Taberyunine D






Names

    • Taberyunine D

Attributes

  • Canonical SMILES

    COC1=C(O)C=C2C(NC3=C(C(OC)=O)C[C@@]4(CC)[C@H]5[C@]32CCN5[C@H](C6=C(OC)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)[C@@H]%12[C@H]4O%12)=C1OC

  • InChI

    InChI=1S/C45H52N4O10/c1-8-42-17-21(38(51)56-6)34-44(11-13-49(40(42)44)37-28(19-42)58-37)23-14-20(27(53-3)16-25(23)46-34)30-33-36(59-33)43(9-2)18-22(39(52)57-7)35-45(10-12-48(30)41(43)45)24-15-26(50)31(54-4)32(55-5)29(24)47-35/h14-16,28,30,33,36-37,40-41,46-47,50H,8-13,17-19H2,1-7H3/t28-,30+,33+,36+,37-,40-,41-,42+,43+,44-,45-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 156.11999999999998
  • #RotBonds: 8
  • MW: 808.9289999999997
  • HBD: 3
  • HBA: 14
  • logP: 4.998500000000005
  • Chemical Formula: C45H52N4O10


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • 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

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) -5.42
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 1198.87
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 157466.09
    Distribution Blood-Brain Barrier (Central Nervous System) -3.26
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.74
    Plasma Protein Binding 46.97
    Steady State Volume of Distribution 2.58
    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 Non-Inhibitor
    Excretion Clearance 5.38
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -3662.03
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.03
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 4.13
    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 -285794400.55
    Rat (Acute) 2.47
    Rat (Chronic Oral) 2.24
    Fathead Minnow 360756.72
    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 32139359.96
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -4.89
    Log(P) 3.57
    Log S -5.13
    Log(Vapor Pressure) -1058246.08
    Melting Point 237.33
    pKa Acid -7661.51
    pKa Basic -33.78