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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-22 23:33:52 UTC
HMDB IDHMDB0000370
Secondary Accession Numbers
  • HMDB00370
Metabolite Identification
Common Name2-Amino-3-phosphonopropionic acid
Description2-Amino-3-phosphonopropionic acid (AP-3) is a normal human metabolite found in diverse tissues, such as liver, intestine and spleen. (PMID 2627760 ) AP-3 is a metabotropic glutamate receptor agonist (PMID 8836635 ) shown to block the amyloid precursor protein (APP) release evoked by glutamate receptor stimulation in neurons of the cortex and hippocampus; APP accumulation is believed to produce the damage in Alzheimer disease (PMID 7644542 ).
Structure
Data?1582752127
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
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
2-Amino-3-phosphonopropionic acid, sodium saltHMDB
2-Amino-3-phosphonopropionic acid, (DL)-isomerHMDB
L-AP3HMDB
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
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility34.7 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0006-0977300000-4d443df31909d1853a23Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-0977300000-4d443df31909d1853a23Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-9500000000-25e7ef18b28da038081fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8910000000-350d551b33d8dcc00403Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9200000000-08200d2cb234cf50b916Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-3900000000-c9c889a41769a47adbb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9200000000-08200d2cb234cf50b916Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-8b77aaf1b45a8474d0e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ufr-4900000000-a387ee1964c407a1e324Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-d60e9dd01c1955aa2a29Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-bfdad272f458c80ee240Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-d4bd00a29f208f0b6c4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0fk9-0900000000-7849997de5f05d38e107Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0fk9-0900000000-8a8d71c41991a12e2d3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-052r-0900000000-44aa8996de047417f313Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-053i-6900000000-59ba18558489e038f56cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-003u-9100000000-cdd1bec9118104602debSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-8b77aaf1b45a8474d0e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ufr-4900000000-a387ee1964c407a1e324Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d60e9dd01c1955aa2a29Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-bfdad272f458c80ee240Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d4bd00a29f208f0b6c4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fk9-0900000000-7849997de5f05d38e107Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-45d697c64347f275ee31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-6edd7e15764a7a402a22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-4a8ae3dee523a44eb0dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-5ff068071928da7730adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00pj-8900000000-b93eb66e26a07668eb5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-3a5413c9c3e2d6c726b4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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)Download (PDF)
General References
  1. Lueken A, Juhl-Strauss U, Krieger G, Witte I: Synergistic DNA damage by oxidative stress (induced by H2O2) and nongenotoxic environmental chemicals in human fibroblasts. Toxicol Lett. 2004 Feb 28;147(1):35-43. [PubMed:14700526 ]
  2. Chan P, Mahler J: NTP technical report on the toxicity studies of Glyphosate (CAS No. 1071-83-6) Administered In Dosed Feed To F344/N Rats And B6C3F1 Mice. Toxic Rep Ser. 1992 Jul;16:1-D3. [PubMed:12209170 ]
  3. Dickson SJ, Meinhold RH, Beer ID, Koelmeyer TD: Rapid determination of glyphosate in postmortem specimens using 31P NMR. J Anal Toxicol. 1988 Sep-Oct;12(5):284-6. [PubMed:3226127 ]
  4. Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. [PubMed:890917 ]
  5. Wester RC, Melendres J, Sarason R, McMaster J, Maibach HI: Glyphosate skin binding, absorption, residual tissue distribution, and skin decontamination. Fundam Appl Toxicol. 1991 May;16(4):725-32. [PubMed:1884912 ]
  6. Acquavella JF, Alexander BH, Mandel JS, Burns CJ, Gustin C: Exposure misclassification in studies of agricultural pesticides: insights from biomonitoring. Epidemiology. 2006 Jan;17(1):69-74. [PubMed:16357597 ]
  7. Kintzios S, Pistola E, Panagiotopoulos P, Bomsel M, Alexandropoulos N, Bem F, Ekonomou G, Biselis J, Levin R: Bioelectric recognition assay (BERA). Biosens Bioelectron. 2001 Jun;16(4-5):325-36. [PubMed:11390221 ]
  8. Tan SA, Tan LG: Distribution of ciliatine (2-aminoethylphosphonic acid) and phosphonoalanine (2-amino-3-phosphonopropionic acid) in human tissues. Clin Physiol Biochem. 1989;7(6):303-9. [PubMed:2627760 ]
  9. Sorrentino G, Singh IN, Massarelli R, Kanfer JN: Stimulation of phospholipase C activity by norepinephrine, t-ACPD and bombesin in LA-N-2 cells. Eur J Pharmacol. 1996 Jul 11;308(1):81-6. [PubMed:8836635 ]
  10. Lee RK, Wurtman RJ, Cox AJ, Nitsch RM: Amyloid precursor protein processing is stimulated by metabotropic glutamate receptors. Proc Natl Acad Sci U S A. 1995 Aug 15;92(17):8083-7. [PubMed:7644542 ]