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1-Amino-propan-2-one-3-phosphate (M2MDB000559)

Record Information
Version2.0
Creation Date2012-05-31 14:02:14 -0600
Update Date2015-06-03 15:54:37 -0600
Secondary Accession Numbers
  • ECMDB04014
Identification
Name:1-Amino-propan-2-one-3-phosphate
Description1-amino-propan-2-one-3-phosphate is a normal E coli 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
MOLSDFPDBSMILESInChI
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
Weight:Average: 169.0731
Monoisotopic: 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
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
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2-Amino-3-oxo-4-phosphonooxybutyrate + Hydrogen ion > 1-Amino-propan-2-one-3-phosphate + Carbon dioxide
1-Amino-propan-2-one-3-phosphate + 1-Deoxy-D-xylulose 5-phosphate > Hydrogen ion + Pyridoxine 5'-phosphate + Phosphate + Water
SMPDB Pathways:Not Available
KEGG Pathways:
  • Phosphonate and phosphinate metabolism ec00440
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0006-0977300000-4d443df31909d1853a23View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-0977300000-4d443df31909d1853a23View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-9500000000-25e7ef18b28da038081fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8910000000-350d551b33d8dcc00403View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-8b77aaf1b45a8474d0e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ufr-4900000000-a387ee1964c407a1e324View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d60e9dd01c1955aa2a29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-bfdad272f458c80ee240View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d4bd00a29f208f0b6c4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fk9-0900000000-7849997de5f05d38e107View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-45d697c64347f275ee31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-6edd7e15764a7a402a22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-4a8ae3dee523a44eb0dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-5ff068071928da7730adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00pj-8900000000-b93eb66e26a07668eb5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-3a5413c9c3e2d6c726b4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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 ID28388
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

Enzymes

Protein Details
1. 4-hydroxythreonine-4-phosphate dehydrogenase
General function:
Involved in 4-hydroxythreonine-4-phosphate dehydrogenase activity
Specific function:
Catalyzes the NAD(P)-dependent oxidation of 4- (phosphohydroxy)-L-threonine (HTP) into 2-amino-3-oxo-4- (phosphohydroxy)butyric acid which spontaneously decarboxylates to form 3-amino-2-oxopropyl phosphate (AHAP)
Gene Name:
pdxA
Uniprot ID:
P19624
Molecular weight:
35114
Reactions
4-(phosphonooxy)-L-threonine + NAD(+) = (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + NADH.