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Showing metabocard for Ethyl carbamate (HMDB0031219)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:41 UTC
Update Date2023-02-21 17:20:06 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 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. In case of contact with eyes, irrigate opened eyes for several minutes under running water. Metabolism is mediated by cytochrome P450 2E1.
Structure
Data?1677000006
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031219 (Ethyl carbamate)

4827
  Mrv1652305271900112D          

  6  5  0  0  0  0            999 V2000
    3.0791    0.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  6  1  0  0  0  0
  2  6  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0031219 (Ethyl carbamate)

HMDB0031219
     RDKit          3D
Ethyl carbamate
 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.0480    0.6745    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632   -0.3683   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725    0.2158    0.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577   -0.4710   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389    0.1014    0.2514 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768   -1.6581   -0.4861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462    1.2215   -0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    1.3757    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9451    0.1653    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793   -0.5976   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756   -1.2942    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -0.0440    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.6789   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  5 12  1  0
  5 13  1  0
M  END
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3D SDF for HMDB0031219 (Ethyl carbamate)

4827
  Mrv1652305271900112D          

  6  5  0  0  0  0            999 V2000
    3.0791    0.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  6  1  0  0  0  0
  2  6  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031219

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)

> <INCHI_KEY>
JOYRKODLDBILNP-UHFFFAOYSA-N

> <FORMULA>
C3H7NO2

> <MOLECULAR_WEIGHT>
89.0932

> <EXACT_MASS>
89.047678473

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.64441327256789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl carbamate

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.054189237333333376

> <ALOGPS_LOGS>
0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.473281507740328

> <JCHEM_POLAR_SURFACE_AREA>
52.32

> <JCHEM_REFRACTIVITY>
20.8381

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
urethane

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0031219 (Ethyl carbamate)

HMDB0031219
     RDKit          3D
Ethyl carbamate
 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.0480    0.6745    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632   -0.3683   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725    0.2158    0.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577   -0.4710   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389    0.1014    0.2514 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768   -1.6581   -0.4861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462    1.2215   -0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    1.3757    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9451    0.1653    0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793   -0.5976   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756   -1.2942    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -0.0440    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.6789   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  5 12  1  0
  5 13  1  0
M  END
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PDB for HMDB0031219 (Ethyl carbamate)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4827                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       5.748   0.678   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081  -1.632   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.415   0.678   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.414  -0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080   0.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -0.092   0.000  0.00  0.00           C+0
CONECT    1    4    6                                                       
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    1    5                                                       
CONECT    5    4                                                            
CONECT    6    1    2    3                                                  
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0031219 (Ethyl carbamate)

COMPND    HMDB0031219
HETATM    1  C1  UNL     1      -2.048   0.675   0.084  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.963  -0.368  -0.205  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.273   0.216   0.100  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.458  -0.471  -0.054  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.739   0.101   0.251  1.00  0.00           N  
HETATM    6  O2  UNL     1       1.377  -1.658  -0.486  1.00  0.00           O  
HETATM    7  H1  UNL     1      -2.346   1.222  -0.811  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.691   1.376   0.879  1.00  0.00           H  
HETATM    9  H3  UNL     1      -2.945   0.165   0.492  1.00  0.00           H  
HETATM   10  H4  UNL     1      -1.079  -0.598  -1.301  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.176  -1.294   0.369  1.00  0.00           H  
HETATM   12  H6  UNL     1       3.214  -0.044   1.164  1.00  0.00           H  
HETATM   13  H7  UNL     1       3.189   0.679  -0.484  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3   10   11
CONECT    3    4
CONECT    4    5    6    6
CONECT    5   12   13
END
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SMILES for HMDB0031219 (Ethyl carbamate)

CCOC(N)=O
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INCHI for HMDB0031219 (Ethyl carbamate)

InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental roleBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point48.5 - 50 °CNot Available
Boiling Point185.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility480 mg/mL at 15 °CNot Available
LogP-0.15Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1296181
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

Enzyme Details
1. Cytosolic phospholipase A2
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 ]
Enzyme Details
2. Aldehyde oxidase
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 ]
Enzyme Details
3. Myeloperoxidase
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 ]