Record Information
Version1.0
Creation date2011-04-11 17:01:47 UTC
Update date2019-11-26 03:20:54 UTC
Primary IDFDB021820
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyridoxal 5'-phosphate
DescriptionThis is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia [HMDB]. Pyridoxal 5'-phosphate is found in many foods, some of which are linden, kai-lan, nance, and rose hip.
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0gb9-2690000000-c9bacb7e657461e28407JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-2690000000-c9bacb7e657461e28407JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0910000000-0408f3957221fc9882cdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-1790000000-b01115fa8b4cfd3612c7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9520000000-bfd574b2e5355694902aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9152000000-26c9f631195663322986JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fxx-8900000000-ee972556340c61650528JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9100000000-3cc29fb51820adecd59cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0090000000-9b86e80a9dd0de14ab59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03dj-9800000000-9313aa9cbf19bc6311c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9500000000-7ce120a58879e2214ce5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9200000000-7e6bd8c298613e59fb5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-4c05178b1645bf01f3faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-3920000000-6c5e6106f5658d1d6c50JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-3920000000-f96097815e6922356131JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9000000000-2c4e243699a95e3a0f88JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9000000000-8aa111485891af9f0d02JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0090000000-9b86e80a9dd0de14ab59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03dj-9800000000-9313aa9cbf19bc6311c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9500000000-7ce120a58879e2214ce5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9200000000-7e6bd8c298613e59fb5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-4c05178b1645bf01f3faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-2c4e243699a95e3a0f88JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-8aa111485891af9f0d02JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1790000000-1dcb07cd1110c71f7005JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ca6aab7f31a36863a417JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-053802b9c0533d7943eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9080000000-12ca63d34d39d59f6b42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-144099ec201adbbc4684JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-70a9559d65e78c488e7eJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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