19,20-Didehydroervatamine






Names

    • Methyl (3R,7E,8S)-7-ethylidene-5-methyl-10-oxo-5,12-diazatetracyclo(9.7.0.0,.0,)octadeca-1(11),13,15,17-tetraene-3-carboxylic acid
    • 33228-82-9
    • Methyl (3R,7E,8S)-7-ethylidene-5-methyl-10-oxo-5,12-diazatetracyclo[9.7.0.0,.0,]octadeca-1(11),13,15,17-tetraene-3-carboxylic acid
    • 19,20-Didehydroervatamine
    • methyl (3R,7E,8S)-7-ethylidene-5-methyl-10-oxo-5,12-diazatetracyclo[9.7.0.03,8.013,18]octadeca-1(11),13,15,17-tetraene-3-carboxylate
    • methyl (3R,7E,8S)-7-ethylidene-5-methyl-10-oxo-5,12-diazatetracyclo(9.7.0.03,8.013,18)octadeca-1(11),13,15,17-tetraene-3-carboxylate

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C21H24N2O3/c1-4-13-11-23(2)12-21(20(25)26-3)10-15-14-7-5-6-8-17(14)22-19(15)18(24)9-16(13)21/h4-8,16,22H,9-12H2,1-3H3/b13-4-/t16-,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.400000000000006
  • #RotBonds: 1
  • MW: 352.4340000000001
  • HBD: 1
  • HBA: 4
  • logP: 2.964100000000001
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    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).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • 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) -4.82
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.82
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.54
    Distribution Blood-Brain Barrier (Central Nervous System) -2.07
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.75
    Plasma Protein Binding 55.2
    Steady State Volume of Distribution 5.39
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 14.69
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.36
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.03
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.64
    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 -3.19
    Rat (Acute) 2.92
    Rat (Chronic Oral) 1.85
    Fathead Minnow 4.56
    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 420.95
    Hydration Free Energy -7.26
    Log(D) at pH=7.4 2.59
    Log(P) 2.97
    Log S -3.72
    Log(Vapor Pressure) -8.9
    Melting Point 190.09
    pKa Acid 7.06
    pKa Basic 6.35