Vobtusine






Names

    • 2134-83-0
    • C09253
    • Vobtusine
    • Vobasine
    • Methyl (1R,14R,15E)-15-ethylidene-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate

Attributes

  • Canonical SMILES

    COC1=CC=CC2=C1N3C[C@]4(C[C@H]5[C@]3([C@]26CCN7[C@H]6[C@@]8(C5)CCO[C@H]8CC7)O)CN9CC[C@@]12[C@@H]9[C@@]3([C@H]4OCC3)CC(=C1NC1=CC=CC=C21)C(=O)OC

  • InChI

    InChI=1S/C43H50N4O6/c1-50-30-9-5-7-28-32(30)47-24-38(20-25-21-39-13-18-52-31(39)10-15-45-17-12-42(28,36(39)45)43(25,47)49)23-46-16-11-41-27-6-3-4-8-29(27)44-33(41)26(34(48)51-2)22-40(35(41)46)14-19-53-37(38)40/h3-9,25,31,35-37,44,49H,10-24H2,1-2H3/t25-,31+,35+,36+,37+,38+,39-,40+,41+,42-,43-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 95.97000000000001
  • #RotBonds: 2
  • MW: 718.8950000000001
  • HBD: 2
  • HBA: 10
  • logP: 4.1624000000000025
  • Chemical Formula: C43H50N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pachysiphon Nigeria, Netherlands 403125 HXJ20171220
    T. sphaerocarpa Indonesia 761099 AP070902

External Databases


References

  • Biscarpamontamines A and B, an aspidosperma-iboga bisindole alkaloid and an aspidosperma-aspidosperma bisindole alkaloid, from Tabernaemontana sphaerocarpa. J Nat Prod, 2009 (PMID 19711971).
  • Tabernaesines A-I, Cytotoxic Aspidosperma-Aspidosperma-Type Bisindole Alkaloids from Tabernaemontana pachysiphon. J Nat Prod, 2020 (PMID 33112136).

Compound-Protein Relationships


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) -5.57
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 109.59
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 15054.77
    Distribution Blood-Brain Barrier (Central Nervous System) -2.79
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.15
    Plasma Protein Binding 76.47
    Steady State Volume of Distribution 4.95
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 3.53
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -354.55
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.44
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.45
    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 Toxic
    T. Pyriformis -27325636.35
    Rat (Acute) 3.46
    Rat (Chronic Oral) 2.11
    Fathead Minnow 34493.43
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 3070519.28
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.79
    Log(P) 3.31
    Log S -4.64
    Log(Vapor Pressure) -101002.13
    Melting Point 336.85
    pKa Acid -681.49
    pKa Basic 9.02