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Bovine Metabolome Database



Showing metabocard for 4-Pyridoxic acid (BMDB00017)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-10 13:13:42
Accession Number BMDB00017
Common Name 4-Pyridoxic acid
Description 4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) which is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced in persons with riboflavin deficiency. 4-Pyridoxic acid is formed by the action of aldehyde oxidase I (an endogenous enzyme) and by microbial enzymes (pyridoxal 4-dehydrogenase), an NAD-dependent aldehyde dehydrogenase. 4-pyridoxic acid can be further broken down by the gut microflora via 4-pyridoxic acid dehydrogenase. This enzyme catalyzes the four electron oxidation of 4-pyridoxic acid to 3-hydroxy-2-methylpyridine-4,5-dicarboxylate, using nicotinamide adenine dinucleotide as a cofactor.
Synonyms
  1. 2-Methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridine
  2. 3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylate
  3. 3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylic acid
  4. 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinate
  5. 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinic acid
  6. 3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinsaeure
  7. 3-hydroxy-5-(hydroxymethyl)-2-methyl-Isonicotinate
  8. 3-hydroxy-5-(hydroxymethyl)-2-methyl-Isonicotinic acid
  9. 3-hydroxy-5-hydroxymethyl-2-methyl-isonicotinate
  10. 3-hydroxy-5-hydroxymethyl-2-methyl-isonicotinic acid
  11. 4-Pyridoxate
  12. 4-Pyridoxinate
  13. 4-Pyridoxinecarboxylate
  14. 4-Pyridoxinecarboxylic acid
  15. 4-Pyridoxinic acid
  16. 4-Pyridoxinsaeure
  17. 4-Pyridoxylate
  18. 4-Pyridoxylic acid
Chemical IUPAC Name 3-hydroxy-5-(hydroxymethyl)-2-methyl-pyridine-4-carboxylic acid
Chemical Formula C8H9NO4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Heterocyclic molecules
Class
  • Pyridoxals and Derivatives
Sub Class
  • Miscellaneous pyridoxals
Family
  • Mammalian_Metabolite
Species
  • primary alcohol; phenol or hydroxyhetarene; carboxylic acid; aromatic compound; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 183.161
Monoisotopic Molecular Weight 183.053162
Isomeric SMILES CC1=NC=C(CO)C(C(O)=O)=C1O
Canonical SMILES CC1=NC=C(CO)C(C(O)=O)=C1O
KEGG Compound ID C00847 Link Image
BioCyc ID CPD-1112 Link Image
BiGG ID 36190 Link Image
Wikipedia Link Not Available
METLIN ID 239 Link Image
PubChem Compound 6723 Link Image
PubChem Substance 149703 Link Image
ChEBI ID 17405 Link Image
CAS Registry Number 82-82-6
InChI Identifier InChI=1/C8H9NO4/c1-4-7(11)6(8(12)13)5(3-10)2-9-4/h2,10-11H,3H2,1H3,(H,12,13)
Synthesis Reference Senkuma, Masahiko; Imada, Katsumi; Sato, Masatada. Preparation of 4-pyridoxic acid. Jpn. Kokai Tokkyo Koho (1992), 2 pp.
Melting Point (Experimental) 247-248 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 53.0 mg/mL [MEYLAN,WM et al. (1996)]; 8.71 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.08 [Predicted by ALOGPS]; 0.1 [Predicted by PubChem via XLOGP]; -0.07 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
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2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location Not Available
Tissue Location
Tissue References
Bladder
Erythrocyte
Kidney
Liver
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Vitamin B6 Metabolism
HMDB Pathways
Name Vitamin B6 Metabolism
Image Show Link Image
KEGG Pathways
Name Vitamin B6 Metabolism
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SimCell Pathways
Name Vitamin B6 Metabolism
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Graph
SBML
General References Not Available