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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 IDHMDB0001491
Secondary Accession Numbers
  • HMDB01491
Metabolite Identification
Common NamePyridoxal 5'-phosphate
DescriptionPyridoxal phosphate, also known as PLP, pyridoxal 5'-phosphate or P5P, is the active form of vitamin B6. It is a coenzyme in a variety of enzymatic reactions. Pyridoxal 5'-phosphate 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 5'-phosphate is a drug which is used for nutritional supplementation and for treating dietary shortage or imbalance. Pyridoxal 5'-phosphate exists in all living species, ranging from bacteria to humans. In humans, pyridoxal 5'-phosphate is involved in glycine and serine metabolism. Outside of the human body, pyridoxal 5'-phosphate is found, on average, in the highest concentration within cow milk. Pyridoxal 5'-phosphate has also been detected, but not quantified in several different foods, such as soursops, italian sweet red peppers, muscadine grapes, european plums, and blackcurrants. Pyridoxal 5'-phosphate, with regard to humans, has been found to be associated with several diseases such as epilepsy, early-onset, vitamin B6-dependent, odontohypophosphatasia, pyridoxamine 5-prime-phosphate oxidase deficiency, and hypophosphatasia. Pyridoxal 5'-phosphate has also been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1600449833
Synonyms
ValueSource
3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehydeChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphateChEBI
CodecarboxylaseChEBI
Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) esterChEBI
PLPChEBI
Pyridoxal 5'-(dihydrogen phosphate)ChEBI
Pyridoxal 5-monophosphoric acid esterChEBI
Pyridoxal 5-phosphateChEBI
Pyridoxal phosphateChEBI
PYRIDOXAL-5'-phosphATEChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acidGenerator
Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) esterGenerator
Pyridoxal 5'-(dihydrogen phosphoric acid)Generator
Pyridoxal 5-monophosphate esterGenerator
Pyridoxal 5-phosphoric acidGenerator
Pyridoxal phosphoric acidGenerator
PYRIDOXAL-5'-phosphoric acidGenerator
Pyridoxal 5'-phosphoric acidGenerator
Apolon b6HMDB
BiosechsHMDB
Coenzyme b6HMDB
HairoxalHMDB
Hexermin-pHMDB
Hi-pyridoxinHMDB
HiadelonHMDB
HimitanHMDB
PAL-pHMDB
PhosphopyridoxalHMDB
Phosphopyridoxal coenzymeHMDB
PidopidonHMDB
PiodelHMDB
PydoxalHMDB
Pyridoxal pHMDB
Pyridoxal-pHMDB
Pyridoxyl phosphateHMDB
PyromijinHMDB
SechvitanHMDB
Vitahexin-pHMDB
VitazechsHMDB
Phosphate, pyridoxalHMDB
Pyridoxal 5 phosphateHMDB
Chemical FormulaC8H10NO6P
Average Molecular Weight247.1419
Monoisotopic Molecular Weight247.024573569
IUPAC Name[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
Traditional Namepyridoxal phosphate
CAS Registry Number54-47-7
SMILES
CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O
InChI Identifier
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)
InChI KeyNGVDGCNFYWLIFO-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
  • Monoalkyl phosphate
  • Hydroxypyridine
  • Methylpyridine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Vinylogous acid
  • Heteroaromatic compound
  • Azacycle
  • Organopnictogen compound
  • Aldehyde
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility28 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker150.53830932474
[M-H]-MetCCS_train_neg146.33630932474
[M+H]+Baker154.76130932474
[M+H]+MetCCS_train_pos151.40430932474
[M-H]-Not Available148.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000339
[M+H]+Not Available152.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000339
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.7 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.75 m³·mol⁻¹ChemAxon
Polarizability20.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.84931661259
DarkChem[M-H]-149.5831661259
AllCCS[M+H]+152.94132859911
AllCCS[M-H]-147.7132859911
DeepCCS[M+H]+147.64330932474
DeepCCS[M-H]-145.28530932474
DeepCCS[M-2H]-179.61530932474
DeepCCS[M+Na]+154.76630932474
AllCCS[M+H]+152.932859911
AllCCS[M+H-H2O]+149.232859911
AllCCS[M+NH4]+156.432859911
AllCCS[M+Na]+157.432859911
AllCCS[M-H]-147.732859911
AllCCS[M+Na-2H]-148.132859911
AllCCS[M+HCOO]-148.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pyridoxal 5'-phosphateCC1=NC=C(COP(O)(O)=O)C(C=O)=C1O2937.5Standard polar33892256
Pyridoxal 5'-phosphateCC1=NC=C(COP(O)(O)=O)C(C=O)=C1O1916.5Standard non polar33892256
Pyridoxal 5'-phosphateCC1=NC=C(COP(O)(O)=O)C(C=O)=C1O2191.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyridoxal 5'-phosphate,1TMS,isomer #1CC1=NC=C(COP(=O)(O)O)C(C=O)=C1O[Si](C)(C)C2203.8Semi standard non polar33892256
Pyridoxal 5'-phosphate,1TMS,isomer #2CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O2183.0Semi standard non polar33892256
Pyridoxal 5'-phosphate,2TMS,isomer #1CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C2256.0Semi standard non polar33892256
Pyridoxal 5'-phosphate,2TMS,isomer #1CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C2134.1Standard non polar33892256
Pyridoxal 5'-phosphate,2TMS,isomer #1CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C2835.0Standard polar33892256
Pyridoxal 5'-phosphate,2TMS,isomer #2CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O2195.9Semi standard non polar33892256
Pyridoxal 5'-phosphate,2TMS,isomer #2CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O2144.7Standard non polar33892256
Pyridoxal 5'-phosphate,2TMS,isomer #2CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O2744.2Standard polar33892256
Pyridoxal 5'-phosphate,3TMS,isomer #1CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C2270.7Semi standard non polar33892256
Pyridoxal 5'-phosphate,3TMS,isomer #1CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C2215.1Standard non polar33892256
Pyridoxal 5'-phosphate,3TMS,isomer #1CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C2487.5Standard polar33892256
Pyridoxal 5'-phosphate,1TBDMS,isomer #1CC1=NC=C(COP(=O)(O)O)C(C=O)=C1O[Si](C)(C)C(C)(C)C2478.3Semi standard non polar33892256
Pyridoxal 5'-phosphate,1TBDMS,isomer #2CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O2420.3Semi standard non polar33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #1CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C2696.5Semi standard non polar33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #1CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C2562.4Standard non polar33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #1CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C3020.2Standard polar33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #2CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O2643.7Semi standard non polar33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #2CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O2552.0Standard non polar33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #2CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O2949.6Standard polar33892256
Pyridoxal 5'-phosphate,3TBDMS,isomer #1CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C2891.0Semi standard non polar33892256
Pyridoxal 5'-phosphate,3TBDMS,isomer #1CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C2755.5Standard non polar33892256
Pyridoxal 5'-phosphate,3TBDMS,isomer #1CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C2790.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (1 MEOX; 3 TMS)splash10-0gb9-2690000000-c9bacb7e657461e284072014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (Non-derivatized)splash10-0gb9-2690000000-c9bacb7e657461e284072017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal 5'-phosphate GC-EI-TOF (Non-derivatized)splash10-004j-0910000000-0408f3957221fc9882cd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyridoxal 5'-phosphate GC-EI-TOF (Non-derivatized)splash10-0gb9-1790000000-b01115fa8b4cfd3612c72017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9520000000-bfd574b2e5355694902a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9152000000-26c9f6311956633229862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyridoxal 5'-phosphate 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 5'-phosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcf2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0fxx-8900000000-ee972556340c616505282012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014l-9100000000-3cc29fb51820adecd59c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0002-0090000000-9b86e80a9dd0de14ab592012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-03dj-9800000000-9313aa9cbf19bc6311c52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0002-9500000000-7ce120a58879e2214ce52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004j-9200000000-7e6bd8c298613e59fb5d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-9000000000-4c05178b1645bf01f3fa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0udi-3920000000-6c5e6106f5658d1d6c502012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0udi-3920000000-f96097815e69223561312012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-002b-9000000000-2c4e243699a95e3a0f882012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-002b-9000000000-8aa111485891af9f0d022012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOFsplash10-0002-0090000000-9b86e80a9dd0de14ab592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOFsplash10-03dj-9800000000-9313aa9cbf19bc6311c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOFsplash10-0002-9500000000-7ce120a58879e2214ce52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOFsplash10-004j-9200000000-7e6bd8c298613e59fb5d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-4c05178b1645bf01f3fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF , negative-QTOFsplash10-002b-9000000000-2c4e243699a95e3a0f882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF , negative-QTOFsplash10-002b-9000000000-8aa111485891af9f0d022017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 10V, Positive-QTOFsplash10-0f6t-1790000000-1dcb07cd1110c71f70052015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 20V, Positive-QTOFsplash10-0udi-0900000000-ca6aab7f31a36863a4172015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 40V, Positive-QTOFsplash10-0udi-9800000000-053802b9c0533d7943ea2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 10V, Negative-QTOFsplash10-0002-9080000000-12ca63d34d39d59f6b422015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 20V, Negative-QTOFsplash10-004i-9000000000-144099ec201adbbc46842015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 40V, Negative-QTOFsplash10-004i-9000000000-70a9559d65e78c488e7e2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H 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
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Erythrocyte
  • Kidney
  • Liver
  • Neuron
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0146-0.0728 uMChildren (1-13 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.046 (0.035-0.06) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.042 (0.0076-1.26) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0572 +/- 0.0193 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.0581 +/- 0.0176 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.205 +/- 0.193 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.030 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.061 +/- 0.052 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.056 +/- 0.042 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.068 +/- 0.015 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.075 +/- 0.022 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0451 (0.00400-0.207) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0047 +/- 0.00072 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0110-0.0340 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0515 +/- 0.0166 uMNewborn (0-30 days old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0431 +/- 0.0193 uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0305 +/- 0.0111 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0207 +/- 0.0069 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0654 +/- 0.0173 uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0531 +/- 0.0186 uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0312 +/- 0.0049 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.032-0.078 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.044-0.089 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000972 +/- 0.000283 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.59 uMChildren (1-13 years old)FemaleOdontohypophosphatasia details
BloodDetected and Quantified0.024 (0.019-0.031) uMAdult (>18 years old)BothRheumatoid arthritis details
BloodDetected and Quantified0.251 (0.0310-1.182) uMAdult (>18 years old)Both
Hypophosphatasia, infantile
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.064 uMChildren (1-13 years old)Not SpecifiedTruncus arteriosus, seizures and dystonia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00243 +/- 0.00138 uMAdult (>18 years old)Not Specifiedceliac disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0119 (0.0036-0.018) uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0036 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.012 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.014 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.018 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00500-0.00600 uMChildren (1-13 years old)FemaleEpilepsy, early-onset, vitamin B6-dependent details
Associated Disorders and Diseases
Disease References
Rheumatoid arthritis
  1. Chiang EP, Smith DE, Selhub J, Dallal G, Wang YC, Roubenoff R: Inflammation causes tissue-specific depletion of vitamin B6. Arthritis Res Ther. 2005;7(6):R1254-62. Epub 2005 Sep 13. [PubMed:16277678 ]
Hypophosphatasia
  1. Chodirker BN, Coburn SP, Seargeant LE, Whyte MP, Greenberg CR: Increased plasma pyridoxal-5'-phosphate levels before and after pyridoxine loading in carriers of perinatal/infantile hypophosphatasia. J Inherit Metab Dis. 1990;13(6):891-6. [PubMed:2079838 ]
Odontohypophosphatasia
  1. Haliloglu B, Guran T, Atay Z, Abali S, Mornet E, Bereket A, Turan S: Infantile loss of teeth: odontohypophosphatasia or childhood hypophosphatasia. Eur J Pediatr. 2013 Jun;172(6):851-3. doi: 10.1007/s00431-012-1868-4. Epub 2012 Oct 24. [PubMed:23093139 ]
Celiac disease
  1. Hallert C, Allenmark S, Larsson-Cohn U, Sedvall G: High level of pyridoxal 5'-phosphate in the cerebrospinal fluid of adult celiac patients. Am J Clin Nutr. 1982 Nov;36(5):851-4. [PubMed:6182788 ]
Pyridoxamine 5-prime-phosphate oxidase deficiency
  1. Ormazabal A, Oppenheim M, Serrano M, Garcia-Cazorla A, Campistol J, Ribes A, Ruiz A, Moreno J, Hyland K, Clayton P, Heales S, Artuch R: Pyridoxal 5'-phosphate values in cerebrospinal fluid: reference values and diagnosis of PNPO deficiency in paediatric patients. Mol Genet Metab. 2008 Jun;94(2):173-7. doi: 10.1016/j.ymgme.2008.01.004. Epub 2008 Feb 21. [PubMed:18294893 ]
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 ]
Associated OMIM IDs
  • 180300 (Rheumatoid arthritis)
  • 241500 (Hypophosphatasia)
  • 146300 (Odontohypophosphatasia)
  • 212750 (Celiac disease)
  • 610090 (Pyridoxamine 5-prime-phosphate oxidase deficiency)
  • 617290 (Epilepsy, early-onset, vitamin B6-dependent)
DrugBank IDDB00114
Phenol Explorer Compound IDNot Available
FooDB IDFDB021820
KNApSAcK IDC00007503
Chemspider ID1022
KEGG Compound IDC00018
BioCyc IDPYRIDOXAL_PHOSPHATE
BiGG ID33526
Wikipedia LinkPyridoxal_phosphate
METLIN ID6275
PubChem Compound1051
PDB IDNot Available
ChEBI ID18405
Food Biomarker OntologyNot Available
VMH IDPYDX5P
MarkerDB IDMDB00000331
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. Akopov MA, Kagan ZS, Berezov TT, Filiptsev PIa: [Kinetics and thermodynamics of heat inactivation of L-threonine-L-serine dehydratase from human liver]. Biokhimiia. 1978 Nov;43(11):2027-32. [PubMed:737218 ]
  19. 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 ]
  20. 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 ]

Only showing the first 10 proteins. There are 87 proteins in total.

Enzymes

General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS2
Uniprot ID:
P22557
Molecular weight:
64632.86
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
General function:
Involved in glycine C-acetyltransferase activity
Specific function:
Not Available
Gene Name:
GCAT
Uniprot ID:
O75600
Molecular weight:
47973.79
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 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:
TAT
Uniprot ID:
P17735
Molecular weight:
50398.895
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:
BCAT1
Uniprot ID:
P54687
Molecular weight:
38644.77

Only showing the first 10 proteins. There are 87 proteins in total.