Tabernaemine I






Names

    • Tabernaemine I

Attributes

  • Canonical SMILES

    OC[C@@H](C(N(C/1)C)CC2=C(NC3=C2C=CC=C3)[C@@H](CCC1=C/C)C4=CC5=C(C=C4OC)N=C6[C@@]5(CCN7CC8C[C@@](C(OC)=O)6C7[C@H](CC)C8)O)C(OC)=O

  • InChI

    InChI=1S/C44H56N4O7/c1-7-25-13-14-29(38-31(28-11-9-10-12-34(28)45-38)19-36(47(3)22-25)32(24-49)40(50)54-5)30-18-33-35(20-37(30)53-4)46-41-43(42(51)55-6)21-26-17-27(8-2)39(43)48(23-26)16-15-44(33,41)52/h7,9-12,18,20,26-27,29,32,36,39,45,49,52H,8,13-17,19,21-24H2,1-6H3/b25-7+/t26?,27-,29+,32+,36?,39?,43+,44+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 136.92
  • #RotBonds: 7
  • MW: 752.9530000000003
  • HBD: 3
  • HBA: 10
  • logP: 5.630100000000007
  • Chemical Formula: C44H56N4O7


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) -5.82
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 57.79
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 8310.54
    Distribution Blood-Brain Barrier (Central Nervous System) -2.4
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.27
    Plasma Protein Binding 75.75
    Steady State Volume of Distribution 2.26
    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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 5.64
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -197.58
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.84
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.05
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -15083536.14
    Rat (Acute) 2.85
    Rat (Chronic Oral) 1.42
    Fathead Minnow 19043.66
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 1692154.16
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.56
    Log(P) 4.56
    Log S -4.99
    Log(Vapor Pressure) -55654.65
    Melting Point 241.7
    pKa Acid -352.69
    pKa Basic 7.25