pyridoxamine (CHEBI:16410)

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CHEBI:16410 - pyridoxamine

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ChEBI Name	pyridoxamine

ChEBI ID	CHEBI:16410

Definition	A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 3, an aminomethyl group at position 4, a hydroxymethyl group at position 5 and a methyl group at position 2. The 4-aminomethyl form of vitamin B₆, it is used (in the form of the hydrochloride salt) for treatment of diabetic nephropathy.

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

Secondary ChEBI IDs	CHEBI:45228, CHEBI:8669, CHEBI:14978, CHEBI:26426

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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24 24 0 0 0 0 999 V2000

1.2159 -0.4350 0.2262 C 0 0 0 0 0 0 0 0 0 5 0 0

-0.1586 -2.3016 -0.4051 N 0 0 0 0 0 0 0 0 0 1 0 0

1.0138 -1.8255 0.0730 C 0 0 0 0 0 0 0 0 0 6 0 0

0.1565 0.4432 -0.1476 C 0 0 0 0 0 0 0 0 0 4 0 0

-1.0536 -0.1102 -0.6481 C 0 0 0 0 0 0 0 0 0 3 0 0

-1.1993 -1.5117 -0.7682 C 0 0 0 0 0 0 0 0 0 2 0 0

2.5131 0.0393 0.7757 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2816 0.7126 2.0097 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.4353 -2.1450 -1.2695 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0137 0.6365 -0.9860 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2489 1.9306 -0.0333 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7449 2.4365 0.9199 N 0 0 0 0 0 0 0 0 0 0 0 0

1.7333 -2.5100 0.3180 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9848 0.7153 0.0598 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2332 -0.7571 0.9751 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1249 1.1588 2.2314 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2734 -1.8742 -0.6242 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6431 -1.7926 -2.2816 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3692 -3.2340 -1.2974 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7724 0.3048 -1.2828 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0802 2.3873 -1.0102 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2107 2.3109 0.3053 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5723 3.4361 1.0413 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5611 1.9852 1.8186 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

3 13 1 0 0 0 0

7 14 1 0 0 0 0

7 15 1 0 0 0 0

8 16 1 0 0 0 0

9 17 1 0 0 0 0

9 18 1 0 0 0 0

9 19 1 0 0 0 0

10 20 1 0 0 0 0

11 21 1 0 0 0 0

11 22 1 0 0 0 0

12 23 1 0 0 0 0

12 24 1 0 0 0 0

M END): 21 ms

reading 24 atoms

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24 atoms created

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Wikipedia	License
Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids.
Read full article at Wikipedia

Formula

C8H12N2O2

Net Charge

Average Mass

168.19316

Monoisotopic Mass

168.08988

InChI

InChI=1S/C8H12N2O2/c1-5-8(12)7(2-9)6(4-11)3-10-5/h3,11-12H,2,4,9H2,1H3

InChIKey

NHZMQXZHNVQTQA-UHFFFAOYSA-N

SMILES

Cc1ncc(CO)c(CN)c1O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Mus musculus (NCBI:txid10090)	From MetaboLights of strain C57bl/6 mouse (NCIT:C14424) See: MetaboLights Study
Escherichia coli (NCBI:txid562)	See: PubMed
Trypanosoma brucei (NCBI:txid5691)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study

Roles Classification
Chemical Role(s):	iron chelator

Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. 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. 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):	nephroprotective agent Any protective agent that is able to prevent damage to the kidney. 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 (CHEBI:16410) has role Escherichia coli metabolite (CHEBI:76971) pyridoxamine (CHEBI:16410) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) pyridoxamine (CHEBI:16410) has role human metabolite (CHEBI:77746) pyridoxamine (CHEBI:16410) has role iron chelator (CHEBI:38157) pyridoxamine (CHEBI:16410) has role mouse metabolite (CHEBI:75771) pyridoxamine (CHEBI:16410) has role nephroprotective agent (CHEBI:76595) pyridoxamine (CHEBI:16410) has role plant metabolite (CHEBI:76924) pyridoxamine (CHEBI:16410) is a aminoalkylpyridine (CHEBI:38198) pyridoxamine (CHEBI:16410) is a hydroxymethylpyridine (CHEBI:38196) pyridoxamine (CHEBI:16410) is a monohydroxypyridine (CHEBI:38182) pyridoxamine (CHEBI:16410) is a vitamin B₆ (CHEBI:27306) pyridoxamine (CHEBI:16410) is conjugate base of pyridoxaminium(1+) (CHEBI:57761)

Incoming	pyridoxamine 5'-phosphate (CHEBI:18335) has functional parent pyridoxamine (CHEBI:16410) pyridoxaminium(1+) (CHEBI:57761) is conjugate acid of pyridoxamine (CHEBI:16410)

IUPAC Name

4-(aminomethyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol

Synonyms	Sources
4-(AMINOMETHYL)-5-(HYDROXYMETHYL)-2-METHYLPYRIDIN-3-OL	PDBeChem
PM	KEGG COMPOUND
Pyridoxamine	KEGG COMPOUND

Manual Xrefs	Databases
1023	ChemSpider
C00007504	KNApSAcK
C00534	KEGG COMPOUND
FDB021819	FooDB
HMDB0001431	HMDB
PXM	PDBeChem
Pyridoxamine	Wikipedia
PYRIDOXAMINE	MetaCyc
View more database links

Registry Numbers	Types	Sources
6993	Reaxys Registry Number	Reaxys
774473	Gmelin Registry Number	Gmelin
85-87-0	CAS Registry Number	ChemIDplus
85-87-0	CAS Registry Number	NIST Chemistry WebBook

Citations	Types	Sources
1400785	PubMed citation	Europe PMC
15369738	PubMed citation	Europe PMC
18434162	PubMed citation	Europe PMC
19212411	PubMed citation	Europe PMC
23504149	PubMed citation	Europe PMC
23841818	PubMed citation	Europe PMC
24094054	PubMed citation	Europe PMC
2580028	PubMed citation	Europe PMC
33535220	PubMed citation	Europe PMC
33665688	PubMed citation	Europe PMC
7710125	PubMed citation	Europe PMC
8054960	PubMed citation	Europe PMC

Last Modified

22 July 2021

CHEBI:16410 - pyridoxamine

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