(3R/3S)-Ethoxyvoacangine






Names

    • (3R/3S)-Ethoxyvoacangine

Attributes

  • Canonical SMILES

    O=C(OC)[C@]12C3=C(CCN(C4OCC)[C@@]1([H])[C@](CC)([H])C[C@@]4([H])C2)C5=CC(OC)=CC=C5N3

  • InChI

    InChI=1S/C24H32N2O4/c1-5-14-11-15-13-24(23(27)29-4)20-17(9-10-26(21(14)24)22(15)30-6-2)18-12-16(28-3)7-8-19(18)25-20/h7-8,12,14-15,21-22,25H,5-6,9-11,13H2,1-4H3/t14-,15-,21-,22?,24+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 63.79
  • #RotBonds: 5
  • MW: 412.53000000000014
  • HBD: 1
  • HBA: 5
  • logP: 3.626400000000002
  • Chemical Formula: C24H32N2O4


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) -4.64
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.43
    Distribution Blood-Brain Barrier (Central Nervous System) -2.56
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.89
    Plasma Protein Binding 57.91
    Steady State Volume of Distribution 5.12
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.0
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.44
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.78
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.06
    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 -58.96
    Rat (Acute) 3.1
    Rat (Chronic Oral) 2.13
    Fathead Minnow 4.05
    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 458.04
    Hydration Free Energy -2.93
    Log(D) at pH=7.4 3.62
    Log(P) 3.47
    Log S -4.05
    Log(Vapor Pressure) -8.35
    Melting Point 194.39
    pKa Acid 9.49
    pKa Basic 7.15