12-Methoxy-4-methylvoachalotine






Names

    • 12-Methoxy-4-methylvoachalotine

Attributes

  • Canonical SMILES

    CN2C1=C(OC)C=CC=C1C3=C2C(CC5\C(C4)=C/C)[N+]4(C)C([C@@](CO)5[C@](OC)=O)C3

  • 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?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 60.690000000000005
  • #RotBonds: 3
  • MW: 411.52200000000016
  • HBD: 1
  • HBA: 5
  • logP: 2.7308000000000003
  • Chemical Formula: C24H31N2O4+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. macrocarpa Indonesia 761080 -

External Databases


References

  • Inhibition of the lethal and myotoxic activities of Crotalus durissus terrificus venom by Tabernaemontana catharinensis: identification of one of the active components. Planta Med, 2000 (PMID 10909261).
  • Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med, 2019 (PMID 31140017).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticrotalic
    • Myotoxicity
    • Antimalarial
    • Lethal
    • Cytotoxicity
    • Antiophidian

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) -5.19
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.75
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.55
    Distribution Blood-Brain Barrier (Central Nervous System) -3.54
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.86
    Plasma Protein Binding 35.76
    Steady State Volume of Distribution 2.68
    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 5.8
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.89
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.26
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.45
    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 -43.82
    Rat (Acute) 3.11
    Rat (Chronic Oral) 1.88
    Fathead Minnow 5.05
    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 498.34
    Hydration Free Energy -4.44
    Log(D) at pH=7.4 2.1
    Log(P) -0.34
    Log S -1.72
    Log(Vapor Pressure) -9.85
    Melting Point 226.61
    pKa Acid 7.12
    pKa Basic 5.77