Showing Compound Card for Pyridoxal 5'-phosphate (CDB005196)

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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
MOLSDFPDBSMILESInChI
Synonyms
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
Predicted GC-MSPyridoxal 5'-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
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.

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Enzymes

Enzyme Details
1. 5-aminolevulinate synthase, erythroid-specific, mitochondrial
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS2
Uniprot ID:
P22557
Molecular weight:
64632.86
Enzyme Details
2. 5-aminolevulinate synthase, nonspecific, mitochondrial
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
Enzyme Details
3. 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial
General function:
Involved in glycine C-acetyltransferase activity
Specific function:
Not Available
Gene Name:
GCAT
Uniprot ID:
O75600
Molecular weight:
47973.79
Enzyme Details
4. Methylenetetrahydrofolate reductase
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
Enzyme Details
5. 4-aminobutyrate aminotransferase, mitochondrial
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
Enzyme Details
6. Tyrosine aminotransferase
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
Enzyme Details
7. Aromatic-L-amino-acid decarboxylase
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
Enzyme Details
8. Aspartate aminotransferase, cytoplasmic
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
Enzyme Details
9. Aspartate aminotransferase, mitochondrial
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
Enzyme Details
10. Branched-chain-amino-acid aminotransferase, cytosolic
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.

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