Record Information
Creation Date2012-05-31 13:59:45 -0600
Update Date2015-09-13 12:56:13 -0600
Secondary Accession Numbers
  • ECMDB03551
Name:Carbamic acid
DescriptionCarbamic 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. 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. 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)
  • Aminoformate
  • Aminoformic acid
  • Carbamate
  • Carbamate ion
  • Carbamic acid
  • Carbamic acid ion
  • Chlorphenesin carbamate
  • Chlorphenesin carbamic acid
  • Maolate
  • Maolic acid
Chemical Formula:CH3NO2
Weight:Average: 61.04
Monoisotopic: 61.016378345
CAS number:463-77-4
IUPAC Name:carbamic acid
Traditional IUPAC Name:carbamic acid
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
  • 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
Physical Properties
Melting point:Not Available
Experimental Properties:
Predicted Properties
Water Solubility379 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Water + Ureidoacrylate peracid > Carbamic acid + Hydrogen ion + Peroxyaminoacrylate
Carbamic acid + 2 Hydrogen ion > Carbon dioxide + Ammonium
Adenosine triphosphate + Carbamic acid <> ADP + Carbamoylphosphate
Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid
Ureidoacrylate peracid + Water <> Peroxyaminoacrylate + Carbamic acid
Ureidoacrylate + Water <> 3-Aminoacrylate + Carbamic acid
Carbamic acid + Hydrogen ion > Ammonia + Carbon dioxide
3-ureidoacrylate + Water > Hydrogen ion + Carbamic acid + 3-Aminoacrylate
Cyanate + Hydrogen carbonate + Hydrogen ion > Carbamic acid + Carbon dioxide
(<i>Z</i>)-2-methylureidoacrylate peracid + Water > (<i>Z</i>)-2-methyl-peroxyaminoacrylate + Carbamic acid + Hydrogen ion
2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water + Ammonia + Carbamic acid + Carboxyphosphate <>2 ADP + Phosphate + L-Glutamate + Carbamoylphosphate
Cyanate + Hydrogen carbonate + 2 Hydrogen ion + Carbamic acid <> Ammonia +2 Carbon dioxide
Ureidoacrylate peracid + Water + Carbamic acid + (Z)-2-Methyl-ureidoacrylate peracid <> Peroxyaminoacrylate + Carbon dioxide + Ammonia + (Z)-2-Methyl-peroxyaminoacrylate
Hydrogen carbonate + Cyanate + Hydrogen ion + Cyanate > Carbamic acid
Carbon dioxide + Water > Carbamic acid
Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Carbamic acid + Hydrogen ion + 3-Aminoacrylate
Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid
Adenosine triphosphate + Carbamic acid <> ADP + Carbamoylphosphate
Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid
SMPDB Pathways:
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Uracil degradation IIIPW002026 ThumbThumb?image type=greyscaleThumb?image type=simple
cyanate degradationPW002099 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Not Available
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-d4ec45366294deee461dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-39800d42e236043754c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-33c2cd9e9f87e70aeee7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-80dc946b5f814bf962fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-db68c8dff28932d0bd97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9000000000-54e827d7f4201ae683bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9000000000-3158c8b265d264989bd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-24350f23db0893ec042cView in MoNA
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Rendon von Osten, J., Epomex, C., Tinoco-Ojanguren, R., Soares, A. M., Guilhermino, L. (2004). "Effect of pesticide exposure on acetylcholinesterase activity in subsistence farmers from Campeche, Mexico." Arch Environ Health 59:418-425. Pubmed: 16268118
  • Schaefer WH: Reaction of primary and secondary amines to form carbamic acid glucuronides. Curr Drug Metab. 2006 Dec;7(8):873-81. Pubmed: 17168688
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
Pubchem Compound ID277
Kegg IDC01563
ChemSpider ID271
WikipediaCarbamic acid
Ligand ExpoOUT


General function:
Involved in cyanate hydratase activity
Specific function:
Catalyzes the reaction of cyanate with bicarbonate to produce ammonia and carbon dioxide
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Molecular weight:
Cyanate + HCO(3)(-) + 2 H(+) = NH(3) + 2 CO(2).
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
ATP + NH(3) + CO(2) = ADP + carbamoyl phosphate
Gene Name:
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Molecular weight:
ATP + NH(3) + CO(2) = ADP + carbamoyl phosphate.
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Specific function unknown
Gene Name:
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Molecular weight:
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Specific function unknown
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:
Uniprot ID:
Molecular weight:
(Z)-3-ureidoacrylate peracid + H(2)O = (Z)-3-peroxyaminoacrylate + NH(3).
(Z)-3-ureidoacrylate + H(2)O = (Z)-3-aminoacrylate + CO(2) + NH(3).
(Z)-2-methyl-ureidoacrylate peracid + H(2)O = (Z)-2-methyl-peroxyaminoacrylate + CO(2) + NH(3).