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Pyridoxal 5'-phosphate (PC000285)

Record Information
Version1.0
Creation date2015-10-09 22:29:39 UTC
Update date2017-01-19 02:36:19 UTC
FoodComEx IDPC000285
FoodDB RecordFDB021820
Chemical Information
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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Apolon b6HMDB
BiosechsHMDB
CodecarboxylaseChEBI
Coenzyme b6HMDB
HairoxalHMDB
Hexermin-PHMDB
Hi-pyridoxinHMDB
HiadelonHMDB
HimitanHMDB
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
PidopidonHMDB
PiodelHMDB
PLPChEBI
PydoxalHMDB
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
PyromijinHMDB
SechvitanHMDB
Vitahexin-PHMDB
VitazechsHMDB
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
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals P991715