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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:18:54 UTC
HMDB IDHMDB0000017
Secondary Accession Numbers
  • HMDB00017
Metabolite Identification
Common Name4-Pyridoxic acid
Description4-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
Data?1582752107
Synonyms
ValueSource
2-Methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridineChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylic acidChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinic acidChEBI
4-Pyridoxinecarboxylic acidChEBI
4-Pyridoxinic acidChEBI
4-PyridoxinsaeureChEBI
4-Pyridoxylic acidChEBI
Pyridoxic acidChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylateGenerator
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinateGenerator
4-PyridoxinecarboxylateGenerator
4-PyridoxinateGenerator
4-PyridoxylateGenerator
PyridoxateGenerator
4-PyridoxateGenerator
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 Pyridoxinic acidMeSH, HMDB
Pyridoxinecarboxylic acidMeSH, HMDB
4 Pyridoxylic acidMeSH, HMDB
4 Pyridoxic acidMeSH, HMDB
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
Process
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point247 - 248 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4337 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Astarita_pos130.030932474
[M+H]+MetCCS_test_pos135.29730932474
[M+H]+MetCCS_train_pos135.79730932474
[M-H]-Not Available130.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000363
[M+H]+Not Available136.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00000363
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.95831661259
DarkChem[M-H]-136.70631661259
AllCCS[M+H]+139.14932859911
AllCCS[M-H]-135.64932859911
DeepCCS[M+H]+141.83230932474
DeepCCS[M-H]-139.19730932474
DeepCCS[M-2H]-175.66330932474
DeepCCS[M+Na]+150.88130932474
AllCCS[M+H]+139.132859911
AllCCS[M+H-H2O]+134.932859911
AllCCS[M+NH4]+143.132859911
AllCCS[M+Na]+144.332859911
AllCCS[M-H]-135.632859911
AllCCS[M+Na-2H]-136.532859911
AllCCS[M+HCOO]-137.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Pyridoxic acidCC1=NC=C(CO)C(C(O)=O)=C1O2644.3Standard polar33892256
4-Pyridoxic acidCC1=NC=C(CO)C(C(O)=O)=C1O1768.2Standard non polar33892256
4-Pyridoxic acidCC1=NC=C(CO)C(C(O)=O)=C1O1786.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Pyridoxic acid,1TMS,isomer #1CC1=NC=C(CO[Si](C)(C)C)C(C(=O)O)=C1O1856.0Semi standard non polar33892256
4-Pyridoxic acid,1TMS,isomer #2CC1=NC=C(CO)C(C(=O)O[Si](C)(C)C)=C1O1837.4Semi standard non polar33892256
4-Pyridoxic acid,1TMS,isomer #3CC1=NC=C(CO)C(C(=O)O)=C1O[Si](C)(C)C1805.1Semi standard non polar33892256
4-Pyridoxic acid,2TMS,isomer #1CC1=NC=C(CO[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1O1875.8Semi standard non polar33892256
4-Pyridoxic acid,2TMS,isomer #2CC1=NC=C(CO[Si](C)(C)C)C(C(=O)O)=C1O[Si](C)(C)C1831.9Semi standard non polar33892256
4-Pyridoxic acid,2TMS,isomer #3CC1=NC=C(CO)C(C(=O)O[Si](C)(C)C)=C1O[Si](C)(C)C1863.9Semi standard non polar33892256
4-Pyridoxic acid,3TMS,isomer #1CC1=NC=C(CO[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1O[Si](C)(C)C1952.4Semi standard non polar33892256
4-Pyridoxic acid,1TBDMS,isomer #1CC1=NC=C(CO[Si](C)(C)C(C)(C)C)C(C(=O)O)=C1O2113.2Semi standard non polar33892256
4-Pyridoxic acid,1TBDMS,isomer #2CC1=NC=C(CO)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1O2099.9Semi standard non polar33892256
4-Pyridoxic acid,1TBDMS,isomer #3CC1=NC=C(CO)C(C(=O)O)=C1O[Si](C)(C)C(C)(C)C2064.3Semi standard non polar33892256
4-Pyridoxic acid,2TBDMS,isomer #1CC1=NC=C(CO[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1O2330.2Semi standard non polar33892256
4-Pyridoxic acid,2TBDMS,isomer #2CC1=NC=C(CO[Si](C)(C)C(C)(C)C)C(C(=O)O)=C1O[Si](C)(C)C(C)(C)C2338.8Semi standard non polar33892256
4-Pyridoxic acid,2TBDMS,isomer #3CC1=NC=C(CO)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2350.0Semi standard non polar33892256
4-Pyridoxic acid,3TBDMS,isomer #1CC1=NC=C(CO[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2591.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Pyridoxic acid GC-MS (3 TMS)splash10-0600-1594000000-399002a1b2bc22455c9f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Pyridoxic acid GC-MS (Non-derivatized)splash10-0600-1594000000-399002a1b2bc22455c9f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Pyridoxic acid GC-EI-TOF (Non-derivatized)splash10-0002-0963000000-5ea1f1ffe15dc2478b632017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-0900000000-fa35397acddd7c3351b82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00c0-6029000000-e59f960993866934b8cc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Pyridoxic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-052r-0900000000-725f61f22b0bc1a28b932012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-IT , negative-QTOFsplash10-000i-0900000000-79e29b063e250dd7037b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QTOF , negative-QTOFsplash10-052r-0900000000-725f61f22b0bc1a28b932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid , negative-QTOFsplash10-000i-0900000000-f82707706c2653c463932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 40V, Negative-QTOFsplash10-0a6r-9700000000-fa58efd48543c8e04f3d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-04b546db90e141edd5212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 40V, Negative-QTOFsplash10-0a6r-9600000000-b2bbb5c7f99ffc199cc62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 10V, Negative-QTOFsplash10-000i-0900000000-309ee2ecc1e80a54652e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 35V, Negative-QTOFsplash10-000i-0900000000-90c708594ad220cbb95b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-d679aa0f3db4859ad5132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 10V, Negative-QTOFsplash10-000i-0900000000-f21704b608b74a56193d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 35V, Negative-QTOFsplash10-0a4r-0900000000-13a9a18c3bb0f24ca0062021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 10V, Negative-QTOFsplash10-052r-0900000000-4c3f36d41dab07f05edc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 20V, Negative-QTOFsplash10-0a4r-0900000000-a3b7bf11b4e3095f26a02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 40V, Negative-QTOFsplash10-0a6r-9400000000-319e023e2b64781bb2902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid 30V, Negative-QTOFsplash10-0a4i-3900000000-2324d43e445f717dc0252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-001i-0900000000-4f9434fb63b0ad0ce9942012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-014i-0900000000-99753fc7dd56422dd4232012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0002-0900000000-6e2e1f60d8bebc0b33402012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0002-6900000000-8c038db01c62f9d4e87b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-9200000000-a94133cf31fe1f8b79382012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-00kb-0900000000-d57234d89d8c011abfb42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-00kb-7900000000-a99b8437514399d65aba2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QQ , positive-QTOFsplash10-001i-0900000000-4f9434fb63b0ad0ce9942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Pyridoxic acid LC-ESI-QQ , positive-QTOFsplash10-014i-0900000000-2c70b549625fa141234a2017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
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 but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
    • Analysis of 30 no...
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 but not QuantifiedNot QuantifiedAdult (>18 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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIron deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified5.701 +/- 3.878 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified1414.9 +/- 737.8 umol/mmol creatinineAdult (>18 years old)Both
Critically ill
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021874
KNApSAcK IDC00052160
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
MarkerDB IDMDB00000008
Good Scents IDrw1699441
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 ]