pyridoxal 5'-phosphate (CHEBI:18405)

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CHEBI:18405 - pyridoxal 5'-phosphate

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ChEBI Name	pyridoxal 5'-phosphate

ChEBI ID	CHEBI:18405

Definition	The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:234571, CHEBI:45145, CHEBI:358848, CHEBI:8668, CHEBI:14977, CHEBI:26424

Supplier Information	ChemicalBook:CB48047867, ChemicalBook:CB22131140, ChemicalBook:CB0257385, eMolecules:1988700, ZINC000001532514

Download	Molfile XML SDF

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26 26 0 0 0 0 999 V2000

-2.0102 -1.2936 1.3622 C 0 0 0 0 0 0 0 0 0 2 0 0

-1.9812 0.1197 1.3216 C 0 0 0 0 0 0 0 0 0 3 0 0

0.1742 0.0247 0.1325 C 0 0 0 0 0 0 0 0 0 5 0 0

-0.9808 -1.9751 0.8024 N 0 0 0 0 0 0 0 0 0 1 0 0

0.0799 -1.3842 0.2061 C 0 0 0 0 0 0 0 0 0 6 0 0

-0.8840 0.7935 0.7136 C 0 0 0 0 0 0 0 0 0 4 0 0

1.3688 0.6392 -0.5204 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0073 -0.0682 -1.4690 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.1010 -2.0641 1.9972 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.9313 0.7607 1.8539 O 0 0 0 0 0 0 0 0 0 0 0 0

4.2834 0.6411 -1.4767 O 0 0 0 0 0 0 0 0 0 0 0 0

3.4748 -0.6388 -3.2628 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8485 2.1891 0.7080 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8372 2.9060 0.6459 O 0 0 0 0 0 0 0 0 0 0 0 0

0.0142 2.6759 0.7404 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1304 0.3710 -2.2958 P 0 0 1 0 0 0 0 0 0 0 0 0

2.7751 1.5820 -2.9994 O 0 0 0 0 0 0 0 0 0 0 0 0

0.8013 -1.9984 -0.1772 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0615 0.8879 0.2896 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0516 1.5710 -0.9972 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0512 -1.8345 1.5117 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9433 -3.1426 1.9351 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1744 -1.7986 3.0538 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6079 0.3546 2.2420 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7344 -1.4356 -2.9954 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3941 2.1174 -3.3220 H 0 0 0 0 0 0 0 0 0 0 0 0

9 1 1 0 0 0 0

1 2 4 0 0 0 0

10 2 1 0 0 0 0

7 3 1 0 0 0 0

1 4 4 0 0 0 0

3 5 4 0 0 0 0

5 4 4 0 0 0 0

2 6 4 0 0 0 0

6 3 4 0 0 0 0

13 6 1 0 0 0 0

8 7 1 0 0 0 0

16 8 1 0 0 0 0

11 16 2 0 0 0 0

12 16 1 0 0 0 0

14 13 2 0 0 0 0

13 15 1 0 0 0 0

16 17 1 0 0 0 0

5 18 1 0 0 0 0

7 19 1 0 0 0 0

7 20 1 0 0 0 0

9 21 1 0 0 0 0

9 22 1 0 0 0 0

9 23 1 0 0 0 0

10 24 1 0 0 0 0

12 25 1 0 0 0 0

17 26 1 0 0 0 0

M END): 23 ms

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Wikipedia	License
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. 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.
Read full article at Wikipedia

Formula

C8H10NO6P

Net Charge

Average Mass

247.14190

Monoisotopic Mass

247.02457

InChI

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)

InChIKey

NGVDGCNFYWLIFO-UHFFFAOYSA-N

SMILES

[H]C(=O)c1c(COP(O)(O)=O)cnc(C)c1O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). (via vitamin B6 phosphate ) EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor A DNA polymerase inhibitor that interferes with the action of a DNA-directed DNA polymerase (EC 2.7.7.7). coenzyme A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via B vitamin )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. (via B vitamin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	pyridoxal 5'-phosphate (CHEBI:18405) has functional parent pyridoxal (CHEBI:17310) pyridoxal 5'-phosphate (CHEBI:18405) has role Escherichia coli metabolite (CHEBI:76971) pyridoxal 5'-phosphate (CHEBI:18405) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) pyridoxal 5'-phosphate (CHEBI:18405) has role coenzyme (CHEBI:23354) pyridoxal 5'-phosphate (CHEBI:18405) has role cofactor (CHEBI:23357) pyridoxal 5'-phosphate (CHEBI:18405) has role EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor (CHEBI:131699) pyridoxal 5'-phosphate (CHEBI:18405) has role human metabolite (CHEBI:77746) pyridoxal 5'-phosphate (CHEBI:18405) has role mouse metabolite (CHEBI:75771) pyridoxal 5'-phosphate (CHEBI:18405) is a methylpyridines (CHEBI:25340) pyridoxal 5'-phosphate (CHEBI:18405) is a monohydroxypyridine (CHEBI:38182) pyridoxal 5'-phosphate (CHEBI:18405) is a pyridinecarbaldehyde (CHEBI:38187) pyridoxal 5'-phosphate (CHEBI:18405) is a vitamin B₆ phosphate (CHEBI:36970) pyridoxal 5'-phosphate (CHEBI:18405) is conjugate acid of pyridoxal 5'-phosphate(2−) (CHEBI:597326)

Incoming	(2R,3R,4S,5R,6R)-3,4-dihydroxy-5-{[(1E)-{3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methylidene]amino}-6-methyltetrahydro-2H-pyran-2-yl [(2R,3S,5R)-3-hydroxy-5-(thymin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen diphosphate (CHEBI:47689) has functional parent pyridoxal 5'-phosphate (CHEBI:18405) 5'-phosphopyridoxal-6-azobenzene-2,4-disulfonic acid (CHEBI:34941) has functional parent pyridoxal 5'-phosphate (CHEBI:18405) pyridoxal 5'-phosphate(2−) (CHEBI:597326) is conjugate base of pyridoxal 5'-phosphate (CHEBI:18405)

IUPAC Name

(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate

Synonyms	Sources
3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde	ChEBI
3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate	ChEBI
codecarboxylase	ChEBI
Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester	ChEMBL
PLP	KEGG COMPOUND
pyridoxal 5'-(dihydrogen phosphate)	ChEBI
Pyridoxal 5'-phosphate	KEGG COMPOUND
pyridoxal 5-monophosphoric acid ester	ChEBI
Pyridoxal 5-phosphate	KEGG COMPOUND
Pyridoxal phosphate	KEGG COMPOUND
PYRIDOXAL-5'-PHOSPHATE	PDBeChem

Manual Xrefs	Databases
3506	DrugCentral
C00007503	KNApSAcK
C00018	KEGG COMPOUND
DB00114	DrugBank
HMDB0001491	HMDB
MOL000108	COMe
PLP	PDBeChem
Pyridoxal_phosphate	Wikipedia
View more database links

Registry Numbers	Types	Sources
234749	Reaxys Registry Number	Reaxys
465416	Gmelin Registry Number	Gmelin
54-47-7	CAS Registry Number	ChemIDplus

Citations

Smith P, Szu PH, Bui C, Liu HW, Tsai SC (2008)
Structure and mutagenic conversion of E1 dehydrase: at the crossroads of dehydration, amino transfer, and epimerization.
Biochemistry 47, 6329-6341 [PubMed:18491919]
[show Abstract]

Chiang EP, Smith DE, Selhub J, Dallal G, Wang YC, Roubenoff R (2005)
Inflammation causes tissue-specific depletion of vitamin B6.
Arthritis research & therapy 7, R1254-62 [PubMed:16277678]
[show Abstract]

Mizushina Y, Xu X, Matsubara K, Murakami C, Kuriyama I, Oshige M, Takemura M, Kato N, Yoshida H, Sakaguchi K (2003)
Pyridoxal 5'-phosphate is a selective inhibitor in vivo of DNA polymerase alpha and epsilon.
Biochemical and biophysical research communications 312, 1025-1032 [PubMed:14651974]
[show Abstract]

Millar DB (1998)
Negative cooperativity in tryptophan synthase alpha subunit dissociation is caused by the bound coenzyme: pyridoxal 5'-phosphate.
Analytical biochemistry 264, 271-278 [PubMed:9866693]
[show Abstract]

Han CN, Iwata C, Metzler DE (1983)
Phosphonate analogues of pyridoxal phosphate with shortened side chains.
Journal of medicinal chemistry 26, 595-598 (Source: ChEMBL) [PubMed:6339724]
[show Abstract]

Modak MJ, Dumaswala UJ (1981)
Divalent cation-dependent pyridoxal 5'-phosphate inhibition of Rauscher leukemia virus DNA polymerase: characterization and mechanism of action.
Biochimica et biophysica acta 654, 227-235 [PubMed:7284379]
[show Abstract]

Last Modified

25 July 2019

CHEBI:18405 - pyridoxal 5'-phosphate

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