(-)-Mehranine






Names

    • (-)-Mehranine

Attributes

  • Canonical SMILES

    COC(C3=C2N(C)C1=CC=CC=C1[C@@]52[C@]4([H])[C@]([C@H](O6)[C@H]6CN4CC5)(CC)C3)=O

  • InChI

    InChI=1S/C22H26N2O3/c1-4-21-11-13(19(25)26-3)17-22(14-7-5-6-8-15(14)23(17)2)9-10-24(20(21)22)12-16-18(21)27-16/h5-8,16,18,20H,4,9-12H2,1-3H3/t16-,18-,20+,21-,22+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.31
  • #RotBonds: 2
  • MW: 366.46100000000024
  • HBD: 0
  • HBA: 5
  • logP: 2.4567000000000005
  • Chemical Formula: C22H26N2O3


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).
  • Taberdines L and M, two new alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2022 (PMID 34933610).
  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).

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) -5.0
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.76
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.81
    Distribution Blood-Brain Barrier (Central Nervous System) -2.43
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.36
    Plasma Protein Binding 27.37
    Steady State Volume of Distribution 2.65
    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 Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 13.14
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.2
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.9
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 8.33
    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 -20.54
    Rat (Acute) 3.34
    Rat (Chronic Oral) 1.45
    Fathead Minnow 4.04
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 442.17
    Hydration Free Energy -4.86
    Log(D) at pH=7.4 2.72
    Log(P) 2.26
    Log S -2.65
    Log(Vapor Pressure) -7.86
    Melting Point 161.89
    pKa Acid 5.24
    pKa Basic 6.84