Showing Metabocard for 4-pyridoxate (BASm0001791)
| Common Name | 4-pyridoxate | ||||||
|---|---|---|---|---|---|---|---|
| Description | 4-Pyridoxic acid is a member of the class of compounds known as methylpyridines. More specifically it is a 2-methylpyridine derivative substituted by a hydroxy group at C-3, a carboxy group at C-4, and a hydroxymethyl group at C-5. 4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) and is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced even further in persons with a 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 the enzyme known as 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 (NAD) as a cofactor. | ||||||
| Structure | |||||||
| Molecular Formula | C8H9NO4 | ||||||
| Average Mass | 183.16140 | ||||||
| Monoisotopic Mass | 183.05316 | ||||||
| IUPAC Name | 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid | ||||||
| Traditional Name | Pyridoxic acid | ||||||
| CAS Registry Number | 82-82-6 | ||||||
| SMILES | Cc1ncc(CO)c(C(=O)[O-])c1O | ||||||
| InChI Identifier | InChI=1S/C8H9NO4/c1-4-7(11)6(8(12)13)5(3-10)2-9-4/h2,10-11H,3H2,1H3,(H,12,13) | ||||||
| InChI Key | HXACOUQIXZGNBF-UHFFFAOYSA-N | ||||||
| CHEBI ID | CHEBI:30959 | ||||||
| HMDB ID | HMDB0000017 | ||||||
| Pathways |
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| State | Solid | ||||||
| Water Solubility | 8.71e+00 g/l | ||||||
| logP | -0.08 | ||||||
| logS | -1.32 | ||||||
| pKa (Strongest Acidic) | 2.55 | ||||||
| pKa (Strongest Basic) | 4.09 | ||||||
| Hydrogen Acceptor Count | 5 | ||||||
| Hydrogen Donor Count | 3 | ||||||
| Polar Surface Area | 90.65 Ų | ||||||
| Rotatable Bond Count | 2 | ||||||
| Physiological Charge | -1 | ||||||
| Formal Charge | 0 | ||||||
| Refractivity | 44.55 m³·mol⁻¹ | ||||||
| Polarizability | 17.19 |