CHEBI:143992 - (2S)-2-amino-4-phosphonobutanoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (2S)-2-amino-4-phosphonobutanoic acid
ChEBI ID CHEBI:143992
ChEBI ASCII Name (2S)-2-amino-4-phosphonobutanoic acid
Definition A non-proteinogenc L-α-amino acid that is L-α-aminobutyric acid in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-λ5-phosphanyl group. It is a potent and selective agonist for the group III metabotropic glutamate receptors (mGluR4/6/7/8).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter TheOtherDave
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C4H10NO5P
Net Charge 0
Average Mass 183.100
Monoisotopic Mass 183.02966
InChI InChI=1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
InChIKey DDOQBQRIEWHWBT-VKHMYHEASA-N
SMILES [C@H](C(=O)O)(N)CCP(=O)(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): metabotropic glutamate receptor agonist
An agonist that selectively binds to and activates a metabotropic glutamate receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2S)-2-amino-4-phosphonobutanoic acid (CHEBI:143992) has role metabotropic glutamate receptor agonist (CHEBI:61966)
(2S)-2-amino-4-phosphonobutanoic acid (CHEBI:143992) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
(2S)-2-amino-4-phosphonobutanoic acid (CHEBI:143992) is a phosphonic acids (CHEBI:26069)
IUPAC Name
(2S)-2-amino-4-phosphonobutanoic acid
Synonyms Sources
(2S)-2-amino-4-phosphonobutyric acid IUPAC
(S)-2-amino-4-phosphonobutanoic acid ChEBI
(S)-2-amino-4-phosphonobutyric acid SUBMITTER
L-(+)-2-amino-4-phosphonobutanoic acid ChEBI
L-(+)-2-amino-4-phosphonobutyric acid SUBMITTER
L-AP-4 ChEBI
L-AP4 ChemIDplus
L-APB SUBMITTER
Manual Xref Database
L-AP4 Wikipedia
View more database links
Registry Number Type Source
23052-81-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12593528 PubMed citation Europe PMC
16531635 PubMed citation Europe PMC
1681998 PubMed citation Europe PMC
18598739 PubMed citation Europe PMC
2055241 PubMed citation Europe PMC
25450419 PubMed citation Europe PMC
29402739 PubMed citation Europe PMC
7525012 PubMed citation Europe PMC
8950003 PubMed citation Europe PMC
9175612 PubMed citation Europe PMC
9251893 PubMed citation Europe PMC
Last Modified
18 July 2019