12-Methoxy-voaphylline






Names

    • 12-Methoxy-voaphylline

Attributes

  • Canonical SMILES

    CC[C@]([C@H]4[C@H](O4)C3)(CC5)CN3CCC1=C5NC2=C1C=CC=C2OC

  • InChI

    InChI=1S/C20H26N2O2/c1-3-20-9-7-15-13(8-10-22(12-20)11-17-19(20)24-17)14-5-4-6-16(23-2)18(14)21-15/h4-6,17,19,21H,3,7-12H2,1-2H3/t17-,19-,20+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 40.79
  • #RotBonds: 2
  • MW: 326.44000000000005
  • HBD: 1
  • HBA: 3
  • logP: 3.1446000000000014
  • Chemical Formula: C20H26N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. dichotoma Sri Lanka, Malaysia - -

External Databases


References

  • Chemical Constituents from Tabernaemontana bufalina Lour. Chem Biodivers, 2019 (PMID 30411487).
  • Dichomine, a novel type of iboga alkaloid*,**. Planta Med, 1983 (PMID 17405059).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Spasmolytic
    • Cytotoxicity
    • Convulsive

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) -5.01
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.96
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.39
    Distribution Blood-Brain Barrier (Central Nervous System) -3.12
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.43
    Plasma Protein Binding 26.87
    Steady State Volume of Distribution 2.13
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-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 14.69
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.16
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.08
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.02
    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 -3.73
    Rat (Acute) 2.62
    Rat (Chronic Oral) 1.41
    Fathead Minnow 4.04
    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 416.84
    Hydration Free Energy -5.25
    Log(D) at pH=7.4 2.75
    Log(P) 3.29
    Log S -3.0
    Log(Vapor Pressure) -7.51
    Melting Point 169.18
    pKa Acid 10.37
    pKa Basic 7.47