Taburnaemine A






Names

    • Taburnaemine A
    • CHEMBL4160272

Attributes

  • Canonical SMILES

    C[C@H](O1)[C@]21[C@@]3([H])C[C@@H](C4=C5C(C(CCN([C@@]6(CC(C)=O)[H])[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/C47H56N4O8/c1-8-25-18-26-21-45(43(53)56-6)40-29(15-16-51(41(25)45)33(26)17-23(2)52)28-13-14-34(55-5)37(39(28)49-40)31-19-35-46(44(54)57-7)22-58-42(47(35)24(3)59-47)50(4)36(46)20-30-27-11-9-10-12-32(27)48-38(30)31/h9-14,24-26,31,33,35-36,41-42,48-49H,8,15-22H2,1-7H3/t24-,25-,26+,31-,33+,35-,36-,41-,42-,45+,46-,47-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 138.72
  • #RotBonds: 7
  • MW: 804.9849999999999
  • HBD: 2
  • HBA: 10
  • logP: 5.7743000000000055
  • Chemical Formula: C47H56N4O8


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) -5.51
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 720.16
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 94890.66
    Distribution Blood-Brain Barrier (Central Nervous System) -3.32
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.02
    Plasma Protein Binding 66.15
    Steady State Volume of Distribution 4.04
    Metabolism Breast Cancer Resistance Protein Non-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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 8.68
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -2207.56
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.93
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 4.22
    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 -172218815.19
    Rat (Acute) 3.09
    Rat (Chronic Oral) 1.84
    Fathead Minnow 217391.26
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 19365641.22
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 2.5
    Log(P) 4.58
    Log S -5.61
    Log(Vapor Pressure) -637624.7
    Melting Point 224.46
    pKa Acid -4592.66
    pKa Basic -6.12