	0	nitrobenzoic acid
aniline [no description available]	2.05	1	0	anilines; primary arylamine
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.	3.34	5	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.	2.15	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.17	1	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.	6.42	51	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
n-hexanal [no description available]	2.03	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	3.98	4	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	2.6	1	0	psoralens	plant metabolite
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	2.05	1	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	1.94	1	0	barbiturates	allergen; xenobiotic
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.	2.96	4	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
fluocinolone acetonide Fluocinolone Acetonide: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). fluocinolone acetonide : A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders.	2.05	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic ketal; fluorinated steroid; glucocorticoid; organic heteropentacyclic compound; primary alpha-hydroxy ketone	anti-inflammatory drug; antipruritic drug
triaziquone Triaziquone: Alkylating antineoplastic agent used mainly for ovarian tumors. It is toxic to skin, gastrointestinal tract, bone marrow and kidneys.. triaziquone : A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which three of the ring hydrogens are replaced by aziridin-1-yl groups.	3.05	1	0	1,4-benzoquinones; aziridines	alkylating agent; antineoplastic agent
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.	2.6	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.	2.9	4	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	2.17	1	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	2.38	2	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
trifluridine Trifluridine: An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557). trifluridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis.	2.6	1	0	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; EC 2.1.1.45 (thymidylate synthase) inhibitor
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	2.15	1	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
dinitrofluorobenzene Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.	2.49	2	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
4-hydroxypropiophenone [no description available]	2.05	1	0	acetophenones
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.	2.46	2	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.	7.72	32	2	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.95	4	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.	2.17	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.	3.08	5	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	2.77	3	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	3.13	4	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.13	1	0	alkene; gas molecular entity	plant hormone; refrigerant
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	1.93	1	0	methylamines; one-carbon compound; primary aliphatic amine	mouse 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.	2.94	4	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
ethanethiol ethanethiol: RN given refers to parent cpd; structure. ethanethiol : An alkanethiol that is ethane substituted by a thiol group at position 1. It is added to odorless gaseous products such as liquefied petroleum gas (LPG) to provide a garlic scent which helps warn of gas leaks.	2.04	1	0	alkanethiol	rodenticide
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.	2.02	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
2-propylamine 2-propylamine: RN given refers to parent cpd	2.6	1	0	alkylamines; primary aliphatic amine
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.	2.71	3	0	tertiary alcohol	human xenobiotic metabolite
tert-amyl alcohol 2-methylbutan-2-ol : A tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups.	2.5	2	0	aliphatic alcohol; tertiary alcohol	protic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	3.31	6	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
pinacol pinacol : A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.	2.31	1	0	glycol
triamcinolone acetonide Triamcinolone Acetonide: An esterified form of TRIAMCINOLONE. It is an anti-inflammatory glucocorticoid used topically in the treatment of various skin disorders. Intralesional, intramuscular, and intra-articular injections are also administered under certain conditions.. triamcinolone acetonide : A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.	2.05	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; cyclic ketal; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
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.	2.1	1	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.99	4	0
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	2.08	1	0	mercaptopropanoic acid	algal metabolite
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	3.15	5	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
isobutyl alcohol isobutyl alcohol: RN given refers to parent cpd	3.54	8	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.	3.4	1	1	2-methyl-branched fatty aldehyde; propanals	Saccharomyces cerevisiae metabolite
2-butanol 2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.	2.46	2	0	secondary alcohol
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	1.97	1	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
acrylamide [no description available]	2.99	4	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.41	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
isobutyric acid isobutyric acid: RN given refers to parent cpd. isobutyric acid : A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.	1.98	1	0	branched-chain saturated fatty acid; fatty acid 4:0; methyl-branched fatty acid	Daphnia magna metabolite; plant metabolite; volatile oil component
camphene camphene : A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.	2.02	1	0	carbobicyclic compound; monoterpene	fragrance; plant metabolite
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	2.58	2	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
cumene hydroperoxide cumene hydroperoxide: RN given refers to parent cpd. cumene hydroperoxide : A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.	2.03	1	0	peroxol	environmental contaminant; Mycoplasma genitalium metabolite; oxidising agent
p-tert-amylphenol p-tert-amylphenol: RN given refers to parent cpd	2.05	1	0	alkylbenzene
methylmethacrylate Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.	3.45	1	1	enoate ester; methyl ester	allergen; polymerisation monomer
dehydrocholic acid Dehydrocholic Acid: A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.. 3,7,12-trioxo-5beta-cholanic acid : An oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton.	2.05	1	0	12-oxo steroid; 3-oxo-5beta-steroid; 7-oxo steroid; oxo-5beta-cholanic acid	gastrointestinal drug
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	2.49	2	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.75	3	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.97	4	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	2.6	1	0	anthraquinone
diisobutyl phthalate diisobutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of isobutanol.	2.07	1	0	diester; phthalate ester	plasticiser; PPAR modulator; teratogenic agent
carbazole carbazole: structure in first source	2.05	1	0	carbazole
salicylanilide salicylanilide: RN given refers to parent cpd. salicylanilide : An amide of salicylic acid and of aniline; it is therefore both a salicylamide and an anilide.	2.6	1	0	benzanilide fungicide; salicylamides; salicylanilides
Ethyl 2-aminobenzoate [no description available]	2.03	1	0	benzoate ester
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	2.6	1	0	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.03	1	0
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.69	3	0	pyrrolidin-2-ones
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.	2.95	4	0	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.44	2	0	hydroxybenzaldehyde	nematicide; plant metabolite
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.	2.6	1	0	aminoacridines; primary amino compound	acid-base indicator; antiinfective agent; antiseptic drug; fluorescent dye; MALDI matrix material; mutagen
quinoline [no description available]	2.05	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	1.98	1	0	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	2.49	2	0	naphthylamine	carcinogenic agent
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.21	1	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.38	2	0	xanthene
phenothiazine 10H-phenothiazine : The 10H-tautomer of phenothiazine.	2.05	1	0	phenothiazine	ferroptosis inhibitor; plant metabolite; radical scavenger
thianthrene thianthrene: in its electron deficient state, effects formation of high-energy phosphate bonds in process of oxidative phosphorylation; structure. thianthrene : The organosulfur heterocyclic compound that is the parent compound of the thianthrenes, a tricyclic structure comprising two benzene rings fused to the b and e sides of 1,4-dithin.	2.05	1	0	mancude organic heterotricyclic parent; organosulfur heterocyclic compound; thianthrenes
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.	2.05	1	0	biphenyls; substituted aniline	carcinogenic agent
1-phenylpropanol 1-phenylpropanol: structure in first source	2.42	2	0	organic molecular entity
styrene glycol styrene glycol: RN given refers to cpd without isomeric designation	2.38	2	0	benzenes
methyl benzoate methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.	2.44	2	0	benzoate ester; methyl ester	insect attractant; metabolite
ethyl benzoate ethyl benzoate : A benzoate ester obtained by condensation of benzoic acid and ethanol. It is a volatile oil component found in ripe kiwifruit, cranberry juice, and palm kernel oil.	2.44	2	0	benzoate ester; ethyl ester	flavouring agent; fragrance; volatile oil component
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)	2.93	4	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
butylparaben [no description available]	2.05	1	0	organic molecular entity
benzothiophene [no description available]	2.05	1	0	1-benzothiophenes; benzothiophene
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	2.05	1	0	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
styrene oxide styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.	2.68	3	0	epoxide	human xenobiotic metabolite
2-methylbutanal 2-methylbutanal: structure in first source. 2-methylbutanal : A methylbutanal in which the methyl substituent is at position 2.	3.31	1	0	2-methyl-branched fatty aldehyde; methylbutanal	plant metabolite; Saccharomyces cerevisiae metabolite; volatile oil component
cyclopentanol [no description available]	2.05	1	0	cyclopentanols
ethyl 2-methylpropanoate ethyl isobutyrate : A fatty acid ethyl ester obtained by the formal condensation of isobutyric acid with ethanol.	2.81	3	0	fatty acid ethyl ester	plant metabolite
ethyl lactate ethyl lactate: RN given refers to cpd with unspecified isomeric designation. ethyl 2-hydroxypropanoate : The ethyl ester obtained of 2-hydroxypropanoic acid.	2.55	2	0	ethyl ester; lactate ester; secondary alcohol	metabolite
furfuryl alcohol furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.	2.03	1	0	furans; primary alcohol	Maillard reaction product
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	3.42	7	0	aldehyde; furans	Maillard reaction product; metabolite
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.	2.05	1	0	phenols	allergen
1-phenethylamine 1-phenethylamine: RN given refers to cpd without isomeric designation. 1-phenylethylamine : A phenylethylamine that is ethylamine substituted by a phenyl group at position 1.	2.51	2	0	phenylethylamine	human metabolite
methylphenyl carbinol 1-phenylethanol : An aromatic alcohol that is ethanol substituted by a phenyl group at position 1.. methylbenzyl alcohol : Members of the class of benzyl alcohols substituted by at least one methyl group.	4.76	9	0	aromatic alcohol	mouse metabolite
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	4.38	20	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.	2.47	2	0	nitroarene; nitrobenzenes
methyl gallate methyl gallate: has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum. methyl 3,4,5-trihydroxybenzoate : A gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties.	2.6	1	0	gallate ester	anti-inflammatory agent; antioxidant; plant metabolite
gamma-terpinene gamma-terpinene: RN given refers to gamma-terpinene; structure. gamma-terpinene : One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.	2.31	1	0	cyclohexadiene; monoterpene	antioxidant; human xenobiotic metabolite; plant metabolite; volatile oil component
4-isopropylphenol [no description available]	2.05	1	0	phenols	flavouring agent
4-hydroxyacetophenone 4-hydroxyacetophenone: promotes secretion of bile & bile salts, which promotes griseofulvin absorption in the duodenum. 4'-hydroxyacetophenone : A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.	2.75	3	0	monohydroxyacetophenone	fungal metabolite; mouse metabolite; plant metabolite
4-chloronitrobenzene [no description available]	2.05	1	0	C-nitro compound
4-nitroaniline [no description available]	2.05	1	0	nitroaniline	bacterial xenobiotic metabolite
ethylbenzene [no description available]	3.15	5	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.	3.27	6	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
benzyl chloride benzyl chloride: RN given refers to unlabeled cpd. chlorophenylmethane : A chlorohydrocarbon that is phenylmethane substituted by a chloro group at unspecified position.. benzyl chloride : A member of the class of benzyl chlorides that is toluene substituted on the alpha-carbon with chlorine.	2.05	1	0	benzyl chlorides
benzonitrile benzonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group.	2.05	1	0	benzenes; nitrile
4-cyanopyridine 4-cyanopyridine: spectroscopic probe for cytochrome P450 BM3	2.03	1	0
nicotinyl alcohol Nicotinyl Alcohol: Alcohol analog of NICOTINIC ACID which is a direct-acting peripheral vasodilator that causes flushing and may decrease blood pressure. It is used in vasospasm and threatened GANGRENE.. 3-pyridinemethanol : A member of the class of pyridines that is pyridine which is substituted by a hydroxymethyl group at position 3 .	2.05	1	0	aromatic primary alcohol; pyridines	antilipemic drug; vasodilator agent
methylaniline methylaniline: RN given refers to parent cpd. methylaniline : A substituted aniline carrying one or more methyl groups at unspecified positions.	2.05	1	0	methylaniline; phenylalkylamine; secondary amine
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.05	1	0	monomethoxybenzene	plant metabolite
ethyl phenylacetate [no description available]	2.17	1	0	benzenes
monobenzone monobenzone: structure. monobenzone : The monobenzyl ether of hydroquinone. It is used as a topical drug for medical depigmentation.	2.6	1	0	benzyl ether	allergen; dermatologic drug; melanin synthesis inhibitor
2-phenylethyl acetate phenethyl acetate : The acetate ester of 2-phenylethanol.	6.98	37	0	acetate ester	metabolite; Saccharomyces cerevisiae metabolite
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	1	0	alkylbenzene
phenetole phenetole : An aromatic ether in which the ether oxygen is bonded to an ethyl and a phenyl group.	2.05	1	0	aromatic ether
1-phenyl-2-propanone 1-phenyl-2-propanone: analog of propiophenone where carbonyl group is on the 2 carbon atom instead of the 1 carbon atom of the side chain. phenylacetone : A propanone that is propan-2-one substituted by a phenyl group at position 1.	2.44	2	0	methyl ketone; propanones
anisyl alcohol anisyl alcohol: structure given in first source	2	1	0	benzyl alcohols
ethyl butyrate ethyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of ethanol with the carboxy group of butyric acid.	2.51	2	0	butyrate ester	plant metabolite
2,4-dimethylphenol 2,4-dimethylphenol: RN given refers to parent cpd. 2,4-xylenol : A member of the class of phenols that phenol substituted by methyl groups at positions 2 and 4.	1.96	1	0	aromatic fungicide; phenols	disinfectant; volatile oil component
citronellal citronellal: aldehyde of citronellol; found in citronella oil. citronellal : A monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma.	4.43	1	1	aldehyde; monoterpenoid	antifungal agent; metabolite
ethyl caprylate ethyl octanoate : A fatty acid ethyl ester resulting from the formal condensation of octanoic acid with ethanol.	2.21	1	0	fatty acid ethyl ester; octanoate ester	metabolite
1,4-dibromobenzene [no description available]	2.05	1	0	dibromobenzene
4-bromophenol 4-bromophenol : A bromophenol containing only hydroxy and bromo substituents that are para to one another.	2.05	1	0	bromophenol	human urinary metabolite; human xenobiotic metabolite; marine metabolite; mouse metabolite; persistent organic pollutant; rat metabolite
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	2.05	1	0	xylene
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	2.02	1	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
acrolein [no description available]	3.83	10	0	enal	herbicide; human xenobiotic metabolite; toxin
glyoxal [no description available]	2.15	1	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.02	1	0	alkane
vinyl acetate [no description available]	2.42	2	0	acetate ester
isobutylmethylcarbinol isobutylmethylcarbinol: RN given refers to cpd without isomeric designation	2.05	1	0
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	2.15	1	0	acyclic carboxylic anhydride	metabolite; reagent
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	1.96	1	0	xylene
3-chlorophenol 3-chlorophenol : A monochlorophenol carrying the chloro substituent at position 3.	2.05	1	0	monochlorophenol
bromobenzene [no description available]	2.05	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar 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.	5.98	9	1	cyclohexanols; secondary alcohol	solvent
n-butyl n-butyrate n-butyl n-butyrate: structure. butyl butanoate : A butanoate ester of butan-1-ol.	2.03	1	0	butyrate ester	metabolite
dibutyl sebacate dibutyl sebacate: used in retail packaging of foods	2.42	2	0	fatty acid ester
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.	4.12	3	1	short-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.08	1	0	alkane; volatile organic compound	non-polar solvent; refrigerant
methyl cellosolve methyl cellosolve: widely used industrial solvent for resins, lacquers, dyes & inks; may cause anemia macrocytosis, appearance of young granulocytes in blood; RN given refers to parent cpd	2.05	1	0	glycol ether	protic solvent; solvent
diethylamine [no description available]	2.05	1	0	secondary aliphatic amine
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.08	1	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.	2.44	2	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.04	1	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
ethyl decanoate ethyl decanoate : A fatty acid ethyl ester of decanoic acid.	2.11	1	0	decanoate ester; fatty acid ethyl ester	metabolite
1,4-butanediol butane-1,4-diol : A butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16degreeC) with a high boiling point (230degreeC), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF).	2.05	1	0	butanediol; glycol	neurotoxin; prodrug; protic solvent
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.	3.55	8	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
1,5-pentanediol [no description available]	2.05	1	0	primary alcohol
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.	2.43	2	0	heptanol; primary alcohol	flavouring agent; fragrance; gap junctional intercellular communication inhibitor; plant metabolite
octyl acetate octyl acetate : The acetate ester of octan-1-ol.	2.03	1	0	acetate ester	plant metabolite
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.	2.01	1	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
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.	2.01	1	0	long-chain primary fatty alcohol; octadecanol	algal metabolite; human metabolite; plant metabolite
mephobarbital Mephobarbital: A barbiturate that is metabolized to PHENOBARBITAL. It has been used for similar purposes, especially in EPILEPSY, but there is no evidence mephobarbital offers any advantage over PHENOBARBITAL.. mephobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by ethyl and phenyl groups.	2.05	1	0	barbiturates	anticonvulsant
2-methylbutanoic acid 2-methylbutanoic acid: RN given refers to parent cpd without isomeric designation. 2-methylbutyric acid : A methylbutyric acid comprising a butyric acid core carrying a 2-methyl substituent. Produced from amino acid leucine during nutrient starvation in bacteria.	2.49	2	0	methylbutyric acid	bacterial metabolite; human metabolite
ethyl salicylate ethyl salicylate: causes erythema after topical application as an aerosol; found in blood	2.03	1	0	hydroxybenzoic acid
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.1	1	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
benzoin [no description available]	2	1	0	benzoins; secondary alpha-hydroxy ketone	EC 3.1.1.1 (carboxylesterase) inhibitor
dimethoxyphenylethylamine Dimethoxyphenylethylamine: A derivative of phenethylamine containing two substituent methoxy groups in the phenyl ring.. 3,4-dimethoxyphenylethylamine : An aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family.	2.08	1	0	alkaloid; aromatic ether; phenylethylamine	allergen; plant metabolite
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	2.05	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
ethyl vanillin ethyl vanillin : A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.	2.03	1	0	aromatic ether; benzaldehydes; phenols	antioxidant; flavouring agent
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	3.34	6	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
triethylamine [no description available]	2	1	0	tertiary amine
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.1	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
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.	2.51	2	0	UDP-D-glucose	fundamental metabolite
methyl anthranilate methyl anthranilate : A benzoate ester that is the methyl ester of anthranilic acid.	2.5	2	0	benzoate ester	flavouring agent; metabolite
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.	2.05	1	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.	2.44	2	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
2-methylbutanol 2-methylbutanol: fragrance; structure in first source. 2-methylbutan-1-ol : A primary alcohol that is isopentane substituted by a hydroxy group at position 1.	2.46	2	0	alkyl alcohol; primary alcohol	Saccharomyces cerevisiae metabolite
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.	2.47	2	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.1	1	0	dihydroxybenzaldehyde
benzyl acetate benzyl acetate : The acetate ester of benzyl alcohol.	2.92	4	0	acetate ester; benzyl ester	metabolite
p-cresyl acetate [no description available]	2.05	1	0	benzoate ester; phenols
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	2.13	1	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	2.44	2	0	monoterpenoid	plant metabolite
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	3.98	12	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.	2.78	3	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	2.6	1	0	dithiocarbamic acids	chelator; copper chelator
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.	2.05	1	0	monomethoxybenzene; phenols
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	2.05	1	0	methoxybenzenes; phenols	metabolite
citronellyl acetate citronellyl acetate: RN given refers to cpd without isomeric designation. citronellol acetate : A monoterpenoid that is the acetate ester of citronellol. It has been isolated from Citrus hystrix.	2.21	1	0	acetate ester; monoterpenoid	plant metabolite
hydroxytryptophol Hydroxytryptophol: 5-Hydroxy-indole-3-ethanol.	2.21	1	0	indoles
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.	4.36	19	0	catechin	antioxidant; plant metabolite
phenanthridine phenanthridine : An azaarene that is the 9-aza derivative of phenanthrene. The parent of the class of phenanthridines.	2.05	1	0	azaarene; mancude organic heterotricyclic parent; phenanthridines; polycyclic 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.	2.54	2	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.68	3	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.04	1	0	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	5	9	1	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.83	3	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	3.14	5	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.52	2	0	diazine; pyrazines	Daphnia magna metabolite
muscarine Muscarine: A toxic alkaloid found in Amanita muscaria (fly fungus) and other fungi of the Inocybe species. It is the first parasympathomimetic substance ever studied and causes profound parasympathetic activation that may end in convulsions and death. The specific antidote is atropine.	2.02	1	0	monosaccharide
2h-benzo(a)quinolizin-2-ol, 2-ethyl-1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy- 2H-Benzo(a)quinolizin-2-ol, 2-Ethyl-1,3,4,6,7,11b-hexahydro-3-isobutyl-9,10-dimethoxy-: Proposed catecholamine depletor.	1.96	1	0
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	2.72	2	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
carbutamide Carbutamide: A sulfonylurea antidiabetic agent with similar actions and uses to CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277)	2.05	1	0	benzenes; sulfonamide
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.	2.05	1	0	fluorophenol; monofluorobenzenes
3-fluorophenol 3-fluorophenol: structure in first source	2.05	1	0
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	2.03	1	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
betamethasone Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)	2.05	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent
beta-cyclocitral beta-cyclocitral: structure in first source. beta-cyclocitral : A monoterpenoid formally derived from citral by cyclisation. It is a volatile compound produced by a cyanobacteria.	2.07	1	0	monoterpenoid	bacterial metabolite
3-fluorophenylalanine 3-fluorophenylalanine: p-fluorophenylalanine is a minor descriptor; RN given refers cpd with unspecified isomeric designation	1.97	1	0
cyanogen cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.	2.31	1	0	dinitrile; pseudohalogen
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	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.	2.05	1	0	monofluorobenzenes	NMR chemical shift reference compound
3,3-dimethyl-2-butanol [no description available]	2.05	1	0
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	2.05	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	3.23	1	0
lucanthone Lucanthone: One of the SCHISTOSOMICIDES, it has been replaced largely by HYCANTHONE and more recently PRAZIQUANTEL. (From Martindale The Extrapharmacopoeia, 30th ed., p46). lucanthone : A thioxanthen-9-one compound having a methyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. Formerly used for the treatment of schistosomiasis. It is a prodrug, being metabolised to hycanthone.	2.6	1	0	thioxanthenes	adjuvant; antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; mutagen; photosensitizing agent; prodrug; schistosomicide drug
cepharanthine cepharanthine: isoquinoline alkaloid from tubers of STEPHANIA; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. cepharanthine : A bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.	2.6	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
aloe emodin aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.	2.6	1	0	aromatic primary alcohol; dihydroxyanthraquinone	antineoplastic agent; plant metabolite
chrysophanic acid chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.	2.6	1	0	dihydroxyanthraquinone	anti-inflammatory agent; antiviral agent; plant metabolite
emetine Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.	2.6	1	0	isoquinoline alkaloid; pyridoisoquinoline	antiamoebic agent; anticoronaviral agent; antiinfective agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; expectorant; plant metabolite; protein synthesis inhibitor
osthol osthol: from Cnidium monnieri and Angelica pubescens (both Apiaceae); structure given in first source	2.6	1	0	botanical anti-fungal agent; coumarins	metabolite
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.	2.6	1	0	flavanones
thymoquinone thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.	3.23	5	0	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
indoline indoline: structure given in first source	2.03	1	0	indoles
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	2.99	4	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
phloroglucinol dimethyl ether phloroglucinol dimethyl ether: structure	2.05	1	0	methoxybenzenes; phenols
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	17.69	413	14	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent
phloretic acid phloretic acid: structure. N-hydroxysuccinimide ester : An ester of N-hydroxysuccinimide.. phloretic acid : A hydroxy monocarboxylic acid consisting of propionic acid having a 4-hydroxyphenyl group at the 3-position.	2.61	2	0	hydroxy monocarboxylic acid	plant metabolite
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.72	3	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	2.05	1	0	propane-1,3-diols	metabolite; protic solvent
methionol methionol: a aroma-active compound. 3-methylthiopropanol : An alkyl sulfide that is propan-1-ol substituted by a methylsulfanyl group at position 3. It is a volatile compound found in wines and produced during fermentation.	2.13	1	0	aliphatic sulfide; methyl sulfide	Saccharomyces cerevisiae metabolite
mustard gas Mustard Gas: Severe irritant and vesicant of skin, eyes, and lungs. It may cause blindness and lethal lung edema and was formerly used as a war gas. The substance has been proposed as a cytostatic and for treatment of psoriasis. It has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP-85-002, 1985) (Merck, 11th ed).. bis(2-chloroethyl) sulfide : An ethyl sulfide that is diethyl sulfide in which a hydrogen from each of the terminal methyl groups is replaced by a chlorine. It is a powerful vesicant regulated under the Chemical Weapons Convention.	2.03	1	0	ethyl sulfide; organochlorine compound	alkylating agent; carcinogenic agent; vesicant
oleanolic acid [no description available]	2.6	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	4.01	3	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	2.02	1	0
angelicin angelicin: used as tranquillizer; sedative; or anticonvulsant; structure	2.6	1	0	furanocoumarin
tryptophol tryptophol : An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.	5.9	12	0	indolyl alcohol	auxin; plant metabolite; Saccharomyces cerevisiae metabolite
methoxyhydroxyphenylglycol Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.	5.72	19	1	methoxybenzenes; phenols
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	2.05	1	0	benzenes
diperodon diperodon: RN given refers to parent cpd; structure given in first source	2.6	1	0	carbamate ester
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.	2.03	1	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
4-iodophenol [no description available]	2.05	1	0	iodophenol
1,2-dichloroethylene 1,2-dichloroethylene: RN given refers to cpd without isomeric designation	2.15	1	0	chloroethenes
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	5.89	92	0	dialdehyde	biomarker
3-hexen-1-ol 3-hexen-1-ol: RN given refers to (Z)-isomer; a green odor chemical. hex-3-en-1-ol : A primary alcohol that is hex-3-ene substituted by a hydroxy group at position 1.	2.75	3	0	alkenyl alcohol; homoallylic alcohol; primary alcohol; volatile organic compound	plant metabolite
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.	2.06	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.04	1	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
lignoceric acid lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.	2.03	1	0	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia tenebrosa metabolite; human metabolite; plant metabolite; volatile oil component
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	2.25	1	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	3.16	5	0	flavonols; monohydroxyflavone
3-methylbenzyl alcohol 3-methylbenzyl alcohol : A methylbenzyl alcohol that is toluene in which one of the meta hydrogens has been replaced by a hydroxymethyl group.	1.96	1	0	methylbenzyl alcohol; primary alcohol
isovalerylaldehyde isovalerylaldehyde: structure in Merck Index, 9th ed, #5093. 3-methylbutanal : A methylbutanal that is butanal substituted by a methyl group at position 3. It occurs as a volatile constituent in olives.	2.13	1	0	methylbutanal	flavouring agent; plant metabolite; Saccharomyces cerevisiae metabolite; volatile oil component
3-bromophenol [no description available]	2.05	1	0
3,5-dichlorophenol 3,5-dichlorophenol : A dichlorophenol in which the two chloro substituents are located at positions 3 and 5.	2.05	1	0	dichlorophenol
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	2.05	1	0
megestrol acetate [no description available]	2.6	1	0	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; steroid ester	antineoplastic agent; appetite enhancer; contraceptive drug; progestin; synthetic oral contraceptive
2-chloropropionic acid 2-chloropropionic acid: RN given refers to parent cpd with specified chlorine locant; structure	1.98	1	0
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.07	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
dansyl chloride dansyl chloride: RN given refers to unlabeled cpd	2.15	1	0	aminonaphthalene; sulfonic acid derivative
galactitol [no description available]	2.03	1	0	hexitol	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
phenylglyoxylic acid phenylglyoxylic acid: styrene metabolite. phenylglyoxylic acid : A 2-oxo monocarboxylic acid that is glyoxylic acid in which the aldehyde hydrogen is substituted by a phenyl group.	1.96	1	0	2-oxo monocarboxylic acid	biomarker; human xenobiotic metabolite
phenacylamine phenacylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6990	2.02	1	0	aromatic ketone
2-hydroxyphenylacetic acid 2-hydroxyphenylacetic acid: structure. (2-hydroxyphenyl)acetic acid : A hydroxy monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 2-hydroxyphenyl group. It is a metabolite of phenylalanine and is excreted in the urine of patients suffering from diseases like phenylketonuria.	2.02	1	0	hydroxy monocarboxylic acid; phenols	human metabolite; mouse metabolite
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.91	12	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
3-isopropylphenol 3-isopropylphenol: RN given refers to parent cpd	2.05	1	0
3-ethylphenol [no description available]	2.05	1	0	phenols
3-hydroxybenzeneacetic acid 3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.	2.02	1	0	monocarboxylic acid; phenols	human xenobiotic metabolite
4-Ethoxyphenol [no description available]	2.05	1	0	aromatic ether; phenols
dimethyl disulfide [no description available]	2.05	1	0	organic disulfide	xenobiotic metabolite
methoxyacetic acid methoxyacetic acid: RN given refers to parent cpd. methoxyacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a methoxy group.	2.03	1	0	ether; monocarboxylic acid	antineoplastic agent; apoptosis inducer; human xenobiotic metabolite; mutagen
2-hexanol hexan-2-ol : A hexanol in which the hydroxy group is at position 2.	2.05	1	0	hexanol; secondary alcohol	human metabolite; plant metabolite; semiochemical
amyl acetate amyl acetate: sources do not specify n-isomer. pentyl acetate : An acetate ester of pentanol.	5.97	5	2	acetate ester	metabolite
hexamethylene glycol hexane-1,6-diol : A diol that is hexane substituted by hydroxy groups at positions 1 and 6.	2.05	1	0	diol; primary alcohol
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	2.07	1	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
4-propylphenol 4-propylphenol: structure given in first source	2.05	1	0	alkylbenzene
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.	1.95	1	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
decan-4-olide gamma-decalactone : A gamma-lactone that is oxolan-2-one substituted by a hexyl group at position 5.	2.15	1	0	gamma-lactone; tetrahydrofuranone	anticonvulsant; flavouring agent; food additive
hydroxychloroquine sulfate [no description available]	2.6	1	0
ethylnitrosourea Ethylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-ethyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by ethyl and nitroso groups.	2.31	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; genotoxin; mutagen
porfiromycin Porfiromycin: Toxic antibiotic of the mitomycin group, obtained from MITOMYCIN and also from Streptomyces ardus and other species. It is proposed as an antineoplastic agent, with some antibiotic properties.	3.45	2	0
4-nitrophenyl acetate [no description available]	2.05	1	0	C-nitro compound; phenyl acetates
1-phenylazo-2-naphthol 1-phenylazo-2-naphthol: RN given refers to cpd without isomeric designation	2.04	1	0
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.	1.95	1	0	alkaloid; C-nitro compound; monochlorobenzenes; pyrroles	antifungal drug; bacterial metabolite
ethambutol Ethambutol: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863). ethambutol : An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.	2.83	3	0	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic
phenylglyoxal [no description available]	2.38	2	0	phenylacetaldehydes
metformin hydrochloride metformin hydrochloride : A hydrochloride resulting from the reaction of metformin with one molar equivalent of hydrogen chloride.	2.6	1	0	hydrochloride	environmental contaminant; hypoglycemic agent; xenobiotic
4-acetylpyridine [no description available]	2.03	1	0
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	2.55	2	0
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.03	1	0	alkali metal hydroxide
arsenic trioxide Arsenic Trioxide: An inorganic compound with the chemical formula As2O3 that is used for the treatment of ACUTE PROMYELOCYTIC LEUKEMIA in patients who have relapsed from, or are resistant to, conventional drug therapy.	2.06	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.	2.04	1	0	pinene	plant metabolite
antimycin a [no description available]	2.6	1	0	benzamides; formamides; macrodiolide; phenols	antifungal agent; mitochondrial respiratory-chain inhibitor; piscicide
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	2.47	2	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial 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.	9	27	3	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	4.24	4	0
bisphenol a-glycidyl methacrylate Bisphenol A-Glycidyl Methacrylate: The reaction product of bisphenol A and glycidyl methacrylate that undergoes polymerization when exposed to ultraviolet light or mixed with a catalyst. It is used as a bond implant material and as the resin component of dental sealants and composite restorative materials.	3.45	1	1	diarylmethane
ethyl isonicotinate ethyl isonicotinate: structure in first source	2.03	1	0
methyl tert-butyl ether methyl tert-butyl ether: used to dissolve gallstones; gasoline additive. methyl tert-butyl ether : An ether having methyl and tert-butyl as the two alkyl components.	3.1	1	0	ether	fuel additive; metabolite; non-polar solvent
4-n-Butylphenol [no description available]	2.05	1	0	phenols
1,2,3,4-butanetetracarboxylic acid 1,2,3,4-butanetetracarboxylic acid: structure in first source	2.31	1	0
5,5'-dimethyl-2,2'-bipyridyl 5,5'-dimethyl-2,2'-bipyridyl: structure in first source	2.6	1	0	bipyridines
dichlorobenzyl alcohol 2,4-dichlorobenzyl alcohol : A member of the class of benzyl alcohols that is benzyl alcohol in which the hydrogens at positions 2 and 4 are replaced by chlorines.	2.6	1	0	benzyl alcohols; dichlorobenzene	antiseptic drug
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	2.52	2	0	organic cation	geroprotector; herbicide
s,n,n'-tripropylthiocarbamate Reward: An object or a situation that can serve to reinforce a response, to satisfy a motive, or to afford pleasure.. vernolate : A monounsaturated fatty acid anion that is the conjugate base of vernolic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.15	1	0	tertiary amine
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.25	1	0	hydroquinones	food antioxidant
3-methoxy-4-hydroxyphenylethanol 3-Methoxy-4-hydroxyphenylethanol: Metabolite of serotonin and norepinephrine.	3.34	7	0	methoxybenzenes; phenols
7,12-dihydroxymethylbenz(a)anthracene 7,12-dihydroxymethylbenz(a)anthracene: structure given in first source	2.07	1	0
stavudine Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase	2.6	1	0	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	2.21	1	0	primary alcohol
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	1.98	1	0	fluorescein isothiocyanate
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	3.24	5	0	thujene	plant metabolite
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.	2.46	2	0	alkenyl alcohol; medium-chain fatty alcohol	antimicrobial agent; fungal metabolite; insect attractant; volatile oil component
mannose mannopyranose : The pyranose form of mannose.	2.17	1	0	D-aldohexose; D-mannose; mannopyranose	metabolite
dimethyl trisulfide [no description available]	2.05	1	0	organic trisulfide
sulfamethomidine sulfamethomidine: structure given in first source	2.05	1	0	organic molecular entity
streptomycin [no description available]	2.38	2	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.13	1	0	carbon oxoanion
divinyl adipate divinyl adipate: structure in first source	2.02	1	0
dideoxyadenosine Dideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.	2.6	1	0	adenosines; purine 2',3'-dideoxyribonucleoside	EC 3.5.4.4 (adenosine deaminase) inhibitor; EC 4.6.1.1 (adenylate cyclase) inhibitor
2-octanol 2-octanol: RN given refers to cpd without isomeric designation. octan-2-ol : An octanol carrying the hydroxy group at position 2.	2.05	1	0	octanol; secondary alcohol	plant metabolite; volatile oil component
fructosamine Fructosamine: An amino sugar formed when glucose non-enzymatically reacts with the N-terminal amino group of proteins. The fructose moiety is derived from glucose by the classical Amadori rearrangement.	2.15	1	0
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.06	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
vidarabine adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.	2.6	1	0	beta-D-arabinoside; purine nucleoside	antineoplastic agent; bacterial metabolite; nucleoside antibiotic
chlorpyrifos-methyl chlorpyrifos-methyl : An organic thiophosphate that is O,O-dimethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.13	1	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	3.82	2	0	cycloalkene; p-menthadiene	human metabolite
3-deazaadenosine 3-deazaadenosine: RN given refers to parent cpd.	2.6	1	0
helenalin helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.	2.01	1	0	cyclic ketone; gamma-lactone; organic heterotricyclic compound; secondary alcohol; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; plant metabolite
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	3.11	5	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	2.52	2	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.42	2	0	chromium group element atom	micronutrient
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.77	3	0	metal allergen; nickel group element atom; platinum group metal atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	2.31	1	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	2.02	1	0	iron group element atom; platinum group metal atom
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	4.41	4	1	titanium group element atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	3.48	7	0	cadmium molecular entity; zinc group element atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.54	2	0	chromium group element atom; metal allergen	micronutrient
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	2.53	2	0	copper group element atom; elemental gold
zalcitabine Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.	2.6	1	0	pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	2.17	1	0	mercury coordination entity	sensitiser
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	2.13	1	0	D-galactosamine; primary amino compound	toxin
diethyl malate diethyl malate: RN given refers to cpd without isomeric designation. diethyl malate : A malate ester obtained by the formal condensation of the two carboxy groups of malic acid with two molecules of ethanol respectively.	2.07	1	0	malate ester	metabolite
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	2.02	1	0	diatomic bromine
sodium sulfate [no description available]	2.82	2	0	inorganic sodium salt
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.08	1	0	calcium phosphate
sodium thiosulfate sodium thiosulfate: do not confuse synonym sodium hyposulfite with sodium hyposulfite, synonym for di-Na salt of dithionous acid. sodium thiosulfate : An inorganic sodium salt composed of sodium and thiosulfate ions in a 2:1 ratio.	2	1	0	inorganic sodium salt	antidote to cyanide poisoning; antifungal drug; nephroprotective agent
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	3.09	5	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.	2.73	3	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	3	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.	2.52	2	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
hydroiodic acid hydrogen iodide : A diatomic molecule containing covalently bonded hydrogen and iodine atoms.	2.1	1	0	gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.01	1	0	inorganic sodium salt; selenite salt	nutraceutical
cadmium chloride Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.	2.46	2	0	cadmium coordination entity
ancitabine Ancitabine: Congener of CYTARABINE that is metabolized to cytarabine and thereby maintains a more constant antineoplastic action.. ancitabine : An organic heterotricyclic compound resulting from the formal condensation of the oxo group of cytidine to the 2' position with loss of water to give the corresponding cyclic ether. A prodrug, it is metabolised to the antineoplastic agent cytarabine, so is used to maintain a more constant antineoplastic action.	2.6	1	0	diol; organic heterotricyclic compound	antimetabolite; antineoplastic agent; prodrug
trolamine salicylate Arthritis: Acute or chronic inflammation of JOINTS.	2.41	2	0
chloropyramine chloropyramine: RN given refers to parent cpd; structure	2.6	1	0	aminopyridine
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	2.1	1	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
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.	2.51	2	0	titanium oxides	food colouring
hydrocortisone-17-butyrate cortisol 17-butyrate : Cortisol esterified with butyric acid at the 17-hydroxy group.	2.05	1	0	butyrate ester; cortisol ester; primary alpha-hydroxy ketone	dermatologic drug; drug allergen
salen disalicylaldehyde ethylenediamine: reagents for determination of iron	2.04	1	0
levamisole Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.	2.6	1	0	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator
4-n-Pentylphenol [no description available]	2.05	1	0	phenols
cromolyn sodium Cromolyn Sodium: A chromone complex that acts by inhibiting the release of chemical mediators from sensitized MAST CELLS. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack.. disodium cromoglycate : An organic sodium salt that is the disodium salt of cromoglycic acid.	1.95	1	0	organic sodium salt	anti-asthmatic drug; drug allergen
n'-nitrosonornicotine N'-nitrosonornicotine: structure; a potent carcinogen in laboratory animals	2.6	1	0	pyridines; pyrrolidines
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	3.88	12	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]	3.45	1	1	halide anion; monoatomic fluorine
ochracin ochracin: produced by Aspergillus alutaceus; structure in first source	2.49	2	0	isochromanes
methyl 2-chloropropionate methyl 2-chloropropionate: used in pesticide synthesis	1.98	1	0
benomyl [no description available]	2.13	1	0	aromatic amide; benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	acaricide; anthelminthic drug; antifungal agrochemical; microtubule-destabilising agent; tubulin modulator
chromium chromium hexavalent ion: a human respiratory carcinogen	2.15	1	0	chromium cation; monoatomic hexacation
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	3.5	2	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
zingerone zingerone: pungent principle of ginger; structure. zingerone : A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.	3.53	2	0	methyl ketone; monomethoxybenzene; phenols	anti-inflammatory agent; antiemetic; antioxidant; flavouring agent; fragrance; plant metabolite; radiation protective agent
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	9.7	83	2	benzenes; phenyl acetates
3-phenyl-1-propanol [no description available]	2.44	2	0	monocyclic arene
phenoxyethanol phenoxyethanol: structure. 2-phenoxyethanol : An aromatic ether that is phenol substituted on oxygen by a 2-hydroxyethyl group.	3.14	5	0	aromatic ether; glycol ether; primary alcohol	antiinfective agent; central nervous system depressant
cetylpyridinium chloride anhydrous tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.	4.22	1	0	chloride salt; organic chloride salt	antiseptic drug; surfactant
4-ethylphenol 4-ethylphenol: RN given refers to parent cpd. 4-ethylphenol : A member of the class of phenols carrying an ethyl substituent at position 4.	3.61	9	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.	2.03	1	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
diethyl succinate diethyl succinate: carboxylesterase substrate	2.59	2	0	fatty acid ester
2,5-dimethylpyrazine [no description available]	2.11	1	0	pyrazines
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.	4.31	18	0	alkyl alcohol; primary alcohol; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite; xenobiotic metabolite
ethyl hexanoate ethyl hexanoate : A fatty acid ethyl ester obtained by the formal condensation of hexanoic acid with ethanol.	2.21	1	0	fatty acid ethyl ester; hexanoate ester	metabolite
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	1.98	1	0	acetate ester	metabolite
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.02	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
isoamyl acetate isoamyl acetate: structure in Merck, 9th ed, #4958. isoamyl acetate : The acetate ester of isoamylol.	3.36	6	0	acetate ester	metabolite; Saccharomyces cerevisiae metabolite
nonanal nonanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism.	2.82	3	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human metabolite; plant metabolite
triamcinolone Triamcinolone: A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739). triamcinolone : A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections.	2.05	1	0	11beta-hydroxy steroid; 16alpha-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.05	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.21	1	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
alkenes [no description available]	2.43	2	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.	3.31	6	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
glucaric acid Glucaric Acid: A sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups.. D-glucaric acid : The D-enantiomer of glucaric acid.. glucaric acid : A hexaric acid derived by oxidation of sugar such as glucose with nitric acid.	2.17	1	0	glucaric acid	antineoplastic agent
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.01	1	0
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	1.98	1	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.88	4	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
4-hydroxy-2-ethyl-5-methyl-3(2h)-furanone 4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone: structure in first source. 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone : A member of the class of furans that is furan-3(2H)-one carrying additional ethyl, hydroxy and methyl substituents at positions 2, 4 and 5 respectively. A key aroma compound in soy sauce and fish sauce.	2.11	1	0	cyclic ketone; enol; furans	Saccharomyces cerevisiae metabolite
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.6	1	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.53	7	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
substance p [no description available]	2.02	1	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
ribavirin Rebetron: Rebetron is tradename	2.6	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	2.03	1	0	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
pyridoxal phosphate [no description available]	2.6	1	0	pyridinecarbaldehyde
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	2.99	4	0	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	3.3	6	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
pirfenidone pirfenidone : A pyridone that is 2-pyridone substituted at positions 1 and 5 by phenyl and methyl groups respectively. An anti-inflammatory drug used for the treatment of idiopathic pulmonary fibrosis.	2.17	1	0	pyridone	antipyretic; non-narcotic analgesic; non-steroidal anti-inflammatory drug
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.77	3	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
nitazoxanide nitazoxanide: a 5-nitrothiazolyl derivative used for a broad range of intestinal parasitic infections including CRYPTOSPORIDIUM and GIARDIA; it is a redox-active nitrothiazolyl-salicylamide prodrug	2.6	1	0	benzamides; carboxylic ester
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	2.6	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
progabide progabide: GABA agonist; structure	2.05	1	0	diarylmethane
oltipraz oltipraz : A 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively.	2.6	1	0	1,2-dithiole; pyrazines	angiogenesis modulating agent; antimutagen; antineoplastic agent; antioxidant; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; neurotoxin; protective agent; schistosomicide drug
fiacitabine fiacitabine: anti-herpes virus agent which also inhibits growth of certain human tumor cell lines in vitro.	2.6	1	0
4-methacryloxyethyltrimellitic acid anhydride 4-methacryloxyethyltrimellitic acid anhydride: monomer used in 4-META resin; which is used as dental resin; structure given in first source; Cover-Up II is a 4-META bases bonding agent	3.45	1	1
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	1.98	1	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	2.15	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
atomoxetine hydrochloride Atomoxetine Hydrochloride: A propylamine derivative and selective ADRENERGIC UPTAKE INHIBITOR that is used in the treatment of ATTENTION DEFICIT HYPERACTIVITY DISORDER.. atomoxetine hydrochloride : The hydrochloride salt of atomoxetine.	3.9	2	1	hydrochloride	adrenergic uptake inhibitor; antidepressant
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	2.54	2	0	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
ranolazine Ranolazine: An acetanilide and piperazine derivative that functions as a SODIUM CHANNEL BLOCKER and prevents the release of enzymes during MYOCARDIAL ISCHEMIA. It is used in the treatment of ANGINA PECTORIS.. N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide : An aromatic amide obtained by formal condensation of the carboxy group of 2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetic acid with the amino group of 2,6-dimethylaniline.. ranolazine : A racemate comprising equal amounts of (R)- and (S)-ranolazine. Used for treatment of chronic angina.	2.6	1	0	aromatic amide; monocarboxylic acid amide; monomethoxybenzene; N-alkylpiperazine; secondary alcohol
brequinar brequinar : A quinolinemonocarboxylic acid that is quinoline substituted by 2'-fluoro[1,1'-biphenyl]-4-yl, methyl, carboxy and fluoro groups at positions 2, 3, 4, and 6, respectively. It is an inhibitor of dihydroorotate dehydrogenase, an enzyme that is required for de novo pyrimidine biosynthesis. The compound exhibits antineoplastic and antiviral properties.	2.6	1	0	biphenyls; monocarboxylic acid; monofluorobenzenes; quinolinemonocarboxylic acid	anticoronaviral agent; antimetabolite; antineoplastic agent; antiviral agent; EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor; immunosuppressive agent; pyrimidine synthesis inhibitor
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.	2.6	1	0	imidazoquinoline	antineoplastic agent; interferon inducer
adefovir adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.	2.6	1	0	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
zileuton [no description available]	2.52	2	0	1-benzothiophenes; ureas	anti-asthmatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; ferroptosis inhibitor; leukotriene antagonist; non-steroidal anti-inflammatory drug
cidofovir anhydrous Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.	2.6	1	0	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent
celgosivir celgosivir: inhibits glycoprotein processing & the growth of HIVs	2.6	1	0
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.6	1	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
lamivudine [no description available]	2.6	1	0	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
duloxetine hydrochloride Duloxetine Hydrochloride: A thiophene derivative and selective NEUROTRANSMITTER UPTAKE INHIBITOR for SEROTONIN and NORADRENALINE (SNRI). It is an ANTIDEPRESSIVE AGENT and ANXIOLYTIC, and is also used for the treatment of pain in patients with DIABETES MELLITUS and FIBROMYALGIA.. (S)-duloxetine hydrochloride : A duloxetine hydrochloride in which the duloxetine moiety has S configuration.	2.11	1	0	duloxetine hydrochloride	antidepressant
irinotecan [no description available]	2.25	1	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
valsartan Valsartan: A tetrazole derivative and ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to treat HYPERTENSION.. valsartan : A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.	2.6	1	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
zanamivir Zanamivir: A guanido-neuraminic acid that is used to inhibit NEURAMINIDASE.	2.6	1	0	guanidines	antiviral agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
3-iodobenzylguanidine 3-Iodobenzylguanidine: A guanidine analog with specific affinity for tissues of the sympathetic nervous system and related tumors. The radiolabeled forms are used as antineoplastic agents and radioactive imaging agents. (Merck Index, 12th ed) MIBG serves as a neuron-blocking agent which has a strong affinity for, and retention in, the adrenal medulla and also inhibits ADP-ribosyltransferase.	2.04	1	0	organoiodine compound
adefovir dipivoxil bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine: structure given in first source. adefovir pivoxil : An organic phosphonate that is the dipivoxil ester of adefovir. A prodrug for adefovir, an HIV-1 reverse transcriptase inhibitor, adefovir pivoxil is used to treat chronic hepatitis B viral infection.	2.6	1	0	6-aminopurines; carbonate ester; ether; organic phosphonate	antiviral drug; DNA synthesis inhibitor; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent; prodrug
emtricitabine Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.	2.6	1	0	monothioacetal; nucleoside analogue; organofluorine compound; pyrimidone	antiviral drug; HIV-1 reverse transcriptase inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.08	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
octyl gallate [no description available]	2.61	2	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
1-octen-3-one 1-octen-3-one: structure in first source	2.05	1	0	olefinic compound
1-n-butylimidazole [no description available]	2.05	1	0
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	2.21	1	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
vanillyl alcohol vanillyl alcohol: structure. vanillyl alcohol : A monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4.	2.21	1	0	benzyl alcohols; guaiacols	plant metabolite
4-vinylphenol 4-vinylphenol: RN given refers to cpd with locants as specified. 4-hydroxystyrene : A member of the class of phenols that is styrene carrying a hydroxy substituent at position 4.	2.72	3	0	phenols	human urinary metabolite; human xenobiotic metabolite
4-ethylguaiacol 4-ethylguaiacol: a constituent of wood creosote; suppresses intestinal smooth muscle contraction	2.46	2	0	methoxybenzenes; phenols
potassium phosphate potassium phosphate: used in dental materials and to treat hypophosphatemia; RN given refers to cpd with unspecified MF. tripotassium phosphate : An inorganic potassium salt that is the tripotassium salt of phosphoric acid.	2.44	2	0	inorganic phosphate salt; inorganic potassium salt
4-methyl-1-phenylpentan-2-ol [no description available]	7.94	14	1	benzenes
urea formaldehyde foam urea formaldehyde foam: widely used foam insulation	2.06	1	0
4,5-dimethyl-3-hydroxy-2(5h)-furanone [no description available]	2.08	1	0	butenolide	metabolite
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	4.31	6	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	2.6	1	0	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
nelfinavir Nelfinavir: A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children.. nelfinavir : An aryl sulfide that is used (as its mesylate salt) for treatment of HIV and also exhibits some anticancer properties.	2.6	1	0	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	8.02	84	0	D-glucopyranose	epitope; mouse metabolite
2',7'-dichlorofluorescein 2',7'-dichlorofluorescein: RN given refers to parent cpd	2.46	2	0	2-benzofurans	fluorochrome
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.	2.71	3	0	organic bromide salt	colorimetric reagent; dye
betulinic acid [no description available]	2.52	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
arctigenin arctigenin: precursor to catechols; in many plants	2.6	1	0	lignan
baicalin [no description available]	2.6	1	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
plerixafor plerixafor: a bicyclam derivate, highly potent & selective inhibitor of HIV-1 & HIV-2. plerixafor : An azamacrocycle consisting of two cyclam rings connected by a 1,4-phenylenebis(methylene) linker. It is a CXCR4 chemokine receptor antagonist and a hematopoietic stem cell mobilizer. It is used in combination with grulocyte-colony stimulating factor (G-CSF) to mobilize hematopoietic stem cells to the perpheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin's lymphoma and multiple myeloma.	2.6	1	0	azacycloalkane; azamacrocycle; benzenes; crown amine; secondary amino compound; tertiary amino compound	anti-HIV agent; antineoplastic agent; C-X-C chemokine receptor type 4 antagonist; immunological adjuvant
amprenavir [no description available]	2.6	1	0	carbamate ester; sulfonamide; tetrahydrofuryl ester	antiviral drug; HIV protease inhibitor
oseltamivir Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.	2.6	1	0	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic
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.	3.44	7	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
gallocatechol gallocatechol: structure give in first source; RN given for (trans-(+-))-omer; inhibits DNA-dependent DNA & RNA polymerases. (+)-gallocatechin : A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.. gallocatechin : A catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii.	2.44	2	0	gallocatechin	antioxidant; metabolite; radical scavenger
10,10'-dimethyl-9,9'-biacridinium 10,10'-dimethyl-9,9'-biacridinium: chemoluminescent probe; RN given refers to dinitrate; Lucigenin refers to dinitrate	2.02	1	0
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose pentagalloylglucose: pentahydroxy gallic acid ester of glucose; a phytogenic antineoplastic agent and antibacterial agent. 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions.	2.44	2	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
cephalotaxine [no description available]	2.6	1	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; cyclic acetal; enol ether; organic heteropentacyclic compound; secondary alcohol; tertiary amino compound
desipramine hydrochloride desipramine hydrochloride : The hydrochloride salt of desipramine.	2.6	1	0	hydrochloride	drug allergen
mefloquine hydrochloride [no description available]	2.6	1	0	hydrochloride
pyrrolidine dithiocarbamate pyrrolidine dithiocarbamic acid: spelled pyrolidine in J Nutr 1979 reference; RN given refers to parent cpd. pyrrolidine dithiocarbamate : A member of the class of dithiocarbamic acids that is the N-dithiocarboxy derivative of pyrrolidine.	2.01	1	0	dithiocarbamic acids; pyrrolidines	anticonvulsant; antineoplastic agent; geroprotector; neuroprotective agent; NF-kappaB inhibitor; radical scavenger
peroxynitric acid [no description available]	2.41	2	0	nitrogen oxoacid
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.76	3	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
erdosteine [no description available]	2.04	1	0	N-acyl-amino acid
aloxistatin aloxistatin: a membrane-permeable cysteine protease inhibitor. aloxistatin : An L-leucine derivative that is the amide obtained by formal condensation of the carboxy group of (2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid with the amino group of N-(3-methylbutyl)-L-leucinamide.	2.6	1	0	epoxide; ethyl ester; L-leucine derivative; monocarboxylic acid amide	anticoronaviral agent; cathepsin B inhibitor
propazole propazole: RN given refers to parent cpd; structure	2.6	1	0	benzimidazoles
prulifloxacin prulifloxacin: structure given in first source	2.6	1	0	fluoroquinolone antibiotic; quinolone antibiotic
telmisartan Telmisartan: A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.. telmisartan : A member of the class of benzimidazoles used widely in the treatment of hypertension.	2.6	1	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
bergenin bergenin: RN refers to (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-isomer; structure	2.6	1	0	trihydroxybenzoic acid	metabolite
benzeneboronic acid [no description available]	2.31	1	0	boronic acids
laurosept Laurosept: RN given refers to bromide	2	1	0
4-nitroso-n,n-diethylaniline 4-nitroso-N,N-diethylaniline: C-nitroso compound	2.02	1	0
phenoxazine phenoxazine: RN given refers to 10H-phenoxazine. 10H-phenoxazine : A member of the class of phenoxazines that is morpholine which is ortho-fused to two benzene rings at positions 2-3 and 5-6.	2.05	1	0	phenoxazine	ferroptosis inhibitor; radical scavenger
cresatin [no description available]	2.05	1	0	benzoate ester; phenols
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.	2.76	2	0	1,2,3-triazole
lupulon lupulon: antibiotic from hops; structure. lupulone : A beta-bitter acid in which the acyl group is specified as 3-methylbutanoyl.. beta-bitter acid : An alicyclic ketone obtained by prenylation at positions 4, 6 and 6 of any 2-acylphloroglucinol. beta-bitter acids are well known for their contribution to the bitter taste of beer.	3.19	1	0	beta-bitter acid	angiogenesis inhibitor; antimicrobial agent; antineoplastic agent; apoptosis inducer
pinocembrin pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.	4.03	3	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.49	2	0	isocoumarins
hydracrylic acid 3-hydroxypropionic acid : A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.	2.11	1	0	3-hydroxy monocarboxylic acid; omega-hydroxy-short-chain fatty acid	Escherichia coli metabolite; human metabolite
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.	1.98	1	0	anthocyanidin chloride
zoledronic acid Zoledronic Acid: An imidobisphosphonate inhibitor of BONE RESORPTION that is used for the treatment of malignancy-related HYPERCALCEMIA; OSTEITIS DEFORMANS; and OSTEOPOROSIS.. zoledronic acid : An imidazole compound having a 2,2-bis(phosphono)-2-hydroxyethane-1-yl substituent at the 1-position.	2.6	1	0	1,1-bis(phosphonic acid); imidazoles	bone density conservation agent
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	2.6	1	0	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
brinzolamide brinzolamide: an antiglaucoma agent	2.6	1	0	sulfonamide; thienothiazine	antiglaucoma drug; EC 4.2.1.1 (carbonic anhydrase) inhibitor
ethylnicotinate [no description available]	2.03	1	0	aromatic carboxylic acid; pyridines
2,4-dihydroxyphenylacetic acid [no description available]	2	1	0
3-propylphenol 3-propylphenol: insect bait; RN from File CHEMID	2.05	1	0
2,3-diaminonaphthalene [no description available]	2.04	1	0
dipropylacetamide dipropylacetamide: structure. valpromide : A fatty amide derived from valproic acid.	2.6	1	0	fatty amide	geroprotector; metabolite; teratogenic agent
oxprenolol hydrochloride [no description available]	2.6	1	0
tyloxapol tyloxapol: non-ionic detergent with surface-active properties; incompatible with metals; surfactant also used in inhalation therapy; N1 is from CA Vol 90 Form Index; N1 in Chemline is same as synonym 8. tyloxapol : A polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions.	2.17	1	0
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	2.94	4	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
opipramol hydrochloride [no description available]	2.6	1	0
moroxydine [no description available]	2.6	1	0	biguanides
thioxolone tioxolone : A 1,3-benzoxathiole having a hydroxy substituent at the 6-position.	2.6	1	0	benzoxathiole	antiseborrheic
hesperetin [no description available]	2.63	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
magnolol [no description available]	2.07	1	0	biphenyls
honokiol [no description available]	2.6	1	0	biphenyls
nobiletin nobiletin : A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.	2.6	1	0	methoxyflavone	antineoplastic agent; plant metabolite
lycorine lycorine: from bulbs of LYCORIS & other plants; RN given refers to (1 alpha,2 beta)-isomer; structure in Merck Index, 9th ed, #5444. lycorine : An indolizidine alkaloid that is 3,12-didehydrogalanthan substituted by hydroxy groups at positions and 2 and a methylenedioxy group across positions 9 and 10. Isolated from Crinum asiaticum, it has been shown to exhibit antimalarial activity.	2.6	1	0	indolizidine alkaloid	anticoronaviral agent; antimalarial; plant metabolite; protein synthesis inhibitor
leupeptin [no description available]	2.6	1	0	aldehyde; tripeptide	bacterial metabolite; calpain inhibitor; cathepsin B inhibitor; EC 3.4.21.4 (trypsin) inhibitor; serine protease inhibitor
phleomycins Phleomycins: Water-soluble, copper-containing low molecular weight polypeptides obtained from the culture medium of Streptomyces verticillus. They are specific inhibitors of DNA synthesis in bacteria and have been found to act as antitumor agents. They have also been used against rust fungi of plants.. phleomycin : A mixture of glycopeptide antibiotics originally isolated from the bacterium Streptomyces verticillus whose components all contain a thiazolinylthiazole moiety and can form complexes with redox-active metals such as Co, Cu, and Fe. (Bleomycins are very similar to phleomycins, but have a bithiazole moiety in place of the thiazolinylthiazole moiety).	1.95	1	0
tetrandrine tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity	2.6	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
calpeptin [no description available]	2.6	1	0	amino acid amide
eburicoic acid eburicoic acid: structure	2.06	1	0
fangchinoline [no description available]	2.6	1	0	aromatic ether; bisbenzylisoquinoline alkaloid; macrocycle	anti-HIV-1 agent; anti-inflammatory agent; antineoplastic agent; antioxidant; neuroprotective agent; plant metabolite
maslinic acid (2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria	2.6	1	0	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; plant metabolite
hydroxyindoleacetaldehyde (5-hydroxyindol-3-yl)acetaldehyde : An aldehyde that is acetaldehyde substituted by a 5-hydroxyindol-3-yl group.	1.97	1	0	hydroxyindoles; indoleacetaldehyde	human metabolite; mouse metabolite
atovaquone Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.	2.6	1	0	hydroxy-1,2-naphthoquinone
pentafluorobenzoyl chloride pentafluorobenzoyl chloride: RN given refers to parent cpd. pentafluorobenzoyl chloride : The acid chloride of pentafluorobenzoic acid. It is a sensitive derivatising reagent for the analysis of amines, amides and phenols by electron capture gas chromatography.	1.97	1	0	acyl chloride; perfluorinated compound	chromatographic reagent
cyclobutanol cyclobutanol: structure in first source	2.05	1	0
4-iodopyrazole [no description available]	2.08	1	0	organoiodine compound; pyrazoles
2',7'-dichlorodihydrofluorescein diacetate [no description available]	2.04	1	0
3,5-dimethoxytoluene 3,5-dimethoxytoluene: a component of rose fragrance; structure in first source. 3,5-dimethoxytoluene : A member of the class of toluenes that is toluene in which the hydrogens at positions 3 and 5 have been replaced by methoxy groups. It is the major scent compound of many rose varieties.	2.11	1	0	methoxybenzenes; toluenes	fragrance; plant metabolite
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	2.05	1	0
rosiglitazone [no description available]	2.48	2	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
1-nitro-2-phenylethane 1-nitro-2-phenylethane: component of Aniba canelilla essential oil with antinociceptive activity; structure in first source	2.6	1	0
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	21.19	795	34	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
3,4-dihydroxymandelic acid 3,4-dihydroxymandelic acid: metabolite of L-dopa; RN given refers to parent cpd without isomeric designation. 3,4-dihydroxymandelic acid : A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.	1.96	1	0	2-hydroxy monocarboxylic acid; catechols	antioxidant; drug metabolite; human metabolite; mouse metabolite
zinniol zinniol: phytotoxin isolated from cultures as of Alternaris spp. and Phoma macdonaldii; structure given in first source	2	1	0	methoxybenzenes
loganin [no description available]	2.6	1	0	beta-D-glucoside; cyclopentapyran; enoate ester; iridoid monoterpenoid; methyl ester; monosaccharide derivative; secondary alcohol	anti-inflammatory agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; EC 3.4.23.46 (memapsin 2) inhibitor; neuroprotective agent; plant metabolite
mebeverine gamma-oryzanol: present in rice bran is associated with various physiological functions; RN given refers to gamma-oryzanol	2.05	1	0
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.06	1	0	iditol	fungal metabolite
moexipril [no description available]	2.6	1	0	peptide
aucubin [no description available]	2.6	1	0	organic molecular entity	metabolite
7-ketocholesterol 7-ketocholesterol: inhibits uptake of cholesterol in rabbit aorta. 7-ketocholesterol : A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7.	2.46	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; 7-oxo steroid; cholestanoid	neuroprotective agent
cadmium telluride cadmium telluride: used in radiation monitoring device	2.08	1	0
catalpol [no description available]	2.6	1	0	organic molecular entity	metabolite
3,4-dihydroxyphenylglycol 3,4-dihydroxyphenylglycol: noradrenaline metabolite in mouse brain; RN given refers to cpd without isomeric designation. 3,4-dihydroxyphenylethyleneglycol : A tetrol composed of ethyleneglycol having a 3,4-dihydroxyphenyl group at the 1-position.	5.68	18	1	catechols; tetrol	metabolite; mouse metabolite
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.44	2	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
salsolinol salsolinol: RN given refers to cpd without isomeric designation; EP to SALSOLINE ALKALOIDS (78-82); on-line search SALSOLINE ALKALOIDS (78-82); Index Medicus search ISOQUINOLINES (78-82). (S)-salsolinol : A 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol that has S-configuration.	2.42	2	0	1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol	human urinary metabolite
triflumizol triflumizol: structure given in first source. triflumizole : A carboxamidine resulting from the formal condensation of the amino group of 4-chloro-2-(trifluoromethyl)aniline with the oxygen of the acetyl group of N-(propoxyacetyl)imidazole. A sterol demethylation inhibitor, it is used as a fungicide for the control of powdery mildew, scab and other diseases on a variety of crops.	2.05	1	0
alpha-curcumene alpha-curcumene: active priniciple in essential oils of Curcuma xanthorrhiza. alpha-curcumene : A sesquiterpene that is 2-methyl-2-heptene in which one of the hydrogens at position 6 is substituted by a p-tolyl group.	2.21	1	0	sesquiterpene
chalcone epoxide chalcone epoxide: activator of epoxide hydrolase; RN given refers to cpd without isomeric designation; structure given in first source	2.03	1	0
4-nitrostyrene oxide 4-nitrostyrene oxide: chemical alkylating agent ; structure given in first source	2.01	1	0
lekoptin (S)-verapamil : A 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile that has S configuration.	2.6	1	0	2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
arginine methyl ester arginine methyl ester: RN given refers to (L)-isomer	2.15	1	0	alpha-amino acid ester
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2	1	0
arabitol arabitol: RN given refers to cpd without isomeric designation. arabinitol : A pentitol that is the sugar alcohol produced by the reduction of arabinose or lyxose. It is found in serum or urine of human infected with Candida albicans.. D-arabinitol : The D-enantiomer of arabinitol.	2.17	1	0	arabinitol
1-phenyl-2-propanol [no description available]	4.23	5	0
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.	1.96	1	0
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.59	2	0	D-glucuronic acid	algal metabolite
1-(4-bromophenyl)ethanol 1-(4-bromophenyl)ethanol: structure in first source	2.96	4	0
1-(2-naphthyl)ethanol [no description available]	2.02	1	0
2-(4-bromo-2,5-dimethoxyphenyl)ethylamine 2-(4-bromo-2,5-dimethoxyphenyl)ethylamine: behaves as a partial agonist toward both alpha1-adrenergic & 5-HT(2) serotonergic receptors. 2,5-dimethoxy-4-bromophenethylamine : A 2-arylethylamine compound where the aryl moiety is 4-bromo-2,5-dimethoxyphenyl.	2.08	1	0	2-arylethylamine
2,2,5,7,8-pentamethyl-1-hydroxychroman 2,2,5,7,8-pentamethyl-1-hydroxychroman: a Vitamin E derivative. chromanol : Any member of the class of chromanes that is chromane substituted by one or more hydroxy groups.	2.31	1	0
phorbolol myristate acetate [no description available]	2.08	1	0
n-methyladenosine N-methyladenosine: is a inhibitor of cell differentiation. N(6)-methyladenosine : A methyladenosine compound with one methyl group attached to N(6) of the adenine nucleobase.	2.6	1	0	methyladenosine
2-amino-4-phenylbutyric acid 2-amino-4-phenylbutanoic acid: structure in first source	2.49	2	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.	2.01	1	0	cobalt group element atom; metal allergen	micronutrient
p-methoxy-n-methylphenethylamine p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.	2.41	1	0	aromatic ether; secondary amino compound	metabolite
s-nitrosoglutathione [no description available]	2.17	1	0	glutathione derivative; nitrosothio compound	bronchodilator agent; nitric oxide donor; platelet aggregation inhibitor; signalling molecule
diacetyldichlorofluorescein diacetyldichlorofluorescein: stable storage form of dichlorofluorescein	2.02	1	0
cp 96345 CP 96345: structure given in first source; potent nonpeptide antagonist of the substance P (NK1) receptor; CP 96344 is enantiomer of CP 96345	2.02	1	0
laurdan laurdan: RN from CA Index Guide	2.17	1	0
paxilline paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.	2.76	3	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
prolinedithiocarbamate prolinedithiocarbamate: do not confuse with pyrrolidine dithiocarbamate which is also abbreviated PDTC	2.02	1	0
s-ethyl glutathione [no description available]	2.1	1	0	oligopeptide
sivelestat sivelestat: inhibitor of neutrophil elastase; structure given in first source	2.6	1	0	N-acylglycine; pivalate ester
pyronaridine [no description available]	2.6	1	0	aminoquinoline
geniposide [no description available]	2.6	1	0	terpene glycoside
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	4.84	7	1	proanthocyanidin
phosphites Phosphites: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed). phosphite(3-) : A trivalent inorganic anion obtained by removal of all three protons from phosphorous acid.	2.03	1	0	phosphite ion; trivalent inorganic anion
deguelin deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.	2.31	1	0	aromatic ether; diether; organic heteropentacyclic compound; rotenones	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; mitochondrial NADH:ubiquinone reductase inhibitor; plant metabolite
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	2.6	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
parthenolide [no description available]	2.45	2	0	germacranolide
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	2.47	2	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.76	3	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	1.95	1	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
3-deoxyglucosone 3-deoxyglucosone: RN given refers to (D)-isomer. 3-deoxyglucosone : A deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position.	2.55	2	0	deoxyglucose; deoxyketohexose
globomycin [no description available]	1.96	1	0	cyclodepsipeptide
sophocarpine [no description available]	2.6	1	0
marimastat marimastat: a matrix metalloproteinase inhibitor active in patients with advanced carcinoma of the pancreas, prostate, or ovary. marimastat : A secondary carboxamide resulting from the foraml condensation of the carboxy group of (2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the alpha-amino group of N,3-dimethyl-L-valinamide.	2.6	1	0	hydroxamic acid; secondary carboxamide	antineoplastic agent; matrix metalloproteinase inhibitor
asiatic acid [no description available]	2.6	1	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
al-01567 alconil: structure given in first source	2	1	0
3,4-dihydroxyphenylacetaldehyde 3,4-dihydroxyphenylacetaldehyde : A phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups.	3.88	12	0	alpha-CH2-containing aldehyde; catechols; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite
elacridar Elacridar: inhibitor of MDR1 PROTEIN; structure given in first source	2.6	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.	3.02	4	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.	2.05	1	0	dipeptide; homodetic cyclic peptide; phenols; pyrrolopyrazine	metabolite
pentosidine pentosidine: structure given in first source. pentosidine : An imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively.	2.15	1	0	imidazopyridine; non-proteinogenic L-alpha-amino acid	biomarker; cross-linking reagent
n-iodosuccinimide [no description available]	2.01	1	0	dicarboximide; pyrrolidinone
titanium tetrafluoride [no description available]	3.45	1	1
prisma-fil heliobond: visible-light-curing monomer component of composite resins	3.45	1	1
5-s-cysteinyldopamine [no description available]	2.05	1	0	S-conjugate
saccharolactone saccharolactone: used as index for assessing induction of hepatic enzymes by anticonvulsants; RN given refers to cpd without isomeric designation. D-glucaro-1,4-lactone : A delta-lactone that is D-glucono-1,4-lactone in which the hydroxy group at position 6 has been oxidised to the corresponding carboxylic acid.	2.17	1	0	aldarolactone; delta-lactone
celastrol [no description available]	2.6	1	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
procyanidin b2 procyanidin B2 : A proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 8' in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine.	2.11	1	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	antioxidant; metabolite
1-adamantaneacetic acid [no description available]	2.05	1	0
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.46	2	0	nitrogen oxoacid
cholecystokinin (27-33) [no description available]	1.97	1	0
n-(n-(3-carboxyoxirane-2-carbonyl)leucyl)isoamylamine N-(N-(3-carboxyoxirane-2-carbonyl)leucyl)isoamylamine: inhibits calcium-activated neutral protease; see also record for E-64; RN given refers to (2-S-(2alpha,3beta)(R*)-isomer)	2.6	1	0	leucine derivative
c & b metabond Super-bond: an adhesive resin composed of 4-methacryloxyethyltrimellitic anhydride (4-META), methylmethacrylates (MMA) and tri-n-butylborane (TBB)	3.82	2	1
n(6)-carboxymethyllysine N(6)-carboxymethyllysine: RN given refers to (L)-isomer; structure given in first source. N(6)-carboxymethyl-L-lysine : An L-lysine derivative with a carboxymethyl substituent at the N(6)-position.	2.15	1	0	L-lysine derivative; non-proteinogenic L-alpha-amino acid	antigen
n,n-dimethylarginine N,N-dimethylarginine: asymmetric dimethylarginine; do not confuse with N,N'-dimethylarginine. N(omega),N(omega)-dimethyl-L-arginine : A L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group.	2.61	2	0	dimethylarginine; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor
vadimezan vadimezan : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 5,6-dimethyl-9-oxoxanthen-4-yl group.	2.6	1	0	monocarboxylic acid; xanthones	antineoplastic agent
e 64 E 64: cysteine protease inhibitor of microbial origin, which inhibits cathepsin B (EC 3.4.22.1) and cathepsin L (EC 3.4.22.-)	2.6	1	0	dicarboxylic acid monoamide; epoxy monocarboxylic acid; guanidines; L-leucine derivative; zwitterion	antimalarial; antiparasitic agent; protease inhibitor
tetrahydrocurcumin tetrahydrocurcumin : A beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds.	2.07	1	0	beta-diketone; diarylheptanoid; polyphenol	metabolite
tiglic acid tiglic acid : A 2-methylbut-2-enoic acid having its double bond in trans-configuration.. 2-methylbut-2-enoic acid : A branched-chain fatty acid consisting of 2-butenoic acid having a methyl group at position 2.	2.02	1	0	2-methylbut-2-enoic acid	plant metabolite
methotrexate [no description available]	3.66	9	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
dihydroethidium dihydroethidium: RN given is for the (+-)-isomer	2.04	1	0
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	2.05	1	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant metabolite
umifenovir umifenovir: an antiviral agent	2.6	1	0	indolyl carboxylic acid
safinamide safinamide: short-acting inhibitor of MOA-B; FCE 26743 is (S)-isomer, FCE 28073 is (R)-isomer; structure in first source	2.6	1	0	amino acid amide
ilomastat CS 610: matrix metalloproteinase inhibitor; structure in first source. ilomastat : An N-acyl-amino acid obtained by formal condensation of the carboxy group of (2R)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the amino group of N-methyl-L-tryptophanamide. A cell permeable broad-spectrum matrix metalloproteinase (MMP) inhibitor	2.6	1	0	hydroxamic acid; L-tryptophan derivative; N-acyl-amino acid	anti-inflammatory agent; antibacterial agent; antineoplastic agent; EC 3.4.24.24 (gelatinase A) inhibitor; neuroprotective agent
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	2.44	2	0	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
xylose xylopyranose: structure in first source	3.14	5	0	D-xylose
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.	2.47	2	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
phenylmorphan phenylmorphan: structure given in first source; RN given refers to (+)-isomer; see also (-)-5-m-hydroxyphenyl-2-methylmorphan (sometimes referred to as phenylmorphan)	2.04	1	0
tamolarizine [no description available]	1.98	1	0
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	2.57	2	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
atazanavir atazanavir : A heavily substituted carbohydrazide that is an antiretroviral drug of the protease inhibitor (PI) class used to treat infection of human immunodeficiency virus (HIV).	2.6	1	0	carbohydrazide	antiviral drug; HIV protease inhibitor
4-dimethylaminophenylacetate 4-N,N-dimethylaminophenylacetic acid: accelerator for dental composite polymerization	1.96	1	0
vx 497 N-3-(3-(3-methoxy-4-oxazol-5-ylphenyl)ureido)benzylcarbamic acid tetrahydrofuran-3-yl ester: structure in first source	2.6	1	0
bcx 1812 [no description available]	2.6	1	0	3-hydroxy monocarboxylic acid; acetamides; cyclopentanols; guanidines	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
paclitaxel 6-prenylnaringenin: from hop plant (Humulus lupulus): structure in first source. 6-prenylnaringenin : A trihydroxyflavanone having a structure of naringenin prenylated at C-6.	2.25	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; trihydroxyflavanone	T-type calcium channel blocker
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.	2.6	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
cinacalcet cinacalcet : A secondary amino compound that is (1R)-1-(naphthalen-1-yl)ethanamine in which one of the hydrogens attached to the nitrogen is substituted by a 3-[3-(trifluoromethyl)phenyl]propyl group.	2.05	1	0	(trifluoromethyl)benzenes; naphthalenes; secondary amino compound	calcimimetic; P450 inhibitor
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.45	7	0	oxygen hydride; oxygen radical; reactive oxygen species
olmesartan olmesartan: an active metabolite of CS 866	2.6	1	0	biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent
telbivudine [no description available]	2.6	1	0	pyrimidine 2'-deoxyribonucleoside	antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
rhodioloside [no description available]	7.14	44	0	glycoside
malvidin malvidin: RN given refers to parent cpd; coloring agent from flowers of Malvaviscus conzatti. malvidin : An anthocyanidin cation that is delphinidin carrying methyl substituents at positions 3' and 5'.	2.15	1	0	5-hydroxyanthocyanidin	biological pigment; metabolite
celastrol methyl ester celastrol methyl ester: isolated from Tripterygium wilfordii; potent inhibitory activity on both Kir2.1 and ERG1 potassium channels, leading to LONG QT SYNDROME	2.6	1	0	carboxylic ester
resiquimod S 28463: structure given in first source	2.6	1	0	imidazoquinoline
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.	2.21	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.44	2	0
vanillactic acid vanillactic acid: metabolite of catecholamines	1.95	1	0	2-oxo monocarboxylic acid
syringopicroside syringopicroside: from leaves of Syringa oblata Lindl.; structure given in first source	2.4	2	0
dopamine quinone dopamine quinone: product of the autoxidation of dopamine. dopaminoquinone : A member of the class of 1,2-benzoquinones that is 1,2-benzoquinone in which a hydrogen at para to one of the oxo groups has been replaced by a 2-aminoethyl group.	2.15	1	0	1,2-benzoquinones; primary amino compound	metabolite
mevaldic acid mevaldic acid: RN given refers to cpd without isomeric designation; structure	2.11	1	0	3-hydroxy monocarboxylic acid; 5-oxo monocarboxylic acid
tanshinone ii a tashinone IIA: a cardiovascular agent with antineoplastic activity; isolated from Salvia miltiorrhiza; structure in first source	2.6	1	0	abietane diterpenoid
2,2,6,6-tetramethylpiperidine-n-oxide-4-amino-4-carboxylic acid 2,2,6,6-tetramethylpiperidine-N-oxide-4-amino-4-carboxylic acid: structure given in first source	2.01	1	0	aminoxyls; piperidinemonocarboxylic acid
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.	2.6	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
elenolic acid elenolic acid: extract of olive plant; RN given refers to (2S-(2alpha,3alpha,4beta))-isomer; structure	7	13	0
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.41	2	0	amino acid zwitterion; angiotensin II	human metabolite
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.02	1	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.71	3	0
migalastat migalastat: a potent inhibitor of glycolipid biosynthesis	2.6	1	0	piperidines
sb 203580 [no description available]	2.71	3	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
erlotinib [no description available]	2.6	1	0	aromatic ether; quinazolines; secondary amino compound; terminal acetylenic compound	antineoplastic agent; epidermal growth factor receptor antagonist; protein kinase inhibitor
erlotinib hydrochloride [no description available]	2.31	1	0	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.03	1	0	divalent inorganic anion; phosphite ion
limonin [no description available]	2.6	1	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.6	1	0	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	2.08	1	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
2,5-dihydroxybenzyl alcohol 2,5-dihydroxybenzyl alcohol: structure; RN given refers to parent cpd. gentisyl alcohol : An aromatic primary alcohol that is benzyl alcohol substituted by hydroxy groups at positions 2 and 5.	2.06	1	0	aromatic primary alcohol; phenols	antineoplastic agent; antioxidant; apoptosis inhibitor; fungal metabolite
etravirine [no description available]	2.6	1	0	aminopyrimidine; aromatic ether; dinitrile; organobromine compound	antiviral agent; HIV-1 reverse transcriptase inhibitor
chelidonine chelidonine: benzophenanthridine derived from scoulerine from Chelidonium majus; RN given refers to parent cpd (chelidonine, (5bR-(5balpha,6beta,12alpha))-isomer)	2.6	1	0	alkaloid antibiotic; alkaloid fundamental parent; benzophenanthridine alkaloid
4-n-butylresorcinol 4-n-butylresorcinol: structure in first source	2.6	1	0	resorcinols
darunavir Darunavir: An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.. darunavir : An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.	2.6	1	0	carbamate ester; furofuran; sulfonamide	antiviral drug; HIV protease inhibitor
dapivirine Dapivirine: effectively prevented human immunodeficiency virus (HIV) infection in cocultures of monocyte-derived dendritic cells and T cells, representing primary targets in sexual transmission	2.6	1	0
lenalidomide [no description available]	2.25	1	0	aromatic amine; dicarboximide; isoindoles; piperidones	angiogenesis inhibitor; antineoplastic agent; immunomodulator
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	2.48	2	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse 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.	1.95	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
cortisone [no description available]	2.44	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
cholesterol alpha-oxide cholesterol alpha-oxide: RN given refers to (3beta,5alpha,6alpha)-isomer; structure	2	1	0	3beta-hydroxy steroid; epoxy steroid; oxysterol
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	2.95	4	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	2.44	2	0	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
3-octanone 3-octanone : A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group.	2.47	2	0	dialkyl ketone	antifeedant; biomarker; fungal metabolite; human urinary metabolite; insect attractant; plant metabolite; toxin
lanosterol [no description available]	2.06	1	0	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nsc 74859 NSC 74859: inhibits Stat3 binding activity; structure in first source. S3I-201 : An amidobenzoic acid obtained by formal condensation of the carboxy group of [(4-methylbenzene-1-sulfonyl)oxy]acetic acid with the amino group of 4-amino-2-hydroxybenzoic acid.	2.6	1	0	amidobenzoic acid; monohydroxybenzoic acid; tosylate ester	STAT3 inhibitor
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	3.05	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.56	2	0
norfentanyl norfentanyl: metabolite of fentanyl; RN given refers to parent cpd; structure given in first source. norfentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of 4-(N'-phenyl)piperidin-4-amine with propanoic acid. A major metabolite of fentanyl.	1.98	1	0	anilide; monocarboxylic acid amide; piperidines	drug metabolite; opioid analgesic
withaferin a withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.	2.31	1	0	27-hydroxy steroid; 4-hydroxy steroid; delta-lactone; enone; epoxy steroid; ergostanoid; primary alcohol; secondary alcohol; withanolide	antineoplastic agent; apoptosis inducer
berbamine [no description available]	2.6	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
u-104 SLC-0111: a carbonic anhydrase inhibitor; structure in first source	2.6	1	0
wortmannin [no description available]	1.99	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
withanolides Withanolides: Ergostane derivatives of 28 carbons with oxygens at C1, C22, and C26 positions and the side chain cyclized. They are found in WITHANIA plant genus and have cytotoxic and other effects.	2.72	2	0
o-iodoxybenzoic acid o-iodoxybenzoic acid: structure in first source. 1-hydroxy-1,3-dioxobenziodoxole : A benziodoxole compound having hydroxy and oxo substituents at the 1-position and an oxo substituent at the 3-position. It is a mild and efficient hypervalent iodine synthetic reagent used to carry out several selective oxidation reactions.	2.46	2	0	benziodoxole	EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; oxidising agent
7-hydroxy-5-methyl-2-(2-oxopropyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]-1-benzopyran-4-one [no description available]	2.6	1	0	glycoside
bortezomib [no description available]	2.61	2	0	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
ritonavir Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	2.6	1	0	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
tizoxanide tizoxanide: major metabolite of nitazoxanide; structure in first source	2.6	1	0	salicylamides
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.95	4	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.	2.13	1	0
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.17	1	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
elastin [no description available]	2.21	1	0	oligopeptide
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.44	2	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
3,4-dihydroxyphenyllactic acid 3,4-dihydroxyphenyllactic acid: from S. miltiorhiza Bge; dilates coronary artery; RN given refers to parent cpd without isomeric designation	2.15	1	0	2-hydroxy monocarboxylic acid; catechols
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	2.05	1	0	myo-inositol trisphosphate	mouse metabolite
puromycin [no description available]	3.45	2	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.53	2	0	taxifolin	metabolite
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.	1.99	1	0	alpha-chloroketone; sulfonamide	alkylating agent; serine proteinase inhibitor
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	2.6	1	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
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.	2.93	4	0	cellotriose
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.	2.6	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
conessine conessine : A steroid alkaloid that is con-5-enine substituted by a N,N-dimethylamino group at position 3. It has been isolated from the plant species of the family Apocynaceae.	2.6	1	0	steroid alkaloid; tertiary amino compound	antibacterial agent; antimalarial; H3-receptor antagonist; plant metabolite
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.	2.05	1	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	2.21	1	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
saquinavir Saquinavir: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.. saquinavir : An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N(2)(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.	2.6	1	0	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor
abacavir abacavir: a carbocyclic nucleoside with potent selective anti-HIV activity. abacavir : A 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection.	2.6	1	0	2,6-diaminopurines	antiviral drug; drug allergen; HIV-1 reverse transcriptase inhibitor
linezolid [no description available]	2.6	1	0	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor
carnosol carnosol: isolated from Lepechinia hastata	2.15	1	0	diterpenoid
cephaelin cephaelin: do not confuse with cephalin of brain; after emetine this is the most important alkaloid of ipecac; protein synthesis inhibitor. cephaeline : A pyridoisoquinoline comprising emetam having a hydroxy group at the 6'-position and methoxy substituents at the 7'-, 10- and 11-positions.	2.6	1	0	pyridoisoquinoline
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.79	3	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
(-)-usnic acid (-)-usnic acid : The (-)-enantiomer of usnic acid.	2.6	1	0	usnic acid	EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	1.98	1	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
alpha bitter acid humulon: antibiotic from hops; structure	3.19	1	0	aromatic ketone; cyclic ketone; diketone; tertiary alpha-hydroxy ketone; triol	antibacterial drug; antioxidant; cyclooxygenase 2 inhibitor; metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	5.06	15	0
acriflavine Acriflavine: 3,6-Diamino-10-methylacridinium chloride mixt. with 3,6-acridinediamine. Fluorescent dye used as a local antiseptic and also as a biological stain. It intercalates into nucleic acids thereby inhibiting bacterial and viral replication.	3.45	2	0
acetylleucyl-leucyl-norleucinal acetylleucyl-leucyl-norleucinal: a proteasome inhibitor. acetylleucyl-leucyl-norleucinal : A tripeptide composed of N-acetylleucyl, leucyl and norleucinal residues joined in sequence.	2.51	2	0	aldehyde; tripeptide	cysteine protease inhibitor
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	2.15	1	0	tripeptide
teprotide Teprotide: A synthetic nonapeptide (Pyr-Trp-Pro-Arg-Pro-Gln-Ile-Pro-Pro) which is identical to the peptide from the venom of the snake, Bothrops jararaca. It inhibits kininase II and ANGIOTENSIN I and has been proposed as an antihypertensive agent.	2.01	1	0	peptide
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.52	2	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.72	9	0	cyclodextrin
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.15	1	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.57	2	0	cinnamic acid	plant metabolite
ergosterol [no description available]	2.82	3	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.05	1	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.69	3	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	3.52	8	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	3.38	5	0	cyclodextrin
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.	6.66	20	0	farnesol	plant metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	7.98	25	1	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	2.31	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.	7.65	17	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.	2.6	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.	5.08	12	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.	2.81	3	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.	2.52	2	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	3.12	4	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	2.81	3	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	1.98	1	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
lycopene [no description available]	2.84	3	0	acyclic carotene	antioxidant; plant metabolite
zithromax Azithromycin: A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.. azithromycin : A macrolide antibiotic useful for the treatment of bacterial infections.	2.6	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; xenobiotic
roflumilast [no description available]	2.6	1	0	aromatic ether; benzamides; chloropyridine; cyclopropanes; organofluorine compound	anti-asthmatic drug; phosphodiesterase IV inhibitor
L-cycloserine L-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has S configuration. An antibiotic isolated from Erwinia uredovora.	2.6	1	0	4-amino-1,2-oxazolidin-3-one	anti-HIV agent; anticonvulsant; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor
h 89 N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.	2.6	1	0	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	12	120	1
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	4.15	5	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.93	4	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
bevirimat bevirimat: an HIV inhibitor; disrupts late step in processing HIV Major Core Protein p24, preventing the capsid precursor p25 from being converted to mature capsid p24. bevirimat : A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.	2.6	1	0	dicarboxylic acid monoester; monocarboxylic acid; pentacyclic triterpenoid	HIV-1 maturation inhibitor; metabolite
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.98	4	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	2.6	1	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
posaconazole [no description available]	2.6	1	0	aromatic ether; conazole antifungal drug; N-arylpiperazine; organofluorine compound; oxolanes; triazole antifungal drug; triazoles	trypanocidal drug
l 743,872 [no description available]	2.57	2	0
gw 257406x maribavir: has antiviral activity against human cytomegalovirus	2.6	1	0
micafungin Micafungin: A cyclic lipo-hexapeptide echinocandin antifungal agent that is used for the treatment and prevention of CANDIDIASIS.. micafungin : A cyclic hexapeptide echinocandin antibiotic which exerts its effect by inhibiting the synthesis of 1,3-beta-D-glucan, an integral component of the fungal cell wall. It is used as the sodium salt for the treatment of invasive candidiasis, and of aspergillosis in patients who are intolerant of other therapy.	2.15	1	0	antibiotic antifungal drug; echinocandin	antiinfective agent
shikonin shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities	2.6	1	0	hydroxy-1,4-naphthoquinone
8-prenylnaringenin 8-prenylnaringenin: a phytogenic antineoplastic agent; structure in first source. sophoraflavanone B : A trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8.	3.65	2	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; trihydroxyflavanone	plant metabolite; platelet aggregation inhibitor
4,4-difluoro-N-[(1S)-3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]-1-cyclohexanecarboxamide [no description available]	2.6	1	0	tropane alkaloid
cmx 001 [no description available]	2.6	1	0
amd 8664 [no description available]	2.6	1	0
bay 41-4109 BAY 41-4109: structure in first source	2.6	1	0
bay 57-1293 pritelivir: herpes simplex virus 1 helicase-primase inhibitor	2.6	1	0
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).	2.31	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
2'-c-methylcytidine 2'-C-methylcytidine: structure in first source	2.6	1	0
isoxanthohumol isoxanthohumol: structure in first source	4	3	0	flavanones
zopiclone 2,3-hexanediol: an aggregation pheromone of cerambycid beetles	2.07	1	0
2-acetyl-1-pyrroline 2-acetyl-1-pyrroline: volatile component of uncooked Khao Dawk Mali 105 brown rice were extracted using indirect steam distillation under reduced pressure and controlled temperature in order to prevent cooking. 2-acetyl-1-pyrroline : A pyrroline that is 1-pyrroline in which the hydrogen at position 2 is replaced by an acetyl group. It is an aroma and flavour compound present in jasmine rice and basmati rice. It is responsible for the 'popcorn' aroma in a large variety of cereal and food products. It is one of the key odourants of the crust of bread and considered to be responsible for the cracker-like odour properties. In bread, it is primarily generated during baking but amounts are influenced by ingredient composition and fermentation conditions.	2.08	1	0	acylimine; methyl ketone; pyrroline	flavouring agent; Maillard reaction product; metabolite
4-(4-chloro-2-methylphenoxy)-n-hydroxybutanamide 4-(4-chloro-2-methylphenoxy)-N-hydroxybutanamide: a c-FLIP inhibitor; structure in first source	2.6	1	0	aromatic ether
mecarbinate [no description available]	2.6	1	0
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.	3.3	5	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
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	4.12	15	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
geraniol [no description available]	8.31	6	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	7.59	70	0
chalcone trans-chalcone : The trans-isomer of chalcone.	2.43	2	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	2.41	1	0	sinapic acid	MALDI matrix material; plant metabolite
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	4.34	7	0	isomethyleugenol
teucrol teucrol: from Teucrium pilosum; structure in first source	2.08	1	0
beta-ionone beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.	2.03	1	0	ionone	antioxidant; fragrance
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	4.53	7	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	5.73	25	0	stilbene
2'-hydroxychalcone 2'-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 2'.	2.02	1	0	chalcones; phenols	anti-inflammatory agent
propolin c propolin C: a PAK1 inhibitor; from Taiwanese propolis; structure in first source. nymphaeol A : A tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy group at positions 5, 7, 3' and 4' and a geranyl group at position 6. Isolated from Macaranga tanarius and propolis collected in Okinawa, it exhibits radical scavenging activity.	2.02	1	0	4'-hydroxyflavanones; tetrahydroxyflavanone	metabolite; radical scavenger
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	3.65	2	0	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	1.98	1	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
acetyl-aspartyl-glutamyl-valyl-aspartal acetyl-aspartyl-glutamyl-valyl-aspartal: a capase inhibitor. Ac-Asp-Glu-Val-Asp-H : A tetrapeptide consisting of two L-aspartic acid residues, an L-glutamyl residue and an L-valine residue with an acetyl group at the N-terminal and with the C-terminal carboxy group reduced to an aldehyde. It is an inhibitor of caspase-3/7.	2.6	1	0	tetrapeptide	protease inhibitor
octotropine methylbromide octotropine methylbromide: minor descriptor (65-86); on line & INDEX MEDICUS search TROPANES (69-86); RN given refers to endo-isomer. anisotropine methylbromide : A quaternary ammonium salt resulting from the reaction of the amino group of anisotropine with methyl bromide.	2.6	1	0
nsc 4347 NSC 4347: structure in first source	3.13	1	0
sesquiterpenes [no description available]	3.57	8	0
mercaptopurine Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.	2.6	1	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	3.91	3	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
jrf 12 N2,N4-dibenzylquinazoline-2,4-diamine: a selective, potent, reversible, and ATP-competitive p97 inhibitor	2.6	1	0
phenylthiourea Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.	1.95	1	0	thioureas	EC 1.14.18.1 (tyrosinase) inhibitor
3,4'-dihydroxyflavone 3,4'-dihydroxyflavone: an antioxidant; structure in first source	2.6	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	6.51	55	0	caffeic acid	geroprotector; mouse metabolite
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	2.5	2	0	alkyl caffeate ester; methyl ester
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	2.59	2	0	methoxycinnamic acid
isoferulic acid isoferulic acid: isomer of ferulic acid; structure. isoferulic acid : A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.	2.6	1	0	ferulic acids	antioxidant; biomarker; metabolite
ethyl ferulate ethyl ferulate: structure in first source	2.45	2	0
cyclouridine cyclouridine: structure given in third source	2.6	1	0
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	2.05	1	0	isoeugenol	plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	8.1	22	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
cinnarizine Cinnarizine: A piperazine derivative having histamine H1-receptor and calcium-channel blocking activity with vasodilating and antiemetic properties but it induces PARKINSONIAN DISORDERS.	2.05	1	0	diarylmethane; N-alkylpiperazine; olefinic compound	anti-allergic agent; antiemetic; calcium channel blocker; geroprotector; H1-receptor antagonist; histamine antagonist; muscarinic antagonist
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.	2.41	2	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
zucapsaicin [no description available]	2.6	1	0	methoxybenzenes; phenols
Jasmone jasmone: RN refers to (Z)-isomer; structure given in first source	2.03	1	0	cyclic ketone
geranyl acetate geranyl acetate: constituted about 90% of the palmarosa oil. geranyl acetate : A monoterpenoid that is the acetate ester derivative of geraniol.	2.48	2	0	acetate ester; monoterpenoid	plant metabolite
nbd 556 [no description available]	2.6	1	0
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	2.11	1	0
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	3.77	10	0	cinnamate ester; tannin	food component; plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	2.6	1	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
D-fructopyranose [no description available]	2.97	4	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.52	2	0	thiocarboxamide	hepatotoxic agent
4,5,6,7-tetrachloroindan-1,3-dione 4,5,6,7-tetrachloroindan-1,3-dione: inhibits ubiquitin C-terminal hydrolase L1	2.6	1	0
tamoxifen [no description available]	2.96	4	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
nadp [no description available]	3.36	6	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)	5.39	21	0
srpin340 SRPIN340: Serine-Arginine-Rich Protein Kinase Inhibitor	2.6	1	0
pr-619 [no description available]	2.6	1	0
p5091 P5091: inhibits ubiquitin-specific protease 7; structure in first source	2.6	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.	2.05	1	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
trovirdine trovirdine: HIV-1 reverse transcriptase inhibitor	2.6	1	0
fti 277 [no description available]	2.6	1	0
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	3.03	4	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
vicriviroc vicriviroc: structure in first source	2.6	1	0	(trifluoromethyl)benzenes
telaprevir [no description available]	2.6	1	0	cyclopentapyrrole; cyclopropanes; oligopeptide; pyrazines	antiviral drug; hepatitis C protease inhibitor; peptidomimetic
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2.72	2	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	2.43	2	0	alkali metal atom
nitrogen dioxide Nitrogen Dioxide: Nitrogen oxide (NO2). A highly poisonous gas. Exposure produces inflammation of lungs that may only cause slight pain or pass unnoticed, but resulting edema several days later may cause death. (From Merck, 11th ed) It is a major atmospheric pollutant that is able to absorb UV light that does not reach the earth's surface.	2.13	1	0	nitrogen oxide
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	2.6	1	0	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
glycodeoxycholic acid Glycodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.. glycodeoxycholic acid : A bile acid glycine conjugate of deoxycholic acid.	2.04	1	0	bile acid glycine conjugate	human metabolite
rtki cpd RTKI cpd: preferentially inhibits human glioma cells expressing truncated rather than wild-type epidermal growth factor receptors	2.07	1	0
dasatinib N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxamide: a dasatinib prodrug; structure in first source. dasatinib (anhydrous) : An aminopyrimidine that is 2-methylpyrimidine which is substituted at position 4 by the primary amino group of 2-amino-1,3-thiazole-5-carboxylic acid and at position 6 by a 4-(2-hydroxyethyl)piperazin-1-yl group, and in which the carboxylic acid group has been formally condensed with 2-chloro-6-methylaniline to afford the corresponding amide. A multi-targeted kinase inhibitor, it is used, particularly as the monohydrate, for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhydrous dasatinib (INN).	2.9	3	0	1,3-thiazoles; aminopyrimidine; monocarboxylic acid amide; N-(2-hydroxyethyl)piperazine; N-arylpiperazine; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antineoplastic agent; tyrosine kinase inhibitor
4-hydroxyphenethylene glycol [no description available]	2.37	2	0	phenols
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	3.12	5	0
yya-021 YYA-021: an HIV entry inhibitor; structure in first source	2.6	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	3	4	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	2.38	2	0	organic sodium salt	detergent; protein denaturant
ro 41-0960 [no description available]	2.11	1	0
sb 415286 3-(3-chloro-4-hydroxyphenylamino)-4-(4-nitrophenyl)-1H-pyrrole-2,5-dione: a glycogen synthase kinase-3 inhibitor; structure in first source	2.6	1	0	C-nitro compound; maleimides; monochlorobenzenes; phenols; secondary amino compound; substituted aniline	antioxidant; apoptosis inducer; EC 2.7.11.26 (tau-protein kinase) inhibitor; neuroprotective agent
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.49	2	0
sitagliptin sitagliptin : A triazolopyrazine that exhibits hypoglycemic activity.	2.6	1	0	triazolopyrazine; trifluorobenzene	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; environmental contaminant; hypoglycemic agent; serine proteinase inhibitor; xenobiotic
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.15	1	0	long-chain fatty acid
nitrocatechol nitrocatechol: structure in first source	2.21	1	0
calceolarioside a calceolarioside A: structure given in first source; isolated from Calceolaria hypericina; induces platelet aggregation	2.1	1	0	hydroxycinnamic acid
calceolarioside b calceorioside B: a cardioprotective agent isolated from Akebia; structure in first source	2.1	1	0	hydroxycinnamic acid	metabolite
fraxetin fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.	3	1	0	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent
farnesoic acid farnesoic acid : A methyl-branched, trienoic fatty acid consisting of dodeca-2,6,10-trienoic acid having three methyl substituents at the 3-, 7- and 11-positions.. (2E,6E)-farnesoic acid : A farnesoic acid in which the double bonds at positions 2 and 6 both have E-configuration.	2.21	1	0	farnesoic acid	animal metabolite
tak-220 TAK-220: structure in first source	2.6	1	0
jtk-303 [no description available]	2.6	1	0	aromatic ether; monochlorobenzenes; organofluorine compound; quinolinemonocarboxylic acid; quinolone	HIV-1 integrase inhibitor
nbd 557 [no description available]	2.6	1	0
quercetin [no description available]	6.22	24	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
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.	4.59	24	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	3.62	3	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
formononetin [no description available]	2.31	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	2.88	3	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.97	4	0	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	3.43	7	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
scopoletin [no description available]	2.1	1	0	hydroxycoumarin	plant growth regulator; plant metabolite
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2.08	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	3.82	3	0	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
5'-o-caffeoylquinic acid trans-5-O-caffeoyl-D-quinic acid : A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid.	2.6	1	0	cinnamate ester; cyclitol carboxylic acid	plant metabolite
luteolin-7-glucoside luteolin-7-glucoside: has both antiasthmatic and antineoplastic activities; has 3C protease inhibitory activity; isolated from Ligustrum lucidum. luteolin 7-O-beta-D-glucoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.63	2	0	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antioxidant; plant metabolite
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	3.84	3	0
apigetrin apigetrin: structure given in first source. apigenin 7-O-beta-D-glucoside : A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.21	1	0	beta-D-glucoside; dihydroxyflavone; glycosyloxyflavone; monosaccharide derivative	antibacterial agent; metabolite; non-steroidal anti-inflammatory drug
cyclosporine [no description available]	2.6	1	0
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	2.4	2	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	3.34	6	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	3.91	3	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
6-ketoprostaglandin f1 alpha 6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.	2.05	1	0	prostaglandins Falpha	human metabolite; mouse metabolite
zeaxanthin Zeaxanthins: Carotenoids found in fruits and vegetables. Zeaxanthin accumulates in the MACULA LUTEA.	3.7	1	1	carotenol	antioxidant; bacterial metabolite; cofactor
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.	3.21	5	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.	2.6	1	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	3.12	5	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.	4.23	5	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
eprosartan eprosartan: angiotensin II receptor antagonist. eprosartan : A member of the class of imidazoles and thiophenes that is an angiotensin II receptor antagonist used for the treatment of high blood pressure.	2.6	1	0	dicarboxylic acid; imidazoles; thiophenes	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
mycophenolate mofetil mycophenolate mofetil : A carboxylic ester resulting from the formal condensation between the carboxylic acid group of mycophenolic acid and the hydroxy group of 2-(morpholin-4-yl)ethanol. In the liver, it is metabolised to mycophenolic acid, an immunosuppressant for which it is a prodrug. It is widely used to prevent tissue rejection following organ transplants as well as for the treatment of certain autoimmune diseases.	2.6	1	0	carboxylic ester; ether; gamma-lactone; phenols; tertiary amino compound	anticoronaviral agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; immunosuppressive agent; prodrug
entacapone entacapone: structure given in first source. entacapone : A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group.	2.6	1	0	2-nitrophenols; catechols; monocarboxylic acid amide; nitrile	antidyskinesia agent; antiparkinson drug; central nervous system drug; EC 2.1.1.6 (catechol O-methyltransferase) inhibitor
jasmonic acid jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.	2.79	3	0	oxo monocarboxylic acid	jasmonates; plant metabolite
2-hexenal, z-isomer 2-hexenal: product of lipid peroxidation in the rat liver; a green odor chemical; do not confuse with the hexabarbital synonym, hexenal; RN given refers to cpd without isomeric designation. 2-hexenal : A hexenal having the double bond at the 2-position.. (2E)-hexenal : A 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices.	2.05	1	0	2-hexenal	antibacterial agent; flavouring agent; plant metabolite
fucoxanthin fucoxanthin: RN given refers to (3S,3'S,5R,5'R,6S,6'R)-isomer. fucoxanthin : An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.	2.25	1	0
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	3.7	1	1	carotenol	food colouring; plant metabolite
cucurbitacin i cucurbitacin I: toxic constituent in edible gourd; see also records for cucurbitacins & specific cucurbitacins. cucurbitacin I : A cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22.	2.11	1	0	cucurbitacin; tertiary alpha-hydroxy ketone	antineoplastic agent; plant metabolite
mezerein mezerein: toxic component of plant Daphne mezereum with anti-leukemic activity against P-388 & P-1210 in mice; can act as a tumor promoter; RN given refers to (12beta(E,E))-isomer; structure	1.98	1	0	diterpenoid
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	2	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	2.81	3	0	alpha-humulene
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	12.16	118	1	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
amentoflavone [no description available]	2.6	1	0	biflavonoid; hydroxyflavone; ring assembly	angiogenesis inhibitor; antiviral agent; cathepsin B inhibitor; P450 inhibitor; plant metabolite
baicalein [no description available]	2.6	1	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	3.19	5	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
galangin 5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.	3.54	8	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
genkwanin genkwanin: structure. genkwanin : A monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated.	2.6	1	0	dihydroxyflavone; monomethoxyflavone	metabolite
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	2.61	2	0	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
mangostin mangostin: xanthone from rind of Garcinia mangostana Linn. fruit. alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.	2.6	1	0	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	2.53	2	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
kaempferide kaempferide: structure in first source. kaempferide : A monomethoxyflavone that is the 4'-O-methyl derivative of kaempferol.	2.6	1	0	7-hydroxyflavonol; monomethoxyflavone; trihydroxyflavone	antihypertensive agent; metabolite
myricetin [no description available]	2.86	3	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
orientin orientin: structure given in first source; RN given refers to the (D-glucopyranosyl)-isomer. orientin : A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.	2.6	1	0	3'-hydroxyflavonoid; C-glycosyl compound; tetrahydroxyflavone	antioxidant; metabolite
quercetagetin quercetagetin: structure given in first source; inhibits aldose reductase in rat lens. quercetagetin : A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 5, 6, 7, 3' and 4' respectively.	1.99	1	0	flavonols; hexahydroxyflavone	antioxidant; antiviral agent; plant metabolite
scutellarein scutellarein: aglycone of scutellarin from Scutellaria baicalensis; carthamidin is 2S isomer of scutellarein; do not confuse with isoscutellarein and/or isocarthamidin which are respective regioisomers, or with the scutelarin protein. scutellarein : Flavone substituted with hydroxy groups at C-4', -5, -6 and -7.	2.6	1	0	tetrahydroxyflavone	metabolite
daidzein [no description available]	2	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
trans-2,3',4,5'-tetrahydroxystilbene trans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrol	2.6	1	0	stilbenoid
polydatin trans-piceid : A stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue.	2.6	1	0	beta-D-glucoside; monosaccharide derivative; polyphenol; stilbenoid	anti-arrhythmia drug; antioxidant; geroprotector; hepatoprotective agent; metabolite; nephroprotective agent; potassium channel modulator
pterostilbene [no description available]	2.41	1	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
chicoric acid chicoric acid: inhibits HIV-1 integrase	2.91	3	0	organooxygen compound	geroprotector; HIV-1 integrase inhibitor
echinacoside echinacoside: from Buddleja species; has antihepatotoxic activity	4.27	5	0	oligosaccharide
forsythiaside forsythiaside: RN given refers to (E)-isomer; structure given in first source; from the unripe fruit of Forsythia suspensa (qinglianquiao)	2.76	3	0	hydroxycinnamic acid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	15.17	730	1	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
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.	3	4	0	rosmarinic acid	geroprotector; plant metabolite
acteoside acteoside: a protein kinase C inhibitor with hepatoprotective, anti-asthmatic, and analgesic activities; a phenylethanoid glycoside related to isoacteoside; from leaves of Lippia multiflora (Verbenaceae). acteoside : A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid.	4.37	18	0	catechols; cinnamate ester; disaccharide derivative; glycoside; polyphenol	anti-inflammatory agent; antibacterial agent; antileishmanial agent; neuroprotective agent; plant metabolite
maytansine Maytansine: An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.. maytansine : An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines.	2.04	1	0	alpha-amino acid ester; carbamate ester; epoxide; maytansinoid; organic heterotetracyclic compound; organochlorine compound	antimicrobial agent; antimitotic; antineoplastic agent; plant metabolite; tubulin modulator
ellagic acid [no description available]	2.47	2	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
cyhalothrin cyhalothrin: acaricidal & insecticidal synthetic pyrethroid; structure given in first source. cyhalothrin : A carboxylic ester obtained by formal condensation between 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol.	2.07	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound; organofluorine compound	agrochemical; pyrethroid ester acaricide; pyrethroid ester insecticide
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	3.9	3	0	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	1.95	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
alpha-ionone alpha-ionone: RN given refers to cpd without isomeric designation; structure	2.03	1	0	enone; ionone; methyl ketone
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	3.33	2	0	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
epoprostenol [no description available]	2.05	1	0	prostaglandins I	mouse metabolite
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	3.41	7	0	thromboxanes B	human metabolite; mouse metabolite
2,4-heptadienal 2,4-heptadienal: structure in first source. (E,E)-hepta-2,4-dienal : A heptadienal in which the two double bonds are located at positions 2 and 4 (the E,E-geoisomer).	2.05	1	0	heptadienal	flavouring agent
2-octenal 2-octenal: RN given refers to cpd without isomeric designation. (E)-oct-2-enal : The (E)-isomer of oct-2-enal.. oct-2-enal : An enal consisting of oct-2-ene having an oxo group at the 1-position.	2.25	1	0	oct-2-enal	antifungal agent; volatile oil component
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	2.47	2	0	4-hydroxynon-2-enal; 4-hydroxynonenal
methyl linoleate [no description available]	2.55	2	0	fatty acid methyl ester	plant metabolite
phenylephrine hydrochloride Nose: A part of the upper respiratory tract. It contains the organ of SMELL. The term includes the external nose, the nasal cavity, and the PARANASAL SINUSES.. phenylephrine hydrochloride : A hydrochloride that is the monohydrochloride salt of phenylephrine.	2.95	4	0	hydrochloride
phenylethyl 3-methylcaffeate phenylethyl 3-methylcaffeate: a caffeic acid ester present in propolis, a natural resin produced by honey bees; structure given in first source	2.1	1	0
sarcophytol a sarcophytol A: structure given in first source; isolated from a soft coral Sarcophyton glaucum	1.98	1	0	cembrane diterpenoid
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.	2.6	1	0	sulfonamide; thiophenes	antiglaucoma drug; antihypertensive agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.55	2	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
topiramate Topiramate: A sulfamate-substituted fructose analog that was originally identified as a hypoglycemic agent. It is used for the treatment of EPILEPSY and MIGRAINE DISORDERS, and may also promote weight loss.. topiramate : A hexose derivative that is 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose in which the hydroxy group has been converted to the corresponding sulfamate ester. It blocks voltage-dependent sodium channels and is used as an antiepileptic and for the prevention of migraine.	2.6	1	0	cyclic ketal; ketohexose derivative; sulfamate ester	anticonvulsant; sodium channel blocker
fluticasone Fluticasone: A STEROID with GLUCOCORTICOID RECEPTOR activity that is used to manage the symptoms of ASTHMA; ALLERGIC RHINITIS, and ATOPIC DERMATITIS.. fluticasone : A trifluorinated corticosteroid used in the form of its propionate ester for treatment of allergic rhinitis.	2.13	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 3-oxo-Delta(4) steroid; corticosteroid; fluorinated steroid; thioester	anti-allergic agent; anti-asthmatic drug
herbimycin herbimycin: herbicidal antibiotic produced by Streptomyces sp.; see also herbimycin B; structure for herbimycin A in second source. herbimycin : A 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It is an ansamycin antibiotic that induces apoptosis and displays antitumour effects.	1.99	1	0	1,4-benzoquinones; lactam; macrocycle	antimicrobial agent; apoptosis inducer; herbicide; Hsp90 inhibitor; tyrosine kinase inhibitor
benzyloxycarbonyl-phe-ala-fluormethylketone cathepsin B inhibitor : A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).	2.6	1	0
lysophosphatidic acid lysophosphatidic acid: RN given refers to parent cpd. 1-oleoyl-sn-glycerol 3-phosphate : A 1-acyl-sn-glycerol 3-phosphate having oleoyl as the 1-O-acyl group.. lysophosphatidic acid : A member of the class of lysophosphatidic acids obtained by hydrolytic removal of one of the two acyl groups of any phosphatidic acid. A 'closed' class.	2.21	1	0	1-acyl-sn-glycerol 3-phosphate
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	2.07	1	0	1-O-acyl-sn-glycero-3-phosphocholine
mdl 100907 Serotonin 5-HT2 Receptor Antagonists: Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes.	2.03	1	0
n-(n-(3,5-difluorophenacetyl)alanyl)phenylglycine tert-butyl ester DAPT : A dipeptide consisting of alanylphenylglycine derivatised as a 3,5-difluorophenylacetamide at the amino terminal and a tert-butyl ester at the carboxy terminal. A gamma-secretase inhibitor.	2.6	1	0	carboxylic ester; difluorobenzene; dipeptide; tert-butyl ester	EC 3.4.23.46 (memapsin 2) inhibitor
stiripentol stiripentol: structure	3.06	1	0
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	2.72	3	0	phosphatidylcholine(1+)
casticin casticin: from fruit of Vitex rotundifolia; structure in second source. casticin : A tetramethoxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6, 7 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii.	2.6	1	0	dihydroxyflavone; tetramethoxyflavone	apoptosis inducer; plant metabolite
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	2.05	1	0	cinnamyl alcohol	plant metabolite
syringin syringin: a phenylpropanoid glycoside; see also eleutherosides & lyoniside for eleutheroside A: 474-58-8. syringin : A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	2.71	3	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
ethyl caffeate (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.	2.03	1	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
beta-farnesene beta-farnesene: structure given in first source	2.21	1	0	beta-farnesene
andrographolide [no description available]	2.11	1	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
icariin [no description available]	2.31	1	0	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
MeJA [no description available]	2.03	1	0	Jasmonate derivatives
beta-ocimene beta-ocimene : The trans-stereoisomer of ocimene.. (Z)-beta-ocimene : A beta-ocimene that consists of octa-1,3,6-triene bearing two methyl substituents at positions 3 and 7 (the 3Z-isomer).	2.03	1	0	beta-ocimene	plant metabolite
5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one 5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one: isolated from the Chinese herb Scutellariae radix. oroxylin A : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-6.	2.6	1	0	dihydroxyflavone; monomethoxyflavone	antineoplastic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor
(E)-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucopyranoside: Tyrosinase inhibitor from Polygonum multiflorum; structure in first source. (E)-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside : A stilbenoid that is trans-stilbene which has been substituted by hydroxy groups at positions 2, 3, 5, and 4', and in which the hydroxy group at positon 2 has then been converted to the corresponding the beta-D-glucoside.	2.6	1	0	beta-D-glucoside; resorcinols; stilbenoid	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; cyclooxygenase 2 inhibitor; platelet aggregation inhibitor
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.07	1	0
tyrphostin ag 555 [no description available]	2.6	1	0
ergosterol-5,8-peroxide ergosterol-5,8-peroxide: also inhibits sulfatase; isolated from fungus Cercospora kikuchii; structure given in first source. ergosterol peroxide : An ergostanoid that is ergosta-6,22-dien-3-ol with a peroxy group between positions 5 and 8 (the 3beta,5alpha,8alpha,22E stereoisomer). Isolated from Ganoderma lucidum and Cordyceps sinensis, it exhibits antimycobacterial, trypanocidal and antineoplastic activities.	2.06	1	0	3beta-sterol; ergostanoid; organic peroxide; phytosterols	antimycobacterial drug; antineoplastic agent; metabolite; trypanocidal drug
sulindac sulfide sulindac sulfide: sulfated analog of indomethacin & inhibitor of prostaglandin synthesis in vitro; RN given refers to cpd without isomeric designation; structure given in first source. sulindac sulfide : An aryl sulfide that is a metabolite of sulindac. A non-steroidal anti-inflammatory drug, which also has anticancer activity.	2.41	2	0	aryl sulfide; monocarboxylic acid; organofluorine compound	antineoplastic agent; apoptosis inducer; non-steroidal anti-inflammatory drug
12-hydroxy-5,8,10,14-eicosatetraenoic acid 12-Hydroxy-5,8,10,14-eicosatetraenoic Acid: A lipoxygenase metabolite of ARACHIDONIC ACID. It is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumor cell metastatic potential through activation of protein kinase C. (J Pharmacol Exp Ther 1995; 274(3):1545-51; J Natl Cancer Inst 1994; 86(15):1145-51)	2.39	2	0
bay 11-7085 BAY11-7085 : A sulfone that is benzene substituted by [(E)-2-cyanoethenyl]sulfonyl and tert-butyl groups at position 1 and 4, respectively. It is an irreversible inhibitor of IkappaB-alpha phosphorylation in cells (IC50 = 10 muM) and prevents the activation of NF-kappaB.	2.93	4	0	benzenes; nitrile; sulfone	anti-inflammatory agent; antibacterial agent; antineoplastic agent; apoptosis inducer; autophagy inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; ferroptosis inducer; NF-kappaB inhibitor
pd 151746 [no description available]	2.6	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.53	2	0	boron group element atom; elemental aluminium; metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.41	1	0	metal atom; pnictogen
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	2.5	2	0	metalloid atom; pnictogen	micronutrient
lisinopril Lisinopril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure.	2.6	1	0	dipeptide	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
verteporfin (2R,2(1)S)-8-ethenyl-2(1),2(2)-bis(methoxycarbonyl)-17-(3-methoxy-3-oxopropyl)-2,7,12,18-tetramethyl-2,2(1)-dihydrobenzo[b]porphyrin-13-propanoic acid : The 2(1),2(2),17-trimethyl ester of (2R,2(1)S)-2(1),2(2)-dicarboxy-8-ethenyl-2,7,12,18-tetramethyl-2,2(1)-dihydrobenzo[b]porphyrin-13,17-dipropanoic acid.	2.6	1	0
batimastat batimastat: structure given in first source; a synthetic matrix metalloproteinase inhibitor. batimastat : A secondary carboxamide resulting from the formal condensation of the carboxy group of (2S,3R)-5-methyl-3-{[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl}-2-[(thiophen-2-ylsulfanyl)methyl]hexanoic acid with the amino group of hydroxylamine. It a broad-spectrum matrix metalloprotease inhibitor.	2.6	1	0	hydroxamic acid; L-phenylalanine derivative; organic sulfide; secondary carboxamide; thiophenes; triamide	angiogenesis inhibitor; antineoplastic agent; matrix metalloproteinase inhibitor
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	2.6	1	0	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.79	3	0	chalcogen; nonmetal atom	macronutrient
beta-damascenone beta-damascenone: from Ipomoea pes-caprea; RN given refers to cpd without isomeric designation; RN 23726-93-4 refers to beta-damascenone; structure given in first source. beta-damascenone : A cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group.	2.49	2	0	apo carotenoid monoterpenoid; cyclic monoterpene ketone; enone	fragrance; plant metabolite; volatile oil component
2-Phenylethyl 3-phenyl-2-propenoate [no description available]	2.08	1	0	cinnamate ester
germacrene d germacrene D: RN in 9th CI Form Index for unspecified stereoisomer: 37839-63-7	2.08	1	0
deoxyribose [no description available]	1.98	1	0	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	3.1	5	0	cysteinium	fundamental metabolite
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	2.11	1	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	3.48	7	0
artepillin c artepillin C: RN refers to (E)-isomer	4.96	6	0
solanesol solanesol : A nonaprenol that is hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol substituted by 9 methyl groups at positions 3, 7, 11, 15, 19, 23, 27, 31 and 35 (the all-trans0stereoisomer).	2.6	1	0	nonaprenol; primary alcohol	plant metabolite
pepstatin pepstatin: inhibits the aspartic protease endothiapepsin	2.6	1	0	pentapeptide; secondary carboxamide	bacterial metabolite; EC 3.4.23.* (aspartic endopeptidase) inhibitor
l 685458 L 685458: a gamma-secretase inhibitor; structure in first source. L-685,458 : A peptide and carboxamide that is L-leucyl-L-phenylalaninamide, L-Leu-L-Phe-NH2, which has been acylated on the N-terminus by a Phe-Phe hydroxyethylene dipeptide isotere, 2R-benzyl-5S-tert-butoxycarbonylamino-4R-hydroxy-6-phenylhexanoic acid. Compounds based on the structure of L-685,458 are potent inhibitors of gamma-secretase, which mediates the final catalytic step that generates the amyloid beta-peptide (Abeta), which assembles into the neurotoxic aggregates in the brains of sufferers of Alzheimer's disease.	2.6	1	0	carbamate ester; monocarboxylic acid amide; peptide; secondary alcohol	EC 3.4.23.46 (memapsin 2) inhibitor; peptidomimetic
3,8-dihydroxy-6h-dibenzo(b,d)pyran-6-one 3,8-dihydroxy-6H-dibenzo(b,d)pyran-6-one: metabolite of ellagic acid	2.05	1	0	coumarins	geroprotector
bms 806 BMS 806: prevents entry of HIV into cells by binding HIV envelope protein gp120; no further info available 4/2002	2.6	1	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone [no description available]	2.6	1	0
tulobuterol hydrochloride [no description available]	2.6	1	0	organic molecular entity
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.1	1	0	2-trans-abscisic acid
salubrinal salubrinal: prevents dephosphorylation of eIF2alpha; structure in first source. salubrinal : A member of the class of quinolines that is a mixed aminal resulting from the formal condensation oftrichloroacetaldehyde with the amide nitrogen of trans-cinnamamide and the primary amino group of 1-quinolin-8-ylthiourea. It is a selective inhibitor of cellular complexes that dephosphorylate eukaryotic translation initiation factor 2 subunit alpha (eIF2alpha).	2.6	1	0	aminal; organochlorine compound; quinolines; secondary carboxamide; thioureas
1,2-dielaidoylphosphatidylethanolamine 1,2-dielaidoylphosphatidylethanolamine: RN given refers to (E,E)-isomer; member of a class of cationic lipid formulations called cytofectins	1.97	1	0
benzyl caffeate benzyl caffeate: isolated from Liaoxi propolis	2.01	1	0
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2.06	1	0	ammonium salt; inorganic sulfate salt	fertilizer
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2.41	1	0	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	3.99	3	0	chalcogen; nonmetal atom	micronutrient
dimethyl hydrogen phosphite dimethyl hydrogen phosphite: intermediate in production of insecticides or herbicides	2.03	1	0
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	2.08	1	0	chalcogen; metalloid atom
triethoxysilane [no description available]	2.25	1	0
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	2.47	2	0
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	2.44	2	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
dihydroactinidiolide dihydroactinidiolide: secretion in tail scent gland of red fox; structure	2.01	1	0
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.17	1	0
germacrone germacrone: isolated from Curcuma wenyujin	2.6	1	0	germacrane sesquiterpenoid; olefinic compound	androgen antagonist; anti-inflammatory agent; antifeedant; antifungal agent; antimicrobial agent; antineoplastic agent; antioxidant; antitussive; antiviral agent; apoptosis inducer; autophagy inducer; hepatoprotective agent; insecticide; neuroprotective agent; plant metabolite; volatile oil component
1-(1-glycero)dodeca-1,3,5,7,9-pentaene 1-(1-glycero)dodeca-1,3,5,7,9-pentaene: fecapentaene mutagen of bacterial origin from human feces; structure given in first source	2	1	0
(2e,4e,6e,10e)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid: an acyclic retinoid that suppresses hepatocellular carcinoma recurrence; structure in first source	2.6	1	0
1,2-dioleoylphosphatidylserine 1,2-dioleoylphosphatidylserine: RN given in first source; RN given refers to (R-(Z,Z))-isomer; RN for cpd without isomeric designation not available 6/90. 1,2-dioleoyl-sn-glycero-3-phospho-L-serine : A 3-sn-phosphatidyl L-serine in which the phosphatidyl acyl groups are both oleoyl.. phosphatidylserine(18:1/18:1) : A 3-sn-phosphatidyl-L-serine in which the 1- and 2-acyl groups are octadecenoyl groups.	1.97	1	0	phosphatidylserine(18:1/18:1)	mouse metabolite
caftaric acid [no description available]	2.57	2	0	hydroxycinnamic acid
lithospermic acid [no description available]	2.6	1	0
mkt 077 MKT 077: structure given in first source	2.15	1	0
laq824 LAQ824: Histone deacetylase inhibitor	2.6	1	0
ekb 569 EKB 569: an EGF receptor kinase inhibitor	2.6	1	0	aminoquinoline; monocarboxylic acid amide; monochlorobenzenes; nitrile	protein kinase inhibitor
rilpivirine [no description available]	2.6	1	0	aminopyrimidine; nitrile	EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor
(1Ar,7aS,10aS,10bS)-1a,5-dimethyl-8-methylidene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one [no description available]	2.6	1	0	germacranolide
4,5-di-O-caffeoylquinic acid [no description available]	2.6	1	0	quinic acid
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	2.6	1	0
isoacteoside isoacteoside: a phenylethanoid glycoside isolated from Indian paintbrush (Verbenaceae) Castilleja linariaefolia; also in other plants; structure given in first source	2.52	2	0	hydroxycinnamic acid
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,.	1.98	1	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.	2.04	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
sq-23377 Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.	2.05	1	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
artesunate artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether	2.6	1	0	artemisinin derivative; cyclic acetal; dicarboxylic acid monoester; hemisuccinate; semisynthetic derivative; sesquiterpenoid	antimalarial; antineoplastic agent; ferroptosis inducer
(3S,6S,9S,12R)-3-[(2S)-Butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone [no description available]	2.6	1	0	oligopeptide
vildagliptin [no description available]	2.6	1	0	amino acid amide
belinostat [no description available]	2.6	1	0	hydroxamic acid; olefinic compound; sulfonamide	antineoplastic agent; EC 3.5.1.98 (histone deacetylase) inhibitor
hdac-42 HDAC-42: structure in first source	2.6	1	0	amidobenzoic acid
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	2.66	2	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
gs-7340 tenofovir alafenamide: component of Biktarvy. tenofovir alafenamide : An L-alanine derivative that is isopropyl L-alaninate in which one of the amino hydrogens is replaced by an (S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl group. A prodrug for tenofovir, it is used (as the fumarate salt) in combination therapy for the treatment of HIV-1 infection.	2.6	1	0	6-aminopurines; ether; isopropyl ester; L-alanine derivative; phosphoramidate ester	antiviral drug; HIV-1 reverse transcriptase inhibitor; prodrug
iniparib [no description available]	2.6	1	0	carbonyl compound; organohalogen compound
n-(2-amino-5-fluorobenzyl)-4-(n-(pyridine-3-acrylyl)aminomethyl)benzamide [no description available]	2.6	1	0
pri-2205 [no description available]	2.6	1	0
mk 0752 [no description available]	2.6	1	0
givinostat [no description available]	2.6	1	0	carbamate ester
pd 144418 [no description available]	2.6	1	0
bicyclol bicyclol: an antihepatitis drug, on the metabolism and hepatotoxicity of aflatoxin B1 (AFB1) in rats.	2.6	1	0
rosavin rosavin: isolated from Rhodiola rosea; structure in first source	4.08	4	0	O-acyl carbohydrate
midostaurin midostaurin : An organic heterooctacyclic compound that is the N-benzoyl derivative of staurosporine.	2.6	1	0	benzamides; gamma-lactam; indolocarbazole; organic heterooctacyclic compound	antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	2.39	2	0	oligopeptide
ly 450139 [no description available]	2.6	1	0	peptide
pentagastrin Pentagastrin: A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid.	2.02	1	0	organic molecular entity
cabazitaxel cabazitaxel: an antineoplastic agent; structure in first source. cabazitaxel : A tetracyclic diterpenoid that is 10-deacetylbaccatin III having O-methyl groups attached at positions 7 and 10 as well as an O-(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl group attached at position 13. Acts as a microtubule inhibitor, binds tubulin and promotes microtubule assembly and simultaneously inhibits disassembly.	2.25	1	0	tetracyclic diterpenoid	antineoplastic agent; microtubule-stabilising agent
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).	4.61	25	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
rivaroxaban Rivaroxaban: A morpholine and thiophene derivative that functions as a FACTOR XA INHIBITOR and is used in the treatment and prevention of DEEP-VEIN THROMBOSIS and PULMONARY EMBOLISM. It is also used for the prevention of STROKE and systemic embolization in patients with non-valvular ATRIAL FIBRILLATION, and for the prevention of atherothrombotic events in patients after an ACUTE CORONARY SYNDROME.. rivaroxaban : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-chlorothiophene-2-carboxylic acid with the amino group of 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. An anticoagulant used for prophylaxis of venous thromboembolism in patients with knee or hip replacement surgery.	2.6	1	0	aromatic amide; lactam; monocarboxylic acid amide; morpholines; organochlorine compound; oxazolidinone; thiophenes	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor
sb 3ct compound SB 3CT compound: a matrix metalloproteinase-2 inhibitor; structure in first source	2.6	1	0	aromatic ether
gw 4064 [no description available]	2.15	1	0	stilbenoid
ginsenoside rb1 [no description available]	2.6	1	0	ginsenoside; glycoside; tetracyclic triterpenoid	anti-inflammatory drug; anti-obesity agent; apoptosis inhibitor; neuroprotective agent; plant metabolite; radical scavenger
rucaparib AG14447: Poly(ADP-ribose) polymerase inhibitor; structure in first source	2.6	1	0	azepinoindole; caprolactams; organofluorine compound; secondary amino compound	antineoplastic agent; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
6h-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide, 4-(4-chlorophenyl)-n-(4-hydroxyphenyl)-2,3,9-trimethyl-, (6s)- [no description available]	2.6	1	0	organonitrogen heterocyclic compound; organosulfur heterocyclic compound
zeolites [no description available]	2.02	1	0
cetilistat cetilistat: lipase inhibitor in randomized, placebo-controlled study of weight reduction in obese patients (3/2007)	2.6	1	0	benzoxazine
ym 201636 6-amino-N-(3-(4-(4-morpholinyl)pyrido(3',2'-4,5)furo(3,2-d)pyrimidin-2-yl)phenyl)-3-pyridinecarboxamide: an antiviral agent; structure in first source	2.6	1	0	aromatic amide
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.08	1	0
linagliptin Linagliptin: A purine and quinazoline derivative that functions as an INCRETIN and DIPEPTIDYL-PEPTIDASE IV INHIBTOR. It is used as a HYPOGLYCEMIC AGENT in the treatment of TYPE II DIABETES MELLITUS.. linagliptin : A xanthine that is 7H-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the R-enantiomer). Used for treatment of type II diabetes.	2.6	1	0	aminopiperidine; quinazolines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
beta-bisabolene (S)-beta-bisabolene : A beta-bisabolene which has (1S)-configuration.. beta-bisabolene : A bisabolene that is cyclohexene substituted by a methyl group at position 1 and a 6-methylhepta-1,5-dien-2-yl group at position 4.	2.08	1	0	beta-bisabolene
azd 6244 AZD 6244: a MEK inhibitor	2.6	1	0	benzimidazoles; bromobenzenes; hydroxamic acid ester; monochlorobenzenes; organofluorine compound; secondary amino compound	anticoronaviral agent; antineoplastic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
cerebroside d cerebroside D: isolated from the fungus Lactarium volemus; structure in first source	2.06	1	0
odanacatib odanacatib: a selective inhibitor of cathepsin K for the treatment of post-menopausal osteoporosis; structure in first source	2.6	1	0
apilimod [no description available]	2.6	1	0
cerevisterol cerevisterol: in mushroom family; Russian. cerevisterol : An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 6 (the 3beta,5alpha,6beta stereoisomer). It has been isolated from the fungus, Xylaria species.	2.06	1	0	3beta-hydroxy steroid; 5alpha-hydroxy steroid; 6beta-hydroxy steroid; ergostanoid	Aspergillus metabolite
apixaban [no description available]	2.6	1	0	aromatic ether; lactam; piperidones; pyrazolopyridine	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor
betrixaban betrixaban: a highly potent, selective, and orally efficacious factor Xa inhibitor; structure in first source. betrixaban : A secondary carboxamide obtained by formal condensation of the carboxy group of 4-(N,N-dimethylcarbamimidoyl)benzoic acid with the amino group of 2-amino-N-(5-chloropyridin-2-yl)-5-methoxybenzamide. A synthetic anticoagulant compound that targets activated factor Xa in the coagulation cascade.	2.6	1	0	benzamides; guanidines; monochloropyridine; monomethoxybenzene; secondary carboxamide	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor
edoxaban edoxaban : A monocarboxylic acid amide that is used (as its tosylate monohydrate) for the treatment of deep vein thrombosis and pulmonary embolism.	2.6	1	0	chloropyridine; monocarboxylic acid amide; tertiary amino compound; thiazolopyridine	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor; platelet aggregation inhibitor
saracatinib [no description available]	2.6	1	0	aromatic ether; benzodioxoles; diether; N-methylpiperazine; organochlorine compound; oxanes; quinazolines; secondary amino compound	anticoronaviral agent; antineoplastic agent; apoptosis inducer; autophagy inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; radiosensitizing agent
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	3.84	9	0
rosarin rosarin: isolated from Rhodiola rosea; structure in first source	2.75	3	0	O-acyl carbohydrate
n-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-(2-((((1,1-dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexan-2-carboxamide boceprevir : A synthetic tripeptide consisting of N-(tert-butylcarbamoyl)-3-methyl-L-valyl, a cyclopropyl-fused prolyl and 3-amino-4-cyclobutyl-2-oxobutanamide residues joined in sequence. Used for treatment of chronic hepatitis C virus genotype 1 infection.	2.6	1	0	tripeptide; ureas	antiviral drug; hepatitis C protease inhibitor; peptidomimetic
ly 411575 [no description available]	2.6	1	0	dibenzoazepine; difluorobenzene; lactam; secondary alcohol	EC 3.4.23.46 (memapsin 2) inhibitor
galidesivir [no description available]	2.6	1	0
sb 215505 SB 215505: a neuroleptic with equivalent or higher antagonist affinity for 5-HT2 than for dopamine D2 receptor	2.03	1	0
5s,12r,18r-trihydroxy-6z,8e,10e,14z,16e-eicosapentaenoic acid 5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-eicosapentaenoic acid: a bioactive oxygenated product of EPA, was identified in human plasma and prepared by total organic synthesis; structure in first source. resolvin E1 : A resolvin that is (6Z,8E,10E,14Z,16E)-icosa-6,8,10,14,16-pentaenoic acid which is substituted at positions 5, 12 and 18 by hydroxy groups (the 5S,12R,18R stereoisomer).	2.21	1	0	hydroxy polyunsaturated fatty acid; long-chain fatty acid; nonclassic icosanoid; resolvin; triol	anti-inflammatory agent; human xenobiotic metabolite
PB28 PB28 : A member of the class of tetralins that is tetralin that is substituted by 3-(4-cyclohexylpiperazin-1-yl)propyl and methoxy groups at positions 1 and 5, respectively. It is a sigma 2 (sigma2) receptor agonist (Ki = 0.68 nM) and exhibits antineoplastic and anti SARS-CoV-2 activities.	2.6	1	0	aromatic ether; piperazines; tetralins	anticoronaviral agent; antineoplastic agent; apoptosis inducer; sigma-2 receptor agonist
2-hydroxy-3-methylanthraquinone 2-hydroxy-3-methylanthraquinone: apoptosis-inducing compound from Hedyotis diffusa WILLD; structure in first source	2.1	1	0
ucn 1028 c calphostin C: structure given in first source; isolated from Cladosporium cladosporioides	2.05	1	0
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.	2.04	1	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
degrasyn degrasyn: a JAK2 kinase inhibitor that induces rapid degradation of c-Myc protein in MM-1 multiple myeloma and other tumor cell lines; structure in first source	2.6	1	0
epoxomicin [no description available]	2.6	1	0	morpholines; tripeptide	proteasome inhibitor
bms 477118 [no description available]	2.6	1	0	adamantanes; azabicycloalkane; monocarboxylic acid amide; nitrile; tertiary alcohol	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
pha 680632 PHA 680632: Aurora kinase inhibitor with potent antitumoral activity; structure in first source	2.6	1	0
tmc 353121 [no description available]	2.6	1	0
procyanidin b1 procyanidin B1 : A proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach.	2.11	1	0	biflavonoid; hydroxyflavan; polyphenol; proanthocyanidin	anti-inflammatory agent; EC 3.4.21.5 (thrombin) inhibitor; metabolite
amd 070 mavorixafor: a derivative of AMD3100; a CXCR4 blocker	2.6	1	0	aminoquinoline
danoprevir [no description available]	2.6	1	0
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	1.95	1	0	nystatins
bms-626529 [no description available]	2.6	1	0
bms-663068 fostemsavir: an HIV-1 attachment inhibitor; structure in first source	2.6	1	0
resolvin d2 resolvin D2: structure in first source; a potent endogenous regulator of excessive inflammatory responses that acts via multiple cellular targets to stimulate resolution and preserve immune vigilance. resolvin D2 : A member of the class of resolvins that is (4Z,8E,10Z,12E,14E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 7, 16 and 17 (the 7S,16R,17S-stereoisomer).	2.21	1	0	hydroxy polyunsaturated fatty acid; resolvin; secondary allylic alcohol; triol	anti-inflammatory agent; anti-obesity agent; estrogen receptor agonist; human xenobiotic metabolite; rat metabolite
ks370g KS370G: antihyperglycemic; structure in first source	2.49	2	0
amenamevir ASP2151: a herpesvirus helicase-primase inhibitor, in a guinea pig model of genital herpes; structure in first source	2.6	1	0
vx 765 belnacasan: a NSAID	2.6	1	0	dipeptide
Dihydrotanshinone I dihydrotanshinone I: extracted from Radix Salviae	2.6	1	0	abietane diterpenoid	anticoronaviral agent
alogliptin alogliptin: structure in first source. alogliptin : A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes.	2.6	1	0	nitrile; piperidines; primary amino compound; pyrimidines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
fr 180204 FR 180204: structure in first source	2.6	1	0	pyrazoles; ring assembly
dorsomorphin dorsomorphin: an AMPK inhibitor. dorsomorphin : A pyrazolopyrimidine that is pyrazolo[1,5-a]pyrimidine which is substituted at positions 3 and 6 by pyridin-4-yl and p-[2-(piperidin-1-yl)ethoxy]phenyl groups, respectively. It is a potent, selective, reversible, and ATP-competitive inhibitor of AMPK (AMP-activated protein kinase, EC 2.7.11.31) and a selective inhibitor of bone morphogenetic protein (BMP) signaling.	2.06	1	0	aromatic ether; piperidines; pyrazolopyrimidine; pyridines	bone morphogenetic protein receptor antagonist; EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} inhibitor
quisinostat [no description available]	2.6	1	0	indoles
carfilzomib [no description available]	2.6	1	0	epoxide; morpholines; tetrapeptide	antineoplastic agent; proteasome inhibitor
hcv 796 HCV 796: inhibits HCV RdRp; structure in first source	2.6	1	0
resminostat resminostat: a histone deacetylase inhibitor; structure in first source	2.6	1	0
crizotinib Crizotinib: A piperidine and aminopyridine derivative that acts as an inhibitor of RECEPTOR PROTEIN-TYROSINE KINASES, including ANAPLASTIC LYMPHOMA KINASE (ALK) and HEPATOCYTE GROWTH FACTOR RECEPTOR (HGFR; c-Met). It is used in the treatment of NON-SMALL CELL LUNG CANCER.. crizotinib : A 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine that has R configuration at the chiral centre. The active enantiomer, it acts as a kinase inhibitor and is used for the treatment of patients with locally advanced or metastatic non-small cell lung cancer (NSCLC)	2.15	1	0	3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine	antineoplastic agent; biomarker; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
2,4,3',5'-tetrahydroxystilbene oleocanthal: newly pressed extra-virgin olive oil contains oleocanthal, acting as a natural anti-inflammatory compound that has a potency and profile strikingly similar to that of ibuprofen; structure in first source. oleocanthal : A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.	5.56	7	0
zk 756326 2-(2-(4-(3-phenoxybenzyl)piperazin-1-yl)ethoxy)ethanol: a CC chemokine receptor CCR8 agonist; structure in first source	2.6	1	0	aromatic ether
balapiravir balapiravir: a prodrug of R1479; structure in first source	2.6	1	0
trametinib [no description available]	2.6	1	0	acetamides; aromatic amine; cyclopropanes; organofluorine compound; organoiodine compound; pyridopyrimidine; ring assembly	anticoronaviral agent; antineoplastic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
deoxyarbutin 4-((tetrahydro-2H-pyran-2-yl)oxy)phenol: has antineoplastic activity; structure in first source	2.6	1	0
abexinostat abexinostat: structure in first source	2.6	1	0	benzofurans
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.	2.11	1	0
silvestrol silvestrol: isolated from the fruit and twig of Aglaia silvestris. silvestrol : An organic heterotricyclic compound that consists of a 2,3,3a,8b-tetrahydro-H-benzo[b]cyclopenta[d]furan framework substituted by hydroxy groups at positions C-1 and C-8b, a methoxycarbonyl group at C-2, a phenyl group at C-3, a 4-methoxyphenyl group at C-3a, a methoxy group at C-8 and a 1,4-dioxan-2-yloxy group at position C-6 which in turn is substituted by a methoxy group at position 3 and a 1,2-dihydroxyethyl group at position 6. Isolated from Aglaia silvestris, it exhibits antineoplastic activity.	2.6	1	0	dioxanes; ether; methyl ester; organic heterotricyclic compound	antineoplastic agent; metabolite
narlaprevir narlaprevir: an antiviral agent that inhibits hepatitis C virus NS3 protease. narlaprevir : An azabicyclohexane that is (1R,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane substituted by [(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]aminoacyl and N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl groups at positions 2S and 3, respectively. It is a hepatitis C virus (HCV) NS3/4A serine protease inhibitor (Ki = 6 nM) that is used for the treatment of chronic hepatitis C.	2.6	1	0	azabicyclohexane; cyclopropanes; pyrrolidinecarboxamide; secondary carboxamide; sulfone; tertiary carboxamide; ureas	anticoronaviral agent; antiviral drug; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; hepatitis C protease inhibitor
teneligliptin [no description available]	2.6	1	0	amino acid amide
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	2	1	0	benzoxazole
dextrothyroxine [no description available]	2.69	2	0
veliparib [no description available]	2.6	1	0	benzimidazoles	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
scopolamine hydrobromide [no description available]	2.69	2	0
dactolisib dactolisib: antineoplastic agent that inhibits both phosphatidylinositol 3-kinase and mTOR. dactolisib : An imidazoquinoline that is 3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinoline substituted at position 1 by a 4-(1-cyanoisopropyl)phenyl group and at position 8 by a quinolin-3-yl group. A dual PI3K/mTOR inhibitor used in cancer treatment.	2.15	1	0	imidazoquinoline; nitrile; quinolines; ring assembly; ureas	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; mTOR inhibitor
pf 03491390 [no description available]	2.6	1	0
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.45	2	0
alloin [no description available]	2.6	1	0	anthracenes; C-glycosyl compound; cyclic ketone; phenols	laxative; metabolite
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.05	1	0
ants Ants: Insects of the family Formicidae, very common and widespread, probably the most successful of all the insect groups. All ants are social insects, and most colonies contain three castes, queens, males, and workers. Their habits are often very elaborate and a great many studies have been made of ant behavior. Ants produce a number of secretions that function in offense, defense, and communication. (From Borror, et al., An Introduction to the Study of Insects, 4th ed, p676)	2.55	2	0
ligstroside ligstroside: structure in first source. ligstroside : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 4-hydroxyphenethyl ester (the 2S,3E,4S stereoisomer). An important phenolic compound present in olive cultivars.	4.11	4	0	beta-D-glucoside; diester; methyl ester; phenols; pyrans; secoiridoid glycoside	antineoplastic agent; plant metabolite
lyoniside lyoniside: see also eleutherosides & syringin for eleutheroside B: 118-34-3; RN given refers to (3beta)-isomer	2.02	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	4.13	5	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
mdv 3100 [no description available]	2.6	1	0	(trifluoromethyl)benzenes; benzamides; imidazolidinone; monofluorobenzenes; nitrile; thiocarbonyl compound	androgen antagonist; antineoplastic agent
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.	4.05	14	0
resolvin e2 resolvin E2: structure in first source; derivative of eicosapentaenoic acid in contrast to resolvin D that derives from docosahexaenoic acid. resolvin E2 : A member of the class of resolvins that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid carrying two hydroxy substituents at positions 5 and 18 (the 5S,18R stereoisomer).	2.21	1	0	diol; hydroxy polyunsaturated fatty acid; resolvin; secondary allylic alcohol	anti-inflammatory agent; human xenobiotic metabolite; rat metabolite
bms-650032 asunaprevir: an NS3 protease inhibitor against hepatitis C virus	2.6	1	0	oligopeptide
rg 7128 2'-fluoro-2'-methyl-3',5'-diisobutyryldeoxycytidine: inhibits HCV polymerase; structure in first source	2.6	1	0
agrimoniin agrimoniin: tannin of Agrimonia pilosa; structure given in first source. agrimoniin : A dimeric hydrolysable tannin in which 2 moles of potentillin monomer are linked via a dehydrogalloyl group; an antitumor tannin of Agrimonia pilosa Ledeb., which induces interleukin-1.	2.03	1	0	tannin
ceruletide Ceruletide: A specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein is similar in action and composition to CHOLECYSTOKININ. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.. ceruletide : A decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction.	2.05	1	0	oligopeptide	diagnostic agent; gastrointestinal drug
vitisin a [no description available]	2.11	1	0	benzofurans
iberiotoxin [no description available]	2.02	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	3.54	2	0
oligonucleotides [no description available]	1.98	1	0
liraglutide [no description available]	3.94	2	0	lipopeptide; polypeptide	glucagon-like peptide-1 receptor agonist; neuroprotective agent
oritavancin oritavancin : A semisynthetic glycopeptide used (as its bisphosphate salt) for the treatment of acute bacterial skin and skin structure infections caused or suspected to be caused by susceptible isolates of designated Gram-positive microorganisms including MRSA.	2.6	1	0	disaccharide derivative; glycopeptide; semisynthetic derivative	antibacterial drug; antimicrobial agent
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3.76	10	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)	2.11	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.96	4	0	1,2-diacyl-sn-glycero-3-phosphocholine
(9R)-9-chloro-11,17-dihydroxy-17-(2-hydroxy-1-oxoethyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one Beclomethasone: An anti-inflammatory, synthetic glucocorticoid. It is used topically as an anti-inflammatory agent and in aerosol form for the treatment of ASTHMA.. beclomethasone : A 17alpha-hydroxy steroid that is prednisolone in which the hydrogens at the 9alpha and 16beta positions are substituted by a chlorine and a methyl group, respectively.	2.41	2	0	21-hydroxy steroid
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	3.05	4	0	chlorophyll; methyl ester	cofactor
pevonedistat pevonedistat: a potent and selective inhibitor of NAE (NEDD8-activating enzyme). pevonedistat : A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine which is substituted by a (1S)-2,3-dihydro-1H-inden-1-ylnitrilo group at position 4 and by a (1S,3S,4S)-3-hydroxy-4-[(sulfamoyloxy)methyl]cyclopentyl group at position 7. It is a potent and selective NEDD8-activating enzyme inhibitor with an IC50 of 4.7 nM, and currently under clinical investigation for the treatment of acute myeloid leukemia (AML) and myelodysplastic syndromes.	2.6	1	0	cyclopentanols; indanes; pyrrolopyrimidine; secondary amino compound; sulfamidate	antineoplastic agent; apoptosis inducer
uk 453,061 UK 453,061: a reverse transcriptase inhibitor/anti-HIV agent; structure in first source	2.6	1	0	aromatic ether
sodium salicylate [no description available]	1.99	1	0	organic molecular entity
N-(2-aminophenyl)-2-pyrazinecarboxamide [no description available]	2.6	1	0	aromatic amide
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	4.61	4	0
argpyrimidine argpyrimidine: structure given in first source. argpyrimidine : A member of the class of hydroxypyrimidines obtained by cyclocondensation of L-arginine and methylglyoxal; a methyl glyoxal-derived advanced glycation end-product (AGE) in familial amyloidotic polyneuropathy and human cancers.	2.15	1	0	hydroxypyrimidine; L-arginine derivative; non-proteinogenic alpha-amino acid	epitope
pinoresinol pinoresinol: in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol. pinoresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl groups.	4.38	7	0
3,4-dihydroxyphenylethanol-elenolic acid dialdehyde oleacein: found in olive oil; structure in first source	5.71	8	0	alcohol; phenols
2'-acetylacteoside 2'-acetylacteoside: hepatoprotective agent isolated from Cistanch deserticola; structure in first source	2.25	1	0
chitosan [no description available]	3.87	10	0
invert sugar invert sugar: mixture of approx 50% dextrose & 50% levulose obtained by acid hydrolysis of cane sugar	1.97	1	0
tegobuvir tegobuvir: a non-structural protein 5B polymerase inhibitor	2.6	1	0
pf-429242 PF-429242: a subtilisin kexin isozyme-1/site-1 protease inhibitor	2.6	1	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	1.96	1	0	3',5'-cyclic purine nucleotide
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	2.61	2	0	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
olaparib [no description available]	2.6	1	0	cyclopropanes; monofluorobenzenes; N-acylpiperazine; phthalazines	antineoplastic agent; apoptosis inducer; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
methyl jasmonate [no description available]	2.46	2	0
cx 4945 [no description available]	2.6	1	0
pci 34051 PCI 34051: an HDAC8 inhibitor	2.6	1	0	indolecarboxamide
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.	2.4	2	0	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lomibuvir lomibuvir: an antiviral agent with polymerase NS5 inhibitory activity	2.6	1	0	thiophenecarboxylic acid
delanzomib [no description available]	2.6	1	0	C-terminal boronic acid peptide; phenylpyridine; secondary alcohol; threonine derivative	antineoplastic agent; apoptosis inducer; proteasome inhibitor
ethyl cellulose [no description available]	2.25	1	0	glycoside
pitavastatin(1-) pitavastatin(1-) : A hydroxy monocarboxylic acid anion that is the conjugate base of pitavastatin, obtained by deprotonation of the carboxy group.	2.6	1	0	hydroxy monocarboxylic acid anion
GRL-0617 GRL-0617 : A benzamide resulting from the formal condensation of the carboxy group of 5-amino-2-methylbenzoic acid with the amino group of (1R)-1-(naphthalen-1-yl)ethan-1-amine. It is a potent noncovalent inhibitor (IC50 = 600 nM) of severe acute respiratory syndrome-coronavirus papain-like protease (SARS-CoV PLpro).	2.6	1	0	benzamides; naphthalenes; secondary carboxamide; substituted aniline	anticoronaviral agent; protease inhibitor
N-[4-[3-[[[7-(hydroxyamino)-7-oxoheptyl]amino]-oxomethyl]-5-isoxazolyl]phenyl]carbamic acid tert-butyl ester CAY10603: a HDAC6 inhibitor	2.6	1	0	carbamate ester
niraparib niraparib: structure in first source. niraparib : A 2-[4-(piperidin-3-yl)phenyl]-2H-indazole-7-carboxamide that has S-configuration. It is a potent inhibitor of PARP1 and PARP2 (IC50 of 3.8 and 2.1 nM, respectively) and approved as a first-line maintenance treatment for women with advanced ovarian cancer after responding to platinum-based chemotherapy.	2.6	1	0	2-[4-(piperidin-3-yl)phenyl]-2H-indazole-7-carboxamide	antineoplastic agent; apoptosis inducer; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; radiosensitizing agent
jzl 184 JZL 184: inhibits monoacylglycerol lipase; structure in first source	2.6	1	0	benzodioxoles
gsk 650394 [no description available]	2.6	1	0	phenylpyridine
oprozomib ONX 0912: antineoplastic; an orally active proteasome inhibitor; structure in first source	2.6	1	0
az 960 [no description available]	2.6	1	0
golgicide a golgicide A: inhibits the cis-golgi ArfGEF GBF1; structure in first source. golgicide A : A diastereoisomeric mixture comprising racemic cis- and racemic trans-goglioside A in a 10:1 ratio. It is a potent and rapidly reversible GBF1 (Golgi-specific brefeldin A-resistance guanine nucleotide exchange factor 1) inhibitor. The (3aS,4R,9bR) isomer is the most active (see Bioorg. Med. Chem. Lett., 2012, 22, 5177-5181).	2.6	1	0	diastereoisomeric mixture	cis-Golgi ArfGEF GBF inhibitor
poziotinib HM781-36B: antitumor irreversible Pan-HER inhibitor for treatment of gastric cancer	2.31	1	0	acrylamides; aromatic ether; dichlorobenzene; diether; monofluorobenzenes; N-acylpiperidine; quinazolines; secondary amino compound; substituted aniline	antineoplastic agent; apoptosis inducer; epidermal growth factor receptor antagonist
cobicistat [no description available]	2.6	1	0	1,3-thiazoles; carbamate ester; monocarboxylic acid amide; morpholines; ureas	P450 inhibitor
bms-790052 daclatasvir: an HCV NS5A inhibitor. daclatasvir : A member of the class of biphenyls that is a potent inhibitor of nonstructural protein 5A and is used (as its hydrochloride salt) for treatment of hepatitis C.	2.6	1	0	biphenyls; carbamate ester; carboxamide; imidazoles; valine derivative	antiviral drug; nonstructural protein 5A inhibitor
ixazomib ixazomib: a proteasome inhibitor with antineoplastic activity; MLN2238 is the biologically active form of MLN9708; structure in first source. ixazomib : A glycine derivative that is the amide obtained by formal condensation of the carboxy group of N-(2,5-dichlorobenzoyl)glycine with the amino group of [(1R)-1-amino-3-methylbutyl]boronic acid. The active metabolite of ixazomib citrate, it is used in combination therapy for treatment of multiple myeloma.	2.6	1	0	benzamides; boronic acids; dichlorobenzene; glycine derivative	antineoplastic agent; apoptosis inducer; drug metabolite; orphan drug; proteasome inhibitor
ucph 101 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile: structure in first source	2.6	1	0
2-hydroxy-5-carboxymethylmuconate semialdehyde 2-hydroxy-5-carboxymethylmuconate semialdehyde: metabolite of 3,4-dihydroxyphenylacetate; structure. 5-formyl-2-hydroxyhepta-2,4-dienedioate : Dicarboxylate anion of 5-formyl-2-hydroxyhepta-2,4-dienedioic acid; major species at pH 7.3.	2.03	1	0
3-deoxygalactosone 3-deoxygalactosone: galactose degradation product isolated from milk products; structure in first source	2.15	1	0
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	2.04	1	0
5-(3-methylsulfonylphenyl)-4-[(1-methyl-5-tetrazolyl)thio]thieno[2,3-d]pyrimidine [no description available]	2.6	1	0	aryl sulfide; thienopyrimidine
baricitinib [no description available]	2.6	1	0	azetidines; nitrile; pyrazoles; pyrrolopyrimidine; sulfonamide	anti-inflammatory agent; antirheumatic drug; antiviral agent; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; immunosuppressive agent
KOM70144 KOM70144 : A benzamide that is GRL-0617 in which one of the hydrogen's of the primary amino group is replaced by an acetyl group. It an inhibitor of SARS-CoV and SARS-CoV-2 papain-like protease (PLpro) with an IC50 of 2.6 muM and 5.0 muM, respectively. It also inhibits SARS-CoV and SARS-CoV-2 infection of Vero E6 cells in vitro (EC50 values are 13.1 and 21 muM, respectively).	2.6	1	0	acetamides; benzamides; naphthalenes; secondary carboxamide	anticoronaviral agent; protease inhibitor
e-52862 [no description available]	2.6	1	0
resolvin d1 resolvin D1: an anti-inflammatory lipid mediator; structure in first source. resolvin D1 : A resolvin that is docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid which is substituted by hydroxy groups at the 7, 8, and 17 positions (the 7S,8R,17S-stereoisomer).	2.21	1	0	hydroxy polyunsaturated fatty acid; resolvin; triol	anti-inflammatory agent
ly2811376 [no description available]	2.6	1	0
5-hydroxymethyl-2'-deoxyuridine 5-hydroxymethyl-2'-deoxyuridine : A pyrimidine 2'-deoxyribonucleoside composed of 2'-deoxyuridine having a 5-hydroxymethyl substituent.	1.98	1	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	6.07	10	1
4-hydroxymellein 4-hydroxymellein: alpha-Glucosidase Inhibitor from Xylaria feejeensis associated with Hintonia latiflora; structure in first source. 4-hydroxymellein : An isochromane that is mellein bearing a hydroxy group at position 4.	2.15	1	0
anagliptin anagliptin: anagliptin hydrochloride salt is the active compound	2.6	1	0	amino acid amide
punicalagin punicalagin: hepatoprotective agent isolated from Terminalia catappa; structure in first source	3.8	1	1	tannin
gardiquimod [no description available]	2.6	1	0
grazoprevir grazoprevir: has antiviral activity; component of Zepatier. grazoprevir : An azamacrocyclic compound that is a hepatitis C protease inhibitor used in combination with elbasvir (under the brand name Zepatier) for treatment of chronic HCV genotypes 1 or 4 infection in adults.	2.6	1	0	aromatic ether; azamacrocycle; carbamate ester; cyclopropanes; lactam; N-sulfonylcarboxamide; quinoxaline derivative	antiviral drug; hepatitis C protease inhibitor; hepatoprotective agent
darendoside a darendoside A: from Scutellaria orientalis subsp. pinnatifida; structure given in first source	1.98	1	0
abt-450 paritaprevir: inhibits HCV NS3 protease. paritaprevir : An azamacrocycle which is used which is in combination with dasabuvir sodium hydrate, ombitasvir and ritonavir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	2.6	1	0
letermovir letermovir: has antiviral activity; structure in first source	2.6	1	0
sofosbuvir Sofosbuvir: A uridine monophosphate analog inhibitor of HEPATITIS C VIRUS (HCV) polymerase NS5B that is used as an ANTIVIRAL AGENT in the treatment of CHRONIC HEPATITIS C.. sofosbuvir : A nucleotide conjugate that is used in combination with ledipasvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.	2.6	1	0	isopropyl ester; L-alanyl ester; nucleotide conjugate; organofluorine compound; phosphoramidate ester	antiviral drug; hepatitis C protease inhibitor; prodrug
5-(4-amino-1-propan-2-yl-3-pyrazolo[3,4-d]pyrimidinyl)-1,3-benzoxazol-2-amine sapanisertib: an mTOR inhibitor	2.6	1	0	benzoxazole
blz 945 [no description available]	2.6	1	0
azd3839 AZD3839: a BACE1 inhibitor; structure in first source	2.6	1	0
pf 3084014 nirogacestat: an antineoplastic agent. nirogacestat : A member of the class of imidazoles that is 1H-imidazole substituted by a 1-[(2,2-dimethylpropyl)amino]-2-methylpropan-2-yl group at position 1 and a {N-[(2S)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]-L-norvalyl}amino group at position 4. It is a gamma-secretase inhibitor whose hydrobromide salt is indicated for adult patients with progressing desmoid tumours who require systemic treatment.	2.6	1	0
unc 0638 UNC 0638: inhibits lysine methyltransferases G9a and GLP; structure in first source	2.6	1	0	quinazolines
gs-9620 [no description available]	2.6	1	0
n-((5-(methanesulfonyl)pyridin-2-yl)methyl)-6-methyl-5-(1-methyl-1h-pyrazol-5-yl)-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide N-((5-(methanesulfonyl)pyridin-2-yl)methyl)-6-methyl-5-(1-methyl-1H-pyrazol-5-yl)-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide: structure in first source	2.6	1	0
bms 708163 BMS 708163: structure in first source	2.6	1	0	oxadiazole; ring assembly
jq1 compound [no description available]	2.6	1	0	carboxylic ester; organochlorine compound; tert-butyl ester; thienotriazolodiazepine	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; bromodomain-containing protein 4 inhibitor; cardioprotective agent; ferroptosis inducer
1-(5-((2,4-difluorophenyl)thio)-4-nitrothiophen-2-yl)ethanone 1-(5-((2,4-difluorophenyl)thio)-4-nitrothiophen-2-yl)ethanone: a USP7 inhibitor; structure in first source	2.6	1	0
gsk525762a molibresib: mimicks acetylated histones; structure in first source	2.6	1	0	benzodiazepine
ML240 ML240 : A member of the class of quinazolines that is quinazoline which is substituted at positions 2, 5 and 8 by 2-amino-1H-benzimidazol-1-yl, benzylnitrilo and methoxy groups, respectively. It is a ATP-competetive inhibitor of AAA ATPase p97, also known as valosin-containing protein (VCP).	2.6	1	0	aromatic amine; aromatic ether; benzimidazoles; primary amino compound; quinazolines; secondary amino compound	antineoplastic agent
birinapant birinapant: a Smac mimetic with antineoplastic activity	2.6	1	0	dipeptide
ly2886721 [no description available]	2.6	1	0
nms-p118 NMS-P118: a PARP-1 inhibitor; structure in first source	2.6	1	0
tubastatin a [no description available]	2.6	1	0	hydroxamic acid; pyridoindole; tertiary amino compound	EC 3.5.1.98 (histone deacetylase) inhibitor
pracinostat pracinostat : A hydroxamic acid that is N-hydroxyacrylamide which is substituted at position 3 by a 2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl group (the E isomer). An orally available pan-histone deacetylase inhibitor with demonstrated activity in the treatment of advanced solid tumours.	2.6	1	0	benzimidazole; hydroxamic acid; olefinic compound; tertiary amino compound	antimalarial; antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
spautin-1 [no description available]	2.6	1	0
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	1.94	1	0
isoquercitrin [no description available]	2	1	0
ldn 57444 LDN 57444: inhibitor of ubiquitin C-terminal hydrolase-L1; structure in first source	2.6	1	0
gsk1210151a GSK1210151A: inhibitor of the BET family of proteins; structure in first source	2.6	1	0	imidazoquinoline
i-bet726 [no description available]	2.6	1	0
vasoactive intestinal peptide Vasoactive Intestinal Peptide: A highly basic, 28 amino acid neuropeptide released from intestinal mucosa. It has a wide range of biological actions affecting the cardiovascular, gastrointestinal, and respiratory systems and is neuroprotective. It binds special receptors (RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE).	3.35	1	0
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	2.03	1	0	polypeptide
acy-1215 ricolinostat: an HDAC6 inhibitor; structure in first source	2.6	1	0	pyrimidinecarboxylic acid
3,4-dihydroxybenzalacetone 3,4-dihydroxybenzalacetone: isolated from Chaga (Inonotus obliquus); structure in first source	2.58	2	0
cudc-907 [no description available]	2.6	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.	7.86	12	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	1.95	1	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
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.	3.17	5	0	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	2.07	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
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
mobic Meloxicam: A benzothiazine and thiazole derivative that acts as a NSAID and cyclooxygenase-2 (COX-2) inhibitor. It is used in the treatment of RHEUMATOID ARTHRITIS; OSTEOARTHRITIS; and ANKYLOSING SPONDYLITIS.. meloxicam : A benzothiazine that is piroxicam in which the pyridin-2-yl group is replaced by a 5-methyl-1,3-thiazol-2-yl group. A non-steroidal anti-inflammatory drug and selective inhibitor of COX-2, it is used particularly for the management of rheumatoid arthritis.	2.6	1	0	1,3-thiazoles; benzothiazine; monocarboxylic acid amide	analgesic; antirheumatic drug; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	5.84	11	0	benzenes; hydroxycoumarin; methyl ketone
tipranavir tipranavir: inhibits HIV-1 protease. tipranavir : A pyridine-2-sulfonamide substituted at C-5 by a trifluoromethyl group and at the sulfonamide nitrogen by a dihydropyrone-containing m-tolyl substituent. It is an HIV-1 protease inhibitor.	2.6	1	0	sulfonamide	antiviral drug; HIV protease inhibitor
tasquinimod tasquinimod: a lead second generation quinoline-3-carboxamide anti-angiogenic agent for the treatment of prostate cancer; structure in first source	2.6	1	0
gsk1265744 [no description available]	2.6	1	0	difluorobenzene; monocarboxylic acid amide; organic heterotricyclic compound; secondary carboxamide	HIV-1 integrase inhibitor
abt-267 ombitasvir: inhibits HCV NS5A protein, component of Viekirax. ombitasvir : A dipeptide derivative which is used which is in combination with dasabuvir sodium hydrate, paritaprevir and ritonavir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	2.6	1	0	aromatic amide; carbamate ester; dipeptide; pyrrolidines	antiviral drug; hepatitis C virus nonstructural protein 5A inhibitor
abt-333 dasabuvir: an antiviral agent. dasabuvir : A member of the class of pyrimidone, which is (as the monohydrate of its sodium salt) in combination with ombitasvir, paritaprevir and ritonavir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	2.6	1	0	aromatic ether; naphthalenes; pyrimidone; sulfonamide	antiviral drug; nonnucleoside hepatitis C virus polymerase inhibitor
rgfp966 [no description available]	2.6	1	0
rg2833 RG2833: a histone deacetylase inhibitor; structure in first source	2.6	1	0
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	2.72	3	0
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	3.21	5	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	3.19	1	0
oleuropein aglycone oleuropein aglycone: an agonist of both TRPA1 and TRPV1 receptors. oleuropein aglycone : A secoiridoid that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2R,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	3.49	6	0	catechols; diester; lactol; methyl ester; pyrans; secoiridoid	anti-inflammatory agent; antioxidant; mTOR inhibitor; neuroprotective agent; plant metabolite; TRPA1 channel agonist
pi-1840 PI-1840: has both antineoplastic and proteasome inhibitory activities; structure in first source	2.6	1	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	2.42	2	0	ketal
acy-738 [no description available]	2.6	1	0
pelabresib CPI-0610: a bromodomain and extra-terminal protein inhibitor with antineoplastic activity; structure in first source	2.6	1	0	monochlorobenzenes; organic heterotricyclic compound; primary carboxamide	antineoplastic agent; bromodomain-containing protein 4 inhibitor
brine brine: not from seawater; contains sodium chloride; calcium chloride; magnesium chloride; one or all of the above	2.13	1	0
gs-5806 presatovir: a respiratory syncytial virus entry inhibitor	2.6	1	0
doravirine [no description available]	2.6	1	0
pyrethrins [no description available]	2.07	1	0
gn6958 GN6958: inhibits SUMO-sentrin specific protease 1 (SENP1); structure in first source	2.6	1	0
vx-787 pimodivir: non‐nucleotide inhibitor of the polymerase basic protein 2 (PB2) subunit of the influenza A that is active against H1N1, H7N9 and H5N1, as well as influenza A strains with reduced susceptibility to NAIs	2.6	1	0
ledipasvir ledipasvir : A benzimidazole derivative that is used in combination with sofosbuvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.	2.6	1	0	azaspiro compound; benzimidazole; bridged compound; carbamate ester; carboxamide; fluorenes; imidazoles; L-valine derivative; N-acylpyrrolidine; organofluorine compound	antiviral drug; hepatitis C protease inhibitor
gs-5816 velpatasvir: an NS5A inhibitor used for treating hepatitis C infections. velpatasvir : A complex organic heteropentacyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with sofosbuvir (under the brand name Epclusa) for treatment of patients with chronic hepatitis C of all six major genotypes.	2.6	1	0	carbamate ester; ether; imidazoles; L-valine derivative; N-acylpyrrolidine; organic heteropentacyclic compound; ring assembly	antiviral drug; hepatitis C virus nonstructural protein 5A inhibitor
g007-lk G007-LK: potent and specific small-molecule tankyrase inhibitor; structure in first source	2.6	1	0
rome Rome: The capital city of Italy.. (2R)-2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-ol : A 2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-ol that has R-configuration. It is a sphingosine kinase-2 inhibitor.	4.51	1	1	2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-ol	EC 2.7.1.91 (sphingosine kinase) inhibitor
4-((1-butyl-3-phenylureido)methyl)-n-hydroxybenzamide 4-((1-butyl-3-phenylureido)methyl)-N-hydroxybenzamide: inhibits HDAC6; structure in first source	2.6	1	0
selinexor selinexor: inhibits karyopherin XPO1	2.6	1	0
verdinexor verdinexor: a selective inhibitor of nuclear export	2.6	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.51	2	0
cb-839 [no description available]	2.6	1	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.	2.6	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
atglistatin atglistatin: inhibits adipose triglyceride lipase; structure in first source. atglistatin : A biphenyl that is 1,1'-biphenyl substituted by (dimethylcarbamoyl)amino and dimethylamino groups at positions 3 and 4', respectively. It is a potent inhibitor of adipose triglyceride lipase activity (IC50 = 700nM).	2.6	1	0
xen445 [no description available]	2.6	1	0
santacruzamate a santacruzamate A: HDAC2 inhibitor from the Panamanian marine cyanobacterium cf. Symploca sp.; structure in first source	2.6	1	0	organonitrogen compound; organooxygen compound
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	3.19	5	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.	2.76	2	0
ldc4297 LDC4297: a CDK7 inhibitor with antineoplastic activity; structure in first source. LDC4297 : A pyrazolotriazine that is pyrazolo[1,5-a][1,3,5]triazine substituted by a piperidin-3-yloxy group, [2-(1H-pyrazol-1-yl)benzyl]nitrilo group and an isopropyl group at positions 2, 4 and 8 respectively. It is a potent and selective CDK7 inhibitor and exhibits antiviral activity.	2.6	1	0	aromatic ether; piperidines; pyrazoles; pyrazolotriazine; secondary amino compound	antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
duramycin duramycin: from Streptomyces cinnamoneus; contains rare amino acids such as lanthionine & lysinoarginine. lancovutide : A 19-membered heterodetic cyclic peptide that is isolated from Streptoverticillium cinnamoneus. It exhibits antiproliferative properties and induces apoptosis in tumour cells and has been used for treatment of cystic fibrosis.	1.97	1	0	heterodetic cyclic peptide; macrocycle	antimicrobial agent; apoptosis inducer; bacterial metabolite
g(m3) ganglioside G(M3) Ganglioside: A ganglioside present in abnormally large amounts in the brain and liver due to a deficient biosynthetic enzyme, G(M3):UDP-N-acetylgalactosaminyltransferase. Deficiency of this enzyme prevents the formation of G(M2) ganglioside from G(M3) ganglioside and is the cause of an anabolic sphingolipidosis.. alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/24:1(15Z)) : A sialotriaosylceramide consisting of beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-Glc attached to the primary hydroxy function of ceramide(d18:1/24:1(15Z)).	2.1	1	0	alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-ceramide; sialodiosylceramide; sialotriaosylceramide	mouse metabolite
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	1.99	1	0
hydroxytyrosyl acetate hydroxytyrosyl acetate: structure in first source	3.95	12	0
enasidenib [no description available]	2.6	1	0	1,3,5-triazines; aminopyridine; aromatic amine; organofluorine compound; secondary amino compound; tertiary alcohol	antineoplastic agent; EC 1.1.1.42 (isocitrate dehydrogenase) inhibitor
diospyros Diospyros: A plant genus of the family EBENACEAE, order Ebenales, subclass Dilleniidae, class Magnoliopsida best known for the edible fruit and the antibacterial activity and compounds of the wood.	2.13	1	0
trichodermin Trichodermin: Antifungal metabolite from several fungi, mainly Trichoderma viride; inhibits protein synthesis by binding to ribosomes; proposed as antifungal and antineoplastic; used as tool in cellular biochemistry.. trichodermin : A tetracyclic spiroepoxide which acts as an antifungal and protein synthesis inhibitor.	2.47	2	0
s 8932 [no description available]	2.6	1	0	aromatic amine; C-nucleoside; carboxylic ester; nitrile; phosphoramidate ester; pyrrolotriazine	anticoronaviral agent; antiviral drug; prodrug
benzylpenicilloic acid benzylpenicilloic acid: RN given refers to parent cpd. benzylpenicilloic acid : A penicilloic acid where the side-chain N-acyl group is specified as phenylacetyl.	1.96	1	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	3.14	5	0
thromboplastin Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.	2.08	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
liriodendrin, 1r-(1alpha,3abeta,4beta,6aalpha)-isomer eleutheroside E: from Eleutherococcus senticosus extract	2.06	1	0
angiogenin angiogenin: human tumor protein which stimulates growth of blood vessels; contains 123 amino acids; member of the pancreatic ribonuclease superfamily; MW 14,400	2.08	1	0
entecavir entecavir (anhydrous) : Guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B.	2.6	1	0	2-aminopurines; oxopurine; primary alcohol; secondary alcohol	antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.6	1	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
nu 1025 NU 1064: structure in first source	2.6	1	0	phenols; quinazolines	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
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.	2.91	4	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	2.94	4	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine tetraphosphate Guanosine Tetraphosphate: Guanosine 5'-diphosphate 2'(3')-diphosphate. A guanine nucleotide containing four phosphate groups. Two phosphate groups are esterified to the sugar moiety in the 5' position and the other two in the 2' or 3' position. This nucleotide serves as a messenger to turn off the synthesis of ribosomal RNA when amino acids are not available for protein synthesis. Synonym: magic spot I.. guanosine 3',5'-bis(diphosphate) : A guanosine bisphosphate having diphosphate groups at both the 3' and 5'-positions.	1.96	1	0	guanosine bisphosphate	Escherichia coli metabolite; mouse metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	4	2	1	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	2.51	2	0
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.55	2	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.36	2	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
didanosine Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.	2.6	1	0	purine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor; geroprotector; HIV-1 reverse transcriptase inhibitor
ganciclovir [no description available]	2.6	1	0	2-aminopurines; oxopurine	antiinfective agent; antiviral drug
valacyclovir Valacyclovir: A prodrug of acyclovir that is used in the treatment of HERPES ZOSTER and HERPES SIMPLEX VIRUS INFECTION of the skin and mucous membranes, including GENITAL HERPES.	2.6	1	0	L-valyl ester	antiviral drug
penciclovir penciclovir : A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topically for treatment of herpes labialis. A prodrug, famciclovir, is used for oral administration.	2.6	1	0	2-aminopurines; propane-1,3-diols	antiviral drug
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.	4.74	29	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
4-hydroxyquinazoline 4-oxo-3,4-dihydroquinazoline: structure in first source	2.6	1	0	quinazolines
tegaserod tegaserod: a nonbenzamide 5-hydroxytryptamine(4) agonist; used in treatment of irritable bowel syndrome; marketing suspended 2007 in US due to higher incidence of MI, stroke, and unstable angina; structure given in first source	2.6	1	0	carboxamidine; guanidines; hydrazines; indoles	gastrointestinal drug; serotonergic agonist
norclozapine norclozapine: structure given in first source. N-desmethylclozapine : A dibenzodoazepine substituted with chloro and piperazino groups which is a major metabolite of clozapine; a potent and selective 5-HT2C serotonin receptor antagonist.	2.6	1	0	dibenzodiazepine; organochlorine compound; piperazines	delta-opioid receptor agonist; metabolite; serotonergic antagonist
pemetrexed pemetrexed disodium : An organic sodium salt that is the disodium salt of N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).	2.6	1	0	N-acyl-L-glutamic acid; pyrrolopyrimidine	antimetabolite; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; EC 2.1.1.45 (thymidylate synthase) inhibitor; EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor
aprepitant Aprepitant: A morpholine neurokinin-1 (NK1) receptor antagonist that is used in the management of nausea and vomiting caused by DRUG THERAPY, and for the prevention of POSTOPERATIVE NAUSEA AND VOMITING.. aprepitant : A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors.	2.82	2	0	(trifluoromethyl)benzenes; cyclic acetal; morpholines; triazoles	antidepressant; antiemetic; neurokinin-1 receptor antagonist; peripheral nervous system drug; substance P receptor antagonist
azilsartan azilsartan: an angiotensin type 1 receptor blocker; receptor blocker. azilsartan : A benzimidazolecarboxylic acid that is benzimidazole-7-carboxylic acid substituted at position 2 by a methoxy group and at position 1 by a 2'-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl group. Used (as the prodrug, azilsartan medoxomil) for treatment of hypertension.	2.6	1	0	1,2,4-oxadiazole; aromatic ether; benzimidazolecarboxylic acid	angiotensin receptor antagonist; antihypertensive agent
hesperadin [no description available]	2.6	1	0
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).	2.13	1	0
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	3.14	5	0	guanosines	biomarker
6-bromoindirubin-3'-acetoxime 6-bromoindirubin-3'-acetoxime: a synthetic derivative of a compound from the Mediterranean mollusk Hexaplex trunculus, protects cells from varicella infection	2.6	1	0
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.	2.31	1	0
imidacloprid imidacloprid: systemic & contact insecticide exhibiting low mammalian toxicity; structure given in first source; it is one of the neonicotinoid insecticides, which acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. imidacloprid : An imidazolidine that is N-nitroimidazolidin-2-imine bearing a (6-chloro-3-pyridinyl)methyl substituent at position 1.	2.72	2	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
n'-(3,4-dihydroxybenzylidene)-3-hydroxy-2-naphthahydrazide [no description available]	2.6	1	0	catechols; hydrazide; hydrazone; naphthols	EC 3.6.5.5 (dynamin GTPase) inhibitor
XL413 XL413 : A benzofuropyrimidine that is 3,4-dihydro[1]benzofuro[3,2-d]pyrimidine substituted by (2S)-pyrrolidin-2-yl, oxo and chloro groups at positions 2, 4, and 8, respectively. It is a potent ATP competitive inhibitor of Cdc7 kinase (IC50 = 3.4 nM) and exhibits anticancer properties.	2.6	1	0	benzofuropyrimidine; organochlorine compound; pyrrolidines	antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
me0328 ME0328: inhibits ARTD3; structure in first source	2.6	1	0
dibutyryl cyclic gmp Dibutyryl Cyclic GMP: N-(1-Oxobutyl)-cyclic 3',5'-(hydrogen phosphate)-2'-butanoate guanosine. A derivative of cyclic GMP. It has a higher resistance to extracellular and intracellular phosphodiesterase than cyclic GMP.	1.96	1	0
nvp-tnks656 [no description available]	2.6	1	0
eye [no description available]	2.33	2	0
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.13	1	0
tauromuricholate tauromuricholic acid: RN given refers to (3 alpha,5 beta,6 beta,7 beta)-isomer	2.15	1	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.65	3	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.48	2	0

Intervention	units on a scale (Geometric Mean)
	Hour 1	Hour 2	Hour 3	Hour 4.5	Hour 6	Hour 8	Hour 10
LY2216684 + Alcohol	-29.13	-96.35	-76.72	-65.06	-39.56	-42.28	-46.78
LY2216684 + Placebo-matching Alcohol	-24.81	-44.3	-34.92	-50.78	-41.34	-46.09	-41.95
Placebo-matching LY2216684 + Alcohol	-30.56	-97.54	-74.27	-52.23	-49.7	-43.65	-34.33
Placebo-matching LY2216684 + Placebo-matching Alcohol	-19.29	-41.64	-30.58	-34.29	-38.86	-35.95	-39.04

Intervention	units on a scale (Least Squares Mean)
	Self-rated Alertness, Hour 1	Self-rated Alertness, Hour 2	Self-rated Alertness, Hour 3	Self-rated Alertness, Hour 4.5	Self-rated Alertness, Hour 6	Self-rated Alertness, Hour 8	Self-rated Alertness, Hour 10	Self-rated Contentment, Hour 1	Self-rated Contentment, Hour 2	Self-rated Contentment, Hour 3	Self-rated Contentment, Hour 4.5	Self-rated Contentment, Hour 6	Self-rated Contentment, Hour 8	Self-rated Contentment, Hour 10
LY2216684 + Alcohol	2.98	17.09	23.67	27.19	23.66	12.69	3.85	3.28	3.72	8.41	16.98	18.14	9.97	2.47
LY2216684 + Placebo-matching Alcohol	3.64	0.76	9.04	16.26	15.13	12.38	11.88	2.77	1.64	5.69	11.39	10.68	9.68	10.16
Placebo-matching LY2216684 + Alcohol	4.57	14.08	26.25	20.74	17.25	3.63	-2.37	0.95	1.5	7.12	8.5	10.85	0.98	0.44
Placebo-matching LY2216684 + Placebo-matching Alcohol	6.06	3.64	1.22	9.82	7.55	3.03	3.02	4.34	2.79	1.32	5.03	4.57	2.7	3.72

Intervention	millisecond (msec) (Least Squares Mean)
	Hour 1	Hour 2	Hour 3	Hour 4.5	Hour 6	Hour 8	Hour 10
LY2216684 + Alcohol	-38.46	104.48	43.69	30.12	-116.69	-116.72	-74.78
LY2216684 + Placebo-matching Alcohol	42.51	59.65	51.53	-121.55	-90.46	55.62	-108.12
Placebo-matching LY2216684 + Alcohol	36.22	316.09	283.63	61.93	46.44	-48.13	-136.62
Placebo-matching LY2216684 + Placebo-matching Alcohol	138.87	197.37	24.55	169.34	-114.87	-120.29	-129.8

Intervention	Units on a scale (Least Squares Mean)
	Hour 1	Hour 2	Hour 3	Hour 4.5	Hour 6	Hour 8	Hour 10
LY2216684 + Alcohol	-0.12	-0.27	-0.2	-0.15	-0.1	-0.03	-0.21
LY2216684 + Placebo-matching Alcohol	-0.1	-0.13	-0.06	-0.2	-0.06	-0.08	-0.16
Placebo-matching LY2216684 + Alcohol	-0.12	-0.29	-0.18	-0.11	-0.09	-0.05	-0.09
Placebo-matching LY2216684 + Placebo-matching Alcohol	-0.02	-0.12	-0.04	-0.2	-0.07	-0.13	-0.06

Intervention	millimoleshours/liters (mmolh/L) (Geometric Mean)
LY2216684 + Alcohol	29.7
Placebo-matching LY2216684 + Alcohol	34.5

Intervention	millimoles/liters (mmol/L) (Geometric Mean)
LY2216684 + Alcohol	11.4
Placebo-matching LY2216684 + Alcohol	13.8

Intervention	nanograms/milliliters (ng/mL) (Geometric Mean)
LY2216684 + Alcohol	60.2
LY2216684 + Placebo-matching Alcohol	58.0

Intervention	hours (Median)
LY2216684 + Alcohol	4.00
LY2216684 + Placebo-matching Alcohol	2.94

Intervention	hours (Median)
LY2216684 + Alcohol	0.92
Placebo-matching LY2216684 + Alcohol	0.92

phenylethyl alcohol

Description

Cross-References

Synonyms (181)

Research Excerpts

Overview

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (96 Product(s))

Product Categories

Products

Roles (5)

Drug Classes (2)

Pathways (8)

Protein Targets (11)

Potency Measurements

Bioassays (51)

Research

Studies (2,607)

Market Indicators

Research Demand Index: 63.70

Study Types

Clinical Trials (8)

Trial Overview

Trial Outcomes

Change From Baseline to 54 Week Endpoint in Clinical Global Impression - Severity (CGI-S)

Change From Baseline to 54 Week Endpoint in EuroQol Questionnaire - 5 Dimension (EQ-5D)

Change From Baseline to 54 Week Endpoint in Hospital Anxiety and Depression Scale (HADS) Anxiety Subscale Score

Change From Baseline to 54 Week Endpoint in Hospital Anxiety and Depression Scale (HADS) Depression Subscale Score

Change From Baseline to 54 Week Endpoint in Massachusetts General Hospital Cognitive and Physical Functioning Questionnaire (CPFQ)

Change From Baseline to 54 Week Endpoint in Quality of Life Enjoyment and Satisfaction Questionnaire-Short Form (Q-LES-Q-SF)

Change From Baseline to 54 Week Endpoint in the Arizona Sexual Experiences (ASEX) Scale

Change From Baseline to Week 54 Endpoint in Pulse Rate

Percentage of Participants Who Meet Remission Criteria of Depressive Symptoms by Week 8

Percentage of Participants Who Meet Response Criteria of Depressive Symptoms by Week 8

Percentage of Participants With Discontinuation-Emergent Adverse Events (DEAEs)

Probability of Meeting the Remission Criteria for Depressive Symptoms at Week 54 Endpoint

Probability of Meeting the Response Criteria for Depressive Symptoms at Week 54 Endpoint

The Number of Participants Experiencing Clinically Significant Effects

Change From Baseline to 54 Week Endpoint in Blood Pressure

Change From Baseline to 54 Week Endpoint in Fatigue Associated With Depression (FAsD) Average Score and Subscale Scores

Change From Baseline to 54 Week Endpoint in Montgomery-Asberg Depression Rating Scale (MADRS) Total Score and Individual Items

Change From Baseline to 54 Week Endpoint in Sheehan Disability Scale (SDS) Total Score and Subscores

Percent of Participants With Suicidal Ideation and Behavior Based on the Columbia-Suicide Severity Rating Scale (C-SSRS)

Percentage of Participants Who Reported Resource Utilization (RU) at Baseline and at the Week 54 Endpoint

Plasma Concentration of LY2216684

The Number of Participants Experiencing Clinically Significant Effects as a Function of CYP2D6 Predicted Phenotype at Week 54 Endpoint

Maximum, Minimum and Average Changes in Diastolic Blood Pressure

Maximum, Minimum and Average Changes in Heart Rate

Maximum, Minimum and Average Changes in Systolic Blood Pressure

Change From Baseline to 10 Hours in Continuity of Attention Composite Score

Change From Baseline to 10 Hours in Postural Stability

Change From Baseline to 10 Hours in Power of Attention Composite Score

Change From Baseline to 10 Hours in Self-Rated Alertness

Pharmacokinetics: Area Under the Concentration Time Curve From Time Zero to the Last Time Point With a Measurable Concentration (AUC[0-tlast]) of Alcohol

Pharmacokinetics: Area Under the Concentration Time Curve Over a Dosing Interval (AUCt) of LY2216684

Pharmacokinetics: Observed Cmax of Alcohol

Pharmacokinetics: Observed Maximum Plasma Concentration (Cmax) of LY2216684

Pharmacokinetics: Observed Time to Maximum Plasma Concentration (Tmax) of LY2216684

Pharmacokinetics: Observed Tmax of Alcohol

Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Episodic Memory

Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Self-Ratings of Calmness and Contentment

Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Speed of Retrieval of Information From Memory

Change From Baseline to 1, 2, 3, 4.5, 6, 8, and 10 Hours in Working Memory

Related Drugs (1,684)

Related Conditions (689)