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CHEBI:138644 - 2-amino-5-phosphonopentanoic acid

ChEBI IDCHEBI:138644
ChEBI Name2-amino-5-phosphonopentanoic acid
Stars
DefinitionThe 5-phosphono derivative of 2-aminopentanoic acid; acts as an N-methyl-D-aspartate receptor antagonist.
Secondary ChEBI IDCHEBI:34257
Last Modified26 March 2015
DownloadsMolfile
FormulaC5H12NO5P
Net Charge0
Average Mass197.127
Monoisotopic Mass197.04531
SMILESNC(CCCP(=O)(O)O)C(=O)O
InChIInChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)
InChIKeyVOROEQBFPPIACJ-UHFFFAOYSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
NMDA receptor antagonist  Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
ChEBI Ontology
Outgoing Relation(s)
2-amino-5-phosphonopentanoic acid (CHEBI:138644) has functional parent 2-aminopentanoic acid (CHEBI:19475)
2-amino-5-phosphonopentanoic acid (CHEBI:138644) has functional parent phosphonic acid (CHEBI:44976)
2-amino-5-phosphonopentanoic acid (CHEBI:138644) has role NMDA receptor antagonist (CHEBI:60643)
2-amino-5-phosphonopentanoic acid (CHEBI:138644) is a non-proteinogenic α-amino acid (CHEBI:83925)
IUPAC Name 
5-phosphononorvaline
Synonyms  Source
2-Amino-5-phosphopentanoic acidKEGG COMPOUND
2-Amino-5-phosphonovaleric acidChemIDplus
2-Amino-5-phosphovaleric acidChemIDplus
Manual XrefsDatabases
C13734KEGG COMPOUND
Registry NumbersSources
Reaxys:2446389Reaxys
CAS:76326-31-3KEGG COMPOUND
CAS:76326-31-3ChemIDplus