Taberine D






Names

    • CHEMBL4648833
    • Taberine D

Attributes

  • Canonical SMILES

    C[C@H](O1)[C@]21[C@@]3([H])C[C@@H](C4=CC(C(CC[N@@](C5)[C@@H]6[C@@]7(C(OC)=O)C[C@@]5([H])C[C@@H]6CC)=C7N8)=C8C=C4OC)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/C44H52N4O7/c1-7-24-14-23-19-42(40(49)52-5)37-26(12-13-48(20-23)38(24)42)27-15-28(33(51-4)18-32(27)46-37)29-16-34-43(41(50)53-6)21-54-39(44(34)22(2)55-44)47(3)35(43)17-30-25-10-8-9-11-31(25)45-36(29)30/h8-11,15,18,22-24,29,34-35,38-39,45-46H,7,12-14,16-17,19-21H2,1-6H3/t22-,23+,24-,29-,34-,35-,38-,39-,42+,43-,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 121.65
  • #RotBonds: 5
  • MW: 748.9210000000002
  • HBD: 2
  • HBA: 9
  • logP: 5.426600000000005
  • Chemical Formula: C44H52N4O7


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).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -5.57
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 124.15
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 16966.15
    Distribution Blood-Brain Barrier (Central Nervous System) -3.11
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.08
    Plasma Protein Binding 66.97
    Steady State Volume of Distribution 4.83
    Metabolism Breast Cancer Resistance Protein 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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 10.48
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -396.65
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -2.02
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.23
    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 -30792227.7
    Rat (Acute) 3.19
    Rat (Chronic Oral) 2.15
    Fathead Minnow 38871.14
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 3459526.29
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.72
    Log(P) 4.96
    Log S -5.14
    Log(Vapor Pressure) -113846.29
    Melting Point 261.92
    pKa Acid -783.34
    pKa Basic 8.24