CHEBI:16199 - urea

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name urea
ChEBI ID CHEBI:16199
Definition A carbonyl group with two C-bound amine groups. The commercially available fertilizer has an analysis of 46-0-0 (N-P2O5-K2O).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46379, CHEBI:9888, CHEBI:15292, CHEBI:27218
Supplier Information ChemicalBook:CB5853861, ChemicalBook:CB11342474, eMolecules:10525132, eMolecules:475133, ZINC000008214514
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Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups (–NH2) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important role in the cellular metabolism of nitrogen-containing compounds by animals and is the main nitrogen-containing substance in the urine of mammals. Urea is Neo-Latin, from French urée, from Ancient Greek οὖρον (oûron) 'urine', itself from Proto-Indo-European *h₂worsom. It is a colorless, odorless solid, highly soluble in water, and practically non-toxic (LD50 is 15 g/kg for rats). Dissolved in water, it is neither acidic nor alkaline. The body uses it in many processes, most notably nitrogen excretion. The liver forms it by combining two ammonia molecules (NH3) with a carbon dioxide (CO2) molecule in the urea cycle. Urea is widely used in fertilizers as a source of nitrogen (N) and is an important raw material for the chemical industry. In 1828, Friedrich Wöhler discovered that urea can be produced from inorganic starting materials, which was an important conceptual milestone in chemistry. This showed for the first time that a substance previously known only as a byproduct of life could be synthesized in the laboratory without biological starting materials, thereby contradicting the widely held doctrine of vitalism, which stated that only living organisms could produce the chemicals of life.
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Formula CH4N2O
Net Charge 0
Average Mass 60.05534
Monoisotopic Mass 60.03236
InChI InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
InChIKey XSQUKJJJFZCRTK-UHFFFAOYSA-N
SMILES NC(N)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
flour treatment agent
A food additive which is added to flour or dough to improve baking quality and/or colour.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
Application(s): flour treatment agent
A food additive which is added to flour or dough to improve baking quality and/or colour.
fertilizer
A fertilizer is any substance that is added to soil or water to assist the growth of plants.
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ChEBI Ontology
Outgoing urea (CHEBI:16199) has functional parent carbonic acid (CHEBI:28976)
urea (CHEBI:16199) has role Daphnia magna metabolite (CHEBI:83056)
urea (CHEBI:16199) has role Escherichia coli metabolite (CHEBI:76971)
urea (CHEBI:16199) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
urea (CHEBI:16199) has role fertilizer (CHEBI:33287)
urea (CHEBI:16199) has role flour treatment agent (CHEBI:64577)
urea (CHEBI:16199) has role human metabolite (CHEBI:77746)
urea (CHEBI:16199) has role mouse metabolite (CHEBI:75771)
urea (CHEBI:16199) is a monocarboxylic acid amide (CHEBI:29347)
urea (CHEBI:16199) is a one-carbon compound (CHEBI:64708)
urea (CHEBI:16199) is tautomer of carbamimidic acid (CHEBI:48376)
Incoming N-ethyl-N-nitrosourea (CHEBI:23995) has functional parent urea (CHEBI:16199)
condensed ureas (CHEBI:36954) has functional parent urea (CHEBI:16199)
selenourea (CHEBI:36957) has functional parent urea (CHEBI:16199)
thiourea (CHEBI:36946) has functional parent urea (CHEBI:16199)
ureas (CHEBI:47857) has functional parent urea (CHEBI:16199)
ammonium sulfate urea (CHEBI:91240) has part urea (CHEBI:16199)
urea ammonium nitrate (CHEBI:88276) has part urea (CHEBI:16199)
urea hydrogen peroxide (CHEBI:75178) has part urea (CHEBI:16199)
[amino(hydroxy)methylidene]amino group (CHEBI:48231) is substituent group from urea (CHEBI:16199)
carbamoylamino group (CHEBI:48349) is substituent group from urea (CHEBI:16199)
carbamimidic acid (CHEBI:48376) is tautomer of urea (CHEBI:16199)
IUPAC Name
urea
INN Source
carbamide ChEBI
Synonyms Sources
1728 PPDB
Carbamide KEGG COMPOUND
carbonyldiamide NIST Chemistry WebBook
E927b ChEBI
H2NC(O)NH2 ChEBI
Harnstoff NIST Chemistry WebBook
Karbamid ChEBI
ur IUPAC
Urea KEGG COMPOUND
UREA PDBeChem
urea UniProt
urée ChEBI
Manual Xrefs Databases
1728 PPDB
4264 DrugCentral
C00007314 KNApSAcK
C00086 KEGG COMPOUND
c0165 UM-BBD
D00023 KEGG DRUG
DB03904 DrugBank
ECMDB04172 ECMDB
HMDB0000294 HMDB
URE PDBeChem
Urea Wikipedia
UREA MetaCyc
YMDB00003 YMDB
View more database links
Registry Numbers Types Sources
1378 Gmelin Registry Number Gmelin
57-13-6 CAS Registry Number KEGG COMPOUND
57-13-6 CAS Registry Number ChemIDplus
57-13-6 CAS Registry Number NIST Chemistry WebBook
635724 Reaxys Registry Number Reaxys
Citations
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
Temnyalov ND (2008)
Endogenous urea as an autacoid: extrarenal and renal focuses.
Autonomic neuroscience : basic & clinical 138, 1-8 [PubMed:18037357]
[show Abstract]
Last Modified
16 October 2020