Conopharyngine






Names

    • DTXSID90997354
    • BRN 0060123
    • Conopharyngine
    • 76-98-2
    • methyl (1S,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
    • METHYL (1S,17S,18S)-17-ETHYL-6,7-DIMETHOXY-3,13-DIAZAPENTACYCLO[13.3.1.0(2),(1)?.0?,?.0(1)(3),(1)?]NONADECA-2(10),4,6,8-TETRAENE-1-CARBOXYLATE
    • Conopharyngine (iboga)
    • 18-Carbomethoxy-12,13-dimethoxyibogamine
    • 4-25-00-01286 (Beilstein Handbook Reference)
    • Ibogamine-18-carboxylic acid, 12,13-dimethoxy-, methyl ester

Attributes

  • Canonical SMILES

    CC[C@H]1CC2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)OC)C(=O)OC

  • InChI

    InChI=1S/C23H30N2O4/c1-5-14-8-13-11-23(22(26)29-4)20-15(6-7-25(12-13)21(14)23)16-9-18(27-2)19(28-3)10-17(16)24-20/h9-10,13-14,21,24H,5-8,11-12H2,1-4H3/t13?,14-,21-,23+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 63.790000000000006
  • #RotBonds: 4
  • MW: 398.50300000000016
  • HBD: 1
  • HBA: 5
  • logP: 3.272400000000002
  • Chemical Formula: C23H30N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291
    T. laeta Brazil 761076 WAG

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • 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).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial
    • 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) -4.65
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.01
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.69
    Distribution Blood-Brain Barrier (Central Nervous System) -2.92
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.77
    Plasma Protein Binding 49.83
    Steady State Volume of Distribution 4.2
    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 Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.68
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.56
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.31
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.8
    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 -34.7
    Rat (Acute) 2.89
    Rat (Chronic Oral) 2.02
    Fathead Minnow 4.11
    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 472.72
    Hydration Free Energy -4.22
    Log(D) at pH=7.4 3.11
    Log(P) 2.47
    Log S -3.74
    Log(Vapor Pressure) -8.28
    Melting Point 212.17
    pKa Acid 9.52
    pKa Basic 7.27