CHEBI:28616 - carbamic acid

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ChEBI Name carbamic acid
ChEBI ID CHEBI:28616
Definition A one-carbon compound that is ammonia in which one of the hydrogens is replaced by a carboxy group. Although carbamic acid derivatives are common, carbamic acid itself has never been synthesised.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3386, CHEBI:44573, CHEBI:22504, CHEBI:23002
Supplier Information No supplier information found for this compound.
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Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]−. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH. Carbamic acid could be seen as both an amine and carboxylic acid, and therefore an amino acid; however, the attachment of the carboxyl group –COOH directly to the nitrogen atom (without any intermediate carbon chain) makes it behave very differently from the amino acids with intermediate carbon chain. (Glycine NH2CH2COOH is generally considered to be the simplest amino acid.) The hydroxyl group –OH attached to the carbon also excludes it from the amide class. The term "carbamic acid" is also used generically for any compounds of the form RR′NCOOH, where R and R′ are organic groups or hydrogen. Deprotonation of a carbamic acid yields a carbamate anion RR′NCOO−, the salts of which can be relatively stable. Carbamate is also a term used for esters of carbamic acids, such as methyl carbamate H2N−C(=O)−OCH3. The carbamoyl functional group RR′N–C(=O)– (often denoted by Cbm) is the carbamic acid molecule minus the OH part of the carboxyl.
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Formula CH3NO2
Net Charge 0
Average Mass 61.04006
Monoisotopic Mass 61.01638
InChI InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4)
InChIKey KXDHJXZQYSOELW-UHFFFAOYSA-N
SMILES NC(O)=O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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ChEBI Ontology
Outgoing carbamic acid (CHEBI:28616) has role Escherichia coli metabolite (CHEBI:76971)
carbamic acid (CHEBI:28616) is a carbon oxoacid (CHEBI:35605)
carbamic acid (CHEBI:28616) is a one-carbon compound (CHEBI:64708)
carbamic acid (CHEBI:28616) is a organonitrogen compound (CHEBI:35352)
carbamic acid (CHEBI:28616) is conjugate acid of carbamate (CHEBI:13941)
Incoming (hydroxymethyl)carbamic acid (CHEBI:185681) has functional parent carbamic acid (CHEBI:28616)
1,3-dicarboxyurea (CHEBI:142879) has functional parent carbamic acid (CHEBI:28616)
1-carboxybiuret (CHEBI:143024) has functional parent carbamic acid (CHEBI:28616)
5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole (CHEBI:48000) has functional parent carbamic acid (CHEBI:28616)
carbamate ester (CHEBI:23003) has functional parent carbamic acid (CHEBI:28616)
chlorphenesin carbamate (CHEBI:3643) has functional parent carbamic acid (CHEBI:28616)
dimethylcarbamic acid (CHEBI:38544) has functional parent carbamic acid (CHEBI:28616)
Dimethylcarbamoyl chloride (CHEBI:82280) has functional parent carbamic acid (CHEBI:28616)
hexylcarbamic acid (CHEBI:156060) has functional parent carbamic acid (CHEBI:28616)
methylcarbamic acid (CHEBI:45379) has functional parent carbamic acid (CHEBI:28616)
phenylcarbamic acid (CHEBI:52496) has functional parent carbamic acid (CHEBI:28616)
piperazine-1-carboxylic acid (CHEBI:41221) has functional parent carbamic acid (CHEBI:28616)
carbamate (CHEBI:13941) is conjugate base of carbamic acid (CHEBI:28616)
carbamoyl group (CHEBI:23004) is substituent group from carbamic acid (CHEBI:28616)
carboxyamino group (CHEBI:37017) is substituent group from carbamic acid (CHEBI:28616)
IUPAC Name
carbamic acid
Synonyms Sources
Aminoameisensäure ChEBI
Aminoformic acid KEGG COMPOUND
Carbamate KEGG COMPOUND
CARBAMIC ACID PDBeChem
Carbamic acid KEGG COMPOUND
Carbamidsäure ChEBI
Manual Xrefs Databases
C01563 KEGG COMPOUND
Carbamic_acid Wikipedia
DB04261 DrugBank
OUT PDBeChem
View more database links
Registry Numbers Types Sources
130345 Gmelin Registry Number Gmelin
1734754 Beilstein Registry Number Beilstein
463-77-4 CAS Registry Number ChemIDplus
Last Modified
13 July 2020