3,3′-(Oxopropyl)dicoronaridine






Names

    • 3,3′-(Oxopropyl)dicoronaridine

Attributes

  • Canonical SMILES

    O=[C@@](OC)[C@]34C2=C(CCN([C@H]5CC(C[C@H]9N8C%10[C@@]([C@](OC)=O)(C[C@@H]9C[C@@H]%10CC)C7=C(CC8)C6=CC=CC=C6N7)=O)C3[C@H](CC)C[C@H]5C4)C1=CC=CC=C1N2

  • InChI

    InChI=1S/C45H54N4O5/c1-5-25-19-27-23-44(42(51)53-3)38-32(30-11-7-9-13-34(30)46-38)15-17-48(40(25)44)36(27)21-29(50)22-37-28-20-26(6-2)41-45(24-28,43(52)54-4)39-33(16-18-49(37)41)31-12-8-10-14-35(31)47-39/h7-14,25-28,36-37,40-41,46-47H,5-6,15-24H2,1-4H3/t25-,26+,27-,28-,36+,37-,40?,41?,44+,45+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 107.72999999999999
  • #RotBonds: 8
  • MW: 730.95
  • HBD: 2
  • HBA: 7
  • logP: 6.610500000000007
  • Chemical Formula: C45H54N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

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) -5.74
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 77.76
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 10898.37
    Distribution Blood-Brain Barrier (Central Nervous System) -2.95
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.4
    Plasma Protein Binding 84.92
    Steady State Volume of Distribution 4.36
    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 9.69
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -257.8
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -2.0
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.02
    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 -19778639.06
    Rat (Acute) 3.14
    Rat (Chronic Oral) 2.05
    Fathead Minnow 24967.69
    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 2220862.53
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 6.24
    Log(P) 5.47
    Log S -5.75
    Log(Vapor Pressure) -73062.8
    Melting Point 299.8
    pKa Acid -479.35
    pKa Basic 6.99