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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:52 UTC
HMDB IDHMDB0001538
Secondary Accession Numbers
  • HMDB01538
Metabolite Identification
Common Name3-Pyridylacetic acid
Description3-Pyridylacetic acid is a breakdown product of nicotine (and other tobacco alkaloids) and is part of the nicotine degradation pathway. It is formed from 4-(3-pyridyl)-butanoate. One alkaloid in particular, myosmine, appears to be a major source for 3-pyridylacetic acid. The alkaloid myosmine is present not only in tobacco products but also in various foods. Myosmine is easily nitrosated, yielding 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB) and the esophageal tobacco carcinogen N'-nitrosonornicotine. The two major metabolites of myosmine metabolism have been identified as 3-pyridylacetic acid (20-26%) and 4-oxo-4-(3-pyridyl)butyric acid (50-60%) (PMID: 16079272 ). 3-pyridylacetatic acid is an analog of nicotinic acid. (PMID 13898750 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC7H7NO2
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
IUPAC Name2-(pyridin-3-yl)acetic acid
Traditional Name3-pyridylacetic acid
CAS Registry Number501-81-5
SMILES
OC(=O)CC1=CN=CC=C1
InChI Identifier
InChI=1S/C7H7NO2/c9-7(10)4-6-2-1-3-8-5-6/h1-3,5H,4H2,(H,9,10)
InChI KeyWGNUNYPERJMVRM-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility58.3 g/LALOGPS
logP0.43ALOGPS
logP-0.59ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.21 m³·mol⁻¹ChemAxon
Polarizability13.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kf-2900000000-aac5c5306dec497de585View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-1900000000-c98d84fdf977d74c2474View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kf-2900000000-aac5c5306dec497de585View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-77c774fbbba55426ddbaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9200000000-805e406695a85dfb497dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-964146db5c3fedc485a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-8f77c7e2475dc6ac6bfeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9000000000-c7a59cf72ca01533f864View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-10149149c6d319e7f980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9700000000-f1b2745c5221401a430cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-32a62918974897c3306fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-4900000000-4f856c8dbfb884e62961View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ko-5900000000-ed528dcebf9acf8cca60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-7900000000-9101833fcccbfe2041c9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.47 +/- 1.55 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022679
KNApSAcK IDNot Available
Chemspider ID106
KEGG Compound IDNot Available
BioCyc ID3-PYRIDYLACETIC-ACID
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6308
PubChem Compound108
PDB IDNot Available
ChEBI ID1220323
References
Synthesis Referenceaquet, Andre; Marison, Ian W.; Meyer, Hans Peter; Von Stockar, Urs. Choice of a method for in situ recovery of 3-pyridylacetic acid formed by biotransformation with Pseudomonas oleovorans. Chimia (1996), 50(9), 426-427.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zwickenpflug W, Tyroller S, Richter E: Metabolism of myosmine in Wistar rats. Drug Metab Dispos. 2005 Nov;33(11):1648-56. Epub 2005 Aug 3. [PubMed:16079272 ]
  2. GINOULHIAC E, TENCONI LT, CHIANCONE FM: 3-Pyridineacetic acid and nicotinic acid: blood levels, urinary elimination and excretion of nicotinic acid derivatives in man. Nature. 1962 Mar 10;193:948-9. [PubMed:13898750 ]