You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:41 UTC
Update Date2019-07-23 06:08:16 UTC
HMDB IDHMDB0031219
Secondary Accession Numbers
  • HMDB31219
Metabolite Identification
Common NameEthyl carbamate
DescriptionEthyl carbamate, also known as aethylurethan or uretan, belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2. Ethyl carbamate is an extremely weak acidic (essentially neutral) compound (based on its pKa). Outside of the human body, Ethyl carbamate has been detected, but not quantified in, alcoholic beverages. This could make ethyl carbamate a potential biomarker for the consumption of these foods. Ethyl carbamate is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. It is readily absorbed from the gastrointestinal tract and the skin. It also tends to induce specific mutations in the Kras oncogene in codon 61 of exon 2 including A:T transversions and A-->G transitions in the second base and A-->T transversions in the third base. Urethane, formerly marketed as an inactive ingredient in Profenil injection, was determined to be carcinogenic and was removed from the Canadian, US, and UK markets in 1963. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. EYES: irrigate opened eyes for several minutes under running water. Metabolism is mediated by cytochrome P450 2E1. INHALATION: supply fresh air.
Structure
Data?1563862096
Synonyms
ValueSource
Carbamic acid ethyl esterChEBI
Carbamate ethyl esterGenerator
Ethyl carbamic acidGenerator
AethylcarbamatHMDB
AethylurethanHMDB
Carbamate, ethylHMDB
Carbamic acid, ethyl esterHMDB
Estane 5703HMDB
Ethyl aminoformateHMDB
Ethyl ester OF carbamic acidHMDB
Ethyl urethanHMDB
Ethyl urethaneHMDB
EthylcarbamateHMDB
Ethylester kyseliny karbaminoveHMDB
EthylurethanHMDB
EthylurethaneHMDB
LeucethaneHMDB
LeucothaneHMDB
NH2COOC2H5HMDB
NSC 746HMDB
O-Ethyl carbamateHMDB
O-Ethyl urethaneHMDB
O-EthylurethaneHMDB
PracarbaminHMDB
PracarbamineHMDB
U-compoundHMDB
UretanHMDB
Uretan etylowyHMDB
UretanoHMDB
UrethanHMDB
UrethaneHMDB
Urethane + ethanol (combination)HMDB
Urethane, innHMDB
Ethyl carbamateChEBI
Chemical FormulaC3H7NO2
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
IUPAC Nameethyl carbamate
Traditional Nameurethane
CAS Registry Number51-79-6
SMILES
CCOC(N)=O
InChI Identifier
InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
InChI KeyJOYRKODLDBILNP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassNot Available
Direct ParentCarboximidic acids and derivatives
Alternative Parents
Substituents
  • Carboximidic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point48.5 - 50 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility480 mg/mL at 15 °CNot Available
LogP-0.15Not Available
Predicted Properties
PropertyValueSource
Water Solubility371 g/LALOGPS
logP-0.14ALOGPS
logP-0.054ChemAxon
logS0.62ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.84 m³·mol⁻¹ChemAxon
Polarizability8.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-ba57e1f4b939a6bb2c1cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-4905daa85aa870eff5d7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-ba57e1f4b939a6bb2c1cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-4905daa85aa870eff5d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-e97e597e9d87bdb17da9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5187886e237ef9d66a60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-9000000000-8c895ae06181b5b4338dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-ec38f306aca381823adbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-f2310b881ad089adcd93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-143896eea6847dbb32c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-51c772011dee8070de89Spectrum
MSMass Spectrum (Electron Ionization)splash10-01r7-9000000000-dbaaf921e6f73cb42292Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04827
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003243
KNApSAcK IDNot Available
Chemspider ID5439
KEGG Compound IDC01537
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl_carbamate
METLIN IDNot Available
PubChem Compound5641
PDB IDNot Available
ChEBI ID17967
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lijinsky W, Taylor HW: Carcinogenesis in Sprague-Dawley rats of N-nitroso-N-alkylcarbamate esters. Cancer Lett. 1976 May;1(5):275-9. [PubMed:828074 ]
  2. Lijinsky W, Reuber MD: Studies of a deuterium isotope effect in carcinogenesis by N-nitroso-N-alkylurethanes in rats. Cancer Lett. 1982 Sep;16(3):273-9. [PubMed:7151047 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
References
  1. Dinnes DL, Santerre JP, Labow RS: Phospholipase A2 pathway association with macrophage-mediated polycarbonate-urethane biodegradation. Biomaterials. 2005 Jun;26(18):3881-9. [PubMed:15626436 ]
  2. Labow RS, Santerre JP, Waghray G: The effect of phospholipids on the biodegradation of polyurethanes by lysosomal enzymes. J Biomater Sci Polym Ed. 1997;8(10):779-95. [PubMed:9297603 ]
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
References
  1. Sugihara K, Kitamura S, Tatsumi K: Involvement of liver aldehyde oxidase in conversion of N-hydroxyurethane to urethane. J Pharmacobiodyn. 1983 Sep;6(9):677-83. [PubMed:6689178 ]
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Kotanidou A, Choi AM, Winchurch RA, Otterbein L, Fessler HE: Urethan anesthesia protects rats against lethal endotoxemia and reduces TNF-alpha release. J Appl Physiol (1985). 1996 Nov;81(5):2305-11. [PubMed:8941558 ]