10,11-Dimethoxy-14,15-didehydrovincanmenine






Names

    • 10,11-Dimethoxy-14,15-didehydrovincanmenine

Attributes

  • Canonical SMILES

    CC[C@@]12C=CCN3[C@]1([H])C4=C(C5=C(C=C(C(OC)=C5)OC)N4C=C2)CC3

  • InChI

    InChI=1S/C21H24N2O2/c1-4-21-7-5-9-22-10-6-14-15-12-17(24-2)18(25-3)13-16(15)23(11-8-21)19(14)20(21)22/h5,7-8,11-13,20H,4,6,9-10H2,1-3H3/t20-,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 26.630000000000003
  • #RotBonds: 3
  • MW: 336.43500000000006
  • HBD: 0
  • HBA: 4
  • logP: 4.008200000000003
  • Chemical Formula: C21H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bovina China, Vietnam 3036760 Cai20150423

External Databases


References

  • Vincan- and eburnan-type alkaloids from Tabernaemontana bovina and their hypoglycemic activity. Phytochemistry, 2021 (PMID 34218044).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Hypoglycemic

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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.54
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.62
    Distribution Blood-Brain Barrier (Central Nervous System) -2.62
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.93
    Plasma Protein Binding 53.29
    Steady State Volume of Distribution 1.95
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.08
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.71
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.05
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.35
    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 -3.62
    Rat (Acute) 3.04
    Rat (Chronic Oral) 1.51
    Fathead Minnow 4.4
    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 445.51
    Hydration Free Energy -5.68
    Log(D) at pH=7.4 3.4
    Log(P) 3.59
    Log S -2.88
    Log(Vapor Pressure) -7.0
    Melting Point 184.63
    pKa Acid 12.13
    pKa Basic 8.52