Voacangine hydroxyindolenine






Names

    • methyl 10-hydroxy-17-(1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2,4(9),5,7-tetraene-1-carboxylate
    • Methyl 9,20-dihydroxy-12-methoxy-16,17-didehydro-9,17-dihydroibogamine-18-carboxylate #
    • Voacristine hydroxyindolenine
    • Voacangine hydroxyindolenine
    • Ibogamine-18-carboxylic acid, 16,17-didehydro-9,17-dihydro-9,20-dihydroxy-12-methoxy-, methyl ester, (20S)-
    • 15215-86-8
    • methyl 10-hydroxy-17-(1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2,4(9),5,7-tetraene-1-carboxylate

Attributes

  • Canonical SMILES

    CC[C@@H]1C2[C@]3(C(OC)=O)C4=NC5=C(C=C(OC)C=C5)C4(O)CC[N@]2C[C@@H](C1)C3

  • InChI

    InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(25)28-3)18(14)24(12-13)8-7-22(26)16-10-15(27-2)5-6-17(16)23-19(21)22/h5-6,10,13-14,18,26H,4,7-9,11-12H2,1-3H3/t13-,14-,18?,21-,22?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.36
  • #RotBonds: 3
  • MW: 384.4760000000002
  • HBD: 1
  • HBA: 6
  • logP: 2.652400000000001
  • Chemical Formula: C22H28N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. australis Brazil - ICN-68457
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. laeta Brazil 761076 WAG
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).
  • 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

    • Anticholinesterase
    • Inhibitory
    • Cytotoxicity
    • 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) -5.07
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.94
    Distribution Blood-Brain Barrier (Central Nervous System) -2.35
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.75
    Plasma Protein Binding 57.93
    Steady State Volume of Distribution 2.55
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.22
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.37
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.07
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.05
    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 -19.6
    Rat (Acute) 3.28
    Rat (Chronic Oral) 1.84
    Fathead Minnow 4.08
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 442.26
    Hydration Free Energy -6.0
    Log(D) at pH=7.4 2.45
    Log(P) 2.22
    Log S -3.33
    Log(Vapor Pressure) -8.02
    Melting Point 187.91
    pKa Acid 7.27
    pKa Basic 6.31