Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000420
Identification
Name: Pyridoxamine 5'-phosphate
Description:Pyradoxamine 5' phosphate or Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes.Vitamin B6 is a water-soluble vitamin. The three major forms of vitamin B6 are pyridoxine (also known as pyridoxol), pyridoxal, and pyridoxamine, which are all converted in to pyridoxal 5-phosphate (PLP) a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen.
Structure
Thumb
Synonyms:
  • PMP
  • PX5'P
  • Pyridoxamine 5'-phosphate
  • Pyridoxamine 5'-phosphoric acid
  • Pyridoxamine phosphate
  • Pyridoxamine phosphoric acid
Chemical Formula: C8H13N2O5P
Average Molecular Weight: 248.173
Monoisotopic Molecular Weight: 248.056208048
InChI Key: ZMJGSOSNSPKHNH-UHFFFAOYSA-N
InChI:InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)
CAS number: 529-96-4
IUPAC Name:{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid
Traditional IUPAC Name: pyridoxamine-5'-phosphate
SMILES:CC1=NC=C(COP(O)(O)=O)C(CN)=C1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyridoxamines. These are pyridoxal derivatives in which the pyridoxal moiety is substituted at position 2 by an amine.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pyridines and derivatives
Sub ClassPyridoxamines
Direct Parent Pyridoxamines
Alternative Parents
Substituents
  • Pyridoxamine
  • Methylpyridine
  • Hydroxypyridine
  • Aralkylamine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.61 mg/mLALOGPS
logP-0.99ALOGPS
logP-2.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)10.11ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.64 m3·mol-1ChemAxon
Polarizability22.14 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0590000000-f2e78df6839a1a6c3c53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900000000-45ff9c035fa30cea77bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-96d22fb2e9dd035fa2e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9080000000-908c35d20c168506f92cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-97480b70e97796d59101View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c77bbc411daf4c046f20View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • 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
  • 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
Synthesis Reference: Katsunishi, Masatoshi; Kondo, Osamu. Pyridoxamine-5'-phosphate. Jpn. Tokkyo Koho (1972), 2 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID18335
HMDB IDHMDB01555
Pubchem Compound ID1053
Kegg IDC00647
ChemSpider ID1024
Wikipedia IDNot Available
BioCyc IDPYRIDOXAMINE-5P
EcoCyc IDPYRIDOXAMINE-5P
Ligand ExpoPMP