Taberdivarine D






Names

    • Taberdivarine D

Attributes

  • Canonical SMILES

    OC1=C(OC)C(OC)=C(NC2=C(C(OC)=O)C[C@@]3(CC)[C@H]4[C@]25CC[N@@+]4([O-])[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/C45H54N4O11/c1-8-42-18-22(38(52)58-6)35-44(10-12-48(40(42)44)37-30(20-42)60-37)24-14-21(29(55-3)16-26(24)46-35)27-17-31(51)43(9-2)19-23(39(53)59-7)36-45(11-13-49(27,54)41(43)45)25-15-28(50)33(56-4)34(57-5)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-,49+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 183.64000000000001
  • #RotBonds: 8
  • MW: 826.9439999999998
  • HBD: 4
  • HBA: 14
  • logP: 4.994700000000005
  • Chemical Formula: C45H54N4O11


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).
  • 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) -5.8
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 850.38
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 111922.45
    Distribution Blood-Brain Barrier (Central Nervous System) -4.12
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.47
    Plasma Protein Binding 59.89
    Steady State Volume of Distribution 1.79
    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 5.15
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -2602.49
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.3
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.38
    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 -203136014.12
    Rat (Acute) 2.66
    Rat (Chronic Oral) 3.19
    Fathead Minnow 256419.58
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 22843107.91
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -1.22
    Log(P) 2.76
    Log S -3.95
    Log(Vapor Pressure) -752119.44
    Melting Point 284.52
    pKa Acid -5430.75
    pKa Basic -17.97