(3S)-3-Cyanoisovoacangine






Names

    • CHEMBL361668
    • (3S)-3-Cyanoisovoacangine

Attributes

  • Canonical SMILES

    O=C(OC)[C@]12C3=C(CCN(C4C#N)[C@@]1([H])[C@](CC)([H])C[C@@]4([H])C2)C5=CC=C(OC)C=C5N3

  • InChI

    InChI=1S/C23H27N3O3/c1-4-13-9-14-11-23(22(27)29-3)20-17(7-8-26(21(13)23)19(14)12-24)16-6-5-15(28-2)10-18(16)25-20/h5-6,10,13-14,19,21,25H,4,7-9,11H2,1-3H3/t13-,14-,19?,21-,23+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 78.35
  • #RotBonds: 3
  • MW: 393.48700000000014
  • HBD: 1
  • HBA: 5
  • logP: 3.1559800000000005
  • Chemical Formula: C23H27N3O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

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) -5.0
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.88
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.54
    Distribution Blood-Brain Barrier (Central Nervous System) -2.89
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.83
    Plasma Protein Binding 54.77
    Steady State Volume of Distribution 3.49
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate 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 9.2
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.36
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.43
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 8.88
    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 -38.06
    Rat (Acute) 3.04
    Rat (Chronic Oral) 1.86
    Fathead Minnow 4.16
    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 463.57
    Hydration Free Energy -4.48
    Log(D) at pH=7.4 3.11
    Log(P) 2.95
    Log S -3.87
    Log(Vapor Pressure) -9.06
    Melting Point 216.49
    pKa Acid 8.51
    pKa Basic 6.71