3-(2-Oxopropyl)voacangine






Names

    • 3-(2-Oxopropyl)voacangine
    • SCHEMBL11959826

Attributes

  • Canonical SMILES

    CC[C@]1([H])C([N@](C2)CC3)[C@](C[C@]2([H])C1)(C(OC)=O)C4=C3C(C=C(OC)C=C5)=C5N4

  • InChI

    InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20?,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.559999999999995
  • #RotBonds: 3
  • MW: 368.4770000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.2638000000000016
  • Chemical Formula: C22H28N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. pauciflora Malaysia 761086 -

External Databases


References

  • Analgesic components from bornean medicinal plants, Tabernaemontana pauciflora Blume and Tabernaemontana pandacaqui Poir. Chem Pharm Bull (Tokyo), 1992 (PMID 1423760).
  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Analgesic
    • 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) -4.78
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.0
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.49
    Distribution Blood-Brain Barrier (Central Nervous System) -2.63
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 58.97
    Steady State Volume of Distribution 5.06
    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 9.69
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.73
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.06
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.57
    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 -14.91
    Rat (Acute) 2.87
    Rat (Chronic Oral) 2.01
    Fathead Minnow 4.03
    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 453.95
    Hydration Free Energy -5.27
    Log(D) at pH=7.4 3.25
    Log(P) 3.19
    Log S -3.81
    Log(Vapor Pressure) -8.27
    Melting Point 230.23
    pKa Acid 10.11
    pKa Basic 7.55