Vobatensine A






Names

    • Vobatensine A

Attributes

  • Canonical SMILES

    C\C=C3/[C@@H]4CC(C5=CC(NC7=C6CCN(C9)C8C7C[C@@H]9CC8[C@H](O)C)=C6C=C5OC)C2=C(CC([C@H]4C(OC)=O)N(C)C3)C1=CC=CC=C1N2

  • InChI

    InChI=1S/C41H50N4O4/c1-6-23-20-44(3)35-17-31-24-9-7-8-10-33(24)42-39(31)30(15-27(23)37(35)41(47)49-5)29-16-34-28(18-36(29)48-4)25-11-12-45-19-22-13-26(21(2)46)40(45)32(14-22)38(25)43-34/h6-10,16,18,21-22,26-27,30,32,35,37,40,42-43,46H,11-15,17,19-20H2,1-5H3/b23-6-/t21-,22+,26?,27+,30?,32?,35?,37+,40?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 93.82000000000002
  • #RotBonds: 4
  • MW: 662.8750000000001
  • HBD: 3
  • HBA: 6
  • logP: 6.1325000000000065
  • Chemical Formula: C41H50N4O4


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) -6.04
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -0.09
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 740.22
    Distribution Blood-Brain Barrier (Central Nervous System) -3.41
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.29
    Plasma Protein Binding 70.27
    Steady State Volume of Distribution 5.35
    Metabolism Breast Cancer Resistance Protein 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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.04
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -16.6
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.48
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.56
    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 -1341938.67
    Rat (Acute) 2.87
    Rat (Chronic Oral) 2.24
    Fathead Minnow 1696.48
    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 147654.89
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.72
    Log(P) 4.81
    Log S -5.45
    Log(Vapor Pressure) -4819.22
    Melting Point 286.95
    pKa Acid -7.04
    pKa Basic 6.88