Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000559
Identification
Name: 1-Amino-propan-2-one-3-phosphate
Description:1-amino-propan-2-one-3-phosphate is a normal Pseudomonas aeruginosa metabolite in pyridoxal 5'-phosphate biosynthesis pathway. It is formed by the conversion from (2S)-2-amino-3-oxo-4-phosphonooxybutanoate. With 1-deoxy-D-xylulose 5-phosphate, it is converted to pyridoxine-5'-phosphate. (EcoCyc)
Structure
Thumb
Synonyms:
  • 1-Amino-3-(phosphohydroxy)propan-2-one
  • 1-Amino-propan-2-one-3-phosphate
  • 1-amino-Propan-2-one-3-phosphoric acid
  • 2-Amino-3-phosphonopropanoate
  • 2-Amino-3-phosphonopropanoic acid
  • 2-Amino-3-phosphonopropionate
  • 2-Amino-3-phosphonopropionic acid
  • 3-Amino-2-oxopropyl phosphate
  • 3-amino-2-Oxopropyl phosphoric acid
  • D-Alanyl-phosphate
  • D-Alanyl-phosphoric acid
  • Glyphosate
  • Glyphosic acid
  • Phosphonoalanine
Chemical Formula: C3H8NO5P
Average Molecular Weight: 169.0731
Monoisotopic Molecular Weight: 169.014008883
InChI Key: LBTABPSJONFLPO-UHFFFAOYSA-N
InChI:InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
CAS number: 5652-28-8
IUPAC Name:2-amino-3-phosphonopropanoic acid
Traditional IUPAC Name: phosphonoalanine
SMILES:NC(CP(O)(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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).
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Alpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility34.7 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.08 m3·mol-1ChemAxon
Polarizability12.97 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
  • Phosphonate and phosphinate metabolism pae00440
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0006-0977300000-4d443df31909d1853a23View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9200000000-08200d2cb234cf50b916View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-3900000000-c9c889a41769a47adbb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9200000000-08200d2cb234cf50b916View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-8b77aaf1b45a8474d0e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ufr-4900000000-a387ee1964c407a1e324View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-d60e9dd01c1955aa2a29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-bfdad272f458c80ee240View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-d4bd00a29f208f0b6c4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0fk9-0900000000-7849997de5f05d38e107View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0fk9-0900000000-8a8d71c41991a12e2d3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-052r-0900000000-44aa8996de047417f313View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-053i-6900000000-59ba18558489e038f56cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-003u-9100000000-cdd1bec9118104602debView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
Synthesis Reference: Smith, 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
External Links:
ResourceLink
CHEBI ID244030
HMDB IDHMDB00370
Pubchem Compound ID3857
Kegg IDC05672
ChemSpider ID3723
Wikipedia IDNot Available
BioCyc ID1-AMINO-PROPAN-2-ONE-3-PHOSPHATE
EcoCyc ID1-AMINO-PROPAN-2-ONE-3-PHOSPHATE