Voacristina






Names

    • Voacristina

Attributes

  • Canonical SMILES

    O[C@H](C)[C@@H]4C(N(C5)CC3)[C@](CC5C4)(C(OC)=O)C2=C3C1=C(N2[H])C=CC(OC)=C1

  • InChI

    InChI=1S/C22H28N2O4/c1-12(25)16-8-13-10-22(21(26)28-3)19-15(6-7-24(11-13)20(16)22)17-9-14(27-2)4-5-18(17)23-19/h4-5,9,12-13,16,20,23,25H,6-8,10-11H2,1-3H3/t12-,13?,16-,20?,22-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 74.79
  • #RotBonds: 3
  • MW: 384.4760000000001
  • HBD: 2
  • HBA: 5
  • logP: 2.2346000000000004
  • Chemical Formula: C22H28N2O4


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) -5.2
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.94
    Distribution Blood-Brain Barrier (Central Nervous System) -2.97
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.67
    Plasma Protein Binding 40.75
    Steady State Volume of Distribution 6.16
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.87
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.29
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.94
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.07
    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 -18.86
    Rat (Acute) 2.92
    Rat (Chronic Oral) 2.1
    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 427.32
    Hydration Free Energy -5.74
    Log(D) at pH=7.4 2.43
    Log(P) 1.63
    Log S -3.1
    Log(Vapor Pressure) -8.62
    Melting Point 206.78
    pKa Acid 8.86
    pKa Basic 7.85