Voacristine hydroxyindolenine






Names

    • Methyl 9,20-dihydroxy-12-methoxy-16,17-didehydro-9,17-dihydroibogamine-18-carboxylate #
    • 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
    • Voacristine hydroxyindolenine
    • 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
    • Ibogamine-18-carboxylic acid, 16,17-didehydro-9,17-dihydro-9,20-dihydroxy-12-methoxy-, methyl ester, (20S)-

Attributes

  • Canonical SMILES

    C[C@H](O)[C@]1([H])C[C@]2([H])C[C@@]3(C(OC)=O)[C@]1([H])N(CCC4(O)C3=NC5=C4C=C(OC)C=C5)C2

  • InChI

    InChI=1S/C22H28N2O5/c1-12(25)15-8-13-10-21(20(26)29-3)18(15)24(11-13)7-6-22(27)16-9-14(28-2)4-5-17(16)23-19(21)22/h4-5,9,12-13,15,18,25,27H,6-8,10-11H2,1-3H3/t12-,13+,15-,18+,21+,22?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 91.59
  • #RotBonds: 3
  • MW: 400.4750000000002
  • HBD: 2
  • HBA: 7
  • logP: 1.6231999999999993
  • Chemical Formula: C22H28N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. corymbosa Malaysia, China 1679252 GK604
    T. heyneana India 2563820 -
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • A new alkaloid and other anti-implantation principles from Tabernaemontana heyneana. Planta Med, 2001 (PMID 11509989).
  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).
  • Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal, 2013 (PMID 23983637).
  • 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

  • No relationship found

Compound Activities

    • Scavenging
    • Uterotrophic
    • Lysosomal acidification
    • Antioxidant
    • Anticholinesterasic
    • Cytotoxicity
    • 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) -5.23
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.97
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.14
    Distribution Blood-Brain Barrier (Central Nervous System) -2.73
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.57
    Plasma Protein Binding 51.29
    Steady State Volume of Distribution 2.52
    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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 3.72
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.49
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.56
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.02
    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 -26.71
    Rat (Acute) 2.92
    Rat (Chronic Oral) 1.88
    Fathead Minnow 4.06
    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 419.79
    Hydration Free Energy -5.25
    Log(D) at pH=7.4 1.73
    Log(P) 0.82
    Log S -2.66
    Log(Vapor Pressure) -9.03
    Melting Point 187.75
    pKa Acid 6.62
    pKa Basic 6.71