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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-15 04:56:50 UTC
NP-MRD IDNP0000061
Secondary Accession NumbersNone
Natural Product 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
Synonyms
ValueSource
3-PyridylacetateGenerator
2-(3-Pyridyl)acetateHMDB
2-(3-Pyridyl)acetic acidHMDB
2-(Pyridin-3-yl)acetateHMDB
2-(Pyridin-3-yl)acetic acidHMDB
3-CarboxymethylpyridineHMDB
a-(3-Pyridyl)acetateHMDB
a-(3-Pyridyl)acetic acidHMDB
alpha-(3-Pyridyl)acetateHMDB
alpha-(3-Pyridyl)acetic acidHMDB
ColetinHMDB
LessterolHMDB
LioxoneHMDB
MinedilHMDB
PiridilHMDB
PiristerolHMDB
Pyridin-3-ylacetateHMDB
Pyridin-3-ylacetic acidHMDB
ToneonHMDB
2-(3-Pyridine)acetic acidHMDB
3-Pyridineacetic acidHMDB
Chemical FormulaC7H7NO2
Average Mass137.1360 Da
Monoisotopic Mass137.04768 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-07-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)V.dorna832021-08-23View Spectrum
Species
Species of Origin
  • Animalia
  • Chemical Taxonomy
    Description Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
    KingdomOrganic compounds
    Super ClassOrganoheterocyclic compounds
    ClassPyridines and derivatives
    Sub ClassNot Available
    Direct ParentPyridines and derivatives
    Alternative Parents
    Substituents
    • Pyridine
    • Heteroaromatic compound
    • Azacycle
    • Monocarboxylic acid or derivatives
    • Carboxylic acid
    • Carboxylic acid derivative
    • Organic nitrogen compound
    • Organic oxygen compound
    • Organopnictogen compound
    • Organic oxide
    • Hydrocarbon derivative
    • Organooxygen compound
    • Organonitrogen compound
    • Carbonyl group
    • Aromatic heteromonocyclic compound
    Molecular FrameworkAromatic heteromonocyclic compounds
    External Descriptors
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point144 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/3-Pyridineacetic-acid#section=Melting-Point
    Boiling PointNot AvailableNot Available
    Water SolubilityNot AvailableNot Available
    LogPNot AvailableNot Available
    Predicted Properties
    PropertyValueSource
    Water Solubility58.3 g/LALOGPS
    logP10(0.43) g/LALOGPS
    logP10(-0.59) g/LChemAxon
    logS10(-0.37) g/LALOGPS
    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
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0001538
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022679
    KNApSAcK IDNot Available
    Chemspider ID106
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6308
    PubChem Compound108
    PDB IDNot Available
    ChEBI ID86390
    Good Scents IDNot Available
    References
    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 ]
    3. Ganna A, Salihovic S, Sundstrom J, Broeckling CD, Hedman AK, Magnusson PK, Pedersen NL, Larsson A, Siegbahn A, Zilmer M, Prenni J, Arnlov J, Lind L, Fall T, Ingelsson E: Large-scale metabolomic profiling identifies novel biomarkers for incident coronary heart disease. PLoS Genet. 2014 Dec 11;10(12):e1004801. doi: 10.1371/journal.pgen.1004801. eCollection 2014 Dec. [PubMed:25502724 ]
    4. Miyamoto Y, Banno Y, Yamashita T, Fujimoto T, Oi S, Moritoh Y, Asakawa T, Kataoka O, Yashiro H, Takeuchi K, Suzuki N, Ikedo K, Kosaka T, Tsubotani S, Tani A, Sasaki M, Funami M, Amano M, Yamamoto Y, Aertgeerts K, Yano J, Maezaki H: Discovery of a 3-pyridylacetic acid derivative (TAK-100) as a potent, selective and orally active dipeptidyl peptidase IV (DPP-4) inhibitor. J Med Chem. 2011 Feb 10;54(3):831-50. doi: 10.1021/jm101236h. Epub 2011 Jan 10. [PubMed:21218817 ]
    5. Liao X, Zhu J, Rubab M, Feng YL, Poon R: An analytical method for the measurement of acid metabolites of tryptophan-NAD pathway and related acids in urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Apr 15;878(13-14):1003-6. doi: 10.1016/j.jchromb.2010.02.017. Epub 2010 Feb 23. [PubMed:20299289 ]