Record Information
Version1.0
Creation date2010-04-08 22:04:37 UTC
Update date2020-09-17 15:41:38 UTC
Primary IDFDB000574
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyridoxine
DescriptionPyridoxine, also known as pyridoxol or vitamin B6, belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. Pyridoxine is a very strong basic compound (based on its pKa). Pyridoxine exists in all living species, ranging from bacteria to humans. Within humans, pyridoxine participates in a number of enzymatic reactions. In particular, pyridoxine can be converted into pyridoxal; which is catalyzed by the enzyme pyridoxine-5'-phosphate oxidase. In addition, pyridoxine can be converted into pyridoxine 5'-phosphate through its interaction with the enzyme pyridoxal kinase. In humans, pyridoxine is involved in vitamin B6 metabolism. Outside of the human body, Pyridoxine is found, on average, in the highest concentration within a few different foods, such as common sages, tarragons, and summer savories and in a lower concentration in hushpuppies, alaska pollocks, and clupeinae (herring, sardine, sprat). Pyridoxine has also been detected, but not quantified in, several different foods, such as ucuhuba, pikeperchs, whiskies, fruit gums, and ginsengs. This could make pyridoxine a potential biomarker for the consumption of these foods. Pyridoxine is a potentially toxic compound.
CAS Number65-23-6
Structure
Thumb
Synonyms
SynonymSource
2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridineChEBI
3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridineChEBI
3-Hydroxy-4,5-dimethylol-alpha-picolineChEBI
5-Hydroxy-6-methyl-3,4-pyridinedimethanolChEBI
PyridoxolChEBI
Vitamin b6ChEBI
3-Hydroxy-4,5-dimethylol-a-picolineGenerator
3-Hydroxy-4,5-dimethylol-α-picolineGenerator
2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridineHMDB
2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridineHMDB
2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridineHMDB
3-Hydroxy-2-picoline-4,5-dimethanolHMDB
AdermineHMDB
GravidoxHMDB
HydoxinHMDB
PiridossinaHMDB
PiridoxinaHMDB
PyridoxinHMDB
PyridoxinumHMDB
PyridoxolumHMDB
Pyridoxol hydrochlorideHMDB
RodexHMDB
Pyridoxine hydrochlorideHMDB
2-methyl-3-hydroxy-4,5-dihydroxymethylpyridinebiospider
2-methyl-4,5-dimethylol-pyridin-3-olbiospider
2-Picoline-4,5-dimethanol, 3-hydroxy-biospider
3-hydroxy-2-Picoline-4,5-dimethanolbiospider
3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-biospider
4,5-Bis(hydroxymethyl)-2-methyl-3-pyridinolbiospider
4,5-bis(hydroxymethyl)-2-methylpyridine-3-olbiospider
5-Hydroxy-6-methyl-3,4-pyridinedimethanol, 9CIdb_source
Aderoxinebiospider
Bezatinbiospider
Hexabetalinbiospider
Hexabionbiospider
Pirivitolbiospider
Pridoxinebiospider
Vitamin B6manual
Vitamin B6, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-0.57ALOGPS
logP-0.95ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)5.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.58 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.11 m³·mol⁻¹ChemAxon
Polarizability17.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H11NO3
IUPAC name4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
InChI IdentifierInChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
InChI KeyLXNHXLLTXMVWPM-UHFFFAOYSA-N
Isomeric SMILESCC1=C(O)C(CO)=C(CO)C=N1
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
Classification
Description Belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridoxines
Direct ParentPyridoxines
Alternative Parents
Substituents
  • Pyridoxine
  • Methylpyridine
  • Hydroxypyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 56.80%; H 6.55%; N 8.28%; O 28.37%DFC
Melting PointMp 160°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-0.77SANGSTER (1993)
Experimental pKapKa2 8.96 (25°, 0.15M NaCl)DFC
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-1003-6900000000-1237eaf82dfadfd54d4bSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
GC-MSPyridoxine, 3 TMS, GC-MS Spectrumsplash10-000t-0940000000-30b4702623a6d8fcb4bbSpectrum
GC-MSPyridoxine, non-derivatized, GC-MS Spectrumsplash10-001j-0690000000-0581e2b42fa48c1ea498Spectrum
GC-MSPyridoxine, 3 TMS, GC-MS Spectrumsplash10-00di-9330000000-32929ff06762b9f5887fSpectrum
GC-MSPyridoxine, 3 TMS, GC-MS Spectrumsplash10-001i-0490000000-34a09ddbbb462aeb02a6Spectrum
GC-MSPyridoxine, non-derivatized, GC-MS Spectrumsplash10-0f6x-9400000000-486db54a30b61c2eb9d4Spectrum
GC-MSPyridoxine, non-derivatized, GC-MS Spectrumsplash10-000t-0940000000-30b4702623a6d8fcb4bbSpectrum
GC-MSPyridoxine, non-derivatized, GC-MS Spectrumsplash10-001j-0690000000-0581e2b42fa48c1ea498Spectrum
GC-MSPyridoxine, non-derivatized, GC-MS Spectrumsplash10-00di-9330000000-32929ff06762b9f5887fSpectrum
GC-MSPyridoxine, non-derivatized, GC-MS Spectrumsplash10-001i-0490000000-34a09ddbbb462aeb02a6Spectrum
GC-MSPyridoxine, non-derivatized, GC-MS Spectrumsplash10-001j-0790000000-6f8f6e679e03f9119a65Spectrum
Predicted GC-MSPyridoxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-0900000000-0f727b3e23c2481951e8Spectrum
Predicted GC-MSPyridoxine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7079000000-2f143e187cb8c078f936Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0vi0-0900000000-bd0de86c072765a5caadSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-3900000000-2018b406a3c75213b733Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0059-9200000000-e69bb531deb2a103a476Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0f6x-9400000000-77c43a946c4ae1abf3b9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-479d4492cc8d634fa366Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-486d6a4e5e1a731b7c54Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-05fr-0900000000-4ef09ce9c04561a1085eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0ab9-1900000000-3298adf6db36689d5d43Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a6r-7900000000-6711954ee96f08344434Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-234e90d43a7febd7a098Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-137080765c0035b45258Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-0900000000-882ee900a8bba08e2c7cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-003r-8900000000-e0e11797b63cea991d81Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0059-9100000000-c25384179219411af02cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0ue9-0900000000-c0e149ce890192397b7fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0v4i-0900000000-f9f378af3d47ab006806Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-479d4492cc8d634fa366Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-486d6a4e5e1a731b7c54Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fr-0900000000-4ef09ce9c04561a1085eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0900000000-eab5b3411261744df750Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0900000000-cc4dc8719602182ef1ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-5900000000-1c2637733578fcdd7c6aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-e89cc69d8b21012ff982Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-0900000000-0ad8d09e042015cb2e33Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-577a3d87899ca47d539fSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID1025
ChEMBL IDCHEMBL1364
KEGG Compound IDC00314
Pubchem Compound ID1054
Pubchem Substance IDNot Available
ChEBI ID16709
Phenol-Explorer IDNot Available
DrugBank IDDB00165
HMDB IDHMDB00239
CRC / DFC (Dictionary of Food Compounds) IDBDV40-Q:BDV40-Q
EAFUS ID3262
Dr. Duke IDVITAMIN-B-6|VIT-B-6|PYRIDOXINE
BIGG ID34590
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPyridoxine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti aggregantDUKE
anti anemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti autistic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti carpal-tunnelDUKE
anti cheiliticDUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti dyskineticDUKE
anti emetic50919 A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.DUKE
anti epileptic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti glossiticDUKE
anti homocystinuricDUKE
anti hyperkineticDUKE
anti hyperventilation52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti infertility52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti lithicDUKE
anti morning sickness52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti monosodium-glutamate-sensitivityDUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuropathicDUKE
anti oxaluricDUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti premenstrual syndrome52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti prolactinDUKE
anti radiationDUKE
anti schizophrenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti seborrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti sicklingDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti TMJDUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti vertigo52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
dopaminergic48560 A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.DUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
progesteronigenicDUKE
Enzymes
NameGene NameUniProt ID
Phosphoserine aminotransferasePSAT1Q9Y617
Pathways
NameSMPDB LinkKEGG Link
Vitamin B6 MetabolismSMP00017 map00750
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).