Taberdivarine C






Names

    • Taberdivarine C

Attributes

  • Canonical SMILES

    OC1=C(OC)C(OC)=C(NC2=C(C(OC)=O)C[C@@]3(CC)[C@H]4[C@]25CCN4[C@H](C6=C(C=C(NC7=C(C(OC)=O)C[C@@]8(CC)[C@H]9[C@]7%10CCN9[C@H]%11[C@H](O%11)C8)C%10=C6)OC)C[C@H]3O)C5=C1

  • InChI

    InChI=1S/C45H54N4O10/c1-8-42-18-22(38(52)57-6)35-44(11-13-49(40(42)44)37-30(20-42)59-37)24-14-21(29(54-3)16-26(24)46-35)27-17-31(51)43(9-2)19-23(39(53)58-7)36-45(10-12-48(27)41(43)45)25-15-28(50)33(55-4)34(56-5)32(25)47-36/h14-16,27,30-31,37,40-41,46-47,50-51H,8-13,17-20H2,1-7H3/t27-,30+,31+,37+,40-,41-,42+,43+,44-,45-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 163.81999999999996
  • #RotBonds: 8
  • MW: 810.9449999999998
  • HBD: 4
  • HBA: 14
  • logP: 4.982100000000006
  • Chemical Formula: C45H54N4O10


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).
  • Trimeric and dimeric Aspidosperma-type alkaloids from leaves of Tabernaemontana divaricata 'Dwaft'. Bioorg Chem, 2021 (PMID 34500306).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Antiinflammatory
    • Acetylcholinesterase inhibitory

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) -5.73
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 624.96
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 82488.46
    Distribution Blood-Brain Barrier (Central Nervous System) -3.5
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.65
    Plasma Protein Binding 50.93
    Steady State Volume of Distribution 2.62
    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 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 Non-Inhibitor
    Excretion Clearance 4.33
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -1919.33
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.06
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 4.57
    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 -149712534.39
    Rat (Acute) 2.51
    Rat (Chronic Oral) 2.51
    Fathead Minnow 188981.91
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 16833782.85
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 1.7
    Log(P) 3.72
    Log S -4.74
    Log(Vapor Pressure) -554242.69
    Melting Point 213.16
    pKa Acid -3986.91
    pKa Basic -0.01