ethylene chlorohydrin profile

Ethylene chlorohydrin, also known as 2-chloroethanol, is a colorless, flammable liquid with a sweet odor. It is a highly reactive chemical used as an intermediate in the production of other chemicals, including ethylene oxide, which is a major component of many industrial products. Ethylene chlorohydrin is produced by the reaction of ethylene with chlorine and water. The reaction is highly exothermic and must be carefully controlled. The effects of ethylene chlorohydrin exposure on human health are significant, as it is a toxic substance that can cause irritation of the skin, eyes, and respiratory system. It is also suspected to be carcinogenic. Ethylene chlorohydrin is studied extensively due to its industrial importance and its potential environmental impact. Researchers are exploring safer and more sustainable methods of production, as well as ways to mitigate the risks associated with its handling and disposal.'
```

Ethylene Chlorohydrin: Used as a solvent, in the manufacture of insecticides, and for treating sweet potatoes before planting. May cause nausea, vomiting, pains in head and chest, stupefaction. Irritates mucous membranes and causes kidney and liver degeneration. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

chloroethanol : An organochlorine compound that is ethanol substituted by at least one chloro group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	34
CHEMBL ID	191244
CHEBI ID	28200
MeSH ID	M0007899

Synonym
.delta.-chloroethanolchloroethylowy alkohol
nsc-122289
monochlorhydrine du glycol
2-hydroxyethyl chloride
nci-c50135
ethyleen-chloorhydrine
ethylene glycol, chlorohydrin
.beta.-hydroxyethyl chloride
aethylenechlorhydrin
ethene, chlorohydrin
2-chloraethanol
2-chloro-1-ethanol
2-chloorethanol
glycolmonochloorhydrine
glycol monochlorohydrin
2-cloroetanolo
2-monochloroethanol
glicol monocloridrina
ethylchlorohydrin
glycomonochlorhydrin
.beta.-chloroethanol
2-chloroethyl alcohol
nsc122289
2-chloro-1-hydroxyethane
ethylene chlorhydrin
wln: q2g
.beta.-chloroethyl alcohol
chloroethanol
ethanol, 2-chloro-
CHEBI:28200 ,
beta-chloroethyl alcohol
beta-chloroethanol
inchi=1/c2h5clo/c3-1-2-4/h4h,1-2h
2-chloro-ethanol
glycolmonochloorhydrine [dutch]
2-cloroetanolo [italian]
einecs 203-459-7
nsc 122289
delta-chloroethanolchloroethylowy alkohol [polish]
2-chloraethanol [german]
beta-hydroxyethyl chloride
chloroethylowy alkohol [polish]
2-chlorethanol [german]
delta-chloroethanol
ethyleen-chloorhydrine [dutch]
hsdb 426
ai3-52326
un1135
brn 0878139
ccris 859
2-chloorethanol [dutch]
glicol monocloridrina [italian]
monochlorhydrine du glycol [french]
aethylenechlorhydrin [german]
C06753
2-chloroethanol ,
glycol chlorohydrin
ethylene chlorohydrin
107-07-3
argogel(tm)-cl, 1 % cross-linked
2-chloroethanol, 99%
2-chloroethanol (ethylene chlorohydrin)
2-chloroethanol, puriss. p.a., >=99.0% (gc)
BMSE000360
chloroalcohol
ethanol, chloro-
59826-67-4
buta-1,3-diene-1,1,4-tricarboxylic acid
CHEMBL191244
AKOS000119040
2-chloranylethanol
A801572
NCGC00247890-01
753n66ihan ,
ec 203-459-7
delta-chloroethanolchloroethylowy alkohol
2-chlorethanol
chloroethylowy alkohol
4-01-00-01372 (beilstein handbook reference)
ethylene chlorohydrin [un1135] [poison]
unii-753n66ihan
cas-107-07-3
NCGC00254022-01
tox21_300043
dtxsid1021877 ,
dtxcid601877
BBL011477
STL146589
2-chloroethanol [hsdb]
ethylene chlorohydrin [mi]
2-chloro ethanol
2-chloroethan-1-ol
2-chloro-ethan-1-ol
2-choroethan-1-ol
ethylenechlorohydrine
ethylenechlorohydrin
ethylene chlorohydrine
ch2clch2oh
1-chloro-2-hydroxyethane
un 1135
mfcd00002829
J-509022
2-chloroethanol, pestanal(r), analytical standard
2-chloroethanol, saj special grade, >=99.0%
Q209354
2-chloroethanol 1000 microg/ml in methanol
2-chloroethanol 100 microg/ml in methanol
857 - ethylene oxide in food products
868 - ethylene oxide in spices

Excerpt	Reference	Relevance
"Chlorate hydrate is commonly used for neonatal sedation, but blood levels are infrequently monitored, reflecting an underemphasis of acute toxic effects."	( Chloral hydrate toxicity in a term infant. Anyebuno, MA; Rosenfeld, CR, 1991)	0.28
" This pattern is consistent with formation of the toxic intermediate in the primary metabolic pathway of each compound."	( Delineation of the role of metabolism in the hepatotoxicity of trichloroethylene and perchloroethylene: a dose-effect study. Buben, JA; O'Flaherty, EJ, 1985)	0.27
" Monocrotaline is the major toxic pyrrolizidine alkaloid of Crotalaria species."	( Effect of 2(3)-tert-butyl-4-hydroxyanisole (BHA) and 2-chloroethanol against pyrrole production and chronic toxicity of monocrotaline in chickens. Braun, RC; Dickinson, JO, 1987)	0.27
" Administered TFE and TFAld were not toxic per se, since their toxicity and metabolism were inhibited by pyrazole."	( 2,2,2-Trifluoroethanol intestinal and bone marrow toxicity: the role of its metabolism to 2,2,2-trifluoroacetaldehyde and trifluoroacetic acid. Fraser, JM; Kaminsky, LS, 1988)	0.27
" In addition, each of the metabolites tested were significantly less developmental toxic than the parent compound, trichloroethylene."	( Evaluation of the developmental toxicity of trichloroethylene and detoxification metabolites using Xenopus. Bantle, JA; Fort, DJ; Hull, M; Rayburn, JR; Stover, EL, 1993)	0.29
" These results indicated that TCE is metabolized in the male reproductive tract, leading to adverse effects that are more severe in the epididymis than in the testis."	( Metabolism and toxicity of trichloroethylene in epididymis and testis. Forkert, PG; Lash, LH; Nadeau, V; Simmonds, A; Tardif, R, 2002)	0.31
"1 to 180 mg/kg and reduced the production of a potential toxic metabolite chloroacetaldehyde (CAA) in animal plasma."	( Protective effects of fomepizole on 2-chloroethanol toxicity. Chen, YT; Hung, DZ; Liao, JW, 2010)	0.36

Excerpt	Reference	Relevance
"8 micrograms/ml, and declined monophasically with a half-life of about 24 min."	( Disposition, pharmacokinetics, and metabolism of 14C-fotemustine in cancer patients. Breen, M; Brownsill, R; Gordon, BH; Gray, AJ; Hiley, M; Ings, RM; Marchant, N; Richards, R; Taylor, AR; Wallace, D, 1990)	0.28
" After termination of treatment the half-life of TCE was 12."	( Pharmacokinetics of chloral hydrate poisoning treated with hemodialysis and hemoperfusion. Buur, T; Larsson, R; Norlander, B, 1988)	0.27
"A physiologically based pharmacokinetic model was used to determine the in vivo metabolic constants of the candidate chlorofluorocarbon replacement 1,1-dichloro-1-fluoroethane (HCFC-141b)."	( Gas-uptake pharmacokinetics and biotransformation of 1,1-dichloro-1-fluoroethane (HCFC-141b). Anders, MW; Loizou, GD, )	0.13
" In all, 40 pharmacokinetic determinations of fotemustine were made at dose levels ranging from 2 x 300 to 2 x 500 mg/m2."	( Phase I pharmacokinetics study of high-dose fotemustine and its metabolite 2-chloroethanol in patients with high-grade gliomas. Biron, P; Evene, E; Giroux, B; Gordon, B; Lucas, C; Mornex, F; Richards, R; Roux, N; Solere, P; Tranchand, B, 1993)	0.29
"A six-compartment physiologically based pharmacokinetic (PBPK) model for the B6C3F1 mouse was developed for trichloroethylene (TCE) and was linked with five metabolite submodels consisting of four compartments each."	( A physiologically based pharmacokinetic model for trichloroethylene and its metabolites, chloral hydrate, trichloroacetate, dichloroacetate, trichloroethanol, and trichloroethanol glucuronide in B6C3F1 mice. Abbas, R; Fisher, JW, 1997)	0.3
"Using the Monte Carlo method and physiologically based pharmacokinetic modeling, an occupational inhalation exposure to trichloroethylene consisting of 7 h of exposure per day for 5 days was simulated in populations of men and women of 5000 individuals each."	( Combining physiologically based pharmacokinetic modeling with Monte Carlo simulation to derive an acute inhalation guidance value for trichloroethylene. Simon, TW, 1997)	0.3
" Blood, urine, and exhaled breath samples were collected for development of a physiologically based pharmacokinetic (PBPK) model for trichloroethylene and its two major P450-mediated metabolites, trichloroacetic acid and free trichloroethanol."	( A human physiologically based pharmacokinetic model for trichloroethylene and its metabolites, trichloroacetic acid and free trichloroethanol. Abbas, R; Fisher, JW; Mahle, D, 1998)	0.3
"A physiologically based pharmacokinetic (PBPK) model for inhaled trichloroethylene (TCE) was developed for B6C3F1 mice."	( Physiologically based pharmacokinetic modeling of inhaled trichloroethylene and its oxidative metabolites in B6C3F1 mice. Burton, GA; Fisher, JW; Greenberg, MS, 1999)	0.3
"Bayesian population analysis of a harmonized physiologically based pharmacokinetic (PBPK) model for trichloroethylene (TCE) and its metabolites was performed."	( Bayesian population analysis of a harmonized physiologically based pharmacokinetic model of trichloroethylene and its metabolites. Chiu, WA; Clewell, HJ; Hack, CE; Jay Zhao, Q, 2006)	0.33

Excerpt	Relevance	Reference
" Dose-response curves were obtained using mice at pressures ranging from 1 to 125 atm for five agents, namely alpha-chloralose, ethylcarbamate, phenobarbital and, for comparison, nitrogen and argon."	( The pressure reversal of a variety of anesthetic agents in mice. Miller, KW; Wilson, MW, 1978)	0.26
" The method has been used to determine plasma levels after therapeutic dosing with chloral preparations."	( Determination of trichloroethanol at therapeutic and overdose levels in blood and urine by electron capture gas chromatography. Berry, DJ, 1975)	0.25
" Multiple dosing of chloral hydrate in preterm infants should be used with caution and frequent monitoring of serum bilirubin concentrations is indicated in such cases."	( Chloral hydrate sedation in neonates and infants--clinical and pharmacologic considerations. Gorecki, DK; Hindmarsh, KW; Kasian, GF; Reimche, LD; Sankaran, K; Tan, L, 1989)	0.28
" The mean total dosage per mouse was 2110."	( [Carcinogenic activity of ethylene oxide and its reaction products 2-chloroethanol, 2-bromoethanol, ethylene glycol and diethylene glycol. III. Research on ethylene glycol and diethylene glycol for carcinogenic effects]. Dunkelberg, H, 1987)	0.27
" Recommendations are made concerning patient supervision, dosage limitations, and degree of sedation."	( Death after chloral hydrate sedation: report of case. Jastak, JT; Pallasch, T, 1988)	0.27
"3 mg, single dosage per mouse) and 2-bromoethanol in 2 dosages (1."	( [Carcinogenic activity of ethylene oxide and its reaction products 2-chlorethanol, 2-bromoethanol, ethylene glycol and diethylene glycol. II. Testing of 2-chlorethanol and 2-bromoethanol for carcinogenic activity]. Dunkelberg, H, 1983)	0.27
" Fischer 344 rats and beagle dogs were dosed orally with TRI and blood was analyzed for TRI, DCA, TCA, and trichloroethanol (TCE)."	( Factors affecting species differences in the kinetics of metabolites of trichloroethylene. Bonate, PL; Bull, RJ; Stenner, RD; Stevens, DK; Templin, MV; Tuman, D, 1995)	0.29
" Jugular vein, duodenum, and bile duct-cannulated Fischer 344 rats were used, with the collection of blood, bile, urine, and feces samples after intraduodenal and intravenous dosing of animals with TRI, TCEOH, and TCA."	( Enterohepatic recirculation of trichloroethanol glucuronide as a significant source of trichloroacetic acid. Metabolites of trichloroethylene. Bull, RJ; Merdink, JL; Springer, DL; Stenner, RD; Stevens, DK, 1997)	0.3
" For oral bolus dosing of TCE with 300, 600, and 2000 mg/kg, model predictions of TCE and several metabolites were in general agreement with observations."	( A physiologically based pharmacokinetic model for trichloroethylene and its metabolites, chloral hydrate, trichloroacetate, dichloroacetate, trichloroethanol, and trichloroethanol glucuronide in B6C3F1 mice. Abbas, R; Fisher, JW, 1997)	0.3
" Male B6C3F1 mice were dosed with TRI, CH, trichloroethanol (TCE), or TCA and metabolic profiles of each were determined."	( The extent of dichloroacetate formation from trichloroethylene, chloral hydrate, trichloroacetate, and trichloroethanol in B6C3F1 mice. Bull, RJ; Gonzalez-Leon, A; Merdink, JL; Schultz, IR, 1998)	0.3
" Additional male mice were dosed as described above and their livers were excised at 24, 48 h, and 7 days after the final dose."	( Tumorigenicity of chloral hydrate, trichloroacetic acid, trichloroethanol, malondialdehyde, 4-hydroxy-2-nonenal, crotonaldehyde, and acrolein in the B6C3F(1) neonatal mouse. Bucci, TJ; Chou, MW; Fu, PP; Kadlubar, FF; Samokyszyn, VM; Von Tungeln, LS; Yi, P, 2002)	0.31
" On the other hand, tissue repair showed a dose-response leading to regression of injury."	( Dose-dependent liver regeneration in chloroform, trichloroethylene and allyl alcohol ternary mixture hepatotoxicity in rats. Anand, SS; Mehendale, HM; Mumtaz, MM, 2005)	0.33
" This analysis provides an important step toward estimating uncertainty of dose-response relationships in noncancer and cancer risk assessment, improving the extrapolation of toxic TCE doses from experimental animals to humans."	( Bayesian population analysis of a harmonized physiologically based pharmacokinetic model of trichloroethylene and its metabolites. Chiu, WA; Clewell, HJ; Hack, CE; Jay Zhao, Q, 2006)	0.33
" We have examined the dose-response relationship for formic aciduria in male and female Fischer 344 rats, the effect of some known metabolites of TCE and examined the response in male Wistar rats to help understand its relevance to renal toxicity."	( Trichloroethylene-induced formic aciduria: effect of dose, sex and strain of rat. Evans, AR; Lock, EA; Yaqoob, N, 2013)	0.39
" Oral dosing with TCE was conducted in subacute (600 mg/kg/d; 5 d; 7 inbred mouse strains) and subchronic (100 or 400 mg/kg/d; 1, 2, or 4 wk; 2 inbred mouse strains) designs."	( Comparative analysis of the relationship between trichloroethylene metabolism and tissue-specific toxicity among inbred mouse strains: liver effects. Ball, LM; Bodnar, WM; Bradford, BU; Collins, LB; Gold, A; Kosyk, O; Rusyn, I; Shymonyak, S; Uehara, T; Yoo, HS, 2015)	0.42
" Oral dosing with TCE was conducted in subacute (600 mg/kg/d; 5 d; 7 inbred mouse strains) and subchronic (100 or 400 mg/kg/d; 1, 2, or 4 wk; 2 inbred mouse strains) designs."	( Comparative analysis of the relationship between trichloroethylene metabolism and tissue-specific toxicity among inbred mouse strains: kidney effects. Ball, LM; Bodnar, WM; Bradford, BU; Collins, LB; Gold, A; Kosyk, O; Rusyn, I; Shymonyak, S; Uehara, T; Yoo, HS, 2015)	0.42
" This new method can be applied for the pharmacokinetic analysis of TCS and its metabolites and the determination of the optimal TCS dosage in children."	( Simple method to detect triclofos and its metabolites in plasma of children by combined use of liquid chromatography tandem-mass spectrometry and gas chromatography-mass spectrometry. Hashimoto, S; Inoue, M; Ito, Y; Kamijima, M; Nakahira, Y; Nakajima, T; Sato, H, 2019)	0.51

Role	Description
xenobiotic metabolite	Any metabolite produced by metabolism of a xenobiotic compound.
[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
chloroethanol	An organochlorine compound that is ethanol substituted by at least one chloro group.
[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
1,2-dichloroethane degradation	1	15

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	32.4533	0.0060	38.0041	19,952.5996	AID1159523
GLI family zinc finger 3	Homo sapiens (human)	Potency	45.8415	0.0007	14.5928	83.7951	AID1259392
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	20.0713	0.0008	17.5051	59.3239	AID1159527; AID1159531
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID384212	Mutagenic activity in Salmonella Typhimurium TA100 assessed as logarithm of his+ revertant number increasing activity by amens test	2008	Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10	Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (HAA) mutagenicity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	154 (49.20)	18.7374
1990's	67 (21.41)	18.2507
2000's	57 (18.21)	29.6817
2010's	29 (9.27)	24.3611
2020's	6 (1.92)	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	6 (1.79%)	5.53%
Reviews	5 (1.49%)	6.00%
Case Studies	24 (7.14%)	4.05%
Observational	0 (0.00%)	0.25%
Other	301 (89.58%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	2.37	2	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	1.96	1	0	trichlorobenzene
chloroacetaldehyde [no description available]	2.93	4	0	organochlorine compound
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.39	2	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	8.22	6	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
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.	8.67	10	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.95	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
benzene [no description available]	2.04	1	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
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.	1.99	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
carbamates [no description available]	1.95	1	0	amino-acid anion
carbamyl phosphate Carbamyl Phosphate: The monoanhydride of carbamic acid with PHOSPHORIC ACID. It is an important intermediate metabolite and is synthesized enzymatically by CARBAMYL-PHOSPHATE SYNTHASE (AMMONIA) and CARBAMOYL-PHOSPHATE SYNTHASE (GLUTAMINE-HYDROLYZING).	1.95	1	0	acyl monophosphate; one-carbon compound	Escherichia coli metabolite; mouse metabolite
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	1.98	1	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
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.	2.96	4	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
chloroacetic acid chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.	3.09	5	0	chlorocarboxylic acid; haloacetic acid	alkylating agent; herbicide
choline [no description available]	1.95	1	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.42	2	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.	1.97	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.11	1	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
methylmalonic acid Methylmalonic Acid: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA.. methylmalonic acid : A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group.	2.45	2	0	C4-dicarboxylic acid	human metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.36	2	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
glyoxylic acid glyoxylic acid: RN given refers to parent cpd. glyoxylic acid : A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.	1.99	1	0	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
indole [no description available]	2.03	1	0	indole; polycyclic heteroarene	Escherichia coli 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.	2.37	2	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.01	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	2.67	3	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
phenol [no description available]	1.98	1	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
pqq cofactor PQQ Cofactor: A pyrrolo-quinoline having two adjacent keto-groups at the 4 and 5 positions and three acidic carboxyl groups. It is a coenzyme of some DEHYDROGENASES.. pyrroloquinoline quinone : A pyrroloquinoline having oxo groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions.	2.02	1	0	orthoquinones; pyrroloquinoline cofactor; tricarboxylic acid	anti-inflammatory agent; antioxidant; cofactor; water-soluble vitamin (role)
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.65	3	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	1.99	1	0	pyrazole
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.67	3	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	1.95	1	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid: An IBOTENIC ACID homolog and glutamate agonist. The compound is the defining agonist for the AMPA subtype of glutamate receptors (RECEPTORS, AMPA). It has been used as a radionuclide imaging agent but is more commonly used as an experimental tool in cell biological studies.	2	1	0	non-proteinogenic alpha-amino acid
1-aminobenzotriazole [no description available]	2.04	1	0
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	1.98	1	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
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.	2.36	2	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	1.98	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
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.	2.36	2	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	2.76	3	0	quaternary ammonium ion
chloral hydrate [no description available]	8.92	60	1	aldehyde hydrate; ethanediol; organochlorine compound	general anaesthetic; mouse metabolite; sedative; xenobiotic
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.	3.34	1	1	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; 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.	2.01	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
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	3.34	1	1	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
disulfiram [no description available]	2.05	1	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.11	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
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.	2.01	1	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
flunitrazepam Flunitrazepam: A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.. flunitrazepam : A 1,4-benzodiazepinone that is nitrazepam substituted by a methyl group at position 1 and by a fluoro group at position 2'. It is a potent hypnotic, sedative, and amnestic drug used to treat chronic insomnia.	3.34	1	1	1,4-benzodiazepinone; C-nitro compound; monofluorobenzenes	anxiolytic drug; GABAA receptor agonist; sedative
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.	2.05	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
halothane [no description available]	2.39	2	0	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	1.96	1	0	barbiturates
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	2.44	2	0	organofluorine compound	inhalation anaesthetic
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	1.95	1	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	1.99	1	0	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
lomustine [no description available]	1.95	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
muscimol Muscimol: A neurotoxic isoxazole isolated from species of AMANITA. It is obtained by decarboxylation of IBOTENIC ACID. Muscimol is a potent agonist of GABA-A RECEPTORS and is used mainly as an experimental tool in animal and tissue studies.. muscimol : A member of the class of isoxazoles that is 1,2-oxazol-3(2H)-one substituted by an aminomethyl group at position 5. It has been isolated from mushrooms of the genus Amanita.	2.39	2	0	alkaloid; isoxazoles; primary amino compound	fungal metabolite; GABA agonist; oneirogen; psychotropic drug
neostigmine Neostigmine: A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.. neostigmine : A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.	1.93	1	0	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.06	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
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).	3.34	1	1	1,4-benzodiazepinone; C-nitro compound	anticonvulsant; antispasmodic drug; drug metabolite; GABA modulator; sedative
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	1.98	1	0	barbiturates	GABAA receptor agonist
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.	3.21	6	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	2	1	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	1.93	1	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	1.96	1	0	diarylmethane
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.	1.99	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
quipazine Quipazine: A pharmacologic congener of serotonin that contracts smooth muscle and has actions similar to those of tricyclic antidepressants. It has been proposed as an oxytocic.	1.98	1	0	piperazines; pyridines
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.	2.02	1	0	ether; organofluorine compound	central nervous system depressant; inhalation anaesthetic; platelet aggregation inhibitor
sodium iodide Sodium Iodide: A compound forming white, odorless deliquescent crystals and used as iodine supplement, expectorant or in its radioactive (I-131) form as an diagnostic aid, particularly for thyroid function tests.. sodium iodide : A metal iodide salt with a Na(+) counterion.	3.05	1	0	inorganic sodium salt; iodide salt
iodoacetic acid Iodoacetic Acid: A derivative of ACETIC ACID that contains one IODINE atom attached to its methyl group.. iodoacetic acid : A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.	2.04	1	0	haloacetic acid; organoiodine compound	alkylating agent
thiabendazole Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate	1.96	1	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
triclofos triclofos: derivative 7 metabolic precursor of trichloroethanol; RN given refers to parent cpd; structure	3.79	2	1	monoalkyl phosphate
urethane [no description available]	2.67	3	0	carbamate ester	fungal metabolite; mutagen
piperonyl butoxide [no description available]	1.96	1	0	benzodioxoles	pesticide synergist
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	1.93	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.36	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.03	1	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.	1.98	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
chlorobutanol [no description available]	1.98	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.	1.93	1	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.01	1	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening 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.	2.93	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.01	1	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
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.	4.01	4	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	1.97	1	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
aniline [no description available]	1.98	1	0	anilines; primary arylamine
uridine triphosphate Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.	2.93	1	0	pyrimidine ribonucleoside 5'-triphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
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.	2	1	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
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.	2.91	4	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
bromoacetate [no description available]	2.04	1	0
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.	1.99	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	4.33	6	0	chloroethanes	polar solvent
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.	5.17	15	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
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	2.04	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	1.95	1	0	alkane; gas molecular entity	plant metabolite; refrigerant
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	1.92	1	0	alkene; gas molecular entity	plant hormone; refrigerant
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	1.96	1	0	boranes; mononuclear parent hydride
vinyl chloride Vinyl Chloride: A gas that has been used as an aerosol propellant and is the starting material for polyvinyl resins. Toxicity studies have shown various adverse effects, particularly the occurrence of liver neoplasms.. chloroethene : A monohaloethene that is ethene in which one of the hydrogens has been replaced by a chloro group.	7.86	4	0	chloroethenes; gas molecular entity; monohaloethene	carcinogenic agent
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	5.81	30	0	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
boron trifluoride [no description available]	1.96	1	0	boron fluoride	NMR chemical shift reference compound
2-bromopropane 2-bromopropane: used as a substitute for freon	2.04	1	0
tetramethylammonium tetramethylammonium: RN given refers to parent cpd. tetramethylammonium : The simplest quaternary ammonium cation, comprising a central nitrogen linked to four methyl groups.	1.93	1	0	quaternary ammonium ion
tribromoethanol tribromoethanol: major descriptor (66-90); on-line search ETHANOL (66-90); INDEX MEDICUS search TRIBROMOETHANOL (66-90)	1.99	1	0	alcohol; organobromine compound
trichloroacetaldehyde trichloroacetaldehyde : An organochlorine compound that consists of acetaldehyde where all the methyl hydrogens are replaced by chloro groups.	3.83	4	0	aldehyde; organochlorine compound	mouse metabolite
trifluoroethanol Trifluoroethanol: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications.	3.36	7	0	fluoroalcohol
tribromoacetic acid [no description available]	2.04	1	0
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	9.46	72	1	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	1.97	1	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	1.96	1	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
2,3-dichloro-1-propene 2,3-dichloro-1-propene: soil fumigant	2.04	1	0
2-chloro-1-propanol [no description available]	2.39	2	0
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
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	9.68	66	1	chloroethenes	inhalation anaesthetic; mouse metabolite
dichloroacetaldehyde [no description available]	1.99	1	0	organochlorine compound
acrylamide [no description available]	3.49	2	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
2,2-dichloroacetyl chloride dichloroacetyl chloride : The acyl chloride obtained by displacement of the hydroxy group of dichloroacetic acid by chloride.	2.04	1	0	acyl chloride	hapten
dichloroacetic acid [no description available]	6.26	13	1	monocarboxylic acid; organochlorine compound	astringent; marine metabolite
2,4-diaminotoluene 2,4-diaminotoluene: RN given refers to unlabeled parent cpd; structure. 2,4-diaminotoluene : An aminotoluene that is para-toluidine with an additional amino group at position 2.	1.98	1	0	aminotoluene	metabolite
1,3-dichloro-2-propanol 1,3-dichloro-2-propanol: RN given refers to cpd with specified locants. 1,3-dichloropropan-2-ol : A secondary alcohol that is isopropanol in which one hydrogen of each methyl group is substituted by a chlorine. A liquid at room temperature (melting point -4degreeC, boiling point 174degreeC at 760 mm Hg), it is used as a solvent for hard resins and nitrocellulose.	2.4	2	0	organochlorine compound; secondary alcohol	cross-linking reagent; protic solvent
alpha-chlorohydrin alpha-Chlorohydrin: A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents.. 3-chloropropane-1,2-diol : A chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3.	2.36	2	0	chloropropane-1,2-diol
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	1.98	1	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
4-chloroaniline 4-chloroaniline: RN given refers to parent cpd; structure. 4-chloroaniline : A chloroaniline in which the chloro atom is para to the aniline amino group.	2.38	2	0	chloroaniline; monochlorobenzenes
1,2-epoxybutane 1,2-epoxybutane: RN given refers to cpd with unspecified isomeric designation	1.96	1	0	epoxide
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	2.65	3	0	epoxide; organochlorine compound
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	3.77	3	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
acrolein [no description available]	2.01	1	0	enal	herbicide; human xenobiotic metabolite; toxin
allyl chloride [no description available]	2.04	1	0	organochlorine compound
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	2.02	1	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	1.95	1	0	alkane
chlorobenzene [no description available]	1.96	1	0	monochlorobenzenes	solvent
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	2.01	1	0	glycol ether	protic solvent; solvent
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.	2.38	2	0	pyrrole; secondary amine
2-ethoxyethanol 2-ethoxyethanol : A hydroxyether that is the ethyl ether derivative of ethylene glycol.	1.97	1	0	glycol ether; primary alcohol	protic solvent; teratogenic agent
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	2.02	1	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
diethylene glycol glycol ether : A hydroxyether which contains both an ether and alcohol functional groups. It is one of the most versatile classes of organic solvents which are commonly used in paints, cleaners, adhesives, pharmaceuticals and cosmetics.	1.97	1	0	hydroxyether
2,2,2-trichloroethanol [no description available]	12.53	166	2	chloroethanol	mouse metabolite
dicofol Dicofol: An organochlorine insecticide.. dicofol : A tertiary alcohol that is DDT in which the benzylic hydrogen has been replaced by a hydroxy group.	1.93	1	0	monochlorobenzenes; organochlorine acaricide; tertiary alcohol
benzyl acetate benzyl acetate : The acetate ester of benzyl alcohol.	1.98	1	0	acetate ester; benzyl ester	metabolite
methohexital Methohexital: An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia.. methohexital : A barbiturate, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by allyl and 1-methylpent-2-ynyl groups.	1.99	1	0	acetylenic compound; barbiturates	drug allergen; intravenous anaesthetic
cyclohexene oxide cyclohexene oxide: inhibitor of epoxide hydrase; structure	1.98	1	0
thiazoles [no description available]	1.98	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
monocrotaline Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.	2.38	2	0	pyrrolizidine alkaloid
2-fluoroethanol [no description available]	2.36	2	0
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	1.98	1	0	thiazolidine
chlormethiazole Chlormethiazole: A sedative and anticonvulsant often used in the treatment of alcohol withdrawal. Chlormethiazole has also been proposed as a neuroprotective agent. The mechanism of its therapeutic activity is not entirely clear, but it does potentiate GAMMA-AMINOBUTYRIC ACID receptors response and it may also affect glycine receptors.	1.95	1	0	thiazoles
tricaprylin tricaprylin: 13C-labeled trioctanoin used in breath tests to detect fat malabsorption. trioctanoin : A triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease.	1.96	1	0	octanoate ester; triglyceride	anticonvulsant; plant metabolite
ethylene bromohydrin ethylene bromohydrin: RN given refers to 2-bromo cpd	3.58	9	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.4	2	0	dialdehyde	biomarker
bis(chloromethyl) ether Bis(Chloromethyl) Ether: A substance that is an irritant to the eyes and respiratory tract and may be carcinogenic.. bis(chloromethyl) ether : An ether that is dimethyl ether in which one of the hydrogens attached to each of the methyl group has replaced by a chlorine.	3.05	1	0	ether; organochlorine compound	alkylating agent; carcinogenic agent
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2.52	2	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
3-nitrophenol [no description available]	2	1	0	3-nitrophenols
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	2.17	1	0	bis(azo) compound
succinimide succinimide: RN given refers to parent cpd. succinimide : A dicarboximide that is pyrrolidine which is substituted by oxo groups at positions 2 and 5.	3.05	1	0	dicarboximide; pyrrolidinone
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.68	3	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
ethoxyacetic acid [no description available]	1.97	1	0	carboxylic acid
3-Bromo-1-propanol [no description available]	2.04	1	0	primary alcohol
dibromoacetic acid dibromoacetic acid : A monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are replaced by bromo groups.	2.04	1	0	2-bromocarboxylic acid; monocarboxylic acid	apoptosis inducer; geroprotector; marine metabolite
c.i. 42510 Rosaniline Dyes: Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS.. basic fuchsin : A four-component mixture of chemically related dyes comprising pararosanilin, rosanilin, magenta II and new fuchsin in varying amounts. rosanilin : A hydrochloride that is the monohydrochloride of 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline. One of the major constituents of Basic fuchsin, together with pararosanilin, magenta II and new fuchsin.	2.73	3	0
2,2-dichloroacetamide [no description available]	3.05	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.	1.97	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; genotoxin; mutagen
glycinaldehyde glycinaldehyde: structure	1.96	1	0	epoxide
2,6-diaminotoluene 2,6-diaminotoluene: RN given refers to parent cpd. 2,6-diaminotoluene : A diamine that is toluene in which both of the hydrogens ortho- to the methyl group are replaced by amino groups.	1.98	1	0	diamine; primary amino compound	mutagen
dodecylamine dodecylamine: RN given refers to parent cpd	2.02	1	0	primary aliphatic amine
stearylamine stearylamine: RN given refers to parent cpd. octadecan-1-amine : An 18-carbon primary aliphatic amine.	2.02	1	0	primary aliphatic amine	film-forming compound
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	1.98	1	0	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
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.	1.98	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	2.4	2	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	2.01	1	0	N-acetyl-D-glucosamine	epitope
chloroethylene oxide chloroethylene oxide: postulated metabolite of vinyl chloride; structure	1.95	1	0	organochlorine compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.67	3	0	diatomic chlorine; gas molecular entity	bleaching agent
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.	2.08	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
2-bromoacrolein [no description available]	2.04	1	0
fluorides [no description available]	1.96	1	0	halide anion; monoatomic fluorine
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	3.36	7	0	benzenes; phenyl acetates
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.	1.99	1	0	alkyl alcohol; primary alcohol; volatile organic compound	antifungal agent; Saccharomyces cerevisiae metabolite; xenobiotic 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.	1.93	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
thiodiacetic acid thiodiacetic acid: vinyl chloride metabolite in urine of rats	2.36	2	0	dicarboxylic acid
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	4.92	4	0	chlorocarbon; chloroethenes	nephrotoxic agent
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	2.35	2	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	2	1	0
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.	2.35	2	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
2-oxothiazolidine-4-carboxylic acid 2-oxothiazolidine-4-carboxylic acid: analog of 5-oxoproline in which the 4-methylene moiety is replaced by sulfur; acts as 5-oxo-L-prolinase substrate; structure in first source; RN given refers to parent cpd without isomeric designation; Procysteine is a trade name	1.98	1	0
trifluoroacetaldehyde [no description available]	1.97	1	0
bromosuccinimide Bromosuccinimide: A brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations. (From Miall's Dictionary of Chemistry, 5th ed; Hawley's Condensed Chemical Dictionary, 12th ed,).	1.97	1	0	dicarboximide; organobromine compound; pyrrolidinone	reagent
leucomalachite green [no description available]	2.11	1	0	benzenoid aromatic compound
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.	2.04	1	0	1,2,3-triazole
heptafluorobutyric anhydride heptafluorobutyric anhydride: structure. heptafluorobutyric anhydride : An acyclic carboxylic anhydride that is perfluorinated butyric anhydride. It is used as a derivatising reagent for gas chromatographic analyses.	1.96	1	0	acyclic carboxylic anhydride; organofluorine compound	chromatographic reagent
3-cresol purple 3-cresol purple: structure given in first source	2	1	0
coenzyme a [no description available]	1.96	1	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	1.93	1	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
alpha,beta-methyleneadenosine 5'-triphosphate alpha,beta-methyleneadenosine 5'-triphosphate: do not confuse with beta,gamma-methylene ATP; RN given refers to parent cpd	3.33	2	0	nucleoside triphosphate analogue
icig 1163 ICIG 1163: RN given refers to parent cpd; structure in first source	1.96	1	0
monocrotaline pyrrole monocrotaline pyrrole: RN given refers to (13alpha,14alpha)-isomer	1.98	1	0
fotemustine fotemustine: structure given in first source. fotemustine : A racemate comprising equimolar amounts of (R)- and (S)-fotemustine. It is an alkylating agent used in the treatment of malignant melanoma.. diethyl (1-{[(2-chloroethyl)(nitroso)carbamoyl]amino}ethyl)phosphonate : A member of the class of N-nitrosoureas that is ethyl diethylphosphonate in the hydrogen at position 1 of the ethyl group attached to the phosphorus has been replaced by a [(2-chloroethyl)(nitroso)carbamoyl]amino group.	3.77	2	1	N-nitrosoureas; organic phosphonate; organochlorine compound
dimyristoylphosphatidylglycerol [no description available]	1.97	1	0
n-acetyl-s-(2-hydroxyethyl)cysteine N-acetyl-S-(2-hydroxyethyl)cysteine: RN given refers to cpd without isomeric designation	1.96	1	0	N-acyl-amino acid
bromodichloroacetic acid [no description available]	2.04	1	0
gr 113808 GR 113808: structure given in first source; a 5-HT(4) receptor antagonist: GR 125487 is the HCl salt. GR 113808 : An indolyl carboxylate ester obtained by formal condensation between the carboxy group of 1-methylindole-3-carboxylic acid with the hydroxy group of N-{2-[4-(hydroxymethyl)piperidin-1-yl]ethyl}methanesulfonamide.	1.99	1	0	indolyl carboxylate ester; piperidines; sulfonamide	serotonergic antagonist
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	1.96	1	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
1,1,2-trichloroethanol 1,1,2-trichloroethanol: metabolite of 1,1,2-trichloroethylene	4.59	10	0
n'-(2-chloroethyl)-n-(2-(methylsulfonyl)ethyl)-n'-nitrosourea N'-(2-chloroethyl)-N-(2-(methylsulfonyl)ethyl)-N'-nitrosourea: structure given in first source	1.97	1	0
s-trichlorovinyl-n-acetylcysteine [no description available]	1.99	1	0	N-acyl-L-amino acid
n'-(2-chloroethyl)-n-(2-(methylsulfinyl)ethyl)-n'-nitrosourea N'-(2-chloroethyl)-N-(2-(methylsulfinyl)ethyl)-N'-nitrosourea: structure given in first source	1.97	1	0
n,n'-bis((2-chloroethyl)nitrosocarbamoyl)cystamine N,N'-bis((2-chloroethyl)nitrosocarbamoyl)cystamine: structure given in first source	1.97	1	0
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2.11	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.25	1	0	oxygen hydride; oxygen radical; reactive oxygen species
lilly 18947 Lilly 18947: RN given refers to parent cpd; Lilly 18947 refers to HBr salt	1.96	1	0
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	3.34	1	1
carbocysteine Carbocysteine: A compound formed when iodoacetic acid reacts with sulfhydryl groups in proteins. It has been used as an anti-infective nasal spray with mucolytic and expectorant action.. S-carboxymethyl-L-cysteine : An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.	2.36	2	0	L-cysteine thioether; non-proteinogenic L-alpha-amino acid	mucolytic
estramustine Estramustine: A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.. estramustine : A carbamate ester obtained by the formal condensation of the hydroxy group of 17beta-estradiol with the carboxy group of bis(2-chloroethyl)carbamic acid.	1.95	1	0	17beta-hydroxy steroid; carbamate ester; organochlorine compound	alkylating agent; antineoplastic agent; radiation protective agent
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.	1.95	1	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
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.	2.01	1	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
2-butenal crotonaldehyde : An enal consisting of propene having a formyl group at the 1-position.	2.01	1	0	enal
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	2.04	1	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
geraniol [no description available]	1.99	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	2.02	1	0
1,4-dichloro-2-butene 1,4-dichloro-2-butene: RN given refers to parent cpd without isomeric designation; structure	2.04	1	0	organochlorine compound
mitobronitol Mitobronitol: Brominated analog of MANNITOL which is an antineoplastic agent appearing to act as an alkylating agent.	2.04	1	0	alcohol; organobromine compound
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.03	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
nadp [no description available]	2.4	2	0
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2.04	1	0
cystine [no description available]	1.99	1	0
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	1.95	1	0
diethyl maleate diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	1.98	1	0	ethyl ester; maleate ester	glutathione depleting agent
bilirubin [no description available]	3.3	2	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
11-cis-retinal Rhodopsin: A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm.. 11-cis-retinal : A retinal having 2E,4Z,6E,8E-double bond geometry.	1.95	1	0	retinal	chromophore; human metabolite; mouse metabolite
ethchlorvynol Ethchlorvynol: A sedative and hypnotic that has been used in the short-term management of INSOMNIA. Its use has been superseded by other drugs.. ethchlorvynol : Propargyl alcohol in which the methylene hydrogens are substituted by ethyl and 2-chlorovinyl groups. A hypnotic and sedative, it is used for treatment of insomnia in some cases where an intolerance or allergy to more commonly used drugs exists.	3.74	2	1
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.	2.01	1	0	4-hydroxynon-2-enal; 4-hydroxynonenal
adp beta s adenosine 5'-O-(2-thiodiphosphate): partial agonist toward platelet aggregation; see also record for 1-thiodiphosphate cpd	2.93	1	0
diphenylhexatriene Diphenylhexatriene: A fluorescent compound that emits light only in specific configurations in certain lipid media. It is used as a tool in the study of membrane lipids.	1.97	1	0	alkatriene	fluorochrome
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.88	4	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.52	2	0	cysteinium	fundamental metabolite
coomassie brilliant blue [no description available]	2.43	2	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.	2.67	3	0
s-(1,2-dichlorovinyl)cysteine S-(1,2-dichlorovinyl)cysteine: RN given refers to (L-Cys)-isomer; structure given in first source. S-(cis-1,2-dichlorovinyl)-L-cysteine : An S-(1,2-dichlorovinyl)-L-cysteine in which the dichlorovinyl group has cis- (Z-) geometry.	2.52	2	0	S-(1,2-dichlorovinyl)-L-cysteine
s-(1,2-dichlorovinyl)glutathione [no description available]	2.52	2	0	peptide
chloralose Chloralose: A derivative of CHLORAL HYDRATE that was used as a sedative but has been replaced by safer and more effective drugs. Its most common use is as a general anesthetic in animal experiments.	2.65	3	0
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.17	1	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
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	1.99	1	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
melitten Melitten: Basic polypeptide from the venom of the honey bee (Apis mellifera). It contains 26 amino acids, has cytolytic properties, causes contracture of muscle, releases histamine, and disrupts surface tension, probably due to lysis of cell and mitochondrial membranes.	1.96	1	0
iberiotoxin [no description available]	2.01	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.37	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
ethyl glucuronide ethyl glucuronide: structure given in first source; RN given refers to (BETA-D)-isomer. ethyl glucuronide : A beta-D-glucosiduronic acid that is the ethyl derivative of beta-D-glucuronic acid.	2.05	1	0	beta-D-glucosiduronic acid	human urinary metabolite
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	1.97	1	0
mannans [no description available]	2.31	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2	1	0
gibberellins [no description available]	2.36	2	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	1.95	1	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	1.93	1	0
deoxyguanosine [no description available]	1.98	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.93	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	1.99	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
eye [no description available]	6.93	1	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.4	2	0

Condition	Relationship Strength	Studies	Trials
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.61	9	0
Acute Liver Injury, Drug-Induced [description not available]	4.01	5	0
Allergic Reaction [description not available]	2.52	2	0
Dermatoses [description not available]	2.4	2	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.52	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.68	3	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.4	2	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	4.01	5	0
Cancer of Stomach [description not available]	2.4	2	0
Infections, Helicobacter [description not available]	2.21	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.4	2	0
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.21	1	0
Chromosome-Defective Micronuclei [description not available]	2.08	1	0
Allergic Contact Dermatitis [description not available]	2.71	3	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.71	3	0
Anaphylactic Reaction [description not available]	2.11	1	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	2.11	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.15	1	0
Cardiac Diseases [description not available]	2.06	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.06	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	3.09	5	0
Experimental Hepatoma [description not available]	2.01	1	0
Dermatitis, Irritant A non-allergic contact dermatitis caused by prolonged exposure to irritants and not explained by delayed hypersensitivity mechanisms.	2.01	1	0
Cancer of Kidney [description not available]	2.01	1	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.94	4	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.01	1	0
Diseases, Occupational [description not available]	3.57	9	0
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	3.34	7	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	4.14	6	0
Liver Dysfunction [description not available]	3.59	3	0
Liver Diseases Pathological processes of the LIVER.	3.59	3	0
Acute Disease Disease having a short and relatively severe course.	2.89	4	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.03	1	0
Chemical Dependence [description not available]	2.42	2	0
Substance-Related Disorders Disorders related to substance use or abuse.	2.42	2	0
ENT Diseases [description not available]	3.34	1	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	3.34	1	1
Arrhythmia [description not available]	2.36	2	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.36	2	0
Experimental Neoplasms [description not available]	2.37	2	0
Hyaline Membrane Disease A respiratory distress syndrome in newborn infants, usually premature infants with insufficient PULMONARY SURFACTANTS. The disease is characterized by the formation of a HYALINE-like membrane lining the terminal respiratory airspaces (PULMONARY ALVEOLI) and subsequent collapse of the lung (PULMONARY ATELECTASIS).	1.96	1	0
Leukemia L5178 An experimental lymphocytic leukemia of mice.	1.96	1	0
Enlarged Spleen [description not available]	1.96	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	1.96	1	0
Bacterial Disease [description not available]	1.96	1	0
Bacterial Infections Infections by bacteria, general or unspecified.	1.96	1	0
Pleural Effusion Presence of fluid in the pleural cavity resulting from excessive transudation or exudation from the pleural surfaces. It is a sign of disease and not a diagnosis in itself.	1.96	1	0
Cadaver A dead body, usually a human body.	1.95	1	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	1.96	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	2.38	2	0
Dizzyness [description not available]	1.96	1	0
Creeping Eruption [description not available]	1.96	1	0
Ache [description not available]	2.38	2	0
Emesis [description not available]	1.96	1	0
Dizziness An imprecise term which may refer to a sense of spatial disorientation, motion of the environment, or lightheadedness.	1.96	1	0
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	1.96	1	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.38	2	0
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	1.96	1	0
Anasarca [description not available]	1.95	1	0
Penile Diseases Pathological processes involving the PENIS or its component tissues.	1.95	1	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	1.95	1	0
Erythema Redness of the skin produced by congestion of the capillaries. This condition may result from a variety of disease processes.	1.95	1	0
Benign Neoplasms, Brain [description not available]	3.78	2	1
Glial Cell Tumors [description not available]	3.37	1	1
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	3.78	2	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	3.37	1	1
Lactic Acidosis [description not available]	4.7	2	1
Acidosis, Lactic Acidosis caused by accumulation of lactic acid more rapidly than it can be metabolized. It may occur spontaneously or in association with diseases such as DIABETES MELLITUS; LEUKEMIA; or LIVER FAILURE.	4.7	2	1
Cancer of Lung [description not available]	1.99	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	1.99	1	0
Cheilitis Inflammation of the lips. It is of various etiologies and degrees of pathology.	1.99	1	0
Hematologic Malignancies [description not available]	1.99	1	0
Cancer of Pancreas [description not available]	2.39	2	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.39	2	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	1.99	1	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	1.99	1	0
Abnormality, Heart [description not available]	1.99	1	0
Delayed Effects, Prenatal Exposure [description not available]	1.99	1	0
Heart Defects, Congenital Developmental abnormalities involving structures of the heart. These defects are present at birth but may be discovered later in life.	1.99	1	0
Adipocere [description not available]	2	1	0
Poisoning, Mercury [description not available]	2	1	0
Mercury Poisoning Poisoning that results from chronic or acute ingestion, injection, inhalation, or skin absorption of MERCURY or MERCURY COMPOUNDS.	2	1	0
Benign Neoplasms [description not available]	2.67	3	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.67	3	0
Alcohol Abuse [description not available]	2	1	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	2	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	2.39	2	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	2.01	1	0
Chronic Insomnia [description not available]	3.34	1	1
Sleep Initiation and Maintenance Disorders Disorders characterized by impairment of the ability to initiate or maintain sleep. This may occur as a primary disorder or in association with another medical or psychiatric condition.	3.34	1	1
Leucocythaemia [description not available]	2.37	2	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	2.37	2	0
Organophosphorus Poisoning [description not available]	1.95	1	0
Organophosphate Poisoning Poisoning due to exposure to ORGANOPHOSPHORUS COMPOUNDS, such as ORGANOPHOSPHATES; ORGANOTHIOPHOSPHATES; and ORGANOTHIOPHOSPHONATES.	1.95	1	0
Liver Steatosis [description not available]	1.95	1	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	1.95	1	0
Cancer of Ovary [description not available]	1.97	1	0
Cancer of Prostate [description not available]	1.97	1	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	1.97	1	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	1.97	1	0
Leukemia, Lymphocytic [description not available]	1.97	1	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	1.97	1	0
Kahler Disease [description not available]	1.97	1	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	1.97	1	0
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	1.97	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	1.97	1	0
Infant, Newborn, Diseases Diseases of newborn infants present at birth (congenital) or developing within the first month of birth. It does not include hereditary diseases not manifesting at birth or within the first 30 days of life nor does it include inborn errors of metabolism. Both HEREDITARY DISEASES and METABOLISM, INBORN ERRORS are available as general concepts.	2.89	1	0
Delayed Hypersensitivity [description not available]	1.97	1	0
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	1.97	1	0
Infections, Staphylococcal [description not available]	1.97	1	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	1.97	1	0
Asystole [description not available]	1.97	1	0
Heart Arrest Cessation of heart beat or MYOCARDIAL CONTRACTION. If it is treated within a few minutes, heart arrest can be reversed in most cases to normal cardiac rhythm and effective circulation.	1.97	1	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	1.97	1	0

ethylene chlorohydrin

Description

Cross-References

Synonyms (109)

Research Excerpts

Toxicity

Pharmacokinetics

Dosage Studied

Roles (1)

Drug Classes (1)

Pathways (1)

Protein Targets (3)

Potency Measurements

Bioassays (1)

Research

Studies (313)

Market Indicators

Research Demand Index: 52.76

Study Types