Metabolite Card

Formula: C8H12N2O2 (168.0899)
SMILES: CC1=C(O)C(CN)=C(CO)C=N1

Synonyms [en]

pyridoxamine; 4-(AMINOMETHYL)-5-(HYDROXYMETHYL)-2-METHYLPYRIDIN-3-OL; 2-methyl-4-aminomethyl-5-hydroxymethyl-3-Pyridinol; Pyridoxylamine; PM; 4-(Aminomethyl)-5-(hydroxymethyl)-2-methyl-3-pyridinol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Pyridoxamine. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000017017). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Pyridoxamine 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. Pyridoxamine, also known as PM, belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position. Within humans, pyridoxamine participates in a number of enzymatic reactions. In particular, pyridoxamine can be converted into pyridoxal; which is mediated by the enzyme pyridoxine-5'-phosphate oxidase. In addition, pyridoxamine can be converted into pyridoxamine 5'-phosphate; which is catalyzed by the enzyme pyridoxal kinase. Pyridoxamine also inhibits the formation of advanced lipoxidation endproducts during lipid peroxidation reactions by reaction with dicarbonyl intermediates. In humans, pyridoxamine is involved in vitamin B6 metabolism. Outside of the human body, pyridoxamine has been detected, but not quantified in several different foods, such as nutmegs, sparkleberries, fennels, turmerics, and swiss chards. Pyridoxamine inhibits the Maillard reaction and can block the formation of advanced glycation endproducts, which are associated with medical complications of diabetes. Pyridoxamine is hypothesized to trap intermediates in the formation of Amadori products released from glycated proteins, possibly preventing the breakdown of glycated proteins by disrupting the catalysis of this process through disruptive interactions with the metal ions crucial to the redox reaction. One research study found that pyridoxamine specifically reacts with the carbonyl group in Amadori products, but inhibition of post-Amadori reactions (that can lead to advanced glycation endproducts) is due in much greater part to the metal chelation effects of pyridoxamine.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 524-36-7
  • CAS Registry Number: 85-87-0
  • PubChem: 1052
  • ChEBI: ChEBI:16410
  • HMDB: HMDB0001431
  • KEGG: C00534
  • BioCyc: PYRIDOXAMINE
  • NCBI MeSH: Pyridoxamine
  • Wikipedia: Pyridoxamine
  • DrugBank: DB11673
  • RefMet: RM0136099
  • MoNA: BAF_UVA_POS000210
  • MoNA: BAF_UVA_POS000211
  • MoNA: BAF_UVA_POS000212
  • MoNA: BAF_UVA_POS000213
  • MoNA: BAF_UVA_POS000884
  • MoNA: CCMSLIB00000479731
  • MoNA: CCMSLIB00000577987
  • MoNA: CCMSLIB00000578232
  • MoNA: CCMSLIB00005464185
  • MoNA: CCMSLIB00005464186
  • MoNA: CCMSLIB00005464259
  • MoNA: CCMSLIB00005720429
  • MoNA: CCMSLIB00005720728
  • MoNA: EMBL-MCF_spec120647
  • MoNA: EMBL-MCF_spec120690
  • MoNA: EMBL-MCF_spec120696
  • MoNA: EMBL-MCF_spec50210
  • MoNA: EMBL_MCF_2_0_HRMS_Library000044
  • MoNA: EMBL_MCF_2_0_HRMS_Library000232
  • MoNA: FiehnHILIC000719
  • MoNA: FiehnHILIC001473
  • MoNA: HMDB0001431_c_ms_1667
  • MoNA: HMDB0001431_ms_ms_1574
  • MoNA: HMDB0001431_ms_ms_1575
  • MoNA: HMDB0001431_ms_ms_1576
  • MoNA: KO001725
  • MoNA: KO001726
  • MoNA: KO001727
  • MoNA: KO001728
  • MoNA: KO001729
  • MoNA: MoNA001947
  • MoNA: MoNA001948
  • MoNA: MoNA001949
  • MoNA: MoNA011301
  • MoNA: MoNA011302
  • MoNA: MoNA011303
  • MoNA: MoNA011304
  • MoNA: MoNA016944
  • MoNA: MoNA024127
  • MoNA: MoNA032132
  • MoNA: MoNA032136
  • MoNA: MoNA032139
  • MoNA: MoNA034085
  • MoNA: MoNA034086
  • MoNA: MoNA034087
  • MoNA: MoNA037178
  • MoNA: MoNA_0007602
  • MoNA: MoNA_0007603
  • MoNA: MoNA_0007604
  • MoNA: MoNA_0007605
  • MoNA: MoNA_0007606
  • MoNA: MoNA_0007617
  • MoNA: MoNA_0007984
  • MoNA: MoNA_0007986
  • MoNA: MoNA_0008263
  • MoNA: MoNA_0008264
  • MoNA: MoNA_0008265
  • MoNA: MoNA_0009813
  • MoNA: MoNA_0009814
  • MoNA: MoNA_0009815
  • MoNA: MoNA_0009816
  • MoNA: MoNA_0009822
  • MoNA: OUF00435
  • MoNA: PR010024
  • MoNA: PR100056
  • MoNA: PR100057
  • MoNA: PR100512
  • MoNA: PS009901
  • MoNA: PS009902
  • MoNA: PS009903
  • MoNA: PS009904
  • Metlin: METLIN_238
  • Coconut NaturalProduct: CNP0195117.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01710 1.4.3.5 pyridoxamine:oxygen oxidoreductase (deaminating)
KEGG:R01712 2.6.1.30 pyridoxamine:pyruvate aminotransferase
KEGG:R01713 2.6.1.31 pyridoxamine:oxaloacetate aminotransferase
KEGG:R02493 2.7.1.35 ATP:pyridoxal 5'-phosphotransferase
KEGG:R02494 3.1.3.74 pyridoxamine-5'-phosphate phosphohydrolase
KEGG:R05839 2.6.1.54 pyridoxamine:2-oxoglutarate aminotransferase
BioCyc:TRANS-RXN0-213 PYRIDOXAMINE --> PYRIDOXAMINE
BioCyc:PYROXALTRANSAM-RXN 2.6.1.31 PYRIDOXAMINE + OXALACETIC_ACID<=>PYRIDOXAL + L-ASPARTATE
BioCyc:PYRAMKIN-RXN 2.7.1.35 ATP + PYRIDOXAMINE --> PROTON + ADP + PYRIDOXAMINE-5P
BioCyc:RXN-14203 1.4.3.- PYRIDOXAMINE + OXYGEN-MOLECULE + WATER --> PYRIDOXAL + AMMONIUM + HYDROGEN-PEROXIDE
BioCyc:RXN-14046 3.1.3.74 PYRIDOXAMINE-5P + WATER --> PYRIDOXAMINE + Pi
BioCyc:2.6.1.30-RXN 2.6.1.30 PYRUVATE + PYRIDOXAMINE<=>L-ALPHA-ALANINE + PYRIDOXAL
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Organism Source

Taxonomy Source

  1. Abrus precatorius [ncbi taxid: 3816]
  2. Allium sativum [ncbi taxid: 4682]
  3. Arabidopsis thaliana [ncbi taxid: 3702]
  4. Citrullus lanatus [ncbi taxid: 3654]
  5. Escherichia coli [ncbi taxid: 562]
  6. FOOD SAKE [ncbi taxid: ]
  7. Homo sapiens [ncbi taxid: 9606]
  8. Mus musculus [ncbi taxid: 10090]
  9. Saccharomyces cerevisiae [ncbi taxid: 4932]

Pathway Synthetic

pathway id name
BioCyc:TRYPANO_PYRIDOXAMINEANABOLISM pyridoxamine anabolism
BioCyc:LEISH_PYRIDOXAMINEANABOLISM pyridoxamine anabolism
BioCyc:LEISH_PLPSAL-PWY pyridoxal 5'-phosphate salvage pathway
BioCyc:TRYPANO_PLPSAL-PWY pyridoxal 5'-phosphate salvage pathway
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-OAU-1119534 Pyridoxal 5'-phosphate salvage pathway
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-MES-2867929 Cofactor biosyntheses
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-OMI-1119534 Pyridoxal 5'-phosphate salvage pathway
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-2867929 Cofactor biosyntheses
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-PVU-2744345 Metabolism and regulation
Plant Reactome:R-BRA-1119534 Pyridoxal 5'-phosphate salvage pathway
Plant Reactome:R-OPU-1119534 Pyridoxal 5'-phosphate salvage pathway
Plant Reactome:R-DCA-1119534 Pyridoxal 5'-phosphate salvage pathway
Plant Reactome:R-CCA-2867929 Cofactor biosyntheses
Plant Reactome:R-EGR-1119534 Pyridoxal 5'-phosphate salvage pathway
View All Pathways