CHEBI:28388 - 2-amino-3-phosphonopropanoic acid

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ChEBI Name 2-amino-3-phosphonopropanoic acid
ChEBI ID CHEBI:28388
Definition A non-proteinogenc α-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-λ5-phosphanyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:999, CHEBI:19451
Supplier Information
Download Molfile XML SDF
Formula C3H8NO5P
Net Charge 0
Average Mass 169.07310
InChI InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
InChIKey LBTABPSJONFLPO-UHFFFAOYSA-N
SMILES NC(CP(O)(O)=O)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in the human liver, intestine and spleen. See: PubMed
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 antagonist
An antagonist at the metabotropic glutamate receptor.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 2-amino-3-phosphonopropanoic acid (CHEBI:28388) has role human metabolite (CHEBI:77746)
2-amino-3-phosphonopropanoic acid (CHEBI:28388) has role metabotropic glutamate receptor antagonist (CHEBI:63963)
2-amino-3-phosphonopropanoic acid (CHEBI:28388) is a alanine derivative (CHEBI:22278)
2-amino-3-phosphonopropanoic acid (CHEBI:28388) is a non-proteinogenic α-amino acid (CHEBI:83925)
2-amino-3-phosphonopropanoic acid (CHEBI:28388) is a phosphonic acids (CHEBI:26069)
IUPAC Name
3-phosphonoalanine
Synonyms Sources
2-amino-3-phosphono-propanoic acid ChEBI
2-amino-3-phosphono-propionic acid ChemIDplus
2-amino-3-phosphonopropanoic acid ChEBI
2-amino-3-phosphonopropionic acid ChemIDplus
2-amino-3-phosphopropionic acid ChemIDplus
2-amino-3-phosprop ChemIDplus
2-AP3 ChEBI
2-azanyl-3-phosphono-propanoic acid ChEBI
phosphonoalanine KEGG COMPOUND
Manual Xrefs Databases
C05672 KEGG COMPOUND
FDB021989 FooDB
HMDB0000370 HMDB
View more database links
Registry Number Type Source
5652-28-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19191873 PubMed citation Europe PMC
20504719 PubMed citation Europe PMC
2627760 PubMed citation Europe PMC
30119975 PubMed citation Europe PMC
4622267 PubMed citation Europe PMC
8836635 PubMed citation Europe PMC
Last Modified
18 September 2019