Voacinol






Names

    • Voacinol

Attributes

  • Canonical SMILES

    OCC[C@]35CC(C(OC)=O)=C([C@]42[C@H]3N(CC(CCC9=C[C@@]8(CCO)CC(C(OC)=O)=C7NC6=CC=CC=C6[C@@](CC%10)7[C@H]8N%10C9)C5)CC4)NC1=C2C=CC=C1

  • InChI

    InChI=1S/C44H52N4O6/c1-53-37(51)29-23-41(15-19-49)21-27(25-47-17-13-43(39(41)47)31-7-3-5-9-33(31)45-35(29)43)11-12-28-22-42(16-20-50)24-30(38(52)54-2)36-44(14-18-48(26-28)40(42)44)32-8-4-6-10-34(32)46-36/h3-10,21,28,39-40,45-46,49-50H,11-20,22-26H2,1-2H3/t28?,39-,40-,41-,42-,43-,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 123.60000000000001
  • #RotBonds: 9
  • MW: 732.9219999999998
  • HBD: 4
  • HBA: 10
  • logP: 5.001300000000003
  • Chemical Formula: C44H52N4O6


Species

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

External Databases


References

  • Tabernaesines A-I, Cytotoxic Aspidosperma-Aspidosperma-Type Bisindole Alkaloids from Tabernaemontana pachysiphon. J Nat Prod, 2020 (PMID 33112136).

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) -5.58
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 79.51
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 11135.35
    Distribution Blood-Brain Barrier (Central Nervous System) -2.31
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.02
    Plasma Protein Binding 74.88
    Steady State Volume of Distribution 3.55
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 8.61
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -264.01
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.65
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.47
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -20213618.48
    Rat (Acute) 2.79
    Rat (Chronic Oral) 3.0
    Fathead Minnow 25518.75
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 2270021.68
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.78
    Log(P) 3.97
    Log S -4.46
    Log(Vapor Pressure) -74645.14
    Melting Point 204.25
    pKa Acid -485.63
    pKa Basic 7.55