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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:08 UTC
HMDB IDHMDB00239
Secondary Accession Numbers
  • HMDB02075
Metabolite Identification
Common NamePyridoxine
DescriptionThe 4-methanol form of vitamin B6 which is converted to pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Although pyridoxine and Vitamin B6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Pyridoxine is one of the compounds that can be called vitamin B6. Pyridoxine assists in the balancing of sodium and potassium as well as promoting red blood cell production. It is linked to cancer immunity and helps fight the formation of homocysteine. It has been suggested that Pyridoxine might help children with learning difficulties, and may also prevent dandruff, eczema, and psoriasis. In addition, pyridoxine can help balance hormonal changes in women and aid in immune system. Lack of pyridoxine may cause anemia, nerve damage, seizures, skin problems, and sores in the mouth. -- Wikipedia Deficiency, though rare because of widespread distribution in foods, leads to the development of peripheral neuritis in adults and affects the central nervous system in children (DOSE - 3rd edition).
Structure
Thumb
Synonyms
  1. 2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine
  2. 2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine
  3. 2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine
  4. 3-Hydroxy-2-Picoline-4,5-dimethanol
  5. 3-Hydroxy-4,5-dimethylol-alpha-picoline
  6. 5-Hydroxy-6-methyl-3,4-pyridinedimethanol
  7. Adermine
  8. Gravidox
  9. Hydoxin
  10. Piridossina
  11. Piridoxina
  12. Pyridoxin
  13. Pyridoxine
  14. Pyridoxinum
  15. Pyridoxol
  16. Pyridoxolum
Chemical FormulaC8H11NO3
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
IUPAC Name4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
Traditional Namepyridoxine
CAS Registry Number65-23-6
SMILES
CC1=NC=C(CO)C(CO)=C1O
InChI Identifier
InChI=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
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassPyridines and Derivatives
Sub ClassPyridoxines
Other Descriptors
  • Pyridines and Derivatives
  • Water-soluble vitamins(KEGG)
  • a vitamin B6(Cyc)
  • hydroxymethylpyridine(ChEBI)
  • methylpyridines(ChEBI)
  • monohydroxypyridine(ChEBI)
  • vitamin B6(ChEBI)
Substituents
  • Primary Alcohol
Direct ParentPyridoxines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point159 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility79 mg/mLNot Available
LogP-0.77SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility16.1ALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.11 m3·mol-1ChemAxon
Polarizability17.11 Å3ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Erythrocyte
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Vitamin B6 MetabolismSMP00017map00750
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.025 (0.007-0.060) uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified<1 nmol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.119 +/- 0.038 uMAdult (>18 years old)BothHomozygous sickle cell disease details
Associated Disorders and Diseases
Disease References
Homozygous sickle cell disease
  1. van der Dijs FP, Schnog JJ, Brouwer DA, Velvis HJ, van den Berg GA, Bakker AJ, Duits AJ, Muskiet FD, Muskiet FA: Elevated homocysteine levels indicate suboptimal folate status in pediatric sickle cell patients. Am J Hematol. 1998 Nov;59(3):192-8. Pubmed: 9798656
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000574
KNApSAcK IDNot Available
Chemspider ID1025
KEGG Compound IDC00314
BioCyc IDCPD-455
BiGG ID34590
Wikipedia LinkPyridoxine
NuGOwiki LinkHMDB00239
Metagene LinkHMDB00239
METLIN ID5245
PubChem Compound1054
PDB IDNot Available
ChEBI ID16709
References
Synthesis ReferenceItov, Z. I.; Stepanova, S. V.; El'yanov, B. S.; Gunar, V. I. Synthesis of pyridoxine under high pressure. Khimiko-Farmatsevticheskii Zhurnal (1987), 21(7), 858-62.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Amoroso A, Pirulli D, Florian F, Puzzer D, Boniotto M, Crovella S, Zezlina S, Spano A, Mazzola G, Savoldi S, Ferrettini C, Berutti S, Petrarulo M, Marangella M: AGXT gene mutations and their influence on clinical heterogeneity of type 1 primary hyperoxaluria. J Am Soc Nephrol. 2001 Oct;12(10):2072-9. Pubmed: 11562405
  2. Plecko B, Stockler-Ipsiroglu S, Paschke E, Erwa W, Struys EA, Jakobs C: Pipecolic acid elevation in plasma and cerebrospinal fluid of two patients with pyridoxine-dependent epilepsy. Ann Neurol. 2000 Jul;48(1):121-5. Pubmed: 10894227
  3. Henderson JM, Codner MA, Hollins B, Kutner MH, Merrill AH: The fasting B6 vitamer profile and response to a pyridoxine load in normal and cirrhotic subjects. Hepatology. 1986 May-Jun;6(3):464-71. Pubmed: 3710434
  4. Chiang EP, Selhub J, Bagley PJ, Dallal G, Roubenoff R: Pyridoxine supplementation corrects vitamin B6 deficiency but does not improve inflammation in patients with rheumatoid arthritis. Arthritis Res Ther. 2005;7(6):R1404-11. Epub 2005 Oct 14. Pubmed: 16277693
  5. Manyam BV, Ferraro TN, Hare TA: Isoniazid-induced alteration of CSF neurotransmitter amino acids in Huntington's disease. Brain Res. 1987 Apr 7;408(1-2):125-30. Pubmed: 2885064
  6. Temesvari P, Szilagyi I, Eck E, Boda D: Effects of an antenatal load of pyridoxine (vitamin B6) on the blood oxygen affinity and prolactin levels in newborn infants and their mothers. Acta Paediatr Scand. 1983 Jul;72(4):525-9. Pubmed: 6624427
  7. McCully KS: Homocysteine, vitamins, and prevention of vascular disease. Mil Med. 2004 Apr;169(4):325-9. Pubmed: 15132238
  8. Chen S, Ito M, Saijo T, Naito E, Kuroda Y: Molecular genetic analysis of pyridoxine-nonresponsive homocystinuric siblings with different blood methionine levels during the neonatal period. J Med Invest. 1999 Aug;46(3-4):186-91. Pubmed: 10687314
  9. Wasilewska A, Narkiewicz M, Rutkowski B, Lysiak-Szydlowska W: Is there any relationship between lipids and vitamin B levels in persons with elevated risk of atherosclerosis? Med Sci Monit. 2003 Mar;9(3):CR147-51. Pubmed: 12640345
  10. Kidd GS, Dimond R, Kark JA, Whorton N, Vigersky RA: The effects of pyridoxine on pituitary hormone secretion in amenorrhea-galactorrhea syndromes. J Clin Endocrinol Metab. 1982 Apr;54(4):872-5. Pubmed: 6801073
  11. Pirulli D, Marangella M, Amoroso A: Primary hyperoxaluria: genotype-phenotype correlation. J Nephrol. 2003 Mar-Apr;16(2):297-309. Pubmed: 12768081
  12. Tolis G, Laliberte R, Guyda H, Naftolin F: Ineffectiveness of pyridoxine (B6) to alter secretion of growth hormone and prolactin and absence of therapeutic effects on galactorrhea-amenorrhea syndromes. J Clin Endocrinol Metab. 1977 Jun;44(6):1197-9. Pubmed: 559690
  13. Esteve-Romero J, Capella-Peiro ME, Monferrer-Pons L, Gil-Agusti M: Micellar liquid chromatography in clinical chemistry: application to the monitorization of B6 vitamins. Clin Chim Acta. 2004 Oct;348(1-2):69-77. Pubmed: 15369738

Enzymes

General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular weight:
74595.895
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
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 + Oxygen → Pyridoxal + Hydrogen peroxidedetails
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Only known pyridoxal phosphate-dependent enzyme that contains heme. Important regulator of hydrogen sulfide, especially in the brain, utilizing cysteine instead of serine to catalyze the formation of hydrogen sulfide. Hydrogen sulfide is a gastratransmitter with signaling and cytoprotective effects such as acting as a neuromodulator in the brain to protect neurons against hypoxic injury (By similarity).
Gene Name:
CBS
Uniprot ID:
P35520
Molecular weight:
60586.05
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
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 transport
Specific function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:
ALB
Uniprot ID:
P02768
Molecular weight:
69365.9
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