Pyridoxine 5'-phosphate (PAMDB000338)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000338
Identification
Name: Pyridoxine 5'-phosphate
Description:Pyridoxine 5'-phosphate is a substrate for Pyridoxine-5'-phosphate oxidase and Pyridoxal kinase.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphate
  • 5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphoric acid
  • 5-Hydroxy-6-methyl-3,4-pyridinedimethanol a( 3)-(dihydrogen phosphate)
  • 5-Hydroxy-6-methyl-3,4-pyridinedimethanol a( 3)-(dihydrogen phosphoric acid)
  • 5-Hydroxy-6-methyl-3,4-Pyridinedimethanol alpha( 3)-(dihydrogen phosphate)
  • 5-Hydroxy-6-methyl-3,4-pyridinedimethanol alpha( 3)-(dihydrogen phosphoric acid)
  • 5-Hydroxy-6-methyl-3,4-pyridinedimethanol α( 3)-(dihydrogen phosphate)
  • 5-Hydroxy-6-methyl-3,4-pyridinedimethanol α( 3)-(dihydrogen phosphoric acid)
  • Pyn5'P
  • Pyridoxine 5'-phosphate
  • Pyridoxine 5'-phosphoric acid
  • Pyridoxine 5-phosphate
  • Pyridoxine 5-phosphoric acid
  • Pyridoxine-5'-phosphate
  • Pyridoxine-5'-phosphoric acid
  • Pyridoxine-5-phosphate
  • Pyridoxine-5-phosphoric acid
  • Pyridoxine-5P
  • Pyridoxine-P
  • Pyridoxine-phosphate
  • Pyridoxine-phosphoric acid
  • Pyridoxol 5-phosphate
  • Pyridoxol 5-phosphoric acid
  • Pyridoxol-5'-phosphate
  • Pyridoxol-5'-phosphoric acid
  • Pyridoxyl-5-phosphate
  • Pyridoxyl-5-phosphoric acid
  • [5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyl phosphate
  • [5-Hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyl phosphoric acid
Chemical Formula: C8H12NO6P
Average Molecular Weight: 249.1577
Monoisotopic Molecular Weight: 249.040223633
InChI Key: WHOMFKWHIQZTHY-UHFFFAOYSA-N
InChI:InChI=1S/C8H12NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2,10-11H,3-4H2,1H3,(H2,12,13,14)
CAS number: 447-05-2
IUPAC Name:{[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methoxy}phosphonic acid
Traditional IUPAC Name: pyridoxine-5'-phosphate
SMILES:CC1=NC=C(COP(O)(O)=O)C(CO)=C1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyridoxine-5'-phosphates. These are pyridoxines that carry a phosphate group at the 5-position.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pyridines and derivatives
Sub ClassPyridoxines
Direct Parent Pyridoxine-5'-phosphates
Alternative Parents
Substituents
  • Pyridoxine-5'-phosphate
  • Methylpyridine
  • Hydroxypyridine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.41 mg/mLALOGPS
logP-0.8ALOGPS
logP-3.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)5.55ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.11 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.98 m3·mol-1ChemAxon
Polarizability21.72 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
1-Deoxy-D-xylulose 5-phosphate + NAD + O-Phospho-4-hydroxy-L-threonine > Carbon dioxide + Hydrogen ion +2 Water + NADH + Pyridoxine 5'-phosphate + Phosphate
Water + Pyridoxine 5'-phosphate > Phosphate + Pyridoxine
Adenosine triphosphate + Pyridoxine <> ADP + Pyridoxine 5'-phosphate
3-Amino-2-oxopropyl phosphate + 1-Deoxy-D-xylulose 5-phosphate + 3-Amino-2-oxopropyl phosphate <> Pyridoxine 5'-phosphate + Phosphate +2 Water
1-Amino-propan-2-one-3-phosphate + 1-Deoxy-D-xylulose 5-phosphate > Hydrogen ion + Pyridoxine 5'-phosphate + Phosphate + Water
Adenosine triphosphate + Pyridoxine > Hydrogen ion + ADP + Pyridoxine 5'-phosphate
Oxygen + Pyridoxine 5'-phosphate > Hydrogen peroxide + Pyridoxal 5'-phosphate
Pyridoxamine 5'-phosphate + Water + Oxygen + Pyridoxine 5'-phosphate <> Pyridoxal 5'-phosphate + Ammonia + Hydrogen peroxide
1-Deoxy-D-xylulose 5-phosphate + 2-Amino-3-phosphonopropionic acid + 1-Deoxy-D-xylulose 5-phosphate + 2-Amino-3-phosphonopropionic acid > Pyridoxine 5'-phosphate + Phosphate + Hydrogen ion +2 Water
Pyridoxine + Adenosine triphosphate > Pyridoxine 5'-phosphate + Adenosine diphosphate + Hydrogen ion + ADP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0590000000-68640055ed308d852fd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900000000-1450b9f084acf6421d59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-4900000000-8fd6492e6f2a6bea9879View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-8090000000-65f73f2c7a460a3fca23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-5b0859a6a40a458fcc9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a6fead236e12d88986b8View in MoNA
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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Argoudelis, Chris J. Preparation of crystalline pyridoxine 5'-phosphate and some of its properties. Journal of Agricultural and Food Chemistry (1986), 34(6), 995-8.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28803
HMDB IDHMDB01319
Pubchem Compound ID1055
Kegg IDC00627
ChemSpider ID1026
Wikipedia IDNot Available
BioCyc IDPYRIDOXINE-5P
EcoCyc IDPYRIDOXINE-5P
Ligand ExpoPXP