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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:30 UTC
HMDB IDHMDB0001545
Secondary Accession Numbers
  • HMDB01545
Metabolite Identification
Common NamePyridoxal
DescriptionPyridoxal is a pyridinecarbaldehyde that is pyridine-4-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 5 respectively. Pyridoxal, also known as pyridoxaldehyde, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives 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. Pyridoxal is one form of vitamin B6. Pyridoxal exists in all living species, ranging from bacteria to humans. In humans, pyridoxal is involved in glycine and serine metabolism. Pyridoxal has been detected, but not quantified in several different foods, such as sourdoughs, lichee, arctic blackberries, watercress, and cottonseeds. Some medically relevant bacteria, such as those in the genera Granulicatella and Abiotrophia, require pyridoxal for growth. This nutritional requirement can lead to the culture phenomenon of satellite growth. In in vitro culture, these pyridoxal-dependent bacteria may only grow in areas surrounding colonies of bacteria from other genera ("satellitism") that are capable of producing pyridoxal. Pridoxal has a role as a cofactor, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.
Structure
Data?1582752209
Synonyms
ValueSource
3-HYDROXY-5-(hydroxymethyl)-2-methylisonicotinaldehydeChEBI
PyridoxaldehydeChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehydeHMDB
Chemical FormulaC8H9NO3
Average Molecular Weight167.162
Monoisotopic Molecular Weight167.058243159
IUPAC Name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
Traditional Namepyridoxal
CAS Registry Number66-72-8
SMILES
CC1=NC=C(CO)C(C=O)=C1O
InChI Identifier
InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
InChI KeyRADKZDMFGJYCBB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridine carboxaldehydes
Direct ParentPyridoxals and derivatives
Alternative Parents
Substituents
  • Pyridoxal
  • Aryl-aldehyde
  • Hydroxypyridine
  • Methylpyridine
  • Vinylogous acid
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Aldehyde
  • Alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M-H]-Not Available130.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000472
AllCCS[M+H]+Not Available132.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000472
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.7 g/LALOGPS
logP10(0.02) g/LALOGPS
logP10(0.18) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Acidic)7.97ChemAxon
pKa (Strongest Basic)4.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.42 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.87 m³·mol⁻¹ChemAxon
Polarizability16.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.67531661259
DarkChem[M-H]-132.18931661259
AllCCS[M+H]+135.63332859911
AllCCS[M-H]-133.13532859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyridoxal,1TMS,#1CC1=NC=C(CO[Si](C)(C)C)C(C=O)=C1O1712.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pyridoxal,1TMS,#2CC1=NC=C(CO)C(C=O)=C1O[Si](C)(C)C1697.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pyridoxal,2TMS,#1CC1=NC=C(CO[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C1828.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pyridoxal,1TBDMS,#1CC1=NC=C(CO[Si](C)(C)C(C)(C)C)C(C=O)=C1O1949.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pyridoxal,1TBDMS,#2CC1=NC=C(CO)C(C=O)=C1O[Si](C)(C)C(C)(C)C1980.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pyridoxal,2TBDMS,#1CC1=NC=C(CO[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C2300.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pyridoxal GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2690000000-5d018202be238b10582a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0aou-3974000000-8c963fdc714896ad343a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0590000000-ed8a55680a0c9fa9cbaf2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal GC-MS (1 MEOX; 2 TMS)splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal GC-MS (1 MEOX; 2 TMS)splash10-0aor-5895000000-e55e01ca30d17d2a8a722014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal GC-MS (Non-derivatized)splash10-0a4i-5695000000-bd3bb22a5dd4a600cb6c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal GC-MS (Non-derivatized)splash10-0aor-5895000000-e55e01ca30d17d2a8a722017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyridoxal GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1900000000-56d1f96c5ac868ce42a62016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyridoxal GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-6190000000-78d7f54ce0c5338f815f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyridoxal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-c49b207cafcf1c21302d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-0900000000-cad83f5f123a879fa0bb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0a4i-0900000000-4f12feae0e11a6d9016b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a4i-2900000000-56fcdbb9b4363c84d2d02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-056r-9400000000-9700c9585f6c540bf0072012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-05n0-0900000000-f468a00d88bedc1164852012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-c49b207cafcf1c21302d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-bf0686eb8e3c28c30e852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ , negative-QTOFsplash10-0a4i-0900000000-686848e0f222273e50892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ , negative-QTOFsplash10-0a4i-2900000000-99577e7f4a39e47c5c422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ , negative-QTOFsplash10-056r-9400000000-9700c9585f6c540bf0072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QTOF , negative-QTOFsplash10-05n0-0900000000-f468a00d88bedc1164852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 10V, Negative-QTOFsplash10-000i-0900000000-bd97f5bc4d391b1814542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 20V, Negative-QTOFsplash10-0a4r-1900000000-f03c6e67ec131201e09e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 40V, Negative-QTOFsplash10-05r0-9300000000-98ede09bbd66557527152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0002-0900000000-4ce3f52baa36006ef4b22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kg-9500000000-658a96f6cda4a96de0452012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0gbc-9000000000-233fc8ab067b0dcd1f142012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0gb9-0900000000-e646a99b0c1521d1c8dd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0udi-0900000000-8fce1a7d8ceb3fced3ed2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0udl-6900000000-e2fc0eaa17e57d0a25562012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-00kf-9200000000-0bda29931f8b6f2fcc772012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014l-9000000000-469c127d1aef4f8a51d72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0udi-2900000000-63ebef5a0818d6a1ccb82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal LC-ESI-QQ , positive-QTOFsplash10-0gb9-0900000000-e646a99b0c1521d1c8dd2017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.251 +/- 0.051 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0160-0.0560 uMChildren (1-13 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.036 +/- 0.031 uMAdult (>18 years old)BothSickle cell disease-SS (SCD-SS) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.015 uMChildren (1-13 years old)FemaleEpilepsy, early-onset, vitamin B6-dependent details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Sickle cell anemia
  1. Nelson MC, Zemel BS, Kawchak DA, Barden EM, Frongillo EA Jr, Coburn SP, Ohene-Frempong K, Stallings VA: Vitamin B6 status of children with sickle cell disease. J Pediatr Hematol Oncol. 2002 Aug-Sep;24(6):463-9. [PubMed:12218594 ]
Epilepsy, early-onset, vitamin B6-dependent
  1. Darin N, Reid E, Prunetti L, Samuelsson L, Husain RA, Wilson M, El Yacoubi B, Footitt E, Chong WK, Wilson LC, Prunty H, Pope S, Heales S, Lascelles K, Champion M, Wassmer E, Veggiotti P, de Crecy-Lagard V, Mills PB, Clayton PT: Mutations in PROSC Disrupt Cellular Pyridoxal Phosphate Homeostasis and Cause Vitamin-B6-Dependent Epilepsy. Am J Hum Genet. 2016 Dec 1;99(6):1325-1337. doi: 10.1016/j.ajhg.2016.10.011. [PubMed:27912044 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
  • 603903 (Sickle cell anemia)
  • 617290 (Epilepsy, early-onset, vitamin B6-dependent)
  • 114500 (Colorectal cancer)
DrugBank IDDB00147
Phenol Explorer Compound IDNot Available
FooDB IDFDB011169
KNApSAcK IDC00007509
Chemspider ID1021
KEGG Compound IDC00250
BioCyc IDPYRIDOXAL
BiGG ID34393
Wikipedia LinkPyridoxal
METLIN ID6312
PubChem Compound1050
PDB IDNot Available
ChEBI ID17310
Food Biomarker OntologyNot Available
VMH IDPYDX
MarkerDB IDMDB00000335
Good Scents IDNot Available
References
Synthesis ReferenceFujimoto, Yasuo. Pyridoxal. Jpn. Tokkyo Koho (1971), 2 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rajamohan F, Nelms L, Joslin DL, Lu B, Reagan WJ, Lawton M: cDNA cloning, expression, purification, distribution, and characterization of biologically active canine alanine aminotransferase-1. Protein Expr Purif. 2006 Jul;48(1):81-9. Epub 2006 Jan 30. [PubMed:16495081 ]
  2. 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 ]
  3. 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 ]
  4. el-Habet AE, el-Sewedy SM, el-Sharaky A, Gaafar NK, Abdel-Rafee A, Hamoud F: Biochemical studies on bilharzial and nonbilharzial hyperoxaluria: effect of pyridoxine and allopurinol treatment. Biochem Med Metab Biol. 1987 Aug;38(1):1-8. [PubMed:3663392 ]
  5. Mehansho H, Henderson LM: Transport and accumulation of pyridoxine and pyridoxal by erythrocytes. J Biol Chem. 1980 Dec 25;255(24):11901-7. [PubMed:7440576 ]
  6. Kark JA, Bongiovanni R, Hicks CU, Tarassoff PG, Hannah JS, Yoshida GY: Modification of intracellular hemoglobin with pyridoxal and pyridoxal 5'-phosphate. Blood Cells. 1982;8(2):299-314. [PubMed:7159754 ]
  7. Bosse TR, Donald EA: The vitamin B6 requirement in oral contraceptive users. I. Assessment by pyridoxal level and transferase activity in erythrocytes. Am J Clin Nutr. 1979 May;32(5):1015-23. [PubMed:433818 ]
  8. Linares P, Luque de Castro MD, Valcarcel M: Simultaneous determination of pyridoxal and pyridoxal 5-phosphate in human serum by flow injection analysis. Anal Chem. 1985 Sep;57(11):2101-6. [PubMed:4051187 ]
  9. Schenker S, Johnson RF, Mahuren JD, Henderson GI, Coburn SP: Human placental vitamin B6 (pyridoxal) transport: normal characteristics and effects of ethanol. Am J Physiol. 1992 Jun;262(6 Pt 2):R966-74. [PubMed:1621875 ]
  10. Brenner A, Wapnir RA: A pyridoxine-dependent behavioral disorder unmasked by isoniazid. Am J Dis Child. 1978 Aug;132(8):773-6. [PubMed:150790 ]
  11. Kark JA, Tarassoff PG, Bongiovanni R: Pyridoxal phosphate as an antisickling agent in vitro. J Clin Invest. 1983 May;71(5):1224-9. [PubMed:6853710 ]
  12. Yiakouvaki A, Savovic J, Al-Qenaei A, Dowden J, Pourzand C: Caged-iron chelators a novel approach towards protecting skin cells against UVA-induced necrotic cell death. J Invest Dermatol. 2006 Oct;126(10):2287-95. Epub 2006 May 18. [PubMed:16710308 ]
  13. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Pyridoxal + Oxygen + Water → 4-Pyridoxic acid + Hydrogen peroxidedetails
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
Pyridoxamine + Water + Oxygen → Pyridoxal + Ammonia + Hydrogen peroxidedetails
Pyridoxine + Oxygen → Pyridoxal + Hydrogen peroxidedetails
General function:
Involved in lyase activity
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The P protein binds the alpha-amino group of glycine through its pyridoxal phosphate cofactor; CO(2) is released and the remaining methylamine moiety is then transferred to the lipoamide cofactor of the H protein.
Gene Name:
GLDC
Uniprot ID:
P23378
Molecular weight:
112728.805
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 + Pyridoxal → ADP + Pyridoxal 5'-phosphatedetails
References
  1. Tang L, Li MH, Cao P, Wang F, Chang WR, Bach S, Reinhardt J, Ferandin Y, Galons H, Wan Y, Gray N, Meijer L, Jiang T, Liang DC: Crystal structure of pyridoxal kinase in complex with roscovitine and derivatives. J Biol Chem. 2005 Sep 2;280(35):31220-9. Epub 2005 Jun 28. [PubMed:15985434 ]
  2. Adams JB, George F, Audhya T: Abnormally high plasma levels of vitamin B6 in children with autism not taking supplements compared to controls not taking supplements. J Altern Complement Med. 2006 Jan-Feb;12(1):59-63. [PubMed:16494569 ]
  3. Newman JA, Das SK, Sedelnikova SE, Rice DW: The crystal structure of an ADP complex of Bacillus subtilis pyridoxal kinase provides evidence for the parallel emergence of enzyme activity during evolution. J Mol Biol. 2006 Oct 20;363(2):520-30. Epub 2006 Aug 12. [PubMed:16978644 ]
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
Pyridoxal 5'-phosphate + Water → Pyridoxal + Phosphatedetails
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
Pyridoxal 5'-phosphate + Water → Pyridoxal + Phosphatedetails