Conolodinine B






Names

    • Conolodinine B

Attributes

  • Canonical SMILES

    COC1=CC=C2C(NC3=C(C(OC)=O)C[C@@]4(CC)[C@H]5[C@]32CCN5[C@H](C6=C(C=C(NC7=C(C(OC)=O)C[C@@]8(CC)[C@H]9[C@]7%10CCN9[C@@H]%11[C@@H](O%11)C8)C%10=C6)OC)C[C@H]4O)=C1O

  • InChI

    InChI=1S/C44H52N4O9/c1-7-41-18-22(37(51)55-5)34-44(12-14-48(39(41)44)36-30(20-41)57-36)25-15-21(29(54-4)16-26(25)45-34)27-17-31(49)42(8-2)19-23(38(52)56-6)35-43(11-13-47(27)40(42)43)24-9-10-28(53-3)33(50)32(24)46-35/h9-10,15-16,27,30-31,36,39-40,45-46,49-50H,7-8,11-14,17-20H2,1-6H3/t27-,30-,31+,36-,39-,40-,41+,42+,43-,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 154.58999999999997
  • #RotBonds: 7
  • MW: 780.9190000000001
  • HBD: 4
  • HBA: 13
  • logP: 4.973500000000006
  • Chemical Formula: C44H52N4O9


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

  • 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).
  • 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

    • Cytotoxicity
    • 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) -5.79
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 256.35
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 34303.6
    Distribution Blood-Brain Barrier (Central Nervous System) -3.36
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.8
    Plasma Protein Binding 55.32
    Steady State Volume of Distribution 2.77
    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 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 4.28
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -798.43
    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 5.7
    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 -62259306.28
    Rat (Acute) 2.57
    Rat (Chronic Oral) 2.46
    Fathead Minnow 78590.7
    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 6997863.26
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.4
    Log(P) 3.6
    Log S -4.77
    Log(Vapor Pressure) -230354.29
    Melting Point 218.87
    pKa Acid -1629.23
    pKa Basic 9.34