pyridoxine (CHEBI:16709)

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CHEBI:16709 - pyridoxine

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ChEBI Name	pyridoxine

ChEBI ID	CHEBI:16709

Definition	A hydroxymethylpyridine with hydroxymethyl groups at positions 4 and 5, a hydroxy group at position 3 and a methyl group at position 2. The 4-methanol form of vitamin B₆, it is converted intoto pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid.

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

Secondary ChEBI IDs	CHEBI:8671, CHEBI:14981, CHEBI:26429

Supplier Information	ZINC000001532705

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

UEG - Ideal conformer

Mrv1927 06292110063D

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Time for openFile(UEG - Ideal conformer

Mrv1927 06292110063D

23 23 0 0 0 0 999 V2000

3.1500 1.4530 -0.0130 O 0 0 0 0 0 0 0 0 0 0 0 0

2.4690 0.2080 -0.1770 C 0 0 1 0 0 0 0 0 0 0 0 0

0.9820 0.4330 -0.0920 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4780 1.7040 0.1170 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8220 1.9120 0.1930 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.6910 0.9280 0.0750 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2620 -0.3740 -0.1360 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1030 -0.6290 -0.2270 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6130 -2.0280 -0.4620 C 0 0 1 0 0 0 0 0 0 0 0 0

0.8180 -2.6760 0.7950 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1620 -1.3850 -0.2570 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.1660 1.2210 0.1700 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1140 1.3830 -0.0570 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7170 -0.2160 -1.1510 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7780 -0.4810 0.6090 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1580 2.5360 0.2200 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5570 1.4450 -0.8230 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6840 0.3520 0.5760 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3250 2.0780 0.8240 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4530 -1.5470 -1.1640 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1190 -2.5880 -1.0440 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5550 -1.9840 -1.0070 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1470 -3.5830 0.7200 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

2 3 1 0 0 0 0

3 4 2 0 0 0 0

3 8 1 0 0 0 0

4 5 1 0 0 0 0

5 6 2 0 0 0 0

6 7 1 0 0 0 0

6 12 1 0 0 0 0

7 8 2 0 0 0 0

7 11 1 0 0 0 0

8 9 1 0 0 0 0

9 10 1 0 0 0 0

9 21 1 0 0 0 0

9 22 1 0 0 0 0

1 13 1 0 0 0 0

2 14 1 0 0 0 0

2 15 1 0 0 0 0

4 16 1 0 0 0 0

12 17 1 0 0 0 0

12 18 1 0 0 0 0

12 19 1 0 0 0 0

11 20 1 0 0 0 0

10 23 1 0 0 0 0

M END): 19 ms

reading 23 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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23 atoms created

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Molfile expand

Wikipedia	License
Erythrose 4-phosphate is a phosphate of the simple sugar erythrose. It is an intermediate in the pentose phosphate pathway and the Calvin cycle. The enzyme transaldolase catalyzes the formation of erythrose 4-phosphate and fructose 6-phosphate from sedoheptulose 7-phosphate and glyceraldehyde 3-phosphate. This reaction is a part of the non-oxidative phase of the pentose phosphate pathway. In the Calvin cycle, the enzyme fructose-bisphosphate aldolase catalyzes the formation of sedoheptulose 1,7-bisphosphate from erythrose 4-phosphate and dihydroxyacetone phosphate. In addition, it serves as a precursor in the biosynthesis of the aromatic amino acids tyrosine, phenylalanine, and tryptophan. It is used in the first step of the shikimate pathway. At this stage, phosphoenolpyruvate and erythrose-4-phosphate react to form 3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzyme DAHP synthase. It also used in 3-hydroxy-1-aminoacetone phosphate biosynthesis, which is a precursor of vitamin B6 in DXP-dependent pathway. Erythrose-4-phosphate dehydrogenase is used to produce erythronate-4-phosphate.
Read full article at Wikipedia

Formula

C8H11NO3

Net Charge

Average Mass

169.180

Monoisotopic Mass

169.07389

InChI

InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3

InChIKey

LXNHXLLTXMVWPM-UHFFFAOYSA-N

SMILES

CC1=C(O)C(CO)=C(CO)C=N1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in urine (BTO:0001419). See: PubMed
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study

Roles Classification
Biological Role(s):	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 ). 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). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). 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	pyridoxine (CHEBI:16709) has role Escherichia coli metabolite (CHEBI:76971) pyridoxine (CHEBI:16709) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) pyridoxine (CHEBI:16709) has role cofactor (CHEBI:23357) pyridoxine (CHEBI:16709) has role human metabolite (CHEBI:77746) pyridoxine (CHEBI:16709) has role mouse metabolite (CHEBI:75771) pyridoxine (CHEBI:16709) is a hydroxymethylpyridine (CHEBI:38196) pyridoxine (CHEBI:16709) is a methylpyridines (CHEBI:25340) pyridoxine (CHEBI:16709) is a monohydroxypyridine (CHEBI:38182) pyridoxine (CHEBI:16709) is a vitamin B₆ (CHEBI:27306)

Incoming	5'-O-β-D-glucosylpyridoxine (CHEBI:17382) has functional parent pyridoxine (CHEBI:16709) pyridoxine 5'-phosphate (CHEBI:28803) has functional parent pyridoxine (CHEBI:16709) pyridoxine hydrochloride (CHEBI:30961) has part pyridoxine (CHEBI:16709)

IUPAC Name

4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol

INNs	Sources
pyridoxina	WHO MedNet
pyridoxine	WHO MedNet
pyridoxine	WHO MedNet
pyridoxinum	WHO MedNet

Synonyms	Sources
2-methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine	ChemIDplus
2-methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine	ChemIDplus
2-Methyl-3-hydroxy-4,5-dihydroxymethyl-pyridin	ChemIDplus
2-methyl-3-hydroxy-4,5-dihydroxymethylpyridine	NIST Chemistry WebBook
2-methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine	ChemIDplus
2-methyl-4,5-dimethylol-pyridin-3-ol	ChEBI
3-hydroxy-2-picoline-4,5-dimethanol	ChemIDplus
3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine	ChEBI
3-hydroxy-4,5-dimethylol-α-picoline	NIST Chemistry WebBook
4,5-bis(hydroxymethyl)-2-methyl-pyridin-3-ol	ChEBI
5-hydroxy-6-methyl-3,4-pyridinedimethanol	NIST Chemistry WebBook
piridossina	HMDB
pyridoxine	UniProt
Pyridoxol	KEGG COMPOUND
pyridoxolum	HMDB
vitamin B₆	NIST Chemistry WebBook

Manual Xrefs	Databases
1025	ChemSpider
2836	DrugCentral
C00001551	KNApSAcK
C00314	KEGG COMPOUND
D08454	KEGG DRUG
DB00165	DrugBank
FDB000574	FooDB
HMDB0000239	HMDB
LSM-5324	LINCS
Pyridoxine	Wikipedia
PYRIDOXINE	MetaCyc
UEG	PDBeChem
View more database links

Registry Numbers	Types	Sources
139854	Reaxys Registry Number	Reaxys
563676	Gmelin Registry Number	Gmelin
65-23-6	CAS Registry Number	ChemIDplus
65-23-6	CAS Registry Number	NIST Chemistry WebBook

Citations	Types	Sources
10687314	PubMed citation	Europe PMC
10894227	PubMed citation	Europe PMC
11562405	PubMed citation	Europe PMC
12640345	PubMed citation	Europe PMC
12768081	PubMed citation	Europe PMC
13046427	PubMed citation	Europe PMC
15132238	PubMed citation	Europe PMC
15369738	PubMed citation	Europe PMC
15756083	PubMed citation	Europe PMC
16236150	PubMed citation	Europe PMC
16277693	PubMed citation	Europe PMC
16690736	PubMed citation	Europe PMC
17044573	PubMed citation	Europe PMC
22932811	PubMed citation	Europe PMC
24035968	PubMed citation	Europe PMC
24601602	PubMed citation	Europe PMC
2580028	PubMed citation	Europe PMC
27113583	PubMed citation	Europe PMC
2885064	PubMed citation	Europe PMC
31093449	PubMed citation	Europe PMC
32105687	PubMed citation	Europe PMC
33549283	PubMed citation	Europe PMC
33665688	PubMed citation	Europe PMC
3710434	PubMed citation	Europe PMC
559690	PubMed citation	Europe PMC
6624427	PubMed citation	Europe PMC
6801073	PubMed citation	Europe PMC
9625217	PubMed citation	Europe PMC
IND607198670	Agricola citation	Europe PMC

Last Modified

29 June 2021

CHEBI:16709 - pyridoxine

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