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 ChemicalBook:CB8895262, eMolecules:5748034, ZINC000034926229
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Pyridoxamine (PM) is one form of vitamin B6. Chemically it is based on a pyridine ring structure, with hydroxyl, methyl, aminomethyl, and hydroxymethyl substituents. It differs from pyridoxine by the substituent at the 4-position. The hydroxyl at position 3 and aminomethyl group at position 4 of its ring endow pyridoxamine with a variety of chemical properties, including the scavenging of free radical species and carbonyl species formed in sugar and lipid degradation and chelation of metal ions that catalyze Amadori reactions.
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Formula C8H12N2O2
Net Charge 0
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
Richts B, Commichau FM (2021)
Underground metabolism facilitates the evolution of novel pathways for vitamin B6 biosynthesis.
Applied microbiology and biotechnology 105, 2297-2305 [PubMed:33665688]
[show Abstract]
Pereira ENGDS, Silvares RR, Rodrigues KL, Flores EEI, Daliry A (2021)
Pyridoxamine and Caloric Restriction Improve Metabolic and Microcirculatory Abnormalities in Rats with Non-Alcoholic Fatty Liver Disease.
Journal of vascular research1-10 [PubMed:33535220]
[show Abstract]
Nagai R, Shirakawa J, Ohno R, Moroishi N, Nagai M (2014)
Inhibition of AGEs formation by natural products.
Amino acids 46, 261-266 [PubMed:23504149]
[show Abstract]
Almeida F, Santos-Silva D, Rodrigues T, Matafome P, Crisóstomo J, Sena C, Gonçalves L, Seiça R (2013)
Pyridoxamine reverts methylglyoxal-induced impairment of survival pathways during heart ischemia.
Cardiovascular therapeutics 31, e79-85 [PubMed:23841818]
[show Abstract]
Huang S, Zhang J, Wu M, Wu Q, Huang L (2013)
Enzymatic transamination of pyridoxamine in tobacco plants.
Plant science : an international journal of experimental plant biology 212, 55-59 [PubMed:24094054]
[show Abstract]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM (2009)
Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression.
Nature 457, 910-914 [PubMed:19212411]
[show Abstract]
Adrover M, Vilanova B, Frau J, Muñoz F, Donoso J (2008)
The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect.
Bioorganic & medicinal chemistry 16, 5557-5569 [PubMed:18434162]
[show Abstract]
Esteve-Romero J, Capella-Peiró ME, Monferrer-Pons L, Gil-Agustí M (2004)
Micellar liquid chromatography in clinical chemistry: application to the monitorization of B6 vitamins.
Clinica chimica acta; international journal of clinical chemistry 348, 69-77 [PubMed:15369738]
[show Abstract]
Berzas Nevado JJ, Murillo Pulgarín JA, Gómez Laguna MA (1995)
Determination of pyridoxamine in urine by matrix isopotential synchronous fluorescence spectrometry.
The Analyst 120, 171-174 [PubMed:7710125]
[show Abstract]
Rokitzki L, Sagredos AN, Reuss F, Büchner M, Keul J (1994)
Acute changes in vitamin B6 status in endurance athletes before and after a marathon.
International journal of sport nutrition 4, 154-165 [PubMed:8054960]
[show Abstract]
Sharma SK, Dakshinamurti K (1992)
Determination of vitamin B6 vitamers and pyridoxic acid in biological samples.
Journal of chromatography 578, 45-51 [PubMed:1400785]
[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
22 July 2021