Showing metabocard for 2-Amino-3-phosphonopropionic acid (BMDB0000370)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:28 UTC
Update Date2020-05-11 20:52:44 UTC
BMDB IDBMDB0000370
Secondary Accession Numbers
  • BMDB00370
Metabolite Identification
Common Name2-Amino-3-phosphonopropionic acid
Description2-Amino-3-phosphonopropionic acid, also known as 2-amino-3-phosphono-propanoate or phosphonoalanine, 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). 2-Amino-3-phosphonopropionic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on 2-Amino-3-phosphonopropionic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-3-phosphono-propanoic acidChEBI
2-Amino-3-phosphono-propionic acidChEBI
2-Amino-3-phosphopropionic acidChEBI
2-Amino-3-phospropChEBI
2-AP3ChEBI
2-Azanyl-3-phosphono-propanoic acidChEBI
PhosphonoalanineChEBI
2-Amino-3-phosphono-propanoateGenerator
2-Amino-3-phosphono-propionateGenerator
2-Amino-3-phosphopropionateGenerator
2-Azanyl-3-phosphono-propanoateGenerator
2-Amino-3-phosphonopropionateGenerator
2-Amino-3-phosphonopropionic acid, (DL)-isomerHMDB
2-Amino-3-phosphonopropionic acid, sodium saltHMDB
3-Phosphono-L-alanineHMDB
L-AP3HMDB
1-Amino-3-(phosphohydroxy)propan-2-oneHMDB
1-Amino-propan-2-one-3-phosphateHMDB
2-Amino-3-phosphonopropanoateHMDB
2-Amino-3-phosphonopropanoic acidHMDB
3-Amino-2-oxopropyl phosphateHMDB
D-Alanyl-phosphateHMDB
GlyphosateHMDB
Chemical FormulaC3H8NO5P
Average Molecular Weight169.0731
Monoisotopic Molecular Weight169.014008883
IUPAC Name2-amino-3-phosphonopropanoic acid
Traditional Namephosphonoalanine
CAS Registry Number5652-28-8
SMILES
NC(CP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
InChI KeyLBTABPSJONFLPO-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
  • Organophosphonic acid
  • Organophosphonic acid derivative
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.5ALOGPS
logP-3.8ChemAxon
logS-0.69ALOGPS
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.08 m³·mol⁻¹ChemAxon
Polarizability12.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000370
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021989
KNApSAcK IDNot Available
Chemspider ID3723
KEGG Compound IDC05672
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5359
PubChem Compound3857
PDB IDNot Available
ChEBI ID28388
References
Synthesis ReferenceSmith, Edward C. R.; McQuaid, Loretta A.; Paschal, Jonathan W.; DeHoniesto, Juel. An enantioselective synthesis of D-(-)- and L-(+)-2-amino-3-phosphonopropanoic acid. Journal of Organic Chemistry (1990), 55(14), 4472-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available