3′-Oxotabernaelegantine C






Names

    • 3′-Oxotabernaelegantine C

Attributes

  • Canonical SMILES

    CC[C@@H]3[C@@H]4C[C@@H]([C@]5=C(NC7=C6CCN(C9=O)C8C(C(OC)=O)7CC9C[C@@H]8CC)C6=CC=C5OC)C2=C(C[C@@H]([C@@H]4C(OC)=O)N(C)C3)C1=CC=CC=C1N2

  • 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: 116.96000000000001
  • #RotBonds: 6
  • MW: 720.9110000000002
  • HBD: 2
  • HBA: 7
  • logP: 6.095400000000007
  • 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) -5.74
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 29.55
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4604.4
    Distribution Blood-Brain Barrier (Central Nervous System) -2.89
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.14
    Plasma Protein Binding 76.09
    Steady State Volume of Distribution 5.63
    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 11.99
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -111.17
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.78
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.11
    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 -8355209.3
    Rat (Acute) 3.03
    Rat (Chronic Oral) 2.56
    Fathead Minnow 10550.88
    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 935913.99
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.62
    Log(P) 5.71
    Log S -5.47
    Log(Vapor Pressure) -30768.15
    Melting Point 283.66
    pKa Acid -181.34
    pKa Basic 6.45