16′-Decarbomethoxydihydrovoacamine






Names

    • 16′-Decarbomethoxydihydrovoacamine

Attributes

  • Canonical SMILES

    C\C=C3/C4CC(C5=CC(NC7=C6CCN(C9)C8C7C[C@@H]9CC8CC)=C6C=C5OC)C2=C(CC([C@H]4C(OC)=O)N(C)C3)C1=CC=CC=C1N2

  • InChI

    InChI=1S/C41H50N4O3/c1-6-23-14-22-15-32-38-26(12-13-45(20-22)40(23)32)28-19-36(47-4)29(17-34(28)43-38)30-16-27-24(7-2)21-44(3)35(37(27)41(46)48-5)18-31-25-10-8-9-11-33(25)42-39(30)31/h7-11,17,19,22-23,27,30,32,35,37,40,42-43H,6,12-16,18,20-21H2,1-5H3/b24-7-/t22-,23?,27?,30?,32?,35?,37-,40?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 73.59
  • #RotBonds: 4
  • MW: 646.8760000000001
  • HBD: 2
  • HBA: 5
  • logP: 7.161700000000009
  • Chemical Formula: C41H50N4O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Vobatensines A-F, Cytotoxic Iboga-Vobasine Bisindoles from Tabernaemontana corymbosa. J Nat Prod, 2016 (PMID 26918761).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Growth 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) -5.88
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -1.64
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 522.85
    Distribution Blood-Brain Barrier (Central Nervous System) -3.3
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.42
    Plasma Protein Binding 63.41
    Steady State Volume of Distribution 5.68
    Metabolism Breast Cancer Resistance Protein 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 Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.59
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -9.71
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.42
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 8.12
    Micronucleos Toxic
    NR-AhR Safe
    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 -947536.18
    Rat (Acute) 2.81
    Rat (Chronic Oral) 2.17
    Fathead Minnow 1199.72
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 103372.28
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.7
    Log(P) 6.47
    Log S -5.82
    Log(Vapor Pressure) -3374.25
    Melting Point 274.11
    pKa Acid 1.25
    pKa Basic 7.12