Voacangine






Names

    • methyl ethyl(methoxy)[?]carboxylate
    • DTXSID50965276
    • 9SY76D3YUK
    • 12-Methoxyibogamine-18-carboxylic acid methyl ester
    • (-)-Voacangine
    • FS-7615
    • UNII-9SY76D3YUK
    • Methyl (1S)-3,13-diaza-17-ethyl-7-methoxypentacyclo[13.3.1.0<2,10>.0<4,9>.0<13,18>]nonadeca-2(10),4,6,8-tetraenecarboxylate
    • Methyl 12-methoxyibogamine-18-carboxylate
    • methyl (6xi)-12-methoxy-2alpha-ibogamine-18-carboxylate
    • Voacangine
    • 12-Methoxyibogamine-18-carboxylate methyl ester
    • 510-22-5
    • 10-METHOXYCORONARIDINE
    • Carbomethoxyibogaine
    • MMAYTCMMKJYIAM-RUGRQLENSA-N
    • Ibogamine-18-carboxylic acid, 12-methoxy-, methyl ester
    • BDBM50329104
    • methyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
    • CHEMBL182120
    • CHEBI:141966
    • methyl (1S,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC

  • InChI

    InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.56
  • #RotBonds: 3
  • MW: 368.4770000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.2638000000000016
  • Chemical Formula: C22H28N2O3


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. australis Brazil - ICN-68457
    T. bufalina China 403123 Cai20170220
    T. calcarea Madagascar 761054 -
    T. catharinensis Brazil 403124 UEC117862
    T. citrifolia Caribbean 141615 C.Sastre/J.Fournet2652
    T. corymbosa Malaysia, China 1679252 GK604
    T. crassa Ghana 761062 20161116
    T. cymosa Colombia 761066 JBC3243
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. heyneana India 2563820 -
    T. inconspicua Cameroon 761075 NHC61026
    T. laeta Brazil 761076 WAG
    T. pauciflora Malaysia 761086 -
    T. psorocarpa Ghana, Ivory Coast 761091 8134

External Databases


References

  • Extraction of indole alkaloids from Tabernaemontana catharinensis using supercritical CO2+ethanol: an evaluation of the process variables and the raw material origin The Journal of Supercritical Fluids, 2004 (DOI).
  • Antioxidant Activity of Methanol Extract of Tinospora crispa and Tabernaemontana corymbosa Sains Malaysiana, 2013 (DOI).
  • New Monoterpenoid Indole Alkaloids from Tabernaemontana crassa Inhibit β-Amyloid42 Production and Phospho-Tau (Thr217). Int J Mol Sci, 2023 (PMID 36675001).
  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).
  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).
  • Virtual Screening of compounds from Tabernaemontana divaricata for potential anti-bacterial activity. Bioinformation, 2014 (PMID 24748755).
  • Antimycobacterial Activity of Alkaloids and Extracts from Tabernaemontana alba and T. arborea. Planta Med, 2022 (PMID 32392600).
  • Tertiary indole alkaloids of Tabernaemontana dichotoma seeds. Planta Med, 1983 (PMID 6635015).
  • 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).
  • Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq. Molecules, 2021 (PMID 34205626).
  • Three New Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2018 (PMID 29754315).
  • Alkaloid studies. 8. Isolation and characterization of alkaloids of Tabernaemontana heyneana Wall and antifertility properties of coronaridine. J Pharm Sci, 1973 (PMID 4714135).
  • Antimycobacterial activity of chemically defined natural substances from the Caribbean flora in Guadeloupe. FEMS Immunol Med Microbiol, 1998 (PMID 9626931).
  • 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).
  • In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res, 2022 (PMID 35075954).
  • Alkaloids from Tabernaemontana psorocarpa. Planta Med, 1983 (PMID 17405098).
  • Monoterpene bisindole alkaloids, from the African medicinal plant Tabernaemontana elegans, induce apoptosis in HCT116 human colon carcinoma cells. J Ethnopharmacol, 2013 (PMID 23872252).
  • Analgesic components from bornean medicinal plants, Tabernaemontana pauciflora Blume and Tabernaemontana pandacaqui Poir. Chem Pharm Bull (Tokyo), 1992 (PMID 1423760).
  • Cytotoxicity and genotoxicity of coronaridine from Tabernaemontana catharinensis A.DC in a human laryngeal epithelial carcinoma cell line (Hep-2). Genet Mol Biol, 2013 (PMID 23569415).
  • 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).
  • 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).
  • Two new monoterpenoid indole alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2019 (PMID 30445827).
  • Effect of an alkaloidal fraction of Tabernaemontana elegans (Stapf.) on selected micro-organisms. J Ethnopharmacol, 2012 (PMID 22313627).
  • A new natural auaternary indole alkaloid isolated from Tabernaemontana laeta Mart. (Apocynaceae) Journal of the Brazilian Chemical Society, 2001 (DOI).
  • A new cytotoxic indole alkaloid from Tabernaemontana inconspicua stapf. Nat Prod Res, 2021 (PMID 31305139).
  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).
  • Tabercarpamines A-J, apoptosis-inducing indole alkaloids from the leaves of Tabernaemontana corymbosa. J Nat Prod, 2014 (PMID 24773071).
  • Plant anticancer agents V: new bisindole alkaloids from Tabernaemontana johnstonii stem bark. J Pharm Sci, 1978 (PMID 621649).
  • Coronaridine, an iboga type alkaloid from Tabernaemontana divaricata, inhibits the Wnt signaling pathway by decreasing β-catenin mRNA expression. Bioorg Med Chem Lett, 2015 (PMID 26231157).
  • Antiviral effect of compounds derived from the seeds of Mammea americana and Tabernaemontana cymosa on Dengue and Chikungunya virus infections. BMC Complement Altern Med, 2017 (PMID 28100218).
  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).

Compound-Protein Relationships

Compound Activities

    • Genotoxicity
    • Analgesic
    • Antiinflammatory
    • Antinociceptive
    • Antioxidant
    • Ambulatory
    • Scavenging
    • Growth inhibitory
    • Antibacterial
    • Apoptotic
    • Antiviral
    • Anticholinesterasic
    • Spasmolytic
    • Inhibitory
    • Antiaddictive
    • Lysosomal acidification
    • Cytotoxicity
    • Cidal
    • Estrogenic
    • Antimycobacterial
    • Antifertility
    • Anticancer
    • Antiproliferative
    • Xanthine oxidase inhibitory
    • Antidepressant
    • Antitumor
    • Acetylcholinesterase inhibitory
    • Acetylbutyrylcholinesterase inhibitory
    • Anticholinesterase

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) -4.71
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.0
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.54

    Distribution Blood-Brain Barrier (Central Nervous System) -2.67
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 57.45
    Steady State Volume of Distribution 5.07

    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor

    Excretion Clearance 9.88
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.29
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.06
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.61
    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 -13.52
    Rat (Acute) 2.86
    Rat (Chronic Oral) 2.02
    Fathead Minnow 3.96
    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 455.72
    Hydration Free Energy -5.34
    Log(D) at pH=7.4 3.3
    Log(P) 3.02
    Log S -3.8
    Log(Vapor Pressure) -8.3
    Melting Point 217.72
    pKa Acid 10.02
    pKa Basic 7.48