3′-Oxotabernaelegantine D






Names

    • 3′-Oxotabernaelegantine D

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2=O)CCC4=C3NC5=C4C=CC(=C5[C@@H]6C[C@H]7[C@@H](CN([C@H]([C@H]7C(=O)OC)CC8=C6NC9=CC=CC=C89)C)CC)OC)C(=O)OC

  • InChI

    InChI=1S/C43H52N4O6/c1-7-22-17-24-20-43(42(50)53-6)38-27(15-16-47(39(22)43)40(24)48)26-13-14-33(51-4)35(37(26)45-38)30-18-28-23(8-2)21-46(3)32(34(28)41(49)52-5)19-29-25-11-9-10-12-31(25)44-36(29)30/h9-14,22-24,28,30,32,34,39,44-45H,7-8,15-21H2,1-6H3/t22-,23+,24+,28-,30-,32-,34-,39-,43+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 116.96000000000002
  • #RotBonds: 6
  • MW: 720.9110000000002
  • HBD: 2
  • HBA: 7
  • logP: 6.095400000000006
  • Chemical Formula: C43H52N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Vobasinyl-Iboga Alkaloids from Tabernaemontana elegans: Cell Cycle Arrest and Apoptosis-Inducing Activity in HCT116 Colon Cancer Cells. J Nat Prod, 2016 (PMID 27704811).

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) -5.86
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 29.48
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4604.55
    Distribution Blood-Brain Barrier (Central Nervous System) -3.4
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.21
    Plasma Protein Binding 89.28
    Steady State Volume of Distribution 5.1
    Metabolism Breast Cancer Resistance Protein 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 Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 11.94
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -111.51
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.44
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.41
    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 -8355210.72
    Rat (Acute) 2.96
    Rat (Chronic Oral) 2.94
    Fathead Minnow 10550.69
    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 935929.61
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.64
    Log(P) 5.52
    Log S -5.36
    Log(Vapor Pressure) -30762.16
    Melting Point 325.39
    pKa Acid -183.1
    pKa Basic 5.02