19-Acetonylvoacangine






Names

    • 19-Acetonylvoacangine

Attributes

  • Canonical SMILES

    C(OC)(=O)[C@]12[C@]3([N@]([C@H](CC(C)=O)[C@@](C1)(C[C@@H]3CC)[H])CCC4=C2NC=5C4=CC(OC)=CC5)[H]

  • InChI

    InChI=1S/C25H32N2O4/c1-5-15-11-16-13-25(24(29)31-4)22-18(19-12-17(30-3)6-7-20(19)26-22)8-9-27(23(15)25)21(16)10-14(2)28/h6-7,12,15-16,21,23,26H,5,8-11,13H2,1-4H3/t15-,16+,21+,23-,25+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.63
  • #RotBonds: 5
  • MW: 424.5410000000002
  • HBD: 1
  • HBA: 5
  • logP: 3.611500000000002
  • Chemical Formula: C25H32N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. officinalis China - Cai20120227

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • 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

    • Lysosomal acidification
    • 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) -4.71
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.79
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.77
    Distribution Blood-Brain Barrier (Central Nervous System) -3.17
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.99
    Plasma Protein Binding 67.27
    Steady State Volume of Distribution 3.65
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.84
    Organic Cation Transporter 2 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 -1.14
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.83
    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 -83.45
    Rat (Acute) 3.14
    Rat (Chronic Oral) 1.78
    Fathead Minnow 4.14
    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 466.31
    Hydration Free Energy -2.57
    Log(D) at pH=7.4 3.25
    Log(P) 2.69
    Log S -3.83
    Log(Vapor Pressure) -9.17
    Melting Point 211.43
    pKa Acid 9.04
    pKa Basic 6.59