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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:34:27 UTC
Update Date2019-01-11 19:17:39 UTC
HMDB IDHMDB0003551
Secondary Accession Numbers
  • HMDB03551
Metabolite Identification
Common NameCarbamic acid
DescriptionCarbamic acid is occasionally found as carbamate in workers exposed to pesticides. Carbamates, particularly carbofuran, seem to be more associated with exuberant and diversified symptomatology of pesticide exposure than organophosphates. Neurological symptoms occur among farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides such as carbamates. Carbamic acid products of several amines, such as beta-N-methylamino-L-alanine (BMAA), ethylenediamine, and L-cysteine have been implicated in toxicity. Studies suggested that a significant portion of amino-compounds in biological samples (that naturally contain CO2/bicarbonate) can be present as a carbamic acid. The formation of carbamate glucuronide metabolites has been described for numerous pharmaceuticals and they have been identified in all of the species commonly used in drug metabolism studies (rat, dog, mouse, rabbit, guinea pig, and human). There has been no obvious species specificity for their formation and no preference for 1 or 2 degree amines. Many biological reactions have also been described in the literature that involve the reaction of CO2 with amino groups of biomolecules. For example, CO2 generated from cellular respiration is expired in part through the reversible formation of a carbamate between CO2 and the -amino groups of the alpha and beta-chains of hemoglobin. Glucuronidation is an important mechanism used by mammalian systems to clear and eliminate both endogenous and foreign chemicals. Many functional groups are susceptible to conjugation with glucuronic acid, including hydroxyls, phenols, carboxyls, activated carbons, thiols, amines, and selenium. Primary and secondary amines can also react with carbon dioxide (CO2) via a reversible reaction to form a carbamic acid. The carbamic acid is also a substrate for glucuronidation and results in a stable carbamate glucuronide metabolite. The detection and characterization of these products has been facilitated greatly by the advent of soft ionization mass spectrometry techniques and high field NMR instrumentation. (PMID: 16268118 , 17168688 , 12929145 ).
Structure
Data?1547234259
Synonyms
ValueSource
AminoameisensaeureChEBI
Aminoformic acidChEBI
CarbamateChEBI
CarbamidsaeureChEBI
AminoformateGenerator
Carbamate ionHMDB
Chlorphenesin carbamateHMDB
MaolateHMDB
Calcium carbamateHMDB
Carbamic acid, potassium saltHMDB
Carbamic acid, sodium saltHMDB
Sodium carbamateHMDB
Ammonium carbamateHMDB
Carbamic acid, ammonia saltHMDB
Carbamic acid, calcium saltHMDB
Potassium carbamateHMDB
Chemical FormulaCH3NO2
Average Molecular Weight61.04
Monoisotopic Molecular Weight61.016378345
IUPAC Namecarbamic acid
Traditional Namecarbamic acid
CAS Registry Number463-77-4
SMILES
NC(O)=O
InChI Identifier
InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)
InChI KeyKXDHJXZQYSOELW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic carbonic acids and derivatives. Organic carbonic acids and derivatives are compounds comprising the organic carbonic acid or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassNot Available
Direct ParentOrganic carbonic acids and derivatives
Alternative Parents
Substituents
  • Carbonic acid derivative
  • Carbamic acid derivative
  • Carbamic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility379 g/LALOGPS
logP-1.1ALOGPS
logP-0.56ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.32 m³·mol⁻¹ChemAxon
Polarizability4.68 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-d4ec45366294deee461dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-39800d42e236043754c2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-33c2cd9e9f87e70aeee7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-80dc946b5f814bf962fcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-db68c8dff28932d0bd97JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9000000000-54e827d7f4201ae683bfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9000000000-3158c8b265d264989bd7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-24350f23db0893ec042cJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Neuron
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04261
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023195
KNApSAcK IDNot Available
Chemspider ID271
KEGG Compound IDC01563
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbamic_acid
METLIN ID6950
PubChem Compound277
PDB IDNot Available
ChEBI ID28616
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rendon von Osten J, Epomex C, Tinoco-Ojanguren R, Soares AM, Guilhermino L: Effect of pesticide exposure on acetylcholinesterase activity in subsistence farmers from Campeche, Mexico. Arch Environ Health. 2004 Aug;59(8):418-25. [PubMed:16268118 ]
  2. Schaefer WH: Reaction of primary and secondary amines to form carbamic acid glucuronides. Curr Drug Metab. 2006 Dec;7(8):873-81. [PubMed:17168688 ]
  3. Smit LA, van-Wendel-de-Joode BN, Heederik D, Peiris-John RJ, van der Hoek W: Neurological symptoms among Sri Lankan farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides. Am J Ind Med. 2003 Sep;44(3):254-64. [PubMed:12929145 ]