Ibogamine-16-carboxylic acid-17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester






Names

    • Ibogamine-16-carboxylic acid-17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester

Attributes

  • Canonical SMILES

    O=C(C1=C([C@@]2(C(OC)=O)[C@@]3([H])[N@@]4C[C@@H](C[C@@H]3CC)C2)NC5=CC=C(OC)C=C51)C4=O

  • InChI

    InChI=1S/C22H24N2O5/c1-4-12-7-11-9-22(21(27)29-3)18-16(17(25)20(26)24(10-11)19(12)22)14-8-13(28-2)5-6-15(14)23-18/h5-6,8,11-12,19,23H,4,7,9-10H2,1-3H3/t11-,12-,19-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 88.70000000000002
  • #RotBonds: 3
  • MW: 396.4430000000001
  • HBD: 1
  • HBA: 5
  • logP: 2.4306
  • Chemical Formula: C22H24N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. inconspicua Cameroon 761075 NHC61026

External Databases


References

  • A new cytotoxic indole alkaloid from Tabernaemontana inconspicua stapf. Nat Prod Res, 2021 (PMID 31305139).

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) -4.94
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.8
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.87
    Distribution Blood-Brain Barrier (Central Nervous System) -3.24
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.83
    Plasma Protein Binding 58.69
    Steady State Volume of Distribution 2.61
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.7
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.49
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.77
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.32
    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 -33.32
    Rat (Acute) 3.0
    Rat (Chronic Oral) 2.45
    Fathead Minnow 4.03
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 474.41
    Hydration Free Energy -4.84
    Log(D) at pH=7.4 2.66
    Log(P) 2.49
    Log S -4.49
    Log(Vapor Pressure) -8.71
    Melting Point 274.18
    pKa Acid 7.4
    pKa Basic 5.46