4-Pyridoxic acid
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.
Structure for HMDB00017 (4-Pyridoxic acid)
C8H9NO4
183.1614
183.053157781
3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid
pyridoxic acid
82-82-6
HXACOUQIXZGNBF-UHFFFAOYSA-N
This compound belongs to the class of chemical entities known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
Chemical entities
Organic compounds
Organoheterocyclic compounds
Pyridines and derivatives
Pyridinecarboxylic acids
Aromatic heteromonocyclic compounds
Detected and Quantified
Not Available
Not Available
Solid
GC-MS Spectrum – GC-MS (3 TMS)splash10-0600-1594000000-399002a1b2bc22455c9fView in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-4f9434fb63b0ad0ce994View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-0900000000-99753fc7dd56422dd423View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-0900000000-6e2e1f60d8bebc0b3340View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0002-6900000000-8c038db01c62f9d4e87bView in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9200000000-a94133cf31fe1f8b7938View in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-0900000000-d57234d89d8c011abfb4View in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kb-7900000000-a99b8437514399d65abaView in MoNA
LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0900000000-725f61f22b0bc1a28b93View in MoNA
LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-000i-0900000000-79e29b063e250dd7037bView in MoNA
LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-000i-0900000000-f82707706c2653c46393View in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-014i-0900000000-2c70b549625fa141234aView in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0002-0900000000-2a37bda24c0b0f98132bView in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-0002-6900000000-d3f955b006cc32330eddView in MoNA
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-014i-9200000000-8f0fa7a53eb7325318baView in MoNA
LC-MS/MS Spectrum – , positivesplash10-014i-0900000000-df0aa00e8733225ac266View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Normal
Normal
Normal
Normal
Eosinophilic esophagitis
Critically ill
None
None
Not Available
Not Available
Not Available
Not Available
FDB021874
Not Available
6467
C00847
CPD-1112
36190
Not Available
HMDB00017
HMDB00017
239
6723
Not Available
17405
- Huang YC, Lan PH, Cheng CH, Lee BJ, Kan MN: Vitamin B6 intakes and status of mechanically ventilated critically ill patients in Taiwan. Eur J Clin Nutr. 2002 May;56(5):387-92. [PubMed:12001008 ]
- Kodentsova VM, Vrzhesinskaia OA, Sokolnikov AA, Beketova NA, Spirichev VB: [The effect of riboflavin supply on metabolism of water-soluble vitamins]. Vopr Med Khim. 1993 Sep-Oct;39(5):29-33. [PubMed:8279138 ]
- Masse PG, Mahuren JD, Tranchant C, Dosy J: B-6 vitamers and 4-pyridoxic acid in the plasma, erythrocytes, and urine of postmenopausal women. Am J Clin Nutr. 2004 Oct;80(4):946-51. [PubMed:15447904 ]
- Huang YC, Chang HH, Huang SC, Cheng CH, Lee BJ, Cheng SY, Su KH: Plasma pyridoxal 5-phosphate is a significant indicator of immune responses in the mechanically ventilated critically ill. Nutrition. 2005 Jul-Aug;21(7-8):779-85. [PubMed:15975484 ]
- Ericson KL, Mahuren JD, Zubovic YM, Coburn SP: Use of chlorite to improve HPLC detection of pyridoxal 5-phosphate. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 5;823(2):218-20. [PubMed:16054880 ]
- Driskell JA, Chrisley BM: Plasma B-6 vitamer and plasma and urinary 4-pyridoxic acid concentrations in young women as determined using high performance liquid chromatography. Biomed Chromatogr. 1991 Sep;5(5):198-201. [PubMed:1742549 ]
- Chiang EP, Smith DE, Selhub J, Dallal G, Wang YC, Roubenoff R: Inflammation causes tissue-specific depletion of vitamin B6. Arthritis Res Ther. 2005;7(6):R1254-62. Epub 2005 Sep 13. [PubMed:16277678 ]
- Rybak ME, Pfeiffer CM: Clinical analysis of vitamin B(6): determination of pyridoxal 5-phosphate and 4-pyridoxic acid in human serum by reversed-phase high-performance liquid chromatography with chlorite postcolumn derivatization. Anal Biochem. 2004 Oct 15;333(2):336-44. [PubMed:15450810 ]
- Huang YC, Chang SJ, Chiu YT, Chang HH, Cheng CH: The status of plasma homocysteine and related B-vitamins in healthy young vegetarians and nonvegetarians. Eur J Nutr. 2003 Apr;42(2):84-90. [PubMed:12638029 ]
- Midttun O, Hustad S, Solheim E, Schneede J, Ueland PM: Multianalyte quantification of vitamin B6 and B2 species in the nanomolar range in human plasma by liquid chromatography-tandem mass spectrometry. Clin Chem. 2005 Jul;51(7):1206-16. [PubMed:15976101 ]
- Chang SJ, Huang YC, Hsiao LJ, Lee YC, Hsuen SY: Determination of vitamin B-6 estimated average requirement and recommended dietary allowance for children aged 7-12 years using vitamin B-6 intake, nutritional status and anthropometry. J Nutr. 2002 Oct;132(10):3130-4. [PubMed:12368406 ]
Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Not Available
- Gene Name:
- AOX1
- Uniprot ID:
- Q06278
- Molecular weight:
- 147916.735
Reactions
References
- Stanulovic M, Jeremic V, Leskovac V, Chaykin S: New pathway of conversion of pyridoxal to 4-pyridoxic acid. Enzyme. 1976;21(4):357-69. [PubMed:939227 ]