Vobatensine C






Names

    • Vobatensine C

Attributes

  • Canonical SMILES

    CC[C@@H]1C2C[C@H](C3=C(C4=CC=CC=C4N3)CC(N(C1)C)[C@@H]2C(OC)=O)C5=CC(N[C@@]67[C@@H]([C@@]8([H])N(CC7)C9)C[C@@]9([H])C[C@@H]8CC)=C(C=C5OC)C6=O

  • InChI

    InChI=1S/C41H52N4O4/c1-6-23-14-22-15-31-38(23)45(20-22)13-12-41(31)39(46)30-19-35(48-4)27(17-33(30)43-41)28-16-26-24(7-2)21-44(3)34(36(26)40(47)49-5)18-29-25-10-8-9-11-32(25)42-37(28)29/h8-11,17,19,22-24,26,28,31,34,36,38,42-43H,6-7,12-16,18,20-21H2,1-5H3/t22-,23+,24+,26?,28+,31-,34?,36-,38+,41+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 86.9
  • #RotBonds: 5
  • MW: 664.8910000000002
  • HBD: 2
  • HBA: 7
  • logP: 6.487500000000007
  • Chemical Formula: C41H52N4O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).
  • Vobatensines A-F, Cytotoxic Iboga-Vobasine Bisindoles from Tabernaemontana corymbosa. J Nat Prod, 2016 (PMID 26918761).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • α-glucosidase inhibitory
    • Butyrylcholinesterase
    • Antimicrobial
    • Growth inhibitory

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) -5.77
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 0.16
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 759.7
    Distribution Blood-Brain Barrier (Central Nervous System) -3.19
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.48
    Plasma Protein Binding 93.8
    Steady State Volume of Distribution 4.76
    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 Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.96
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -17.28
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.88
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.83
    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 -1378581.97
    Rat (Acute) 2.82
    Rat (Chronic Oral) 2.13
    Fathead Minnow 1742.1
    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 152025.28
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.39
    Log(P) 5.51
    Log S -5.0
    Log(Vapor Pressure) -4946.83
    Melting Point 275.01
    pKa Acid -9.61
    pKa Basic 7.32