Record Information
Version1.0
Created at2020-04-17 19:18:58 UTC
Updated at2020-11-18 16:39:30 UTC
CannabisDB IDCDB005196
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Pyridoxal 5'-phosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight247.14
Monoisotopic Molecular Weight247.0246
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility28 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5-aminolevulinate synthase, erythroid-specific, mitochondrialALAS2Xp11.21P22557 details
5-aminolevulinate synthase, nonspecific, mitochondrialALAS13p21.1P13196 details
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrialGCAT22q13.1O75600 details
Methylenetetrahydrofolate reductaseMTHFR1p36.3P42898 details
4-aminobutyrate aminotransferase, mitochondrialABAT16p13.2P80404 details
Tyrosine aminotransferaseTAT16q22.1P17735 details
Aromatic-L-amino-acid decarboxylaseDDC7p12.2P20711 details
Aspartate aminotransferase, cytoplasmicGOT110q24.1-q25.1P17174 details
Aspartate aminotransferase, mitochondrialGOT216q21P00505 details
Branched-chain-amino-acid aminotransferase, cytosolicBCAT112p12.1P54687 details
KynureninaseKYNU2q22.2Q16719 details
Glucose-6-phosphate 1-dehydrogenaseG6PDXq28P11413 details
Glycogen phosphorylase, liver formPYGL14q21-q22P06737 details
Glycogen phosphorylase, muscle formPYGM11q12-q13.2P11217 details
Glycogen phosphorylase, brain formPYGB20p11.21P11216 details
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADAT4q33Q8N5Z0 details
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT25p13Q9BYV1 details
Ornithine aminotransferase, mitochondrialOAT10q26P04181 details
Kynurenine--oxoglutarate transaminase 1CCBL19q34.11Q16773 details
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT219q13O15382 details
Cystathionine gamma-lyaseCTH1p31.1P32929 details
L-serine dehydratase/L-threonine deaminaseSDS12q24.13P20132 details
Pyridoxine-5'-phosphate oxidasePNPO17q21.32Q9NVS9 details
Formimidoyltransferase-cyclodeaminaseFTCD21q22.3O95954 details
Glutamate decarboxylase 2GAD210p11.23Q05329 details
Glutamate decarboxylase 1GAD12q31Q99259 details
Cystathionine beta-synthaseCBS21q22.3P35520 details
Serine--pyruvate aminotransferaseAGXT2q37.3P21549 details
Serine hydroxymethyltransferase, mitochondrialSHMT212q12-q14P34897 details
Serine hydroxymethyltransferase, cytosolicSHMT117p11.2P34896 details
Glycine dehydrogenase [decarboxylating], mitochondrialGLDC9p22P23378 details
Alanine aminotransferase 1GPT8q24.3P24298 details
Phosphoserine aminotransferasePSAT19q21.2Q9Y617 details
Histidine decarboxylaseHDC15q21-q22P19113 details
Serine palmitoyltransferase 1SPTLC19q22.2O15269 details
Serine palmitoyltransferase 2SPTLC214q24.3O15270 details
Cysteine sulfinic acid decarboxylaseCSAD12q13.11-q14.3Q9Y600 details
Ornithine decarboxylaseODC12p25P11926 details
Sphingosine-1-phosphate lyase 1SGPL110q21O95470 details
Pyridoxal kinasePDXK21q22.3O00764 details
Arginine decarboxylaseADC1p35.1Q96A70 details
Phosphatidylserine decarboxylase proenzymePISD22q12.2Q9UG56 details
Cysteine desulfurase, mitochondrialNFS120q11.22Q9Y697 details
Proline synthase co-transcribed bacterial homolog proteinPROSC8p11.2O94903 details
Aminoadipate aminotransferase, isoform CRA_bAADAT4q33Q4W5N8 details
Threonine synthase-like 1THNSL110p12.1Q8IYQ7 details
Ethanolamine-phosphate phospho-lyaseAGXT2L14q25Q8TBG4 details
Alanine aminotransferase 2GPT216q12.1Q8TD30 details
Pyridoxal phosphate phosphatasePDXP22q12.3Q96GD0 details
Selenocysteine lyaseSCLY2q37.3Q96I15 details
Pyridoxal phosphate phosphatase PHOSPHO2PHOSPHO22q31.1Q8TCD6 details
Putative aspartate aminotransferase, cytoplasmic 2GOT1L18p11.23Q8NHS2 details
5-phosphohydroxy-L-lysine phospho-lyaseAGXT2L25q35.3Q8IUZ5 details
Glutamate decarboxylase-like protein 1GADL13p24.1-p23Q6ZQY3 details
Kynurenine--oxoglutarate transaminase 3CCBL21p22.2Q6YP21 details
Molybdenum cofactor sulfuraseMOCOS18q12Q96EN8 details
Pyridoxal-dependent decarboxylase domain-containing protein 1PDXDC116p13.11Q6P996 details
Pyridoxal-dependent decarboxylase domain-containing protein 2PDXDC216q22.1Q6P474 details
Serine dehydratase-likeSDSL12q24.13Q96GA7 details
O-phosphoseryl-tRNA(Sec) selenium transferaseSEPSECS4p15.2Q9HD40 details
Serine palmitoyltransferase 3SPTLC320p12.1Q9NUV7 details
Serine racemaseSRR17p13Q9GZT4 details
Threonine synthase-like 2THNSL22p11.2Q86YJ6 details
Serine hydroxymethyltransferaseSHMT117p11.2A8MYA6 details
Aspartate aminotransferaseGIG18Q2TU84 details
GAD1 proteinGAD12q31Q49AK1 details
Dopa decarboxylase (Aromatic L-amino acid decarboxylase)DDC7p12.2Q53Y41 details
PhosphorylaseQ59GM9 details
Aminolevulinate, delta-, synthase 1, isoform CRA_aALAS13p21.1Q5JAM2 details
Aminolevulinate, delta-, synthase 2ALAS2Q5JZF5 details
Glutamate decarboxylase 2 (Pancreatic islets and brain, 65kDa)GAD210p11.23Q5VZ29 details
Putative L-Dopa decarboxylaseDDC7p12.2Q5W5T9 details
DDC proteinDDC7p12.2Q6IBS8 details
CSAD proteinCSAD12q13.11-q14.3Q86V02 details
PDXDC1 proteinPDXDC116p13.11Q86XE2 details
Glutamate decarboxylase 1 (Brain, 67kDa)GAD12q31Q8IVA8 details
P-selectin cytoplasmic tail-associated protein (PCAP)pcap1q42.2-q43Q96JQ3 details
Glutamic acid decarboxylaseGAD65Q9UGI5 details
Cysteine sulfinic acid decarboxylase, isoform CRA_cCSAD12q13.11-q14.3Q9Y602 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cystathionine beta-synthaseCBS21q22.3P35520 details
Pyridoxal phosphate phosphatasePDXP22q12.3Q96GD0 details
Pyridoxal phosphate phosphatase PHOSPHO2PHOSPHO22q31.1Q8TCD6 details
Molybdenum cofactor sulfuraseMOCOS18q12Q96EN8 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Sphingosine-1-phosphate lyase 1SGPL110q21O95470 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Cystathionine gamma-lyaseCTH1p31.1P32929 details
Concentrations Data
Not Available
HMDB IDHMDB0001491
DrugBank IDDB00114
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 85 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 85 proteins in total.