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 ZINC000001532705
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Pyridoxal (PL) is one form of vitamin B6. Some medically relevant bacteria, such as those in the genera Granulicatella and Abiotrophia, require pyridoxal for growth. This nutritional requirement can lead to the culture phenomenon of satellite growth. In in vitro culture, these pyridoxal-dependent bacteria may only grow in areas surrounding colonies of bacteria from other genera ("satellitism") that are capable of producing pyridoxal. Pyridoxal is involved in what is believed to be the most ancient reaction of aerobic metabolism on Earth, about 2.9 billion years ago, a forerunner of the Great Oxidation Event.
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Formula C8H10NO6P
Net Charge 0
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 Types Sources
14651974 PubMed citation Europe PMC
16277678 PubMed citation Europe PMC
18491919 PubMed citation Europe PMC
6339724 PubMed citation ChEMBL
7284379 PubMed citation Europe PMC
9866693 PubMed citation Europe PMC
Last Modified
25 July 2019