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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:06 UTC
Update Date2023-02-21 17:17:47 UTC
HMDB IDHMDB0012271
Secondary Accession Numbers
  • HMDB12271
Metabolite Identification
Common NameO-Ureidohomoserine
DescriptionO-Ureidohomoserine is involved in the canavanine biosynthesis pathway. It can be generated from the enzymatic reduction of canavaninosuccinate or enzymatic oxidation of L-canaline. The canavanine biosynthesis pathway is analogous to the animal Krebs-Henseleit ornithine-urea cycle. Feeding experiments demonstrated the existence of enzyme activities of canaline-dependent ornithine carbamyltransferase, ureidohomoserine-dependent argininosuccinate synthetase, and canavaninosuccinate-dependent argininosuccinate lyase in Canavalia lineate. The canaline-dependent ornithine carbamyltransferase has been purified subsequently. The synthesis of ureidohomoserine is probably the rate-limiting step. Ureidohomoserine interacted with canaline or canavanine to affect synergistically L. minor growth by enhancing individual canavanine or canaline toxicity and increasing the additive growth reduction caused by canavanine plus canaline. The ornithineurea cycle amino acids effectively counteracted both the additive and synergistic growth-inhibiting properties of the canaline-urea cycle compounds.(PMID: 16659513 ).
Structure
Thumb
Synonyms
ValueSource
alpha-amino-gamma-Ureidooxybutyric acidHMDB
O-((Aminocarbonyl)amino)-L-homoserineHMDB
O-ureido-L-HomoserineHMDB
2-Amino-4-{[(C-hydroxycarbonimidoyl)amino]oxy}butanoateGenerator
O-UreidohomoserineMeSH
Chemical FormulaC5H11N3O4
Average Molecular Weight177.1585
Monoisotopic Molecular Weight177.074955855
IUPAC Name2-amino-4-{[(C-hydroxycarbonimidoyl)amino]oxy}butanoic acid
Traditional Name2-amino-4-[(C-hydroxycarbonimidoylamino)oxy]butanoic acid
CAS Registry Number51767-67-0
SMILES
NC(CCONC(O)=N)C(O)=O
InChI Identifier
InChI=1S/C5H11N3O4/c6-3(4(9)10)1-2-12-8-5(7)11/h3H,1-2,6H2,(H,9,10)(H3,7,8,11)
InChI KeySFYVZOSIAIZWQU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Fatty acid
  • Carbonic acid derivative
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Route of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028907
KNApSAcK IDNot Available
Chemspider ID19993690
KEGG Compound IDNot Available
BioCyc IDO-UREIDOHOMOSERINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21126175
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rosenthal GA, Gulati DK, Sabharwal PS: Additive and Synergistic Growth-inhibiting Properties of the Canaline-Urea Cycle Amino Acids. Plant Physiol. 1976 Apr;57(4):493-6. [PubMed:16659513 ]