P. aeruginosa Metabolome Database: Carbamic acid (PAMDB000513)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000513

Identification

Name:

Carbamic acid

Description:

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. 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)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Aminoformate
Aminoformic acid
Carbamate
Carbamate ion
Carbamic acid
Carbamic acid ion
Chlorphenesin carbamate
Chlorphenesin carbamic acid
Maolate
Maolic acid

Chemical Formula:

CH₃NO₂

Average Molecular Weight:

61.04

Monoisotopic Molecular Weight:

61.016378345

InChI Key:

KXDHJXZQYSOELW-UHFFFAOYSA-N

InChI:

InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)

CAS number:

463-77-4

IUPAC Name:

carbamic acid

Traditional IUPAC Name:

carbamic acid

SMILES:

NC(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as carbamic acids. These are compounds containing the carbamic acid functional group, with the general structure RN(R')C(=O)OH or RN(R')C(=O)[O-] where R,R' = H or organyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Carbamic acids

Alternative Parents

Substituents

Carbamic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:28616 )
organonitrogen compound (CHEBI:28616 )
carbon oxoacid (CHEBI:28616 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	379.0 mg/mL	ALOGPS
logP	-1.1	ALOGPS
logP	-0.56	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	11.32 m³·mol^-1	ChemAxon
Polarizability	4.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

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
(<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

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Metabolic pathways pae01100
Nitrogen metabolism pae00910
Pyrimidine metabolism pae00240

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-33c2cd9e9f87e70aeee7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9000000000-80dc946b5f814bf962fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-db68c8dff28932d0bd97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-9000000000-54e827d7f4201ae683bf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-9000000000-3158c8b265d264989bd7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-24350f23db0893ec042c	View in MoNA

References

References:

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)

Links

External Links:

Resource	Link
CHEBI ID	28616
HMDB ID	HMDB03551
Pubchem Compound ID	277
Kegg ID	C01563
ChemSpider ID	271
Wikipedia	Carbamic acid
BioCyc ID	CARBAMATE
EcoCyc ID	CARBAMATE
Ligand Expo	OUT

Carbamic acid (PAMDB000513)

Structure for Carbamic acid (PAMDB000513)