Vobasine






Names

    • C09253
    • Methyl (1R,14R,15E)-15-ethylidene-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate
    • Vobasine
    • 2134-83-0

Attributes

  • Canonical SMILES

    C/C=C\1/CN([C@H]2CC3=C(C(=O)C[C@@H]1[C@@H]2C(=O)OC)NC4=CC=CC=C34)C

  • InChI

    InChI=1S/C21H24N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h4-8,14,17,19,22H,9-11H2,1-3H3/b12-4-/t14-,17-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.4
  • #RotBonds: 1
  • MW: 352.434
  • HBD: 1
  • HBA: 4
  • logP: 2.9625000000000012
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. alba Mexico 761051 132793, 133359, 161424 to 161427
    T. arborea Mexico, Costa Rica 681494 132793, 133359, 161424 to 161427
    T. bufalina China 403123 Cai20170220
    T. catharinensis Brazil 403124 UEC117862
    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. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. holstii Kenya - -
    T. inconspicua Cameroon 761075 NHC61026
    T. laeta Brazil 761076 WAG
    T. officinalis China - Cai20120227
    T. ventricosa Kenya 761103 AM2017/04

External Databases


References

  • Characterization of a Suspension Culture of Tabernaemontana elegans on Growth, Nutrient Uptake, and Accumulation of Indole Alkaloids*. Planta Med, 1989 (PMID 17262332).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).
  • Vobatensines A-F, Cytotoxic Iboga-Vobasine Bisindoles from Tabernaemontana corymbosa. J Nat Prod, 2016 (PMID 26918761).
  • Quantification of Anti-Addictive Alkaloids Ibogaine and Voacangine in In Vivo- and In Vitro-Grown Plants of Two Mexican Tabernaemontana Species. Chem Biodivers, 2016 (PMID 27448833).
  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Monoterpene bisindole alkaloids, from the African medicinal plant Tabernaemontana elegans, induce apoptosis in HCT116 human colon carcinoma cells. J Ethnopharmacol, 2013 (PMID 23872252).
  • A New Antimicrobial Phenylpropanol from the Leaves of Tabernaemontana inconspicua Stapf. (Apocynaceae) Inhibits Pathogenic Gram-Negative Bacteria. Antibiotics (Basel), 2022 (PMID 35052998).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal, 2013 (PMID 23983637).
  • Tertiary indole alkaloids from leaves of Tabernaemontana dichotoma. Planta Med, 1983 (PMID 17404903).
  • Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans. Bioorg Med Chem Lett, 2009 (PMID 19525111).
  • Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc, 2008 (PMID 18797794).
  • Antimycobacterial Activity of Alkaloids and Extracts from Tabernaemontana alba and T. arborea. Planta Med, 2022 (PMID 32392600).
  • Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species. Nat Prod Res, 2022 (PMID 33459049).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Central nervous system activity of a Tabernaemontana arborea alkaloid extract involves serotonergic and opioidergic neurotransmission in murine models. Fitoterapia, 2023 (PMID 37423501).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Plant anticancer agents III: Isolation of indole and bisindole alkaloids from Tabernaemontana holstii roots. J Pharm Sci, 1977 (PMID 561182).
  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).
  • Dichomine, a novel type of iboga alkaloid*,**. Planta Med, 1983 (PMID 17405059).

Compound-Protein Relationships


Compound Activities

    • Antinociceptive
    • Antioxidant
    • Ambulatory
    • Antimicrobial
    • Scavenging
    • Growth inhibitory
    • Convulsive
    • Anticholinesterasic
    • Spasmolytic
    • Inhibitory
    • Antiaddictive
    • Cytotoxicity
    • Apoptosis
    • Reproducible
    • Antimycobacterial
    • Anticancer
    • Xanthine oxidase inhibitory
    • Antidepressant
    • Antileishmanial
    • Acetylbutyrylcholinesterase inhibitory

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) -4.74
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.92
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.64
    Distribution Blood-Brain Barrier (Central Nervous System) -2.04
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.97
    Plasma Protein Binding 62.28
    Steady State Volume of Distribution 4.36
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 15.63
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.71
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.84
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.76
    Micronucleos Toxic
    NR-AhR Toxic
    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 -4.02
    Rat (Acute) 2.75
    Rat (Chronic Oral) 1.86
    Fathead Minnow 4.48
    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 429.25
    Hydration Free Energy -6.9
    Log(D) at pH=7.4 2.44
    Log(P) 2.74
    Log S -3.62
    Log(Vapor Pressure) -9.44
    Melting Point 208.78
    pKa Acid 8.19
    pKa Basic 5.27