Conophyllinine






Names

    • CHEMBL4520335
    • SCHEMBL4166578
    • Conophyllinine

Attributes

  • Canonical SMILES

    CC[C@@]12CC(C(OC)=O)=C3[C@@]4(C5=C(C=C6C([C@H]7[C@H]([C@H](O)[C@]8(CC)CC(C(OC)=O)=C9[C@@]%10(C%11=CC(O)=C(OC)C(OC)=C%11N9)[C@]8([H])N7CC%10)O6)=C5)N3)[C@]1([H])N(C[C@H](O)[C@H]2O)CC4

  • InChI

    InChI=1S/C44H52N4O11/c1-7-41-16-20(37(53)57-5)33-43(9-11-47(39(41)43)18-26(50)35(41)51)22-13-19-27(15-24(22)45-33)59-32-29(19)48-12-10-44-23-14-25(49)30(55-3)31(56-4)28(23)46-34(44)21(38(54)58-6)17-42(8-2,36(32)52)40(44)48/h13-15,26,29,32,35-36,39-40,45-46,49-52H,7-12,16-18H2,1-6H3/t26-,29-,32+,35+,36-,39+,40+,41-,42-,43+,44+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 191.75
  • #RotBonds: 6
  • MW: 812.917
  • HBD: 6
  • HBA: 15
  • logP: 2.9512
  • Chemical Formula: C44H52N4O11


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

  • Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata. Org Biomol Chem, 2003 (PMID 12929658).
  • Conolodinines A-D, Aspidosperma- Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa. J Nat Prod, 2019 (PMID 30869890).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative
    • Growth 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) -6.15
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 792.4
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 104399.7
    Distribution Blood-Brain Barrier (Central Nervous System) -4.05
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.71
    Plasma Protein Binding 65.96
    Steady State Volume of Distribution 1.85
    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 0.88
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -2428.87
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.14
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.71
    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 -189477966.89
    Rat (Acute) 2.65
    Rat (Chronic Oral) 2.4
    Fathead Minnow 239177.11
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 21305728.05
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 0.75
    Log(P) 2.24
    Log S -4.53
    Log(Vapor Pressure) -701493.67
    Melting Point 279.53
    pKa Acid -5051.42
    pKa Basic -8.02