14-Isovoafoline






Names

    • 14-Isovoafoline
    • CHEMBL4758429

Attributes

  • Canonical SMILES

    CC[C@]1(C[C@@]2([H])C[C@@]3(CN4CC[C@@]56[C@@H]4[C@@]7([C@H]3OCC7)CC(C(OC)=O)=C5NC8=CC=CC=C86)CN9C%10=CC=CC=C%10[C@@]%11(CC%12)[C@]29[H])[C@@H]%11N%12C[C@@H]%13[C@H]1O%13

  • InChI

    InChI=1S/C42H48N4O4/c1-3-39-19-24-18-38(23-46-29-11-7-5-9-27(29)42(32(24)46)13-15-44(35(39)42)21-30-33(39)50-30)22-45-16-12-41-26-8-4-6-10-28(26)43-31(41)25(34(47)48-2)20-40(36(41)45)14-17-49-37(38)40/h4-11,24,30,32-33,35-37,43H,3,12-23H2,1-2H3/t24-,30-,32+,33-,35+,36+,37+,38-,39-,40+,41+,42+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 69.81
  • #RotBonds: 2
  • MW: 672.87
  • HBD: 1
  • HBA: 8
  • logP: 4.832200000000005
  • Chemical Formula: C42H48N4O4


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) -5.52
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 16.96
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 2921.55
    Distribution Blood-Brain Barrier (Central Nervous System) -2.8
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.24
    Plasma Protein Binding 68.26
    Steady State Volume of Distribution 2.98
    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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 5.81
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -72.89
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.33
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.62
    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 -5305363.88
    Rat (Acute) 3.65
    Rat (Chronic Oral) 1.71
    Fathead Minnow 6697.06
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 594425.84
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.05
    Log(P) 4.33
    Log S -4.86
    Log(Vapor Pressure) -19462.07
    Melting Point 292.4
    pKa Acid -102.97
    pKa Basic 8.19