Stebisimine






Names

    • DTXSID70205464', "2H-1,24:12,15-Dietheno-6,10-metheno-16H-pyrido(2',3':17,18)(1,10)dioxacycloeicosino(2,3,4-ij)isoquinoline, 3,5,18,19-tetrahydro-9,21,22,26-tetramethoxy-", '6,20,21,25-tetramethoxy-8,23-dioxa-15,30-diazaheptacyclo(22.6.2.29,12.13,7.114,18.027,31.022,33)hexatriaconta-1(30),3(36),4,6,9(35),10,12(34),14,18,20,22(33),24,26,31-tetradecaene
    • DTXCID70127955
    • 6,20,21,25-tetramethoxy-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-1(30),3(36),4,6,9(35),10,12(34),14,18,20,22(33),24,26,31-tetradecaene
    • 5692-04-6
    • Stebisimine

Attributes

  • Canonical SMILES

    COC1=C2C=C(CC3=NCCC4=CC(=C(C=C43)OC5=C6C(=CC(=C5OC)OC)CCN=C6CC7=CC=C(O2)C=C7)OC)C=C1

  • InChI

    InChI=1S/C36H34N2O6/c1-39-29-10-7-22-16-27-26-20-32(30(40-2)18-23(26)11-13-37-27)44-36-34-24(19-33(41-3)35(36)42-4)12-14-38-28(34)15-21-5-8-25(9-6-21)43-31(29)17-22/h5-10,17-20H,11-16H2,1-4H3

  • Molecule Class: Alkaloids
  • TPSA: 80.10000000000001
  • #RotBonds: 4
  • MW: 590.6760000000004
  • HBD: 0
  • HBA: 8
  • logP: 6.7948000000000075
  • Chemical Formula: C36H34N2O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. johnstonii Kenya - -

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Plant anticancer agents V: new bisindole alkaloids from Tabernaemontana johnstonii stem bark. J Pharm Sci, 1978 (PMID 621649).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Reproducible
    • Xanthine oxidase inhibitory
    • Inhibitory
    • Antileukemic
    • 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) -5.57
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.46
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 43.12
    Distribution Blood-Brain Barrier (Central Nervous System) -2.6
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.67
    Plasma Protein Binding 76.18
    Steady State Volume of Distribution 1.09
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.14
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.68
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.11
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.93
    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 Toxic
    T. Pyriformis -83057.37
    Rat (Acute) 3.37
    Rat (Chronic Oral) 1.43
    Fathead Minnow 121.03
    Respiratory Disease Safe
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 4395.28
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 3.17
    Log(P) 6.13
    Log S -6.08
    Log(Vapor Pressure) -197.2
    Melting Point 216.33
    pKa Acid 9.71
    pKa Basic 8.61