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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:16 UTC
HMDB IDHMDB01319
Secondary Accession NumbersNone
Metabolite Identification
Common NamePyridoxine 5'-phosphate
DescriptionPyridoxine 5'-phosphate is a substrate for Pyridoxine-5'-phosphate oxidase and Pyridoxal kinase.
Structure
Thumb
Synonyms
ValueSource
Pyridoxine 5-phosphateKegg
Pyridoxol 5'-phosphateKegg
Pyridoxine 5-phosphoric acidGenerator
Pyridoxine 5'-phosphoric acidGenerator
Pyridoxol 5'-phosphoric acidGenerator
5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphateHMDB
5-Hydroxy-6-methyl-3,4-pyridinedimethanol alpha( 3)-(dihydrogen phosphate)HMDB
Pyridoxine-5'-phosphateHMDB
Pyridoxine-5PHMDB
Pyridoxine-PHMDB
Pyridoxine-phosphateHMDB
Pyridoxol 5-phosphateHMDB
Pyridoxyl-5-phosphateHMDB
Chemical FormulaC8H12NO6P
Average Molecular Weight249.1577
Monoisotopic Molecular Weight249.040223633
IUPAC Name{[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methoxy}phosphonic acid
Traditional Namepyridoxine-5'-phosphate
CAS Registry Number447-05-2
SMILES
CC1=NC=C(COP(O)(O)=O)C(CO)=C1O
InChI Identifier
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)
InChI KeyInChIKey=WHOMFKWHIQZTHY-UHFFFAOYSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridoxines
Direct ParentPyridoxine-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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
HypophosphatasiaSMP00503Not Available
Vitamin B6 MetabolismSMP00017map00750
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.003 (0.0-0.01) uMAdult (>18 years old)FemaleObesity details
Associated Disorders and Diseases
Disease References
Obesity
  1. Driskell JA, Chrisley BM, Reynolds LK, Moak SW: Plasma B6 vitamer and plasma and urinary 4-pyridoxic acid concentrations of middle-aged obese black women. J Chromatogr. 1991 Aug 23;568(2):333-40. [1783639 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022552
KNApSAcK IDNot Available
Chemspider ID1026
KEGG Compound IDC00627
BioCyc IDPYRIDOXINE-5P
BiGG ID35527
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01319
Metagene LinkHMDB01319
METLIN ID6156
PubChem Compound1055
PDB IDPXP
ChEBI ID28803
References
Synthesis ReferenceArgoudelis, 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
General ReferencesNot Available

Enzymes

General function:
Involved in pyridoxamine-phosphate oxidase activity
Specific function:
Catalyzes the oxidation of either pyridoxine 5'-phosphate (PNP) or pyridoxamine 5'-phosphate (PMP) into pyridoxal 5'-phosphate (PLP).
Gene Name:
PNPO
Uniprot ID:
Q9NVS9
Molecular weight:
29987.79
Reactions
Pyridoxine 5'-phosphate + Oxygen → Pyridoxal 5'-phosphate + Hydrogen peroxidedetails
General function:
Involved in pyridoxal kinase activity
Specific function:
Required for synthesis of pyridoxal-5-phosphate from vitamin B6.
Gene Name:
PDXK
Uniprot ID:
O00764
Molecular weight:
35102.105
Reactions
Adenosine triphosphate + Pyridoxine → ADP + Pyridoxine 5'-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Protein serine phosphatase that dephosphorylates 'Ser-3' in cofilin and probably also dephosphorylates phospho-serine residues in DSTN. Regulates cofilin-dependent actin cytoskeleton reorganization. Required for normal progress through mitosis and normal cytokinesis. Does not dephosphorylate phospho-threonines in LIMK1. Does not dephosphorylate peptides containing phospho-tyrosine. Pyridoxal phosphate phosphatase. Has some activity towards pyridoxal 5'-phosphate (PLP), pyridoxine 5'-phosphate (PMP) and pyridoxine 5'-phosphate (PNP), with a highest activity with PLP followed by PNP.
Gene Name:
PDXP
Uniprot ID:
Q96GD0
Molecular weight:
31697.735
Reactions
Pyridoxine + Phosphoric acid → Pyridoxine 5'-phosphate + Waterdetails
General function:
Involved in phosphatase activity
Specific function:
Phosphatase that has high activity toward pyridoxal 5'-phosphate (PLP). Also active at much lower level toward pyrophosphate, phosphoethanolamine (PEA), phosphocholine (PCho), phospho-l-tyrosine, fructose-6-phosphate, p-nitrophenyl phosphate, and h-glycerophosphate.
Gene Name:
PHOSPHO2
Uniprot ID:
Q8TCD6
Molecular weight:
27768.72
Reactions
Pyridoxine + Phosphoric acid → Pyridoxine 5'-phosphate + Waterdetails