Pyridoxal phosphate

Pyridoxal phosphate
	; Idealised skeletal formula
	; Ball-and-stick model based on the crystal structure. Note that the phosphate and pyridine groups have reacted to form a zwitterion and the aldehyde group is hydrated.
Names
	Preferred IUPAC name (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate
	Other names Pyridoxal 5-phosphate, PAL-P, PLP, Vitamin B6 phosphate
Identifiers
CAS Number	54-47-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18405;
ChEMBL	ChEMBL82202 ;
ECHA InfoCard	100.000.190
IUPHAR/BPS	5249;
MeSH	Pyridoxal+Phosphate
PubChem CID	1051;
UNII	F06SGE49M6 ;
CompTox Dashboard (EPA)	DTXSID4048351 ;
	SMILES O=Cc1c(O)c(C)ncc1COP(O)(O)=O;
Properties
Chemical formula	C8H10NO6P
Molar mass	247.142 g/mol
Density	1.638±0.06 g/cm3
Melting point	139 to 142 °C (282 to 288 °F; 412 to 415 K)
Acidity (pKa)	1.56
Pharmacology
ATC code	A11HA06 (WHO)
Hazards
Flash point	296.0±32.9 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P), the active form of vitamin B₆, is a coenzyme in a variety of enzymatic reactions. The International Union of Biochemistry and Molecular Biology has catalogued more than 140 PLP-dependent activities, corresponding to ~4% of all classified activities.^[5] The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates.

^ "CSD Entry: PLPHYD10". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 1974. Archived from the original on 2023-11-04. Retrieved 2023-11-04.
^ Fujiwara T (1973). "The Crystal and Molecular Structure of Vitamin B₆ Derivatives. I. Pyridoxal Phosphate Hydrate and Pyridoxal Phosphate Methyl Hemiacetal". Bull. Chem. Soc. Jpn. 46 (3): 863–871. doi:10.1246/bcsj.46.863.
^ ^a ^b ^c Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2011 ACD/Labs)
^ Kozlov ÉI, L'vova MS (1978). "Stability of water-soluble vitamins and coenzymes. Hydrolysis of pyridoxal-5-phosphate in acidic, neutral, and weakly alkaline solutions". Pharmaceutical Chemistry Journal. 11 (11): 1543–9. doi:10.1007/BF00778244. S2CID 1094223.
^ Percudani R, Peracchi A (September 2003). "A genomic overview of pyridoxal-phosphate-dependent enzymes". EMBO Reports. 4 (9): 850–4. doi:10.1038/sj.embor.embor914. PMC 1326353. PMID 12949584.

[PLPHYD10-1] "CSD Entry: PLPHYD10". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 1974. Archived from the original on 2023-11-04. Retrieved 2023-11-04.

[2] Fujiwara T (1973). "The Crystal and Molecular Structure of Vitamin B₆ Derivatives. I. Pyridoxal Phosphate Hydrate and Pyridoxal Phosphate Methyl Hemiacetal". Bull. Chem. Soc. Jpn. 46 (3): 863–871. doi:10.1246/bcsj.46.863.

[ReferenceA-3] Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2011 ACD/Labs)

[4] Kozlov ÉI, L'vova MS (1978). "Stability of water-soluble vitamins and coenzymes. Hydrolysis of pyridoxal-5-phosphate in acidic, neutral, and weakly alkaline solutions". Pharmaceutical Chemistry Journal. 11 (11): 1543–9. doi:10.1007/BF00778244. S2CID 1094223.

[5] Percudani R, Peracchi A (September 2003). "A genomic overview of pyridoxal-phosphate-dependent enzymes". EMBO Reports. 4 (9): 850–4. doi:10.1038/sj.embor.embor914. PMC 1326353. PMID 12949584.

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Names
Idealised skeletal formula
Ball-and-stick model based on the crystal structure.^[1]^[2] Note that the phosphate and pyridine groups have reacted to form a zwitterion and the aldehyde group is hydrated.
Preferred IUPAC name (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate
Other names Pyridoxal 5-phosphate, PAL-P, PLP, Vitamin B6 phosphate
Identifiers
CAS Number	54-47-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18405
ChEMBL	ChEMBL82202^N
ECHA InfoCard	100.000.190
IUPHAR/BPS	5249
MeSH	Pyridoxal+Phosphate
PubChem CID	1051
UNII	F06SGE49M6^Y
CompTox Dashboard (EPA)	DTXSID4048351
SMILES O=Cc1c(O)c(C)ncc1COP(O)(O)=O
Properties
Chemical formula	C₈H₁₀NO₆P
Molar mass	247.142 g/mol
Density	1.638±0.06 g/cm3^[3]
Melting point	139 to 142 °C (282 to 288 °F; 412 to 415 K)^[4]
Acidity (pK_a)	1.56^[3]
Pharmacology
ATC code	A11HA06 (WHO)
Hazards
Flash point	296.0±32.9 °C^[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references