3′-(2-Oxopropyl)-19,20-dihydrotabernamine






Names

    • 3′-(2-Oxopropyl)-19,20-dihydrotabernamine

Attributes

  • Canonical SMILES

    [H][C@@]12CC3C[C@H](CC)[C@@H]1N(CCC1=C2NC2=C1C=CC(=C2)[C@@H]1C[C@H]2[C@H](CC)CN(C)[C@@H](CC4=C1NC1=CC=CC=C41)[C@H]2C(=O)OC)[C@@H]3CC(C)=O

  • InChI

    InChI=1S/C43H54N4O3/c1-6-24-17-27-18-34-40-30(14-15-47(42(24)34)37(27)16-23(3)48)29-13-12-26(19-36(29)45-40)32-20-31-25(7-2)22-46(4)38(39(31)43(49)50-5)21-33-28-10-8-9-11-35(28)44-41(32)33/h8-13,19,24-25,27,31-32,34,37-39,42,44-45H,6-7,14-18,20-22H2,1-5H3/t24-,25+,27?,31-,32-,34-,37+,38-,39-,42-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 81.43
  • #RotBonds: 6
  • MW: 674.9300000000002
  • HBD: 2
  • HBA: 5
  • logP: 7.580700000000008
  • Chemical Formula: C43H54N4O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Antiinflammatory
    • Acetylcholinesterase inhibitory

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) -5.9
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 3.17
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 1167.0
    Distribution Blood-Brain Barrier (Central Nervous System) -3.36
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.71
    Plasma Protein Binding 104.51
    Steady State Volume of Distribution 4.25
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 12.0
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -27.79
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.83
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.34
    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 Toxic
    T. Pyriformis -2115859.94
    Rat (Acute) 2.9
    Rat (Chronic Oral) 2.11
    Fathead Minnow 2671.81
    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 234980.1
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.93
    Log(P) 6.14
    Log S -5.86
    Log(Vapor Pressure) -7671.03
    Melting Point 310.55
    pKa Acid -22.07
    pKa Basic 5.76