Pyridoxal 5'-phosphate (PAMDB000400)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000400
Identification
Name: Pyridoxal 5'-phosphate
Description:Pyridoxal 5'-phosphate (PLP) is the active form of vitamin B6 serving as a coenzyme for reactions involving transamination, deamination, and decarboxylation. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Apolon B6
  • Biosechs
  • Codecarboxylase
  • Coenzyme B6
  • Hairoxal
  • Hexermin-P
  • Hi-Pyridoxin
  • Hiadelon
  • Himitan
  • PAL-P
  • Phosphopyridoxal
  • Phosphopyridoxal coenzyme
  • Pidopidon
  • Piodel
  • PLP
  • Pydoxal
  • Pyr5'P
  • Pyridoxal 5'-phosphate
  • Pyridoxal 5'-phosphoric acid
  • Pyridoxal 5-phosphate
  • Pyridoxal 5-phosphoric acid
  • Pyridoxal P
  • Pyridoxal phosphate
  • Pyridoxal phosphoric acid
  • Pyridoxal-5P
  • Pyridoxal-P
  • Pyridoxyl phosphate
  • Pyridoxyl phosphoric acid
  • Pyromijin
  • Sechvitan
  • Vitahexin-P
  • Vitamin B6
  • Vitazechs
Chemical Formula: C8H10NO6P
Average Molecular Weight: 247.1419
Monoisotopic Molecular Weight: 247.024573569
InChI Key: NGVDGCNFYWLIFO-UHFFFAOYSA-N
InChI:InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
CAS number: 54-47-7
IUPAC Name:[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
Traditional IUPAC Name: pyridoxal phosphate
SMILES:CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyridoxals and derivatives. These are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pyridines and derivatives
Sub ClassPyridine carboxaldehydes
Direct Parent Pyridoxals and derivatives
Alternative Parents
Substituents
  • Pyridoxal
  • Methylpyridine
  • Hydroxypyridine
  • Monoalkyl phosphate
  • Aryl-aldehyde
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Vinylogous acid
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 255 °C
Experimental Properties:
PropertyValueSource
Water Solubility:28 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.7 mg/mLALOGPS
logP-0.55ALOGPS
logP-2.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.68ChemAxon
pKa (Strongest Basic)4.11ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.95 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.75 m3·mol-1ChemAxon
Polarizability20.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + Pyridoxal 5'-phosphate > Phosphate + Pyridoxal
L-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acid
Adenosine triphosphate + Pyridoxal <> ADP + Hydrogen ion + Pyridoxal 5'-phosphate
D-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acid
Water + Oxygen + Pyridoxamine 5'-phosphate > Hydrogen peroxide + Ammonium + Pyridoxal 5'-phosphate
Adenosine triphosphate + Pyridoxal <> ADP + Pyridoxal 5'-phosphate
Pyridoxamine 5'-phosphate + Water + Oxygen <> Pyridoxal 5'-phosphate + Ammonia + Hydrogen peroxide
Oxygen + Water + Pyridoxamine 5'-phosphate > Hydrogen ion + Hydrogen peroxide + Ammonia + Pyridoxal 5'-phosphate
Oxygen + Pyridoxine 5'-phosphate > Hydrogen peroxide + Pyridoxal 5'-phosphate
Pyridoxamine 5'-phosphate + Oxoglutaric acid <> Pyridoxal 5'-phosphate + D-Glutamic acid
Pyridoxal 5'-phosphate + Water > Pyridoxal + Inorganic phosphate
Pyridoxamine 5'-phosphate + Water + Oxygen + Pyridoxine 5'-phosphate <> Pyridoxal 5'-phosphate + Ammonia + Hydrogen peroxide
Pyridoxal + Adenosine triphosphate > Pyridoxal 5'-phosphate + Adenosine diphosphate + ADP
Pyridoxal 5'-phosphate > 4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0gb9-2690000000-c9bacb7e657461e28407View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fxx-8900000000-ee972556340c61650528View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9100000000-3cc29fb51820adecd59cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0090000000-9b86e80a9dd0de14ab59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03dj-9800000000-9313aa9cbf19bc6311c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9500000000-7ce120a58879e2214ce5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9200000000-7e6bd8c298613e59fb5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-4c05178b1645bf01f3faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-3920000000-6c5e6106f5658d1d6c50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-3920000000-f96097815e6922356131View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9000000000-2c4e243699a95e3a0f88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9000000000-8aa111485891af9f0d02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1790000000-1dcb07cd1110c71f7005View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ca6aab7f31a36863a417View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-053802b9c0533d7943eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9080000000-12ca63d34d39d59f6b42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-144099ec201adbbc4684View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-70a9559d65e78c488e7eView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Chiang EP, Bagley PJ, Roubenoff R, Nadeau M, Selhub J: Plasma pyridoxal 5'-phosphate concentration is correlated with functional vitamin B-6 indices in patients with rheumatoid arthritis and marginal vitamin B-6 status. J Nutr. 2003 Apr;133(4):1056-9. Pubmed: 12672918
  • Chiang EP, Bagley PJ, Selhub J, Nadeau M, Roubenoff R: Abnormal vitamin B(6) status is associated with severity of symptoms in patients with rheumatoid arthritis. Am J Med. 2003 Mar;114(4):283-7. Pubmed: 12681455
  • 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
  • Descombes E, Hanck AB, Fellay G: Water soluble vitamins in chronic hemodialysis patients and need for supplementation. Kidney Int. 1993 Jun;43(6):1319-28. Pubmed: 8315945
  • Fonda ML: Vitamin B6 metabolism and binding to proteins in the blood of alcoholic and nonalcoholic men. Alcohol Clin Exp Res. 1993 Dec;17(6):1171-8. Pubmed: 8116826
  • Heiskanen K, Kallio M, Salmenpera L, Siimes MA, Ruokonen I, Perheentupa J: Vitamin B-6 status during childhood: tracking from 2 months to 11 years of age. J Nutr. 1995 Dec;125(12):2985-92. Pubmed: 7500176
  • Heiskanen K, Siimes MA, Perheentupa J, Salmenpera L: Reference ranges for erythrocyte pyridoxal 5'-phosphate concentration and the erythrocyte aspartate transaminase stimulation test in lactating mothers and their infants. Am J Clin Nutr. 1994 Jun;59(6):1297-303. Pubmed: 8198054
  • Heiskanen K, Siimes MA, Salmenpera L, Perheentupa J: Low vitamin B6 status associated with slow growth in healthy breast-fed infants. Pediatr Res. 1995 Nov;38(5):740-6. Pubmed: 8552443
  • Huang YC, Chang HH, Huang SC, Cheng CH, Lee BJ, Cheng SY, Su KH: Plasma pyridoxal 5'-phosphate is a significant indicator of immune responses in the mechanically ventilated critically ill. Nutrition. 2005 Jul-Aug;21(7-8):779-85. Pubmed: 15975484
  • Huang YC, Chang SJ, Chiu YT, Chang HH, Cheng CH: The status of plasma homocysteine and related B-vitamins in healthy young vegetarians and nonvegetarians. Eur J Nutr. 2003 Apr;42(2):84-90. Pubmed: 12638029
  • Huang YC, Lan PH, Cheng CH, Lee BJ, Kan MN: Vitamin B6 intakes and status of mechanically ventilated critically ill patients in Taiwan. Eur J Clin Nutr. 2002 May;56(5):387-92. Pubmed: 12001008
  • Iqbal SJ, Plaha DS, Linforth GH, Dalgleish R: Hypophosphatasia: diagnostic application of linked DNA markers in the dominantly inherited adult form. Clin Sci (Lond). 1999 Jul;97(1):73-8. Pubmed: 10369796
  • 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
  • Lacour B, Parry C, Drueke T, Touam M, Kreis H, Bailly M, Durand D: Pyridoxal 5'-phosphate deficiency in uremic undialyzed, hemodialyzed, and non-uremic kidney transplant patients. Clin Chim Acta. 1983 Jan 24;127(2):205-15. Pubmed: 6337752
  • Lee BJ, Huang MC, Chung LJ, Cheng CH, Lin KL, Su KH, Huang YC: Folic acid and vitamin B12 are more effective than vitamin B6 in lowering fasting plasma homocysteine concentration in patients with coronary artery disease. Eur J Clin Nutr. 2004 Mar;58(3):481-7. Pubmed: 14985687
  • Longhi RC, Fleisher LD, Tallan HH, Gaull GE: Cystathionine beta-synthase deficiency: a qualitative abnormality of the deficient enzyme modified by vitamin B6 therapy. Pediatr Res. 1977 Feb;11(2):100-3. Pubmed: 840498
  • Schuster K, Bailey LB, Cerda JJ, Gregory JF 3rd: Urinary 4-pyridoxic acid excretion in 24-hour versus random urine samples as a measurement of vitamin B6 status in humans. Am J Clin Nutr. 1984 Mar;39(3):466-70. Pubmed: 6695847
  • Seki T: Combination treatment of high-dose pyridoxal phosphate and low-dose ACTH in children with West syndrome and related disorders. Jpn J Psychiatry Neurol. 1990 Jun;44(2):219-37. Pubmed: 1701836
  • Selvaag E, Bohmer T, Benkestock K: Reduced serum concentrations of riboflavine and ascorbic acid, and blood thiamine pyrophosphate and pyridoxal-5-phosphate in geriatric patients with and without pressure sores. J Nutr Health Aging. 2002;6(1):75-7. Pubmed: 11813090
  • Stolzenberg-Solomon RZ, Albanes D, Nieto FJ, Hartman TJ, Tangrea JA, Rautalahti M, Sehlub J, Virtamo J, Taylor PR: Pancreatic cancer risk and nutrition-related methyl-group availability indicators in male smokers. J Natl Cancer Inst. 1999 Mar 17;91(6):535-41. Pubmed: 10088624
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID18405
HMDB IDHMDB01491
Pubchem Compound ID1051
Kegg IDC00018
ChemSpider ID1022
WikipediaPyridoxal 5'-phosphate
BioCyc IDPYRIDOXAL_PHOSPHATE
EcoCyc IDPYRIDOXAL_PHOSPHATE
Ligand ExpoPLP