Taburnaemine I






Names

    • Taburnaemine I

Attributes

  • Canonical SMILES

    OC[C@@]1(C(OC)=O)[C@@](CC2=C([C@@H](C3=C(OC)C=C4C([C@](CCN(C5)[C@]6([H])[C@@]7(C(OC)=O)C[C@@]5([H])C[C@]6([H])CC)(O)C7=N4)=C3)C[C@]/81[H])NC9=C2C=CC=C9)([H])N(C)CC8=C\C

  • InChI

    InChI=1S/C44H54N4O7/c1-7-25-15-24-20-42(40(50)54-5)38(25)48(21-24)14-13-44(52)32-16-28(35(53-4)19-34(32)46-39(42)44)29-17-31-26(8-2)22-47(3)36(43(31,23-49)41(51)55-6)18-30-27-11-9-10-12-33(27)45-37(29)30/h8-12,16,19,24-25,29,31,36,38,45,49,52H,7,13-15,17-18,20-23H2,1-6H3/b26-8-/t24-,25+,29-,31-,36+,38+,42+,43+,44+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 136.92000000000002
  • #RotBonds: 6
  • MW: 750.937
  • HBD: 3
  • HBA: 10
  • logP: 5.2400000000000055
  • Chemical Formula: C44H54N4O7


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Taburnaemines A-I, Cytotoxic Vobasinyl-Iboga-Type Bisindole Alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2018 (PMID 29319316).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative

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) -6.03
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 71.19
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 10078.3
    Distribution Blood-Brain Barrier (Central Nervous System) -3.0
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.13
    Plasma Protein Binding 85.22
    Steady State Volume of Distribution 2.99
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-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 7.02
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -237.92
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.86
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.73
    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 -18290626.29
    Rat (Acute) 2.86
    Rat (Chronic Oral) 2.19
    Fathead Minnow 23090.8
    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 2053310.51
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.7
    Log(P) 4.43
    Log S -4.98
    Log(Vapor Pressure) -67528.85
    Melting Point 266.97
    pKa Acid -441.08
    pKa Basic 5.4