10-O-methyl ether, voacangine






Names

    • AE-508/21136051
    • Voacangine
    • 10-O-methyl ether, voacangine

Attributes

  • Canonical SMILES

    CC([H])([H])[C@]1([H])C(N(C2)CC3)[C@](CC2C1)(C(OC)=O)C4=C3C(C=C(OC)C=C5)=C5N4

  • InChI

    InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13?,14-,20?,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.559999999999995
  • #RotBonds: 3
  • MW: 368.4770000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.2638000000000016
  • Chemical Formula: C22H28N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Isolation of 10-hydroxycoronaridine from Tabernaemontana penduliflora and its estrogen-like activity. Planta Med, 2000 (PMID 10763593).

Compound-Protein Relationships


Compound Activities

    • Estrogenic

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) -4.77
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.0
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.52
    Distribution Blood-Brain Barrier (Central Nervous System) -2.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 50.16
    Steady State Volume of Distribution 5.05
    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 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 9.72
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.79
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.06
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.61
    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 -12.78
    Rat (Acute) 2.88
    Rat (Chronic Oral) 2.0
    Fathead Minnow 4.2
    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 451.03
    Hydration Free Energy -5.29
    Log(D) at pH=7.4 3.29
    Log(P) 3.13
    Log S -3.79
    Log(Vapor Pressure) -8.25
    Melting Point 213.85
    pKa Acid 10.16
    pKa Basic 7.61