Coronaridine






Names

    • NS00043651
    • NSC 127490
    • (-)-Coronaridine
    • methyl (1S,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
    • CORONARIDINE
    • Ibogamine-18-carboxylic Acid Methyl Ester
    • Coronaridine
    • SCHEMBL2343450
    • DTXSID60963642
    • Coronardine
    • Methyl ibogamine-18-carboxylate
    • HY-121118
    • EINECS 207-398-7
    • FS-8035
    • 467-77-6
    • G13739
    • CS-0079497
    • CHEBI:3887

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC

  • InChI

    InChI=1S/C21H26N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,13-14,19,22H,3,8-12H2,1-2H3/t13-,14-,19-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.33
  • #RotBonds: 2
  • MW: 338.4510000000001
  • HBD: 1
  • HBA: 3
  • logP: 3.255200000000001
  • Chemical Formula: C21H26N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. alba Mexico 761051 132793, 133359, 161424 to 161427
    T. albiflora France - -
    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. 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. heyneana India 2563820 -
    T. holstii Kenya - -
    T. laeta Brazil 761076 WAG
    T. officinalis China - Cai20120227
    T. pauciflora Malaysia 761086 -
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN
    T. psorocarpa Ghana, Ivory Coast 761091 8134
    T. ternifolia Palawan - 2022

External Databases


References

  • A new alkaloid and other anti-implantation principles from Tabernaemontana heyneana. Planta Med, 2001 (PMID 11509989).
  • An iboga alkaloid chemotaxonomic marker from endemic Tabernaemontana ternifolia with antitubercular activity. Nat Prod Res, 2020 (PMID 30773907).
  • 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).
  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).
  • Isolation of 10-hydroxycoronaridine from Tabernaemontana penduliflora and its estrogen-like activity. Planta Med, 2000 (PMID 10763593).
  • 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).
  • [Determination of structures by H NMR at 400 MHz: albifloranine, a new alkaloid from Tabernaemontana albiflora]. Planta Med, 1981 (PMID 17401820).
  • Plant anticancer agents III: Isolation of indole and bisindole alkaloids from Tabernaemontana holstii roots. J Pharm Sci, 1977 (PMID 561182).
  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).
  • Isolation of Coronaridine from the Seeds of Tabernaemontana penduliflora. Planta Med, 1985 (PMID 17342619).
  • 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).
  • 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).
  • Alkaloids from Tabernaemontana psorocarpa. Planta Med, 1983 (PMID 17405098).
  • 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).
  • 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).
  • A new natural auaternary indole alkaloid isolated from Tabernaemontana laeta Mart. (Apocynaceae) Journal of the Brazilian Chemical Society, 2001 (DOI).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • 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).
  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • 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).
  • 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
    • Antimicrobial
    • Antioxidant
    • Ambulatory
    • Antibacterial
    • Apoptotic
    • Convulsive
    • Spasmolytic
    • Inhibitory
    • Antiaddictive
    • Lysosomal acidification
    • Cytotoxicity
    • Cidal
    • Estrogenic
    • Reproducible
    • Antimycobacterial
    • Antifertility
    • Uterotrophic
    • Xanthine oxidase inhibitory
    • Antidepressant
    • Antitumor
    • Acetylcholinesterase inhibitory
    • Acetylbutyrylcholinesterase inhibitory
    • Antituberculosis
    • 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) -4.67
    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 -1.59

    Distribution Blood-Brain Barrier (Central Nervous System) -2.42
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 64.37
    Steady State Volume of Distribution 5.32

    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 9.12
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.32
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.04
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.08
    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 -4.69
    Rat (Acute) 3.0
    Rat (Chronic Oral) 2.07
    Fathead Minnow 3.95
    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 431.05
    Hydration Free Energy -4.34
    Log(D) at pH=7.4 3.23
    Log(P) 2.97
    Log S -3.86
    Log(Vapor Pressure) -8.27
    Melting Point 224.91
    pKa Acid 9.56
    pKa Basic 7.45