Voalenine






Names

    • Voalenine

Attributes

  • Canonical SMILES

    CC[C@]12CC(=O)C3=NC4=CC=CC=C4[C@@]3(CCN(C1)C[C@@H]5[C@H]2O5)O

  • InChI

    InChI=1S/C19H22N2O3/c1-2-18-9-14(22)16-19(23,12-5-3-4-6-13(12)20-16)7-8-21(11-18)10-15-17(18)24-15/h3-6,15,17,23H,2,7-11H2,1H3/t15-,17-,18+,19-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 65.43
  • #RotBonds: 1
  • MW: 326.396
  • HBD: 1
  • HBA: 5
  • logP: 1.8026
  • Chemical Formula: C19H22N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata. Org Biomol Chem, 2003 (PMID 12929658).

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) -5.07
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.76
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.23
    Distribution Blood-Brain Barrier (Central Nervous System) -2.75
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.35
    Plasma Protein Binding 29.0
    Steady State Volume of Distribution 1.83
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 13.03
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.37
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.84
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.55
    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 -3.16
    Rat (Acute) 2.85
    Rat (Chronic Oral) 1.43
    Fathead Minnow 4.03
    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 399.96
    Hydration Free Energy -5.33
    Log(D) at pH=7.4 0.83
    Log(P) 1.12
    Log S -2.2
    Log(Vapor Pressure) -8.65
    Melting Point 189.98
    pKa Acid 5.13
    pKa Basic 6.4