12-Methoxy-Nb-methylvoachalotine






Names

    • 12-Methoxy-Nb-methylvoachalotine
    • (4R,19E)-16-(hydroxymethyl)-12,17-dimethoxy-1,4-dimethyl-17-oxosarpagan-4-ium
    • 12-methoxy-Nb-methylvoachalotine
    • 85O

Attributes

  • Canonical SMILES

    C/C=C\1/C[N@+]2([C@H]3C[C@@H]1[C@@]([C@@H]2CC4=C3N(C5=C4C=CC=C5OC)C)(CO)C(=O)OC)C

  • InChI

    InChI=1S/C24H31N2O4/c1-6-14-12-26(3)18-11-17(14)24(13-27,23(28)30-5)20(26)10-16-15-8-7-9-19(29-4)22(15)25(2)21(16)18/h6-9,17-18,20,27H,10-13H2,1-5H3/q+1/b14-6-/t17-,18-,20-,24+,26-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 60.69
  • #RotBonds: 3
  • MW: 411.5220000000002
  • HBD: 1
  • HBA: 5
  • logP: 2.7308000000000012
  • Chemical Formula: C24H31N2O4+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Application of preparative high-speed counter-current chromatography for the separation of two alkaloids from the roots of Tabernaemontana catharinensis (Apocynaceae). Molecules, 2011 (PMID 21892126).
  • Bio-guided search of active indole alkaloids from Tabernaemontana catharinensis: Antitumour activity, toxicity in silico and molecular modelling studies. Bioorg Chem, 2019 (PMID 30599414).
  • Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal, 2013 (PMID 23983637).
  • Conodurine, conoduramine, and ervahanine derivatives from Tabernaemontana corymbosa. Phytochemistry, 2003 (PMID 12809725).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimycobacterial
    • Anticrotalic
    • Antitumoral
    • Analgesic
    • Anticholinesterasic
    • Antitumor
    • Antiinflammatory
    • Antileishmanial
    • Antioxidant
    • Cytotoxicity
    • Trypanocidal
    • Scavenging

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) -5.15
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.74
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.52
    Distribution Blood-Brain Barrier (Central Nervous System) -3.61
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.86
    Plasma Protein Binding 59.4
    Steady State Volume of Distribution 2.7
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 5.64
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.61
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.25
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.39
    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 -44.49
    Rat (Acute) 3.11
    Rat (Chronic Oral) 1.87
    Fathead Minnow 4.51
    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 509.15
    Hydration Free Energy -4.42
    Log(D) at pH=7.4 2.11
    Log(P) -0.15
    Log S -1.77
    Log(Vapor Pressure) -10.16
    Melting Point 238.44
    pKa Acid 7.16
    pKa Basic 5.66