Voacangine-7-hydroxyindolenine






Names

    • Voacangine-7-hydroxyindolenine

Attributes

  • Canonical SMILES

    CC[C@@H]1[C@H]2[C@]3(C(OC)=O)C4=NC5=CC=C(OC)C=C5C4(O)CC[N@]2C[C@@H](C1)C3

  • InChI

    InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(25)28-3)18(14)24(12-13)8-7-22(26)16-10-15(27-2)5-6-17(16)23-19(21)22/h5-6,10,13-14,18,26H,4,7-9,11-12H2,1-3H3/t13-,14-,18-,21-,22?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.36
  • #RotBonds: 3
  • MW: 384.4760000000003
  • HBD: 1
  • HBA: 6
  • logP: 2.652400000000001
  • Chemical Formula: C22H28N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. cymosa Colombia 761066 JBC3243
    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).
  • Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq. Molecules, 2021 (PMID 34205626).
  • The Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus Strain. Plants (Basel), 2021 (PMID 34201900).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Antiviral
    • Antiinflammatory
    • Antioxidant
    • 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) -5.04
    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 -1.94
    Distribution Blood-Brain Barrier (Central Nervous System) -2.38
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.75
    Plasma Protein Binding 59.26
    Steady State Volume of Distribution 2.56
    Metabolism Breast Cancer Resistance Protein Non-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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.23
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.5
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.07
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.03
    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 -18.47
    Rat (Acute) 3.29
    Rat (Chronic Oral) 1.84
    Fathead Minnow 3.96
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 445.16
    Hydration Free Energy -6.0
    Log(D) at pH=7.4 2.5
    Log(P) 2.1
    Log S -3.34
    Log(Vapor Pressure) -8.11
    Melting Point 193.66
    pKa Acid 7.24
    pKa Basic 6.2