Voacristina hydroxyindolenina






Names

    • Voacristina hydroxyindolenina

Attributes

  • Canonical SMILES

    O[C@H](C)[C@@H]5C3[C@]4(C(OC)=O)C(C(O)2CCN3CC(C5)C4)=NC1=C2C=C(OC)C=C1

  • InChI

    InChI=1S/C22H28N2O5/c1-12(25)15-8-13-10-21(20(26)29-3)18(15)24(11-13)7-6-22(27)16-9-14(28-2)4-5-17(16)23-19(21)22/h4-5,9,12-13,15,18,25,27H,6-8,10-11H2,1-3H3/t12-,13?,15-,18?,21+,22?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 91.59
  • #RotBonds: 3
  • MW: 400.4750000000002
  • HBD: 2
  • HBA: 7
  • logP: 1.6231999999999993
  • Chemical Formula: C22H28N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).

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) -5.23
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.97
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.16
    Distribution Blood-Brain Barrier (Central Nervous System) -2.7
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.57
    Plasma Protein Binding 49.57
    Steady State Volume of Distribution 2.51
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 3.79
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.33
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.57
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.04
    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 -25.91
    Rat (Acute) 2.93
    Rat (Chronic Oral) 1.87
    Fathead Minnow 4.06
    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 416.75
    Hydration Free Energy -5.27
    Log(D) at pH=7.4 1.67
    Log(P) 0.7
    Log S -2.66
    Log(Vapor Pressure) -8.87
    Melting Point 182.75
    pKa Acid 6.61
    pKa Basic 6.88