Methuenine






Names

    • CHEBI:141923
    • (3S,7E,8R)-7-ethylidene-5-methyl-5,12-diazatetracyclo[9.7.0.03,8.013,18]octadeca-1(11),13,15,17-tetraen-10-one', "Pyrido(3',4':4,5)cyclohept(1,2-b)indol-6(2H)-one, 4-ethylidene-1,3,4,4a,5,7,12,12a-octahydro-2-methyl-, (4aR-cis)-", '(3S,7E,8R)-7-ethylidene-5-methyl-5,12-diazatetracyclo(9.7.0.03,8.013,18)octadeca-1(11),13,15,17-tetraen-10-one
    • 63425-00-3
    • CHEMBL520722
    • Methuenine

Attributes

  • Canonical SMILES

    C/C=C\1/CN(C[C@@H]2[C@H]1CC(=O)C3=C(C2)C4=CC=CC=C4N3)C

  • InChI

    InChI=1S/C19H22N2O/c1-3-12-10-21(2)11-13-8-16-14-6-4-5-7-17(14)20-19(16)18(22)9-15(12)13/h3-7,13,15,20H,8-11H2,1-2H3/b12-3-/t13-,15+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 36.1
  • #RotBonds: 0
  • MW: 294.39799999999997
  • HBD: 1
  • HBA: 2
  • logP: 3.4209000000000014
  • Chemical Formula: C19H22N2O


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).

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) -4.8
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.94
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.84
    Distribution Blood-Brain Barrier (Central Nervous System) -2.1
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.86
    Plasma Protein Binding 66.75
    Steady State Volume of Distribution 3.9
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 15.28
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 2.08
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.07
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.38
    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 2.26
    Rat (Acute) 2.84
    Rat (Chronic Oral) 1.84
    Fathead Minnow 4.41
    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 394.78
    Hydration Free Energy -8.58
    Log(D) at pH=7.4 2.19
    Log(P) 3.55
    Log S -3.64
    Log(Vapor Pressure) -9.0
    Melting Point 193.31
    pKa Acid 7.93
    pKa Basic 6.98