Conophyllidine quinone






Names

    • Conophyllidine quinone

Attributes

  • Canonical SMILES

    [H][C@]12N3CC[C@@]1(C(C4=N5)=CC(C(OC)=C4OC)=O)C5=C(C(OC)=O)C[C@](CC)2[C@@H](O)[C@H]6[C@@H]3C(C=C7C(NC8=C(C[C@@]9([C@]%10([H])[C@@]87CCN%10CC=C9)CC)C(OC)=O)=C%11)=C%11O6

  • InChI

    InChI=1S/C44H48N4O9/c1-7-41-10-9-13-47-14-11-43(39(41)47)24-16-21-28(18-26(24)45-34(43)22(19-41)37(51)55-5)57-33-30(21)48-15-12-44-25-17-27(49)31(53-3)32(54-4)29(25)46-35(44)23(38(52)56-6)20-42(8-2,36(33)50)40(44)48/h9-10,16-18,30,33,36,39-40,45,50H,7-8,11-15,19-20H2,1-6H3/t30-,33+,36-,39+,40+,41+,42-,43+,44+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 148.46
  • #RotBonds: 6
  • MW: 776.8869999999998
  • HBD: 2
  • HBA: 13
  • logP: 4.153800000000003
  • Chemical Formula: C44H48N4O9


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) -5.26
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 362.28
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 48098.96
    Distribution Blood-Brain Barrier (Central Nervous System) -3.04
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.82
    Plasma Protein Binding 71.84
    Steady State Volume of Distribution 2.3
    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 Non-Inhibitor
    Excretion Clearance 5.41
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -1122.6
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.25
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 4.37
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Toxic
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -87300241.68
    Rat (Acute) 2.9
    Rat (Chronic Oral) 2.43
    Fathead Minnow 110202.45
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 9814207.39
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.41
    Log(P) 3.27
    Log S -4.52
    Log(Vapor Pressure) -323111.01
    Melting Point 318.09
    pKa Acid -2290.71
    pKa Basic 8.4