Compounds > chloroacetaldehyde
Page last updated: 2024-12-04

chloroacetaldehyde

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID33
CHEMBL ID506976
CHEBI ID27871
MeSH IDM0045789

Synonyms (56)

Synonym
chloroaldehyde
inchi=1/c2h3clo/c3-1-2-4/h2h,1h
acetaldehyde, chloro-
einecs 203-472-8
2-chloro-1-ethanal
ccris 856
rcra waste number p023
alpha-chloroacetaldehyde
rcra waste no. p023
un2232
2-chloroacetaldehyde
brn 1071226
chloroethanal
hsdb 2521
monochloroacetaldehyde
chloroacetaldehyde monomer
107-20-0
C06754
chloroacetaldehyde ,
2-chloroethanal
chloroacetaldehyde (caa)
CHEBI:27871 ,
CHEMBL506976
AKOS000118948
NCGC00248308-01
ec 203-472-8
unii-cf069f5d9c
2-chloroethanal [un2232] [poison]
acetaldehyde, 2-chloro-
4-01-00-03134 (beilstein handbook reference)
cf069f5d9c ,
NCGC00255050-01
cas-107-20-0
dtxcid60292
tox21_301152
dtxsid4020292 ,
BP-13328
STL264246
chloroacetaldehyde [hsdb]
chloroacetaldehyde [mi]
chloracetaldehyde
chloro acetaldehyde
chloroactaldehyde
clch2cho
chloro-acetaldehyde
chloroacetoaldehyde
ch2clcho
un 2232
chloroacetalaldehyde
mfcd00006992
J-509000
2-chloro-acetaldehyde
Q1950418
STR01221
EN300-19136
chloroacetaldehyde (~45per cent in water)

Research Excerpts

Overview

Chloroacetaldehyde (CAA) is a metabolite of the human carcinogen vinyl chloride. It is putatively responsible for renal damage following anti-tumor therapy with IFO.

ExcerptReferenceRelevance
"Chloroacetaldehyde (CAA) is a metabolite of the human carcinogen vinyl chloride. "( DNA damage and mutations produced by chloroacetaldehyde in a CpG-methylated target gene.
Choi, JH; Pfeifer, GP, 2004)		2.04
"Chloroacetaldehyde (CAA) is a metabolite of the alkylating agent ifosfamide (IFO) and putatively responsible for renal damage following anti-tumor therapy with IFO. "( Chloroacetaldehyde as a sulfhydryl reagent: the role of critical thiol groups in ifosfamide nephropathy.
Benesic, A; Freudinger, R; Gekle, M; Groezinger, F; Kirchhoff, A; Mildenberger, S; Schwerdt, G; Wollny, B, 2006)		3.22
"Chloroacetaldehyde (CA) is a nephrotoxic and neurotoxic metabolite of the anticancer drug ifosfamide (IFA) and is a dose-limiting factor in IFA-based chemotherapy. "( High-performance liquid chromatographic-fluorescent method to determine chloroacetaldehyde, a neurotoxic metabolite of the anticancer drug ifosfamide, in plasma and in liver microsomal incubations.
Huang, Z; Waxman, DJ, 1999)		1.98

Effects

ExcerptReferenceRelevance
"Chloroacetaldehyde has been shown to be a urinary metabolite of cyclophosphamide in the rat. "( 2-Chloroacetaldehyde: a metabolite of cyclophosphamide in the rat.
Graham, MI; McLean, AE; Shaw, IC, 1983)		2.43

Toxicity

Cyclophosphamide and ifosfamide are two commonly used DNA-alkylating agents in cancer chemotherapy. They undergo biotransformation to several toxic and non-toxic metabolites. The toxic metabolite of IFO thought to be responsible for IFO-induced kidney damage is chloroacetaldehyde (CAA)

ExcerptReferenceRelevance
" 4-OH-IF and 4-OH-CP were significantly more toxic than the parent drugs."( Toxicity of ifosfamide, cyclophosphamide and their metabolites in renal tubular cells in culture.
Ansorge, S; Brandis, M; Mohrmann, M; Schmich, U; Schönfeld, B, 1994)		0.29
", this toxic effect is not accompanied by an increase in intramyocardial citrate levels."( A 13C NMR study of 2-(13)C-chloroacetaldehyde, a metabolite of ifosfamide and cyclophosphamide, in the isolated perfused rabbit heart model. Initial observations on its cardiotoxicity and cardiac metabolism.
Loqueviel, C; Malet-Martino, M; Martino, R, 1997)		0.59
"Renal injury is a common side effect of the chemotherapeutic agent ifosfamide."( Toxicity of ifosfamide and its metabolite chloroacetaldehyde in cultured renal tubule cells.
Chan, K; Davies, S; Lu, H; Springate, J; Taub, M, 1999)		0.57
" We have developed transgenic cell lines to examine the potential for either human ALDH1A1 or ALDH3A1 to protect against damage mediated by these toxic aldehydes."( Selective protection by stably transfected human ALDH3A1 (but not human ALDH1A1) against toxicity of aliphatic aldehydes in V79 cells.
Bunting, KD; Haynes, RL; Leone-Kabler, S; Szweda, L; Townsend, AJ; Wu, Y, 2001)		0.31
" The sensitivity of pediatric tubules to the toxic effects of CAA and the rate of their CAA uptake were not statistically different from those found in adult tubules."( Toxicity of chloroacetaldehyde is similar in adult and pediatric kidney tubules.
Baverel, G; Cochat, P; Dubourg, L; Michoudet, C; Tanière, P, 2002)		0.69
"Renal injury is a common side effect of the chemotherapeutic agent ifosfamide."( Comparative toxicity of ifosfamide metabolites and protective effect of mesna and amifostine in cultured renal tubule cells.
Springate, JE; Taub, M; Zaki, EL, 2003)		0.32
" With cyclophosphamide it shares a toxicity profile characterized by myelosuppression and urotoxicity, but ifosfamide has additionally disclosed adverse neurological effects."( Neurological toxicity of ifosfamide.
Giometto, B; Nicolao, P, 2003)		0.32
"Renal injury is a common side effect of the chemotherapeutic agent ifosfamide."( Ifosfamide toxicity in cultured proximal renal tubule cells.
Springate, J; Taub, M, 2007)		0.34
" coli genome from the toxic effects of CAA."( AlkB influences the chloroacetaldehyde-induced mutation spectra and toxicity in the pSP189 supF shuttle vector.
Dedon, PC; Delaney, JC; Essigmann, JM; Kim, MY; Taghizadeh, K; Wogan, GN; Zhou, X, 2007)		0.66
" The toxic metabolite of IFO thought to be responsible for IFO-induced kidney damage is chloroacetaldehyde (CAA)."( Ifosfamide nephrotoxicity in children: a mechanistic base for pharmacological prevention.
Chen, N; Hanly, L; Koren, G; Rieder, M, 2009)		0.58
"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)		0.59
"Since all the latter test compounds, like many toxic compounds, negatively interact with cellular metabolic pathways, we also illustrate our biochemical toxicology approach in which we used not only enzymatic but also carbon 13 NMR measurements and mathematical modelling of metabolic pathways."( Use of precision-cut renal cortical slices in nephrotoxicity studies.
Baverel, G; Duplany, A; El Hage, M; Ferrier, B; Gauthier, C; Knouzy, B; Martin, G, 2013)		0.39
"Cyclophosphamide and ifosfamide are two commonly used DNA-alkylating agents in cancer chemotherapy that undergo biotransformation to several toxic and non-toxic metabolites, including acrolein and chloroacetaldehyde (CAA)."( Acrolein and chloroacetaldehyde: an examination of the cell and cell-free biomarkers of toxicity.
Lau, V; MacAllister, SL; Martin-Brisac, N; O'Brien, PJ; Yang, K, 2013)		0.95
" The analysis revealed toxic effects only for the treatment with 35 μmol·liter(-1) for 3 and 14 days."( Nephron Toxicity Profiling via Untargeted Metabolome Analysis Employing a High Performance Liquid Chromatography-Mass Spectrometry-based Experimental and Computational Pipeline.
Dekant, W; Hewitt, P; Huber, CG; Jennings, P; Kohlbacher, O; Limonciel, A; Ranninger, C; Reischl, R; Rurik, M; Ruzek, S; Wilmes, A, 2015)		0.42
" Those results are in agreement with literature data reporting that intracellular CAA toxic concentrations range from 35 to 320 μM, after therapeutic ifosfamide dosing."( Investigation of ifosfamide and chloroacetaldehyde renal toxicity through integration of in vitro liver-kidney microfluidic data and pharmacokinetic-system biology models.
Bois, FY; Hamon, J; Leclerc, E, 2016)		0.72
"The equimolar produced metabolite DCCTX was chosen to reflect chloroacetaldehyde (CAA, a toxic metabolite of CTX) production in rats."( Schisandra chinensis extract decreases chloroacetaldehyde production in rats and attenuates cyclophosphamide toxicity in liver, kidney and brain.
Chen, L; Chen, W; Feng, G; Gao, S; Yin, J; Zhai, J; Zhang, F, 2018)		0.99

Pharmacokinetics

ExcerptReferenceRelevance
" Independent of the route of ifosfamide application on day 1, the terminal half-life on day 3 (when the drug was given by the alternative route) was decreased in 6 out of the 12 patients, thus indicating self-induction of hepatic metabolism."( Metabolism and pharmacokinetics of oral and intravenous ifosfamide.
Cerny, T; Küpfer, A; Kurowski, V; Wagner, T, 1991)		0.28
" As compared with the values obtained on day 1, on day 5 the terminal half-life and AUC values determined for IF were reduced by 30% (6."( Comparative pharmacokinetics of ifosfamide, 4-hydroxyifosfamide, chloroacetaldehyde, and 2- and 3-dechloroethylifosfamide in patients on fractionated intravenous ifosfamide therapy.
Kurowski, V; Wagner, T, 1993)		0.52
" Using pharmacokinetic modeling of experimental data, we show that the median level of chloroacetaldehyde in RT cells is 80 micromol/L, ranging from 35 to 320 micromol/L."( Renal-tubule metabolism of ifosfamide to the nephrotoxic chloroacetaldehyde: pharmacokinetic modeling for estimation of intracellular levels.
Aleksa, K; Ito, S; Koren, G, 2004)		0.79
" The peak concentration and area under the curve (AUC) were determined for the parent compound and the metabolites 4-hydroxyifosfamide and chloracetaldehyde in eight patients who received two cycles of ICE chemotherapy (ifosfamide 5 g/m(2) day 1, carboplatin 300 mg/m(2) day 1, etoposide 100 mg/m(2) days 1-3)."( Influence of short-term use of dexamethasone on the pharmacokinetics of ifosfamide in patients.
Brüggemann, SK; Peters, SO; Pfäffle, S; Wagner, T, 2007)		0.34
" A pharmacokinetic (PK) model described the production of CAA by the hepatocytes and its transport to the renal cells."( Investigation of ifosfamide and chloroacetaldehyde renal toxicity through integration of in vitro liver-kidney microfluidic data and pharmacokinetic-system biology models.
Bois, FY; Hamon, J; Leclerc, E, 2016)		0.72

Dosage Studied

ExcerptRelevanceReference
"3 mmol/l) displaces the dose-response curve for acrolein to the left, indicating an increased toxicity of the combination of acrolein plus Dimesna."( Ifosfamide and mesna: effects on the Na/H exchanger activity in renal epithelial cells in culture (LLC-PK1).
Brandis, M; Küpper, N; Mohrmann, M; Schönfield, B, )		0.13
"0% VC in air produced similar mutant frequencies without a clear dose-response relationship, suggesting saturation of metabolic activation."( Mutagenicity of vinyl chloride and its reactive metabolites, chloroethylene oxide and chloroacetaldehyde, in a metabolically competent human B-lymphoblastoid line.
Chiang, SY; Skopek, TR; Swenberg, JA; Weisman, WH, 1997)		0.52
" Similar dose-response curves were found for both metabolites."( Ifosfamide cytotoxicity on human tumor and renal cells: role of chloroacetaldehyde in comparison to 4-hydroxyifosfamide.
Brüggemann, SK; Kisro, J; Wagner, T, 1997)		0.54
" The kinetics of the excretion were compared following short-term and continuous ifosfamide infusion at a dosage of 3 g/m2."( Excretion kinetics of ifosfamide side-chain metabolites in children on continuous and short-term infusion.
Blaschke, G; Boos, J; Hohenlöchter, B; Jürgens, H; Rossi, R; Silies, H, 1998)		0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
[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]

Pathways (6)

PathwayProteinsCompounds
Cyclophosphamide Action Pathway922
Ifosfamide Action Pathway821
Cyclophosphamide Metabolism Pathway922
Ifosfamide Metabolism Pathway821
Cyclophosphamide Pathway, Pharmacokinetics73
1,2-dichloroethane degradation115

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency54.94100.000229.305416,493.5996AID743075
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency24.54120.001024.504861.6448AID743215
aryl hydrocarbon receptorHomo sapiens (human)Potency76.95880.000723.06741,258.9301AID743085
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1337095Inhibition of human MPO2017ACS medicinal chemistry letters, Feb-09, Volume: 8, Issue:2
From Dynamic Combinatorial Chemistry to
AID1135701Mutagenicity in repair-deficient Bacillus subtilis assessed as growth inhibition at 0.1 M1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Mercaptoimidazolylpropionic acid hydrobromide. Inhibition of tadpole collagenase and related properties.
AID384212Mutagenic activity in Salmonella Typhimurium TA100 assessed as logarithm of his+ revertant number increasing activity by amens test2008Bioorganic & 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]

Research

Studies (202)

TimeframeStudies, This Drug (%)All Drugs %
pre-199050 (24.75)18.7374
1990's68 (33.66)18.2507
2000's51 (25.25)29.6817
2010's30 (14.85)24.3611
2020's3 (1.49)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.42

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.42 (24.57)
Research Supply Index5.38 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index70.64 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (45.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (1.40%)5.53%
Reviews8 (3.74%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other203 (94.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethylene chlorohydrin
Ethylene Chlorohydrin: Used as a solvent, in the manufacture of insecticides, and for treating sweet potatoes before planting. May cause nausea, vomiting, pains in head and chest, stupefaction. Irritates mucous membranes and causes kidney and liver degeneration.. chloroethanol : An organochlorine compound that is ethanol substituted by at least one chloro group.		2.9340chloroethanolxenobiotic metabolite
3-hydroxybenzaldehyde
[no description available]		2.1510hydroxybenzaldehyde
4-hydroxybenzaldehyde
[no description available]		2.1510hydroxybenzaldehydeEC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor;
mouse metabolite;
plant metabolite
ethylene glycol
Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.		2.0310ethanediol;
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.		12.531993aldehydecarcinogenic 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).		7.420ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
adenine
[no description available]		4.191706-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
agmatine
Agmatine: Decarboxylated arginine, isolated from several plant and animal sources, e.g., pollen, ergot, herring sperm, octopus muscle.		2.0310guanidines;
primary amino compound		Escherichia coli metabolite;
mouse metabolite
benzaldehyde
[no description available]		2.4520benzaldehydesEC 3.1.1.3 (triacylglycerol lipase) inhibitor;
EC 3.5.5.1 (nitrilase) inhibitor;
flavouring agent;
fragrance;
odorant receptor agonist;
plant metabolite
benzene
[no description available]		3.0910aromatic annulene;
benzenes;
volatile organic compound		carcinogenic agent;
environmental contaminant;
non-polar solvent
bromide
Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)		2.0210halide anion;
monoatomic bromine
1-butanol
1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.		2.0510alkyl alcohol;
primary alcohol;
short-chain primary fatty alcohol		human metabolite;
mouse metabolite;
protic solvent
aminooxyacetic acid
Aminooxyacetic Acid: A compound that inhibits aminobutyrate aminotransferase activity in vivo, thereby raising the level of gamma-aminobutyric acid in tissues.. (aminooxy)acetic acid : A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues.		1.9810amino acid;
hydroxylamines;
monocarboxylic acid		anticonvulsant;
EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor;
EC 4.2.1.22 (cystathionine beta-synthase) inhibitor;
nootropic agent
methane
Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).		1.9910alkane;
gas molecular entity;
mononuclear parent hydride;
one-carbon compound		bacterial metabolite;
fossil fuel;
greenhouse gas
chloroacetic acid
chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.		2.6930chlorocarboxylic acid;
haloacetic acid		alkylating agent;
herbicide
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		1.9710halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
propionaldehyde
propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.		2.7130alpha-CH2-containing aldehyde;
propanals		Escherichia coli metabolite
4-nitrobenzaldehyde
4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.		2.1510benzaldehydes;
C-nitro compound
cytosine
[no description available]		4.18170aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae 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.		2.94402-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite
formaldehyde
paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy		2.9340aldehyde;
one-carbon compound		allergen;
carcinogenic agent;
disinfectant;
EC 3.5.1.4 (amidase) inhibitor;
environmental contaminant;
Escherichia coli metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
glutaric acid
glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.		3.1110alpha,omega-dicarboxylic acid;
dicarboxylic fatty acid		Daphnia magna metabolite;
human metabolite
glycolaldehyde
[no description available]		7.9340glycolaldehydesfundamental metabolite;
human metabolite
glycolic acid
glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.		1.99102-hydroxy monocarboxylic acid;
primary alcohol		keratolytic drug;
metabolite
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.0310elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
hydroxylamine
amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.		2.3920hydroxylaminesalgal metabolite;
bacterial xenobiotic metabolite;
EC 1.1.3.13 (alcohol oxidase) inhibitor;
EC 4.2.1.22 (cystathionine beta-synthase) inhibitor;
EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor;
nitric oxide donor;
nucleophilic reagent
palmitic acid
Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.		210long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
pentachlorophenol
PENTA: structure given in first source		2.0310aromatic fungicide;
chlorophenol;
organochlorine pesticide;
pentachlorobenzenes		human xenobiotic metabolite
propylene glycol
Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.		2.0310glycol;
propane-1,2-diols		allergen;
human xenobiotic metabolite;
mouse metabolite;
protic solvent
thiosulfates
Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.		1.9710divalent inorganic anion;
sulfur oxide;
sulfur oxoanion		human metabolite
sulfites
Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).		210divalent inorganic anion;
sulfur oxide;
sulfur oxoanion
succinic acid
Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.		210alpha,omega-dicarboxylic acid;
C4-dicarboxylic acid		anti-ulcer drug;
fundamental metabolite;
micronutrient;
nutraceutical;
radiation protective agent
vanillin
Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).		2.1510benzaldehydes;
monomethoxybenzene;
phenols		anti-inflammatory agent;
anticonvulsant;
antioxidant;
flavouring agent;
plant metabolite
amifostine anhydrous
Amifostine: A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.. amifostine : An organic thiophosphate that is the S-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy.		2.7230diamine;
organic thiophosphate		antioxidant;
prodrug;
radiation protective agent
p-aminohippuric acid
p-Aminohippuric Acid: The glycine amide of 4-aminobenzoic acid. Its sodium salt is used as a diagnostic aid to measure effective renal plasma flow (ERPF) and excretory capacity.. p-aminohippurate : A hippurate that is the conjugate base of p-aminohippuric acid, arising from deprotonation of the carboxy group.. p-aminohippuric acid : An N-acylglycine that is the 4-amino derivative of hippuric acid; used as a diagnostic agent in the measurement of renal plasma flow.		2.0310N-acylglycineDaphnia magna metabolite
2-aminothiazole
2-aminothiazole: RN given refers to parent cpd; structure. 1,3-thiazol-2-amine : A primary amino compound that is 1,3-thiazole substituted by an amino group at position 2.		1.97101,3-thiazoles;
primary amino compound
chloral hydrate
[no description available]		8.6130aldehyde hydrate;
ethanediol;
organochlorine compound		general anaesthetic;
mouse metabolite;
sedative;
xenobiotic
diethyl pyrocarbonate
Diethyl Pyrocarbonate: Preservative for wines, soft drinks, and fruit juices and a gentle esterifying agent.. diethyl pyrocarbonate : The diethyl ester of dicarbonic acid.		3.0850acyclic carboxylic anhydride
disulfiram
[no description available]		2.0510organic 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.		3.1810branched-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
ether
Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.		1.9610ether;
volatile organic compound		inhalation anaesthetic;
non-polar solvent;
refrigerant
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.		2.0510pyrazolesantidote;
EC 1.1.1.1 (alcohol dehydrogenase) inhibitor;
protective agent
glutaral
Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.		2.1510dialdehydecross-linking reagent;
disinfectant;
fixative
guanethidine
Guanethidine: An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.. guanethidine : A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group.. guanethidine sulfate : A organic sulfate salt composed of two molecules of guanethidine and one of sulfuric acid.		2.0210azocanes;
guanidines		adrenergic antagonist;
antihypertensive agent;
sympatholytic agent
ethidium
Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.		2.6730phenanthridinesfluorochrome;
intercalator
hydralazine
Hydralazine: A direct-acting vasodilator that is used as an antihypertensive agent.. hydralazine : The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent.		2.1510azaarene;
hydrazines;
ortho-fused heteroarene;
phthalazines		antihypertensive agent;
vasodilator agent
ifosfamide
[no description available]		9.64453ifosfamidesalkylating agent;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
xenobiotic
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.1510carbohydrazideantitubercular agent;
drug allergen
ketoconazole
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.		2.1710dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine
methoxyamine
methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure		1.9810organooxygen compound
methyl methanesulfonate
[no description available]		1.9810methanesulfonate esteralkylating agent;
apoptosis inducer;
carcinogenic agent;
genotoxin;
mutagen
netropsin
Netropsin: A basic polypeptide isolated from Streptomyces netropsis. It is cytotoxic and its strong, specific binding to A-T areas of DNA is useful to genetics research.		2.0210
nifedipine
Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.		2.0610C-nitro compound;
dihydropyridine;
methyl ester		calcium channel blocker;
human metabolite;
tocolytic agent;
vasodilator agent
oxidopamine
Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).		2.0210benzenetriol;
catecholamine;
primary amino compound		drug metabolite;
human metabolite;
neurotoxin
quinone
benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).		3.09101,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
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.		1.9510barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
propidium
Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.		2.0310phenanthridines;
quaternary ammonium ion		fluorochrome;
intercalator
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.		2.0410haloacetic acid;
organoiodine compound		alkylating agent
tetraethylammonium
Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)		2.0310quaternary ammonium ion
urethane
[no description available]		210carbamate esterfungal metabolite;
mutagen
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		1.9810mitomycinalkylating agent;
antineoplastic agent
thymidine
[no description available]		2.6630pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
cysteine
[no description available]		1.9510cysteine zwitterion;
cysteine;
L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid		EC 4.3.1.3 (histidine ammonia-lyase) inhibitor;
flour treatment agent;
human metabolite
2-acetylaminofluorene
2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.		6.97102-acetamidofluorenesantimitotic;
carcinogenic agent;
epitope;
mutagen
chloramphenicol
Amphenicol: Chloramphenicol and its derivatives.		1.9710C-nitro compound;
carboxamide;
diol;
organochlorine compound		antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor
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.		1.9910aspartate 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
adenosine diphosphate
Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.		2.6730adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
uridine
[no description available]		2.3820uridinesdrug metabolite;
fundamental metabolite;
human metabolite
bromodeoxyuridine
Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.		2.0310pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
adenosine monophosphate
Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.		2.3720adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
methylene blue
Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.		7.420organic chloride saltacid-base indicator;
antidepressant;
antimalarial;
antimicrobial agent;
antioxidant;
cardioprotective agent;
EC 1.4.3.4 (monoamine oxidase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 4.6.1.2 (guanylate cyclase) inhibitor;
fluorochrome;
histological dye;
neuroprotective agent;
physical tracer
cytidine
[no description available]		2.8840cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
egtazic acid
Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.		2.110diether;
tertiary amino compound;
tetracarboxylic acid		chelator
bromoacetate
[no description available]		2.0410
tubercidin
Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.		2.2510antibiotic antifungal agent;
N-glycosylpyrrolopyrimidine;
ribonucleoside		antimetabolite;
antineoplastic agent;
bacterial metabolite
histidine
Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.		1.9510amino acid zwitterion;
histidine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
n-pentanol
n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.		2.0510pentanol;
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.		1.9710chloroethanespolar solvent
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		1.9710L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		1.9610erythrose 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
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.		5.6140chloroethenes;
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.		4.86110gas molecular entity;
oxacycle;
saturated organic heteromonocyclic parent		allergen;
mouse metabolite;
mutagen
2-bromopropane
2-bromopropane: used as a substitute for freon		2.0410
propylene oxide
propylene oxide: structure. 1,2-epoxypropane : An epoxide that is oxirane substituted by a methyl group at position 2.		1.9510epoxide
tribromoacetic acid
[no description available]		2.0410
trichloroacetic acid
Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.		2.6930monocarboxylic acid;
organochlorine compound		carcinogenic agent;
metabolite;
mouse metabolite
dimethyl sulfate
dimethyl sulfate: RN given refers to unlabeled cpd; structure. dimethyl sulfate : The dimethyl ester of sulfuric acid.		1.9910alkyl sulfatealkylating agent;
immunosuppressive agent
isobutyraldehyde
isobutyraldehyde : A member of the class of propanals that is propanal substituted by a methyl group at position 2.		2.15102-methyl-branched fatty aldehyde;
propanals		Saccharomyces cerevisiae metabolite
2,3-dichloro-1-propene
2,3-dichloro-1-propene: soil fumigant		2.0410
chloroacetone
[no description available]		6.9610alpha-chloroketone
1,1,2-trichloroethane
1,1,2-trichloroethane: RN given refers to cpd with locants as specified. 1,1,2-trichloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1 and 2.		1.9710chloroethanes
2,2-dichloroacetyl chloride
dichloroacetyl chloride : The acyl chloride obtained by displacement of the hydroxy group of dichloroacetic acid by chloride.		2.0410acyl chloridehapten
dichloroacetic acid
[no description available]		8.3220monocarboxylic acid;
organochlorine compound		astringent;
marine metabolite
2-chlorobenzaldehyde
[no description available]		2.1510
salicylaldehyde
o-hydroxybenzaldehyde: structure in first source		2.1510hydroxybenzaldehydenematicide;
plant metabolite
styrene oxide
styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.		7.2110epoxidehuman xenobiotic 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.		2.0410organochlorine compound;
secondary alcohol		cross-linking reagent;
protic solvent
furaldehyde
Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.		2.4420aldehyde;
furans		Maillard reaction product;
metabolite
thiophene-2-carboxaldehyde
thiophene-2-carboxaldehyde: structure in first source. formylthiophene : An aldehyde that is thiophene substituted by a formyl group at position 2.		2.1510aldehyde;
thiophenes		metabolite
3-nitrobenzaldehyde
[no description available]		2.1510
4-(dimethylamino)benzaldehyde
p-dimethylaminobenzaldehyde: structure in first source. 4-(dimethylamino)benzaldehyde : A member of the class of benzaldehydes that is benzaldehyde carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.		2.1510benzaldehydes;
substituted aniline;
tertiary amino compound		chromogenic compound
phenyl isocyanate
[no description available]		2.1510benzenes;
isocyanates		allergen;
hapten
phenylisothiocyanate
phenylisothiocyanate: structure. phenyl isothiocyanate : An isothiocyanate having a phenyl group attached to the nitrogen; used for amino acid sequencing in the Edman degradation.		7.1510isothiocyanateallergen;
reagent
4-chlorobenzaldehyde
[no description available]		2.1510
ethylene dibromide
Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.		2.0410bromoalkane;
bromohydrocarbon		algal metabolite;
carcinogenic agent;
fumigant;
marine metabolite;
mouse metabolite;
mutagen
acrolein
[no description available]		4.02140enalherbicide;
human xenobiotic metabolite;
toxin
allyl chloride
[no description available]		2.0410organochlorine compound
chloroacetonitrile
[no description available]		7.0810nitrile
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.		2.0510primary allylic alcohol;
propenol		antibacterial agent;
fungicide;
herbicide;
insecticide;
plant metabolite
glyoxal
[no description available]		2.4720dialdehydeagrochemical;
allergen;
pesticide;
plant growth regulator
piperidine
[no description available]		2.3820azacycloalkane;
piperidines;
saturated organic heteromonocyclic parent;
secondary amine		base;
catalyst;
human metabolite;
non-polar solvent;
plant metabolite;
protic solvent;
reagent
bis(2-chloroethyl)ether
bis(2-chloroethyl)ether: structure		1.9610ether
3-hydroxy-3-methylbutene
3-hydroxy-3-methylbutene: narcotic, sleep-producing principle from hops; RN given refers to parent cpd. 3-hydroxy-3-methylbut-1-ene : A tertiary alcohol that is 3-methylbut-1-ene carrying a hydroxy substituent at position 3.		2.0510olefinic compound;
tertiary alcohol		animal metabolite;
fragrance;
pheromone;
plant metabolite
2-Methoxybenzaldehyde
[no description available]		2.1510carbonyl compound
protocatechualdehyde
protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure		2.1510dihydroxybenzaldehyde
sodium cyanide
Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.		1.9710cyanide salt;
one-carbon compound;
sodium salt		EC 1.15.1.1 (superoxide dismutase) inhibitor
thiazoles
[no description available]		2.42201,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
2-aminopurine
2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).. aminopurine : Any purine having at least one amino substituent.. 2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.		2.25102-aminopurines;
nucleobase analogue		antimetabolite
4-methylphenylhydrazine
4-methylphenylhydrazine: RN given refers to parent cpd		2.1510
ethylene bromohydrin
ethylene bromohydrin: RN given refers to 2-bromo cpd		2.0410
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.		2.7430dialdehydebiomarker
2-nitrobenzaldehyde
2-nitrobenzaldehyde: structure given in first source. 2-nitrobenzaldehyde : Benzaldehyde substituted at the ortho-position with a nitro group.		2.1510benzaldehydes;
C-nitro compound
neutral red
Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.		2.0110hydrochlorideacid-base indicator;
dye;
two-colour indicator
4-aminobenzaldehyde
4-aminobenzaldehyde: a yellow colorimetric indicator for detecting fluoride; structure in first source		2.1510benzaldehydes
diepoxybutane
diepoxybutane: difunctional alkylating agent; RN given refers to cpd with unspecified isomeric designation; structure		1.9910epoxidemutagen
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		3.7930acetylcysteine;
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
isovanillin
isovanillin: inhibits aldehyde oxidase. isovanillin : A member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase.		2.1510benzaldehydes;
monomethoxybenzene;
phenols		animal metabolite;
antidiarrhoeal drug;
antifungal agent;
EC 1.2.3.1 (aldehyde oxidase) inhibitor;
HIV protease inhibitor;
plant metabolite
3-Bromo-1-propanol
[no description available]		2.0410primary alcohol
dibromoacetic acid
dibromoacetic acid : A monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are replaced by bromo groups.		2.04102-bromocarboxylic acid;
monocarboxylic acid		apoptosis inducer;
geroprotector;
marine metabolite
2,2-dichloroacetamide
[no description available]		2.0810
methylnitrosourea
Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.		1.9810N-nitrosoureasalkylating agent;
carcinogenic agent;
mutagen;
teratogenic agent
deoxycytidine
[no description available]		2.4220pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
4-(4-nitrobenzyl)pyridine
[no description available]		1.9710
dithiothreitol
1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.		1.98101,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
cladribine
[no description available]		6.9810organochlorine compound;
purine 2'-deoxyribonucleoside		antineoplastic agent;
immunosuppressive agent
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		1.9810beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
acetoxyacetylaminofluorene
Acetoxyacetylaminofluorene: An alkylating agent that forms DNA ADDUCTS at the C-8 position in GUANINE, resulting in single strand breaks. It has demonstrated carcinogenic action.. N-acetoxy-2-acetamidofluorene : A 2-acetamidofluorene compound in which the parent 2-acetamidofluorene is substituted on nitrogen by an acetoxy group.		2.37202-acetamidofluorenescarcinogenic agent;
mutagen
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.0210metal allergen;
nickel group element atom;
platinum group metal atom
silver nitrate
Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.		210inorganic nitrate salt;
silver salt		astringent
chloroethylene oxide
chloroethylene oxide: postulated metabolite of vinyl chloride; structure		4.86110organochlorine compound
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		1.9710dihydrogen
chlorine
Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.		2.7330diatomic 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.		2.2110elemental molecule;
gas molecular entity;
reactive oxygen species;
triatomic oxygen		antiseptic drug;
disinfectant;
electrophilic reagent;
greenhouse gas;
mutagen;
oxidising agent;
tracer
chloramine
[no description available]		7.0810halide
2-bromoacrolein
[no description available]		2.0410
osmium tetroxide
Osmium Tetroxide: (T-4)-Osmium oxide (OsO4). A highly toxic and volatile oxide of osmium used in industry as an oxidizing agent. It is also used as a histological fixative and stain and as a synovectomy agent in arthritic joints. Its vapor can cause eye, skin, and lung damage.. osmium tetroxide : An osmium coordination entity consisting of four oxygen atoms bound to a central osmium atom via covalent double bonds.		3.0850osmium coordination entityfixative;
histological dye;
oxidising agent;
poison
daunorubicin
Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.		1.9910aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.3920benzenes;
phenyl acetates
4-anisaldehyde
4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.		2.1510benzaldehydesbacterial metabolite;
human urinary metabolite;
insect repellent;
plant metabolite
thiodiacetic acid
thiodiacetic acid: vinyl chloride metabolite in urine of rats		2.3720dicarboxylic acid
tetrachloroethylene
Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.		2.0310chlorocarbon;
chloroethenes		nephrotoxic agent
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		1.9910glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
adefovir
adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.		7106-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		3.91130adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
5-methylcytosine
5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.		7.9240methylcytosine;
pyrimidines		human metabolite
glutathione disulfide
Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.		2.0410glutathione derivative;
organic disulfide		Escherichia coli metabolite;
mouse metabolite
1,7-phenanthroline
[no description available]		1.9710phenanthroline
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.		2.02101,2,3-triazole
2,5-dihydroxybenzaldehyde
2,5-dihydroxybenzaldehyde: structure in first source. 2,5-dihydroxybenzaldehyde : A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5.		2.1510dihydroxybenzaldehydehuman metabolite;
mouse metabolite;
Penicillium metabolite
homocysteine
Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.		3.3911amino acid zwitterion;
homocysteine;
serine family amino acid		fundamental metabolite;
mouse metabolite
4-hydroxycyclophosphamide
4-hydroxycyclophosphamide: primary activation metabolite of cyclophosphamide; RN given refers to cpd without isomeric designation. 4-hydroxycyclophosphamide : A phosphorodiamide that consists of 2-amino-1,3,2-oxazaphosphinan-4-ol 2-oxide having two 2-chloroethyl groups attached to the exocyclic nitrogen.		2.0110nitrogen mustard;
organochlorine compound;
phosphorodiamide		alkylating agent;
metabolite
hydroperoxyisophosphamide
hydroperoxyisophosphamide: RN given refers to parent cpd without isomeric designation		2.4120
alpha-bromo-beta-(5-imidazolyl)propionic acid
[no description available]		1.9510
isophosphamide mustard
isophosphamide mustard: antitumor metabolite of ifosfamide; palifosfamide-tris is a salt with tris; structure in first source		2.4120phosphorodiamide
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		3.1810cobalt group element atom;
metal allergen		micronutrient
1,n(6)-ethenoadenine
1,N(6)-ethenoadenine: biologically active fluorescent derivatives of this cpd potentially valuable in studies concerning interactions between adenine cpds & various enzymes for which they serve as substrates or co-factors; structure		3.0750imidazo[2,1-i]purinemutagen
cyanates
Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).		2.1510
1,n(6)-ethenodeoxyadenosine
[no description available]		2.3820purines
bromoacetaldehyde
bromoacetaldehyde: RN given refers to unlabeled cpd		2.8840organobromine compound
aldophosphamide
aldophosphamide: metabolite of cyclophosphamide		2.0310nitrogen mustard
3,n(4)-ethenodeoxycytidine
[no description available]		1.9910
chlorodiethylenetriamine platinum
chlorodiethylenetriamine platinum: RN given refers to parent cpd; structure		1.9810
1,n(6)-ethenoadenosine
1,N(6)-ethenoadenosine: fluorescent probe; structure		3.0750
deoxyglucose
Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.		2.0510
bromodichloroacetic acid
[no description available]		2.0410
dechloroethylcyclophosphamide
dechloroethylcyclophosphamide: structure given in first source; RN given refers to parent cpd		2.7230phosphorodiamide
dechloroethylifosfamide
dechloroethylifosfamide: RN given refers to parent cpd		7.4120organonitrogen heterocyclic compound;
organophosphorus compound
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.		210fatty acid anion 8:0;
straight-chain saturated fatty acid anion		human metabolite;
Saccharomyces cerevisiae metabolite
wye
[no description available]		1.9610
cyclic adp-ribose
Cyclic ADP-Ribose: A pyridine nucleotide that mobilizes CALCIUM. It is synthesized from nicotinamide adenine dinucleotide (NAD) by ADP RIBOSE CYCLASE.		2.0210cyclic purine nucleotide;
nucleotide-sugar		metabolite;
ryanodine receptor agonist
cyclic 1,n(2)-propanodeoxyguanosine
cyclic 1,N(2)-propanodeoxyguanosine: structure given in first source; RN refers to (6R-trans)-isomer		2.0210
1,n(2)-ethenodeoxyguanosine
[no description available]		2.420
1,n(6)-ethenoadenosine 3',5'-monophosphate
1,N(6)-ethenoadenosine 3',5'-monophosphate: fluorescent cyclic AMP analog; structure		1.9610
n(2),3-ethenoguanine
N(2),3-ethenoguanine: formed from 2-halooxiranes. N(2),3-ethenoguanine : A nucleobase analogue obtained by addition of an etheno group across positions N2 and 3 of guanine.		2.8940imidazopurine;
nucleobase analogue
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.4120divalent inorganic anion;
phosphite ion
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.		3.5320L-cysteine thioether;
non-proteinogenic L-alpha-amino acid		mucolytic
4-hydroxyifosfamide
[no description available]		4.2941ifosfamides
s-adenosylhomocysteine
S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.		2.0210adenosines;
amino acid zwitterion;
homocysteine derivative;
homocysteines;
organic sulfide		cofactor;
EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor;
EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor;
epitope;
fundamental metabolite
acetyl coenzyme a
Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.		2.0410acyl-CoAacyl donor;
coenzyme;
effector;
fundamental metabolite
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		2.0710icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
2-butenal
crotonaldehyde : An enal consisting of propene having a formyl group at the 1-position.		2.1510enal
h 89
N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.		2.110N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
tenofovir
tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.		7.0110nucleoside analogue;
phosphonic acids		antiviral drug;
drug metabolite;
HIV-1 reverse transcriptase inhibitor
potassium permanganate
Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)		1.9910
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.		2.04102-bromocarboxylic acid;
monocarboxylic acid;
organochlorine compound
1,4-dichloro-2-butene
1,4-dichloro-2-butene: RN given refers to parent cpd without isomeric designation; structure		2.0410organochlorine compound
mitobronitol
Mitobronitol: Brominated analog of MANNITOL which is an antineoplastic agent appearing to act as an alkylating agent.		2.0410alcohol;
organobromine compound
sodium metabisulfite
sodium metabisulfite: request from searcher; RN given refers to disulfurous acid, di-Na salt. sodium disulfite : An inorganic sodium salt composed of sodium and disulfite ions in a 2:1 ratio.		210inorganic sodium saltfood antioxidant
thiouracil
Thiouracil: Occurs in seeds of Brassica and Crucifera species. Thiouracil has been used as antithyroid, coronary vasodilator, and in congestive heart failure although its use has been largely supplanted by other drugs. It is known to cause blood dyscrasias and suspected of terato- and carcinogenesis.. thiouracil : A nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group.		6.9510nucleobase analogue;
thiocarbonyl compound		antithyroid drug;
metabolite
thiourea
Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.		2.1510one-carbon compound;
thioureas;
ureas		antioxidant;
chromophore
thiouridine
Thiouridine: A photoactivable URIDINE analog that is used as an affinity label.. 4-thiouridine : A thiouridine in which the oxygen replaced by sulfur is that at C-4.		6.9510nucleoside analogue;
thiouridine		affinity label;
antimetabolite
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester
[no description available]		2.110
2,4-dinitrophenylhydrazine
2,4-dinitrophenylhydrazine: structure. 2,4-dinitrophenylhydrazine : A C-nitro compound that is phenylhydrazine substituted at the 2- and 4-positions by nitro groups.		2.4120C-nitro compound;
phenylhydrazines		reagent
sodium borohydride
sodium borohydride: RN given refers to parent cpd		210inorganic sodium salt;
metal tetrahydridoborate
4-dimethylaminocinnamaldehyde
[no description available]		6.9910cinnamaldehydes
cytochalasin b
Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.		7.4220cytochalasin;
lactam;
lactone;
organic heterotricyclic compound		actin polymerisation inhibitor;
metabolite;
mycotoxin;
platelet aggregation inhibitor
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.		8.8121cysteiniumfundamental metabolite
silicon
Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].		2.0110carbon group element atom;
metalloid atom;
nonmetal atom
tetrodotoxin
Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.		2.0210azatetracycloalkane;
oxatetracycloalkane;
quinazoline alkaloid		animal metabolite;
bacterial metabolite;
marine metabolite;
neurotoxin;
voltage-gated sodium channel blocker
hygromycin a
hygromycin A: a cinnamide derivative produced by Streptomyces hygroscopicus; structure differs from HYGROMYCIN B		210hydroxycinnamic acidmetabolite
o-methylthymidine
O-methylthymidine: RN given refers to (beta)-isomer		1.9610
3-methylcytidine
[no description available]		1.9610methylcytidine
nad
NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.		2.9240organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite
anticodon
Anticodon: The sequential set of three nucleotides in TRANSFER RNA that interacts with its complement in MESSENGER RNA, the CODON, during translation in the ribosome.		1.9810
mesna
Mesna: A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.		591organosulfonic acid
hygromycin b
[no description available]		210
s-adenosylmethionine
(R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.		2.0210organic cation;
sulfonium compound		coenzyme;
cofactor;
human metabolite;
micronutrient;
Mycoplasma genitalium metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
piperidines
Piperidines: A family of hexahydropyridines.		2.6730
3-methyluridine
3-methyluridine: isolated from normal human urine & is a minor constituent of tRNA form yeast, rat and human liver; structure		1.9610
deoxyguanosine
[no description available]		7.6830purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxyguanosine triphosphate
[no description available]		1.9810deoxyguanosine phosphate;
guanyl deoxyribonucleotide;
purine 2'-deoxyribonucleoside 5'-triphosphate		Arabidopsis thaliana metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
guanine
[no description available]		3.681002-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
guanosine
ribonucleoside : Any nucleoside where the sugar component is D-ribose.		2.3720guanosines;
purines D-ribonucleoside		fundamental metabolite
3-methyladenine
N3-methyladenine: structure in first source		2.0210
phthivazide
[no description available]		2.1510
trypan blue
Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).		2.0310
methylnitronitrosoguanidine
Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position		2.3720nitroso compoundalkylating agent
3,n(4)-ethanocytosine
[no description available]		3.2460organic heterobicyclic compoundmutagen
1,n(6)-ethanoadenine
[no description available]		2.0610
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.		2.3820
ConditionIndicatedRelationship StrengthStudiesTrials
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)		03.150
Acute Liver Injury, Drug-Induced
[description not available]		02.5520
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.		02.5520
Encephalopathy, Toxic
[description not available]		03.3820
Kidney Failure
A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.		02.2110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.9440
Renal Insufficiency
Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.		02.2110
Breast Cancer
[description not available]		09.0450
Breast Neoplasms
Tumors or cancer of the human BREAST.		04.0450
Benign Neoplasms
[description not available]		06.4963
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.		06.4963
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		04.3370
Cardiac Diseases
[description not available]		02.0610
Heart Diseases
Pathological conditions involving the HEART including its structural and functional abnormalities.		02.0610
HIV Coinfection
[description not available]		02.0110
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.0110
Adenocarcinoma, Basal Cell
[description not available]		02.0210
Colorectal Cancer
[description not available]		02.0210
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.0210
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		02.0210
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.7230
Bone Cancer
[description not available]		02.0310
Osteogenic Sarcoma
[description not available]		02.0310
Bone Neoplasms
Tumors or cancer located in bone tissue or specific BONES.		02.0310
Osteosarcoma
A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)		07.0310
Experimental Neoplasms
[description not available]		02.6730
Hemoglobinopathies
A group of inherited disorders characterized by structural alterations within the hemoglobin molecule.		01.9810
Adult Fanconi Syndrome
[description not available]		01.9810
Carcinoma, Bronchial
[description not available]		01.9810
Cancer of Lung
[description not available]		02.6830
Carcinoma, Bronchogenic
Malignant neoplasm arising from the epithelium of the BRONCHI. It represents a large group of epithelial lung malignancies which can be divided into two clinical groups: SMALL CELL LUNG CANCER and NON-SMALL-CELL LUNG CARCINOMA.		01.9810
Lung Neoplasms
Tumors or cancer of the LUNG.		02.6830
Germinoblastoma
[description not available]		01.9910
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		01.9910
Carcinoma, Non-Small Cell Lung
[description not available]		01.9910
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		01.9910
Angiosarcoma
[description not available]		0210
Cancer of Liver
[description not available]		0210
Hemangiosarcoma
A rare malignant neoplasm characterized by rapidly proliferating, extensively infiltrating, anaplastic cells derived from blood vessels and lining irregular blood-filled or lumpy spaces. (Stedman, 25th ed)		0210
Liver Neoplasms
Tumors or cancer of the LIVER.		0210
B-Cell Leukemia
[description not available]		0210
Leucocythaemia
[description not available]		02.0110
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)		02.0110
Brain Disorders
[description not available]		01.9810
Brain Diseases
Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.		01.9810
Anoxemia
[description not available]		01.9810
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		01.9810
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.8910
Experimental Hepatoma
[description not available]		02.8910
Aneuploid
[description not available]		06.9710
Bleeding
[description not available]		01.9710
Cystitis
Inflammation of the URINARY BLADDER, either from bacterial or non-bacterial causes. Cystitis is usually associated with painful urination (dysuria), increased frequency, urgency, and suprapubic pain.		01.9710
Hemorrhage
Bleeding or escape of blood from a vessel.		01.9710
Cytomegalovirus
A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.		06.9710
Nervous System Disorders
[description not available]		01.9610
Nervous System Diseases
Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.		01.9610
EHS Tumor
[description not available]		01.9710
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		01.9710