Sarpagan-17-oic acid methyl ester






Names

    • BDBM50480289
    • Sarpagan-17-oic acid, methyl ester
    • CHEMBL518926
    • Sarpagan-17-oic acid methyl ester
    • (2R,6S,12bS,13S)-3-Ethylidene-9-hydroxy-1,2,3,7,12,12b-hexahydro-6H-2,6-methano-indolo[2,3-a]quinolizine-13-carboxylic acid methyl ester

Attributes

  • Canonical SMILES

    C/C=C1C=[N+]2[C@H]3C[C@H]/1[C@H](C(OC)=O)[C@@H]2CC4=C3NC5=C4C=C(O)C=C5

  • InChI

    InChI=1S/C20H20N2O3/c1-3-10-9-22-16-8-14-13-6-11(23)4-5-15(13)21-19(14)17(22)7-12(10)18(16)20(24)25-2/h3-6,9,12,16-18,21H,7-8H2,1-2H3/p+1/b10-3-/t12-,16+,17+,18+/m1/s1

  • Molecule Class: Minor compounds
  • TPSA: 65.33
  • #RotBonds: 1
  • MW: 337.39900000000006
  • HBD: 2
  • HBA: 3
  • logP: 2.6916
  • Chemical Formula: C20H21N2O3+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antioxidant

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -4.92
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.83
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.76
    Distribution Blood-Brain Barrier (Central Nervous System) -2.71
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 58.97
    Steady State Volume of Distribution 5.53
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 13.78
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.32
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.99
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.91
    Micronucleos Toxic
    NR-AhR Toxic
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -2.64
    Rat (Acute) 2.65
    Rat (Chronic Oral) 1.92
    Fathead Minnow 4.35
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 464.55
    Hydration Free Energy -6.77
    Log(D) at pH=7.4 2.24
    Log(P) 1.22
    Log S -2.93
    Log(Vapor Pressure) -9.48
    Melting Point 272.17
    pKa Acid 9.19
    pKa Basic 6.51