Voaphylline






Names

    • Voaphylline
    • voaphylline
    • SCHEMBL6240642

Attributes

  • Canonical SMILES

    CC[C@]12CCC3=C(CCN(C1)C[C@@H]4[C@H]2O4)C5=CC=CC=C5N3

  • InChI

    InChI=1S/C19H24N2O/c1-2-19-9-7-16-14(13-5-3-4-6-15(13)20-16)8-10-21(12-19)11-17-18(19)22-17/h3-6,17-18,20H,2,7-12H2,1H3/t17-,18-,19+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 31.56
  • #RotBonds: 1
  • MW: 296.414
  • HBD: 1
  • HBA: 2
  • logP: 3.136000000000001
  • Chemical Formula: C19H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. chippii Ivory Coast - Lg12291
    T. corymbosa Malaysia, China 1679252 GK604
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227

External Databases


References

  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Comparison of terpenoid indole alkaloid production and degradation in two cell lines of Tabernaemontana divaricata. Plant Cell Rep, 1993 (PMID 24196295).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).
  • Tertiary indole alkaloids of Tabernaemontana dichotoma seeds. Planta Med, 1983 (PMID 6635015).
  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Convulsive
    • Xanthine oxidase inhibitory
    • Spasmolytic
    • Inhibitory
    • Antimicrobial
    • 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) -5.0
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.93
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.32
    Distribution Blood-Brain Barrier (Central Nervous System) -3.1
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.41
    Plasma Protein Binding 32.98
    Steady State Volume of Distribution 2.09
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 14.67
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.36
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.19
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.11
    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 -0.71
    Rat (Acute) 2.53
    Rat (Chronic Oral) 1.4
    Fathead Minnow 4.03
    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 404.89
    Hydration Free Energy -5.4
    Log(D) at pH=7.4 2.55
    Log(P) 3.1
    Log S -2.91
    Log(Vapor Pressure) -7.68
    Melting Point 171.07
    pKa Acid 10.47
    pKa Basic 7.36