Conofoline quinone






Names

    • CHEMBL4552198
    • Conofoline quinone

Attributes

  • Canonical SMILES

    O=C1C=C2[C@@]34[C@@]5([H])N([C@@H]([C@@H]6[C@H]([C@]5(CC(C(OC)=O)=C4N=C2C(OC)=C1OC)CC)O6)C7=CC=C(C8=C7)N([C@@]9([H])CC[C@]%10([C@@]%11([H])[C@]98CCN%11C[C@@H]%12[C@H]%10O%12)CC)C)CC3

  • InChI

    InChI=1S/C43H50N4O7/c1-7-40-12-11-28-42(13-15-46(38(40)42)20-27-35(40)53-27)23-17-21(9-10-25(23)45(28)3)30-33-36(54-33)41(8-2)19-22(37(49)52-6)34-43(14-16-47(30)39(41)43)24-18-26(48)31(50-4)32(51-5)29(24)44-34/h9-10,17-18,27-28,30,33,35-36,38-39H,7-8,11-16,19-20H2,1-6H3/t27-,28+,30-,33-,35-,36-,38+,39+,40-,41-,42+,43+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 108.97
  • #RotBonds: 6
  • MW: 734.8939999999997
  • HBD: 0
  • HBA: 11
  • logP: 4.366400000000003
  • Chemical Formula: C43H50N4O7


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) -5.32
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 124.7
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 17011.67
    Distribution Blood-Brain Barrier (Central Nervous System) -2.91
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 53.8
    Steady State Volume of Distribution 2.13
    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 7.9
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -399.15
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.75
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.55
    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 -30879437.96
    Rat (Acute) 3.91
    Rat (Chronic Oral) 1.63
    Fathead Minnow 38981.53
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 3469834.14
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.07
    Log(P) 2.6
    Log S -4.81
    Log(Vapor Pressure) -114168.88
    Melting Point 256.0
    pKa Acid -781.98
    pKa Basic 6.95