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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-18 01:52:42 UTC
HMDB IDHMDB0001319
Secondary Accession Numbers
  • HMDB01319
Metabolite Identification
Common NamePyridoxine 5'-phosphate
DescriptionPyridoxine 5'-phosphate, also known as pyridoxine 5-phosphoric acid or pyridoxine-5p, is a member of the class of compounds known as pyridoxine-5'-phosphates. Pyridoxine-5'-phosphates are pyridoxines that carry a phosphate group at the 5-position. Pyridoxine 5'-phosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Pyridoxine 5'-phosphate can be found primarily in blood. Within the cell, pyridoxine 5'-phosphate is primarily located in the cytoplasm (predicted from logP). Pyridoxine 5'-phosphate exists in all living species, ranging from bacteria to humans. In humans, pyridoxine 5'-phosphate is involved in the vitamin B6 metabolism. Pyridoxine 5'-phosphate is also involved in hypophosphatasia, which is a metabolic disorder. Moreover, pyridoxine 5'-phosphate is found to be associated with obesity. Pyridoxine 5'-phosphate is a substrate for Pyridoxine-5'-phosphate oxidase and Pyridoxal kinase..
Structure
Thumb
Synonyms
ValueSource
Pyridoxine 5'-(dihydrogen phosphate)ChEBI
Pyridoxine 5-phosphateChEBI
Pyridoxine phosphateChEBI
PYRIDOXINE-5'-phosphATEChEBI
Pyridoxol 5'-phosphateChEBI
Pyridoxol 5-phosphateChEBI
Pyridoxyl-5-phosphateChEBI
Pyridoxine 5'-(dihydrogen phosphoric acid)Generator
Pyridoxine 5'-phosphoric acidGenerator
Pyridoxine 5-phosphoric acidGenerator
Pyridoxine phosphoric acidGenerator
PYRIDOXINE-5'-phosphoric acidGenerator
Pyridoxol 5'-phosphoric acidGenerator
Pyridoxol 5-phosphoric acidGenerator
Pyridoxyl-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-5PHMDB
Pyridoxine-PHMDB
Pyridoxine-phosphateHMDB
Pyridoxine 5-phosphate hydrochlorideMeSH
5-PhosphopyridoxineMeSH
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 KeyWHOMFKWHIQZTHY-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
  • Monoalkyl phosphate
  • Hydroxypyridine
  • Methylpyridine
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic alcohol
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.98 m³·mol⁻¹ChemAxon
Polarizability21.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9530000000-1e967afad92165e82beeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9226000000-49f5293644ca681d401bView in MoNA
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)
Biospecimen Locations
  • Blood
Tissue LocationNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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. [PubMed:1783639 ]
Associated OMIM IDs
DrugBank IDDB02209
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022552
KNApSAcK IDC00007505
Chemspider ID1026
KEGG Compound IDC00627
BioCyc IDPYRIDOXINE-5P
BiGG ID35527
Wikipedia LinkNot Available
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