Survey with prize
Record Information
Version1.0
Creation date2011-04-11 17:01:47 UTC
Update date2020-09-17 15:41:03 UTC
Primary IDFDB021820
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyridoxal 5'-phosphate
DescriptionPyridoxal 5'-phosphate, also known as PLP or codecarboxylase, 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 is a strong basic compound (based on its pKa). 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 milk (cow). 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. This could make pyridoxal 5'-phosphate a potential biomarker for the consumption of these foods. The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal. Pyridoxal 5'-phosphate is a potentially toxic compound. 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.
CAS Number54-47-7
Structure
Thumb
Synonyms
SynonymSource
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
3-Hydroxy-2-methyl-5-[(onooxy)methyl]-4-pyridinecarboxaldehydeChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-ateChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-ic acidGenerator
Hexermin-PHMDB
OpyridoxalHMDB
Opyridoxal coenzymeHMDB
Orate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) esterGenerator
oric acid Mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) esterChEBI
PAL-PHMDB
Pyridoxal 5-monoate esterGenerator
Pyridoxal 5-monoic acid esterGenerator
Pyridoxal 5-monooric acid esterChEBI
Pyridoxal 5-ateChEBI
Pyridoxal 5-ic acidGenerator
Pyridoxal 5'-(dihydrogen ate)ChEBI
Pyridoxal 5'-(dihydrogen ic acid)Generator
Pyridoxal 5'-ateChEBI
Pyridoxal 5'-ic acidGenerator
Pyridoxal ateChEBI
Pyridoxal ic acidGenerator
Pyridoxal PHMDB
PYRIDOXAL-5'-ATEChEBI
PYRIDOXAL-5'-ic acidGenerator
Pyridoxal-PHMDB
Pyridoxyl ateHMDB
Vitahexin-PHMDB
Predicted 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
Chemical FormulaC8H10NO6P
IUPAC name[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
InChI IdentifierInChI=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
Isomeric SMILESCC1=NC=C(COP(O)(O)=O)C(C=O)=C1O
Average Molecular Weight247.1419
Monoisotopic Molecular Weight247.024573569
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPyridoxal 5'-phosphate, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-0gb9-2690000000-c9bacb7e657461e28407Spectrum
GC-MSPyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrumsplash10-0gb9-2690000000-c9bacb7e657461e28407Spectrum
GC-MSPyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrumsplash10-004j-0910000000-0408f3957221fc9882cdSpectrum
GC-MSPyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrumsplash10-0gb9-1790000000-b01115fa8b4cfd3612c7Spectrum
Predicted GC-MSPyridoxal 5'-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9520000000-bfd574b2e5355694902aSpectrum
Predicted GC-MSPyridoxal 5'-phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006t-9152000000-26c9f631195663322986Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcfSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fxx-8900000000-ee972556340c61650528Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9100000000-3cc29fb51820adecd59cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0090000000-9b86e80a9dd0de14ab59Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03dj-9800000000-9313aa9cbf19bc6311c5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9500000000-7ce120a58879e2214ce5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9200000000-7e6bd8c298613e59fb5dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-4c05178b1645bf01f3faSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-3920000000-6c5e6106f5658d1d6c50Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-3920000000-f96097815e6922356131Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9000000000-2c4e243699a95e3a0f88Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9000000000-8aa111485891af9f0d02Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0090000000-9b86e80a9dd0de14ab59Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03dj-9800000000-9313aa9cbf19bc6311c5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9500000000-7ce120a58879e2214ce5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9200000000-7e6bd8c298613e59fb5dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-4c05178b1645bf01f3faSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-2c4e243699a95e3a0f88Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-8aa111485891af9f0d02Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1790000000-1dcb07cd1110c71f7005Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ca6aab7f31a36863a417Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-053802b9c0533d7943eaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9080000000-12ca63d34d39d59f6b42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-144099ec201adbbc4684Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-70a9559d65e78c488e7eSpectrum
NMR
TypeDescriptionView
1D NMR1H 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 ID1022
ChEMBL IDCHEMBL82202
KEGG Compound IDC00018
Pubchem Compound ID1051
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00114
HMDB IDHMDB01491
CRC / DFC (Dictionary of Food Compounds) IDHDV11-W:HDV11-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33526
KNApSAcK IDNot Available
HET IDPLP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Tyrosine aminotransferaseTATP17735
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Branched-chain-amino-acid aminotransferase, cytosolicBCAT1P54687
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT2O15382
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrialGCATO75600
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT2Q9BYV1
Serine hydroxymethyltransferase, mitochondrialSHMT2P34897
Serine hydroxymethyltransferase, cytosolicSHMT1P34896
Glycine dehydrogenase [decarboxylating], mitochondrialGLDCP23378
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Serine hydroxymethyltransferaseDKFZp686P09201Q5HYG8
Ornithine aminotransferase, mitochondrialOATP04181
Histidine decarboxylaseHDCP19113
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Alanine aminotransferase 1GPTP24298
Alanine aminotransferase 2GPT2Q8TD30
Selenocysteine lyaseSCLYQ96I15
5-phosphohydroxy-L-lysine phospho-lyaseAGXT2L2Q8IUZ5
Molybdenum cofactor sulfuraseMOCOSQ96EN8
Serine palmitoyltransferase 1SPTLC1O15269
Proline synthase co-transcribed bacterial homolog proteinPROSCO94903
Phosphoserine aminotransferasePSAT1Q9Y617
Glucose-6-phosphate 1-dehydrogenaseG6PDP11413
Glycogen phosphorylase, liver formPYGLP06737
Glycogen phosphorylase, muscle formPYGMP11217
Glycogen phosphorylase, brain formPYGBP11216
Putative aspartate aminotransferase, cytoplasmic 2GOT1L1Q8NHS2
Ornithine decarboxylaseODC1P11926
Cystathionine gamma-lyaseCTHP32929
Glutamate decarboxylase 2GAD2Q05329
Glutamate decarboxylase 1GAD1Q99259
Arginine decarboxylaseADCQ96A70
O-phosphoseryl-tRNA(Sec) selenium transferaseSEPSECSQ9HD40
Sphingosine-1-phosphate lyase 1SGPL1O95470
Cysteine sulfinic acid decarboxylaseCSADQ9Y600
L-serine dehydratase/L-threonine deaminaseSDSP20132
Serine dehydratase-likeSDSLQ96GA7
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADATQ8N5Z0
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Formimidoyltransferase-cyclodeaminaseFTCDO95954
Ethanolamine-phosphate phospho-lyaseAGXT2L1Q8TBG4
Serine racemaseSRRQ9GZT4
Phosphatidylserine decarboxylase proenzymePISDQ9UG56
Threonine synthase-like 1THNSL1Q8IYQ7
Aspartate aminotransferaseGIG18Q2TU84
Serine palmitoyltransferase 2SPTLC2O15270
Serine palmitoyltransferase 3SPTLC3Q9NUV7
Glutamate decarboxylase-like protein 1GADL1Q6ZQY3
Pyridoxal-dependent decarboxylase domain-containing protein 1PDXDC1Q6P996
Pyridoxal-dependent decarboxylase domain-containing protein 2PDXDC2Q6P474
Threonine synthase-like 2THNSL2Q86YJ6
Aminolevulinate, delta-, synthase 1, isoform CRA_aALAS1Q5JAM2
Aminolevulinate, delta-, synthase 2ALAS2Q5JZF5
P-selectin cytoplasmic tail-associated protein (PCAP)pcapQ96JQ3
Glutamic acid decarboxylaseGAD65Q9UGI5
Pathways
NameSMPDB LinkKEGG Link
Glucose-Alanine CycleSMP00127 Not Available
Malate-Aspartate ShuttleSMP00129 Not Available
Vitamin B6 MetabolismSMP00017 map00750
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference