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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:41 UTC
Update Date2018-03-12 22:08:10 UTC
HMDB IDHMDB0031219
Secondary Accession Numbers
  • HMDB31219
Metabolite Identification
Common NameEthyl carbamate
DescriptionEthyl carbamate is found in alcoholic beverages. Common contaminant of fermented beverages Ethyl carbamate (also called urethane) is a substance first prepared in the nineteenth century. Structurally it is an ester of carbamic acid, i. e., ethyl carbamate as shown. Urethane itself is: (NH2-COOC2H5) and is not a component of polyurethanes. This ethyl ester is a white crystalline substance produced by the action of ammonia on ethyl chloroformate or by heating urea nitrate and ethyl alcohol
Structure
Thumb
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
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
DescriptionThis compound belongs to the class of organic compounds known as carboximidic acids and derivatives. These 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-ba57e1f4b939a6bb2c1cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-4905daa85aa870eff5d7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-ba57e1f4b939a6bb2c1cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r7-9000000000-4905daa85aa870eff5d7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-e97e597e9d87bdb17da9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5187886e237ef9d66a60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-9000000000-8c895ae06181b5b4338dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-ec38f306aca381823adbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-f2310b881ad089adcd93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-143896eea6847dbb32c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-51c772011dee8070de89View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01r7-9000000000-dbaaf921e6f73cb42292View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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
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 ]