22-Demethyl derivative of MMV (methoxy-4-methylvoachalotine)






Names

    • 22-Demethyl derivative of MMV (methoxy-4-methylvoachalotine)

Attributes

  • Canonical SMILES

    COC1=CC=CC2=C1N(C)C3=C2C[C@@H](C4(C(O)=O)CO)[N+](C/5)(C)[C@@]3([H])C[C@@H]4C5=C/C

  • InChI

    InChI=1S/C23H28N2O4/c1-5-13-11-25(3)17-10-16(13)23(12-26,22(27)28)19(25)9-15-14-7-6-8-18(29-4)21(14)24(2)20(15)17/h5-8,16-17,19,26H,9-12H2,1-4H3/p+1/b13-5-/t16-,17+,19+,23?,25?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.69
  • #RotBonds: 3
  • MW: 397.4950000000002
  • HBD: 2
  • HBA: 4
  • logP: 2.6424000000000003
  • Chemical Formula: C23H29N2O4+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. macrocarpa Indonesia 761080 -

External Databases


References

  • 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

    • Antimalarial
    • Cytotoxicity

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) -5.77
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.42
    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) -4.33
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.91
    Plasma Protein Binding 63.75
    Steady State Volume of Distribution 0.97
    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 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 4.0
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.07
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.15
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.64
    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 -25.45
    Rat (Acute) 2.58
    Rat (Chronic Oral) 1.56
    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 472.93
    Hydration Free Energy -6.37
    Log(D) at pH=7.4 -0.43
    Log(P) -0.75
    Log S -1.65
    Log(Vapor Pressure) -12.97
    Melting Point 259.11
    pKa Acid 1.43
    pKa Basic 6.86