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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:21:47 UTC
HMDB IDHMDB0000017
Secondary Accession Numbers
  • HMDB00017
Metabolite Identification
Common Name4-Pyridoxic acid
Description4-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
Data?1582752107
Synonyms
ValueSource
2-Methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridineChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinic acidChEBI
4-PyridoxateChEBI
4-Pyridoxinecarboxylic acidChEBI
4-Pyridoxinic acidChEBI
4-Pyridoxylic acidChEBI
Pyridoxic acidChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinateGenerator
4-PyridoxinecarboxylateGenerator
4-PyridoxinateGenerator
4-PyridoxylateGenerator
PyridoxateGenerator
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylateHMDB
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylic acidHMDB
3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinateHMDB
3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinic acidHMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinateHMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinic acidHMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinsaeureHMDB
4-PyridoxinsaeureHMDB
4 Pyridoxinic acidHMDB
Pyridoxinecarboxylic acidHMDB
4 Pyridoxylic acidHMDB
4 Pyridoxic acidHMDB
Chemical FormulaC8H9NO4
Average Molecular Weight183.1614
Monoisotopic Molecular Weight183.053157781
IUPAC Name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid
Traditional Namepyridoxic acid
CAS Registry Number82-82-6
SMILES
CC1=NC=C(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 KeyHXACOUQIXZGNBF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Hydroxypyridine
  • Methylpyridine
  • Vinylogous acid
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic alcohol
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point247 - 248 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.71 g/LALOGPS
logP-0.08ALOGPS
logP-0.75ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.55ChemAxon
pKa (Strongest Basic)4.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.55 m³·mol⁻¹ChemAxon
Polarizability17.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0600-1594000000-399002a1b2bc22455c9fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0600-1594000000-399002a1b2bc22455c9fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0963000000-5ea1f1ffe15dc2478b63Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-0900000000-fa35397acddd7c3351b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00c0-6029000000-e59f960993866934b8ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-4f9434fb63b0ad0ce994Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-0900000000-99753fc7dd56422dd423Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-0900000000-6e2e1f60d8bebc0b3340Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0002-6900000000-8c038db01c62f9d4e87bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9200000000-a94133cf31fe1f8b7938Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-0900000000-d57234d89d8c011abfb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kb-7900000000-a99b8437514399d65abaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0900000000-725f61f22b0bc1a28b93Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0900000000-79e29b063e250dd7037bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-0900000000-725f61f22b0bc1a28b93Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f82707706c2653c46393Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-4f9434fb63b0ad0ce994Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-2c70b549625fa141234aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-2a37bda24c0b0f98132bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-6900000000-d3f955b006cc32330eddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9200000000-8f0fa7a53eb7325318baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0900000000-d57234d89d8c011abfb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-7900000000-a99b8437514399d65abaSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-df0aa00e8733225ac266Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-5860f1285218e1907916Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-0900000000-463662790c3d6c47c8d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-eda84db35c5bfbd25cebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-cdc1e6701650ec6b77f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-fd70f5eeff9dec054259Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-ff1dc4213c27146d1751Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Bladder
  • Erythrocyte
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.027 (0.0062-3.14) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.040 +/- 0.007 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0071 +/- 0.005 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0097 +/- 0.00665 uMAdult (>18 years old)MaleNormal details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00009-0.00300 uMChildren (1-13 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified> 0.33 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.78 +/- 0.45 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.1 (0.4-7.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.975 +/- 2.873 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.157 +/- 0.0613 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected and Quantified0.245 +/- 0.0873 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.407 +/- 0.173 umol/mmol creatinineAdolescent (13-18 years old)FemaleNormal details
UrineDetected and Quantified0.420 +/- 0.187 umol/mmol creatinineAdolescent (13-18 years old)MaleNormal details
UrineDetected and Quantified> 3.0 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified2.99 +/- 5.25 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothIron deficiency details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Children (6 - 18 years old)BothCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified5.701 +/- 3.878 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified1414.9 +/- 737.8 umol/mmol creatinineAdult (>18 years old)Both
Critically ill
details
UrineDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease References
Crohn's disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
  2. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Iron deficiency
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021874
KNApSAcK IDNot Available
Chemspider ID6467
KEGG Compound IDC00847
BioCyc IDCPD-1112
BiGG ID36190
Wikipedia LinkNot Available
METLIN ID239
PubChem Compound6723
PDB IDNot Available
ChEBI ID17405
Food Biomarker OntologyNot Available
VMH ID4PYRDX
References
Synthesis ReferenceSenkuma, Masahiko; Imada, Katsumi; Sato, Masatada. Preparation of 4-pyridoxic acid. Jpn. Kokai Tokkyo Koho (1992), 2 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Kodentsova VM, Vrzhesinskaia OA, Sokol'nikov 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Pyridoxal + Oxygen + Water → 4-Pyridoxic acid + Hydrogen peroxidedetails
References
  1. 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 ]