19-Epi-3-oxovoacristine






Names

    • 19-Epi-3-oxovoacristine

Attributes

  • Canonical SMILES

    CO[C@@]([C@](C4N(C5=O)CC3)(CC5CC4[C@H](O)C)C2=C3C1=CC(OC)=CC=C1N2)=O

  • InChI

    InChI=1S/C22H26N2O5/c1-11(25)15-8-12-10-22(21(27)29-3)18-14(6-7-24(19(15)22)20(12)26)16-9-13(28-2)4-5-17(16)23-18/h4-5,9,11-12,15,19,23,25H,6-8,10H2,1-3H3/t11-,12?,15?,19?,22-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 91.85999999999999
  • #RotBonds: 3
  • MW: 398.4590000000001
  • HBD: 2
  • HBA: 5
  • logP: 1.7611999999999992
  • Chemical Formula: C22H26N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. calcarea Madagascar 761054 -

External Databases


References

  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.15
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.06
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.6
    Distribution Blood-Brain Barrier (Central Nervous System) -2.89
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.62
    Plasma Protein Binding 44.55
    Steady State Volume of Distribution 4.8
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor 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 8.46
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.58
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.35
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.44
    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 -30.45
    Rat (Acute) 3.38
    Rat (Chronic Oral) 2.27
    Fathead Minnow 4.08
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 477.54
    Hydration Free Energy -5.82
    Log(D) at pH=7.4 1.92
    Log(P) 1.1
    Log S -3.25
    Log(Vapor Pressure) -8.95
    Melting Point 231.88
    pKa Acid 8.84
    pKa Basic 7.01