14,15-Didehydro-10,11-dimethoxyvincamine






Names

    • 14,15-Didehydro-10,11-dimethoxyvincamine

Attributes

  • Canonical SMILES

    O[C@@](C[C@@](CC)4C=CC5)(C(OC)=O)N2C1=CC(OC)=C(OC)C=C1C3=C2C4N5CC3

  • InChI

    InChI=1S/C23H28N2O5/c1-5-22-8-6-9-24-10-7-14-15-11-17(28-2)18(29-3)12-16(15)25(19(14)20(22)24)23(27,13-22)21(26)30-4/h6,8,11-12,20,27H,5,7,9-10,13H2,1-4H3/t20?,22-,23-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 73.16
  • #RotBonds: 4
  • MW: 412.4860000000002
  • HBD: 1
  • HBA: 7
  • logP: 2.745700000000001
  • Chemical Formula: C23H28N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Xanthine oxidase inhibitory

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) -4.68
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.84
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.39
    Distribution Blood-Brain Barrier (Central Nervous System) -2.95
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.9
    Plasma Protein Binding 43.38
    Steady State Volume of Distribution 1.96
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.27
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.83
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.25
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.51
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -51.49
    Rat (Acute) 3.08
    Rat (Chronic Oral) 1.76
    Fathead Minnow 4.4
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 460.11
    Hydration Free Energy -3.75
    Log(D) at pH=7.4 2.42
    Log(P) 2.26
    Log S -2.49
    Log(Vapor Pressure) -8.16
    Melting Point 196.04
    pKa Acid 8.04
    pKa Basic 6.73