Taburnaemine C






Names

    • Taburnaemine C
    • CHEMBL4162237

Attributes

  • Canonical SMILES

    C[C@H](O1)[C@]21[C@@]3([H])C[C@@H](C4=C5C(C(CCN(C6=O)[C@]7([H])[C@@]8(C(OC)=O)C[C@@]6([H])C[C@]7([H])CC)=C8N5)=CC=C4OC)C9=C(C[C@]%10([H])N(C)[C@H]2OC[C@@]%103C(OC)=O)C%11=C(N9)C=CC=C%11

  • InChI

    InChI=1S/C44H50N4O8/c1-7-22-16-23-19-42(40(50)53-5)36-26(14-15-48(37(22)42)38(23)49)25-12-13-30(52-4)33(35(25)46-36)28-17-31-43(41(51)54-6)20-55-39(44(31)21(2)56-44)47(3)32(43)18-27-24-10-8-9-11-29(24)45-34(27)28/h8-13,21-23,28,31-32,37,39,45-46H,7,14-20H2,1-6H3/t21-,22-,23+,28-,31-,32-,37-,39-,42+,43-,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 138.72
  • #RotBonds: 5
  • MW: 762.904
  • HBD: 2
  • HBA: 9
  • logP: 4.953200000000004
  • Chemical Formula: C44H50N4O8


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) -5.48
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 190.97
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 25704.35
    Distribution Blood-Brain Barrier (Central Nervous System) -3.23
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.06
    Plasma Protein Binding 65.45
    Steady State Volume of Distribution 4.85
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-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 9.81
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -598.23
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -2.09
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 3.85
    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 -46649946.23
    Rat (Acute) 3.29
    Rat (Chronic Oral) 2.12
    Fathead Minnow 58889.16
    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 5242639.6
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.09
    Log(P) 4.57
    Log S -5.12
    Log(Vapor Pressure) -172575.73
    Melting Point 255.31
    pKa Acid -1210.21
    pKa Basic 8.01