Conofoline






Names

    • CHEMBL2409161
    • CONOFOLINE
    • methyl (1R,12S,13S,15R,16R,20R)-12-ethyl-16-((1S,9S,12S,13S,15R,20R)-12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo(10.7.1.01,9.02,7.013,15.017,20)icosa-2(7),3,5-trien-4-yl)-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo(10.7.1.01,9.02,7.013,15.017,20)icosa-2,4,6,9-tetraene-10-carboxylate
    • Conofoline
    • methyl (1R,12S,13S,15R,16R,20R)-12-ethyl-16-[(1S,9S,12S,13S,15R,20R)-12-ethyl-8-methyl-14-oxa-8,17-diazahexacyclo[10.7.1.01,9.02,7.013,15.017,20]icosa-2(7),3,5-trien-4-yl]-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.01,9.02,7.013,15.017,20]icosa-2,4,6,9-tetraene-10-carboxylate

Attributes

  • Canonical SMILES

    CC[C@]12CC[C@H]3[C@@]4([C@H]1N(CC4)C[C@@H]5[C@H]2O5)C6=C(N3C)C=CC(=C6)[C@@H]7[C@@H]8[C@@H](O8)[C@]9(CC(=C1[C@@]2([C@H]9N7CC2)C2=CC(=C(C(=C2N1)OC)OC)O)C(=O)OC)CC

  • InChI

    InChI=1S/C43H52N4O7/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/h9-10,17-18,27-28,30,33,35-36,38-39,44,48H,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: 111.80000000000003
  • #RotBonds: 6
  • MW: 736.9100000000001
  • HBD: 2
  • HBA: 11
  • logP: 4.998200000000005
  • Chemical Formula: C43H52N4O7


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227

External Databases


References

  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata. Org Biomol Chem, 2003 (PMID 12929658).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Conolodinines A-D, Aspidosperma- Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa. J Nat Prod, 2019 (PMID 30869890).
  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Trimeric and dimeric Aspidosperma-type alkaloids from leaves of Tabernaemontana divaricata 'Dwaft'. Bioorg Chem, 2021 (PMID 34500306).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative
    • Cytotoxicity
    • 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) -5.34
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 124.44
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 17013.03
    Distribution Blood-Brain Barrier (Central Nervous System) -3.11
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.86
    Plasma Protein Binding 51.57
    Steady State Volume of Distribution 2.54
    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 7.48
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -397.5
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.0
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 7.32
    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 -30879440.79
    Rat (Acute) 2.66
    Rat (Chronic Oral) 1.54
    Fathead Minnow 38979.35
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 3469744.26
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.89
    Log(P) 3.26
    Log S -5.0
    Log(Vapor Pressure) -114148.1
    Melting Point 231.02
    pKa Acid -788.62
    pKa Basic 8.79