2α,7α-Dihydroxydihydrovoaphylline






Names

    • 2α,7α-Dihydroxydihydrovoaphylline

Attributes

  • Canonical SMILES

    CC[C@]12CCC3(O)C(C4=CC=CC=C4N3)(O)CCN(C[C@@H]5[C@H]2O5)C1

  • InChI

    InChI=1S/C19H26N2O3/c1-2-17-7-8-19(23)18(22,13-5-3-4-6-14(13)20-19)9-10-21(12-17)11-15-16(17)24-15/h3-6,15-16,20,22-23H,2,7-12H2,1H3/t15-,16-,17+,18?,19?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 68.25999999999999
  • #RotBonds: 1
  • MW: 330.4280000000001
  • HBD: 3
  • HBA: 5
  • logP: 1.6516
  • Chemical Formula: C19H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. officinalis China - Cai20120227

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).

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) -5.32
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.25
    Distribution Blood-Brain Barrier (Central Nervous System) -3.26
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.52
    Plasma Protein Binding 27.07
    Steady State Volume of Distribution 2.27
    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 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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.17
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.95
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.19
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 6.04
    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 Safe
    T. Pyriformis -2.39
    Rat (Acute) 2.93
    Rat (Chronic Oral) 1.87
    Fathead Minnow 4.09
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 403.42
    Hydration Free Energy -6.82
    Log(D) at pH=7.4 0.81
    Log(P) 1.11
    Log S -2.03
    Log(Vapor Pressure) -9.47
    Melting Point 182.95
    pKa Acid 5.93
    pKa Basic 7.28