10-Methoxyibogamine






Names

    • HSIBGVUMFOSJPD-NXWOVTFFSA-N
    • 3,13-Diaza-17-ethyl-7-methoxypentacyclo[13.3.1.0<2,10>.0<4,9>.0<13,18>]nonadeca-2(10),4,6,8-tetraene
    • AKOS032948157
    • 10-Methoxyibogamine
    • C09214
    • Ibogamine, 12-methoxy-
    • NSC-249764
    • 83-74-9
    • AC1L9C9B
    • SCHEMBL21333266
    • CHEBI:471972
    • (1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene
    • BDBM50206577
    • IBOGAINE
    • (-)-Ibogaine
    • CHEMBL222287

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC

  • InChI

    InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13-,17-,20-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 28.26
  • #RotBonds: 2
  • MW: 310.441
  • HBD: 1
  • HBA: 2
  • logP: 3.936600000000003
  • Chemical Formula: C20H26N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. calcarea Madagascar 761054 -
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).
  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).

Compound-Protein Relationships


Compound Activities

    • Antioxidant
    • 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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.71
    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 -1.55
    Distribution Blood-Brain Barrier (Central Nervous System) -3.19
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.51
    Plasma Protein Binding 62.2
    Steady State Volume of Distribution 2.55
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.16
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.19
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.02
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.31
    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 -2.02
    Rat (Acute) 3.03
    Rat (Chronic Oral) 1.67
    Fathead Minnow 4.08
    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 409.34
    Hydration Free Energy -4.72
    Log(D) at pH=7.4 3.27
    Log(P) 3.54
    Log S -3.17
    Log(Vapor Pressure) -7.62
    Melting Point 199.12
    pKa Acid 12.81
    pKa Basic 8.63