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

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ChEBI Name	2-amino-5-phosphonopentanoic acid

ChEBI ID	CHEBI:138644

Definition	The 5-phosphono derivative of 2-aminopentanoic acid; acts as an N-methyl-D-aspartate receptor antagonist.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:34257

Supplier Information

Download	Molfile XML SDF

Formula

C5H12NO5P

Net Charge

Average Mass

197.12620

Monoisotopic Mass

197.04531

InChI

InChI=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)

InChIKey

VOROEQBFPPIACJ-UHFFFAOYSA-N

SMILES

NC(CCCP(O)(O)=O)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	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	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	Sources
2-Amino-5-phosphonovaleric acid	ChemIDplus
2-Amino-5-phosphopentanoic acid	KEGG COMPOUND
2-Amino-5-phosphovaleric acid	ChemIDplus

Last Modified

26 March 2015