Taberdivarine E






Names

    • Taberdivarine E

Attributes

  • Canonical SMILES

    OC1=C(OC)C=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/C44H52N4O9/c1-7-41-18-22(37(51)55-5)34-43(10-12-48(39(41)43)36-32(20-41)57-36)24-13-21(30(53-3)15-26(24)45-34)28-17-33(50)42(8-2)19-23(38(52)56-6)35-44(9-11-47(28)40(42)44)25-14-29(49)31(54-4)16-27(25)46-35/h13-16,28,32-33,36,39-40,45-46,49-50H,7-12,17-20H2,1-6H3/t28-,32-,33+,36-,39-,40-,41+,42+,43-,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 154.58999999999997
  • #RotBonds: 7
  • MW: 780.919
  • HBD: 4
  • HBA: 13
  • logP: 4.973500000000006
  • Chemical Formula: C44H52N4O9


Species

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

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. J Nat Prod, 2018 (PMID 30169038).
  • 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
    • Antiproliferative
    • 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) -5.85
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 247.18
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 33106.8
    Distribution Blood-Brain Barrier (Central Nervous System) -3.27
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.74
    Plasma Protein Binding 55.44
    Steady State Volume of Distribution 3.05
    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 4.81
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -770.87
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.97
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.86
    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 -60088000.87
    Rat (Acute) 2.51
    Rat (Chronic Oral) 2.46
    Fathead Minnow 75850.0
    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 6753711.37
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.24
    Log(P) 3.6
    Log S -4.81
    Log(Vapor Pressure) -222311.76
    Melting Point 222.37
    pKa Acid -1570.45
    pKa Basic 8.94