Common NamePyridoxal 5'-phosphate
DescriptionPyridoxal phosphate, also known as PLP, pyridoxal 5'-phosphate or P5P, is the active form of vitamin B6. It is a coenzyme in a variety of enzymatic reactions. Pyridoxal 5'-phosphate 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 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 cow milk. 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. 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.
Structure
Molecular FormulaC8H10NO6P
Average Mass247.14190
Monoisotopic Mass247.02457
IUPAC Name[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
Traditional Name(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxyphosphonic acid
CAS Registry Number54-47-7
SMILESCc1ncc(COP(=O)([O-])[O-])c(C=O)c1O
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
CHEBI IDCHEBI:597326
HMDB IDHMDB0001491
Pathways
NameSMPDB/PathBank
Alanine, aspartate and glutamate metabolism
Selenocompound metabolism
Nitrogen metabolism
Arginine and proline metabolism
beta-Alanine metabolism
Tyrosine metabolism
One carbon pool by folate
Lysine degradation
Tyrosine metabolism
Starch and sucrose metabolism
Glycine, serine and threonine metabolism
Tryptophan metabolism
Valine, leucine and isoleucine degradation
Propanoate metabolism
Citrullinemia Type I
Carbamoyl Phosphate Synthetase Deficiency
Argininosuccinic Aciduria
Phenylalanine and Tyrosine Metabolism
Cysteine Metabolism
Vitamin B6 Metabolism
Taurine and Hypotaurine Metabolism
Porphyrin Metabolism
Methionine Metabolism
Histidine metabolism
Starch and Sucrose Metabolism
Urea Cycle
Aspartate Metabolism
Glutamate Metabolism
Glucose-Alanine Cycle
Malate-Aspartate Shuttle
2-Hydroxyglutric Aciduria (D And L Form)
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency
3-Methylglutaconic Aciduria Type I
3-Methylglutaconic Aciduria Type III
3-Methylglutaconic Aciduria Type IV
Alkaptonuria
Aromatic L-Aminoacid Decarboxylase Deficiency
Beta-Ketothiolase Deficiency
Canavan Disease
Cystathionine Beta-Synthase Deficiency
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Glutaric Aciduria Type I
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)
Hawkinsinuria
Histidinemia
Hypoacetylaspartia
Malonic Aciduria
Maple Syrup Urine Disease
Methylmalonic Aciduria
Methylmalonic Aciduria Due to Cobalamin-Related Disorders
Ornithine Transcarbamylase Deficiency (OTC Deficiency)
Phenylketonuria
Prolidase Deficiency (PD)
Prolinemia Type II
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency
Tyrosinemia Type I
Methionine Adenosyltransferase Deficiency
Glycine N-methyltransferase Deficiency
Non Ketotic Hyperglycinemia
Propionic Acidemia
3-Methylcrotonyl Coa Carboxylase Deficiency Type I
Isovaleric Aciduria
Saccharopinuria/Hyperlysinemia II
Dimethylglycine Dehydrogenase Deficiency
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Sarcosinemia
Lactic Acidemia
Hyperinsulinism-Hyperammonemia Syndrome
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Hypermethioninemia
Hereditary Coproporphyria (HCP)
Acute Intermittent Porphyria
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease
Porphyria Variegata (PV)
Metachromatic Leukodystrophy (MLD)
Globoid Cell Leukodystrophy
Gaucher Disease
Pyruvate Carboxylase Deficiency
GABA-Transaminase Deficiency
Primary Hyperoxaluria Type I
Argininemia
Hyperprolinemia Type II
Hyperprolinemia Type I
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Ornithine Aminotransferase Deficiency (OAT Deficiency)
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)
Tyrosinemia Type 3 (TYRO3)
Methylmalonate Semialdehyde Dehydrogenase Deficiency
Homocarnosinosis
Disulfiram Action Pathway
Methotrexate Action Pathway
Spermidine and Spermine Biosynthesis
Threonine and 2-Oxobutanoate Degradation
Homocysteine Degradation
Carnitine Synthesis
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
Ureidopropionase Deficiency
Carnosinuria, carnosinemia
Tyrosinemia, transient, of the newborn
Tyrosine hydroxylase deficiency
Dopamine beta-hydroxylase deficiency
Beta-mercaptolactate-cysteine disulfiduria
Malonyl-coa decarboxylase deficiency
Hypophosphatasia
Creatine deficiency, guanidinoacetate methyltransferase deficiency
Hyperornithinemia with gyrate atrophy (HOGA)
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]
L-arginine:glycine amidinotransferase deficiency
Gamma-cystathionase deficiency (CTH)
Homocystinuria, cystathionine beta-synthase deficiency
3-hydroxyisobutyric acid dehydrogenase deficiency
3-hydroxyisobutyric aciduria
Isobutyryl-coa dehydrogenase deficiency
Isovaleric acidemia
Fabry disease
Krabbe disease
Hyperlysinemia I, Familial
Hyperlysinemia II or Saccharopinuria
Monoamine oxidase-a deficiency (MAO-A)
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Glycogen synthetase deficiency
Glycogenosis, Type III. Cori disease, Debrancher glycogenosis
Glycogenosis, Type IV. Amylopectinosis, Anderson disease
Glycogenosis, Type VI. Hers disease
Mucopolysaccharidosis VI. Sly syndrome
Sucrase-isomaltase deficiency
Succinic semialdehyde dehydrogenase deficiency
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type
Pyridoxine dependency with seizures
2-aminoadipic 2-oxoadipic aciduria
3-Phosphoglycerate dehydrogenase deficiency
Cystinosis, ocular nonnephropathic
Folate malabsorption, hereditary
Glutaminolysis and Cancer
Sarcosine Oncometabolite Pathway
StateSolid
Water Solubility5.70e+00 g/l
logP-0.55
logS-1.64
pKa (Strongest Acidic)1.68
pKa (Strongest Basic)4.11
Hydrogen Acceptor Count6
Hydrogen Donor Count3
Polar Surface Area116.95 Ų
Rotatable Bond Count4
Physiological Charge-2
Formal Charge0
Refractivity54.75 m³·mol⁻¹
Polarizability20.91

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