Taburnaemine D






Names

    • Taburnaemine D

Attributes

  • Canonical SMILES

    C[C@H](O1)[C@]21[C@@]3([H])C[C@@H](C4=C(OC)C=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)(O)C8=N5)=C4)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/C47H56N4O9/c1-8-25-16-26-21-44(42(53)57-6)39(25)51(34(26)15-23(2)52)14-13-46(55)31-17-28(35(56-5)20-33(31)49-40(44)46)29-18-36-45(43(54)58-7)22-59-41(47(36)24(3)60-47)50(4)37(45)19-30-27-11-9-10-12-32(27)48-38(29)30/h9-12,17,20,24-26,29,34,36-37,39,41,48,55H,8,13-16,18-19,21-22H2,1-7H3/t24-,25-,26+,29-,34+,36-,37-,39-,41-,44-,45-,46-,47-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 155.52
  • #RotBonds: 7
  • MW: 820.984
  • HBD: 2
  • HBA: 12
  • logP: 5.162900000000005
  • Chemical Formula: C47H56N4O9


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).
  • 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
    • Lysosomal acidification
    • 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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -5.43
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 1027.04
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 134999.22
    Distribution Blood-Brain Barrier (Central Nervous System) -2.94
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.96
    Plasma Protein Binding 68.83
    Steady State Volume of Distribution 2.9
    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 4.84
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -3139.98
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.35
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 4.08
    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 -245014538.33
    Rat (Acute) 2.95
    Rat (Chronic Oral) 1.46
    Fathead Minnow 309281.42
    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 27552866.23
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -1.66
    Log(P) 3.25
    Log S -4.83
    Log(Vapor Pressure) -907221.11
    Melting Point 236.51
    pKa Acid -6554.11
    pKa Basic -21.78