pyridoxamine 5'-phosphate (CHEBI:18335)

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CHEBI:18335 - pyridoxamine 5'-phosphate

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ChEBI Name	pyridoxamine 5'-phosphate

ChEBI ID	CHEBI:18335

Definition	A vitamin B₆ phosphate that is the phosphoric ester derivative of pyridoxamine.

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

Secondary ChEBI IDs	CHEBI:26427, CHEBI:45037, CHEBI:14979, CHEBI:8670, CHEBI:14980

Supplier Information	ChemicalBook:CB5262429, eMolecules:531246, ZINC000001532708

Download	Molfile XML SDF

more structures >>

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29 29 0 0 0 0 999 V2000

0.2778 -0.8795 0.3952 C 0 0 0 0 0 0 0 0 0 5 0 0

-0.2788 -2.7631 -0.9888 N 0 0 0 0 0 0 0 0 0 1 0 0

0.5054 -2.2056 -0.0420 C 0 0 0 0 0 0 0 0 0 6 0 0

-0.7816 -0.1423 -0.2163 C 0 0 0 0 0 0 0 0 0 4 0 0

-1.5823 -0.7833 -1.2028 C 0 0 0 0 0 0 0 0 0 3 0 0

-1.3120 -2.1194 -1.5811 C 0 0 0 0 0 0 0 0 0 2 0 0

1.1365 -0.3598 1.4921 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8504 0.7078 1.1038 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0976 -2.8581 -2.5890 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5436 -0.1753 -1.7503 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.1058 1.2753 0.1330 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9340 2.1588 -1.0269 N 0 0 0 0 0 0 0 0 0 0 0 0

2.6657 1.5789 1.9399 P 0 0 1 0 0 0 0 0 0 0 0 0

3.1518 2.7117 1.1917 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8612 2.0467 3.0440 O 0 0 0 0 0 0 0 0 0 0 0 0

3.7939 0.8375 2.4457 O 0 0 0 0 0 0 0 0 0 0 0 0

1.2528 -2.7887 0.3408 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4599 -0.1230 2.3196 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8281 -1.1165 1.8803 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0389 -2.3406 -3.5476 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1412 -2.9106 -2.2740 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7400 -3.8798 -2.7346 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0450 -0.5590 -2.3631 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1406 1.3479 0.4742 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5001 1.7001 0.9310 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0768 3.1212 -0.7125 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0388 2.0796 -1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5980 3.3389 0.9170 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2262 2.4210 3.7499 H 0 0 0 0 0 0 0 0 0 0 0 0

3 2 4 0 0 0 0

1 3 4 0 0 0 0

4 1 4 0 0 0 0

5 4 4 0 0 0 0

6 5 4 0 0 0 0

6 2 4 0 0 0 0

7 1 1 0 0 0 0

8 7 1 0 0 0 0

9 6 1 0 0 0 0

10 5 1 0 0 0 0

11 4 1 0 0 0 0

12 11 1 0 0 0 0

13 8 1 0 0 0 0

14 13 1 0 0 0 0

15 13 1 0 0 0 0

16 13 2 0 0 0 0

3 17 1 0 0 0 0

7 18 1 0 0 0 0

7 19 1 0 0 0 0

9 20 1 0 0 0 0

9 21 1 0 0 0 0

9 22 1 0 0 0 0

10 23 1 0 0 0 0

11 24 1 0 0 0 0

11 25 1 0 0 0 0

12 26 1 0 0 0 0

12 27 1 0 0 0 0

14 28 1 0 0 0 0

15 29 1 0 0 0 0

M END): 26 ms

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Formula

C8H13N2O5P

Net Charge

Average Mass

248.17306

Monoisotopic Mass

248.05621

InChI

InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)

InChIKey

ZMJGSOSNSPKHNH-UHFFFAOYSA-N

SMILES

Cc1ncc(COP(O)(O)=O)c(CN)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). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. 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 ) 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	pyridoxamine 5'-phosphate (CHEBI:18335) has functional parent pyridoxamine (CHEBI:16410) pyridoxamine 5'-phosphate (CHEBI:18335) has role Escherichia coli metabolite (CHEBI:76971) pyridoxamine 5'-phosphate (CHEBI:18335) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) pyridoxamine 5'-phosphate (CHEBI:18335) has role human metabolite (CHEBI:77746) pyridoxamine 5'-phosphate (CHEBI:18335) has role mouse metabolite (CHEBI:75771) pyridoxamine 5'-phosphate (CHEBI:18335) is a aminoalkylpyridine (CHEBI:38198) pyridoxamine 5'-phosphate (CHEBI:18335) is a methylpyridines (CHEBI:25340) pyridoxamine 5'-phosphate (CHEBI:18335) is a monohydroxypyridine (CHEBI:38182) pyridoxamine 5'-phosphate (CHEBI:18335) is a vitamin B₆ phosphate (CHEBI:36970) pyridoxamine 5'-phosphate (CHEBI:18335) is conjugate acid of pyridoxamine 5'-phosphate(1−) (CHEBI:58451)

Incoming	pyridoxamine 5'-phosphate(1−) (CHEBI:58451) is conjugate base of pyridoxamine 5'-phosphate (CHEBI:18335)

IUPAC Name

[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methyl dihydrogen phosphate

Synonyms	Sources
4'-DEOXY-4'-AMINOPYRIDOXAL-5'-PHOSPHATE	PDBeChem
pyridoxamine 5'-(dihydrogen phosphate)	ChEBI
Pyridoxamine 5'-phosphate	KEGG COMPOUND
Pyridoxamine 5'-phosphoric acid	HMDB
Pyridoxamine 5-phosphate	KEGG COMPOUND
Pyridoxamine 5-phosphoric acid	HMDB
Pyridoxamine phosphate	KEGG COMPOUND

Manual Xrefs	Databases
C00007506	KNApSAcK
C00647	KEGG COMPOUND
HMDB0001555	HMDB
MOL000123	COMe
PMP	PDBeChem
View more database links

Registry Numbers	Types	Sources
233653	Reaxys Registry Number	Reaxys
529-96-4	CAS Registry Number	KEGG COMPOUND
529-96-4	CAS Registry Number	ChemIDplus
529-96-4	CAS Registry Number	ChemIDplus

Citations

Jankowska M, Marszałł M, Dębska-Ślizień A, Carrero JJ, Lindholm B, Czarnowski W, Rutkowski B, Trzonkowski P (2013)
Vitamin B6 and the immunity in kidney transplant recipients.
Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation 23, 57-64 [PubMed:22445054]
[show Abstract]

Objective

The study aimed to determine vitamin B6 status in elderly (age ≥ 60 years) and younger (age <60 years) recipients of allogeneic kidney graft and to investigate associations between vitamin B6 status and immunity markers.

Design

A retrospective observational study.

Setting

The study was conducted at the Medical University of Gdańsk, Poland.

Subjects

We recruited 34 kidney allograft recipients (17 males and 17 females) and allocated them into 2 groups: patients aged ≥ 60 years (18 patients) and those aged <60 years (16 patients). Exclusion criteria included patients receiving vitamin B6 supplementation or drugs known to influence vitamin B6 metabolism.

Main outcome measure

Plasma levels of pyridoxal 5'-phosphate (PLP), pyridoxal, pyridoxine, pyridoxamine, pyridoxamine 5'-phosphate, and 4 pyridoxic acid were determined by high-performance liquid chromatography. Measured immunity markers were serum cytokines (interleukin-6, interleukin-10, and transforming growth factor-β), levels of T-lymphocyte subsets, and the proliferative ability of peripheral blood mononuclear cells.

Results

Concentrations of all vitamin B6 vitamers in plasma (PLP, pyridoxal, pyridoxamine 5'-phosphate, pyridoxamine, pyridoxine, 4 pyridoxic acid) were comparable in the 2 studied groups. There were no cases of PLP deficiency in the study population, but 29% of patients had PLP concentrations more than the upper reference limit. Vitamin B6 vitamer concentrations were not influenced by gender, estimated glomerular filtration rate, and circulating phosphate concentration. There was no difference in immunity markers according to age. However, the plasma concentrations of vitamin B6 vitamers were inversely associated with levels of CD28(+) lymphocyte subsets, as well as with the proliferative response of peripheral blood mononuclear cells in both groups.

Conclusions

No cases of vitamin B6 deficiency were found among kidney allograft recipients, and we report inverse links between vitamin B6 vitamer concentrations and markers of cellular immunity, suggesting that bioactive vitamin B6 concentration in kidney allograft recipients merits further investigation.

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]

Driskell JA, Chrisley BM, Reynolds LK, Moak SW (1991)
Plasma B6 vitamer and plasma and urinary 4-pyridoxic acid concentrations of middle-aged obese black women.
Journal of chromatography 568, 333-340 [PubMed:1783639]
[show Abstract]

Brandon DL, Corse JW, Windle JJ, Layton LL (1985)
Two homogeneous immunoassays for pyridoxamine.
Journal of immunological methods 78, 87-94 [PubMed:2580028]
[show Abstract]

Last Modified

09 September 2016