19-(2-Oxopropyl)conodurine






Names

    • DTXSID70420418
    • NSC289069
    • CONODURINE, 19-(2-OXOPROPYL)
    • 64192-91-2
    • 19-(2-Oxopropyl)conodurine
    • NSC-289069

Attributes

  • Canonical SMILES

    CC([C@H]1C[C@@H]2C[C@]3(C(OC)=O)[C@H]1[N@@](CCC4=C3NC5=C4C=CC(OC)=C5[C@H]6C[C@@H]7[C@H](C(OC)=O)[C@@H](N(C)C/C7=C/C)CC8=C6NC9=CC=CC=C89)C2)=O

  • InChI

    InChI=1S/C43H50N4O6/c1-7-24-21-46(3)33-18-30-25-10-8-9-11-32(25)44-37(30)31(17-29(24)35(33)41(49)52-5)36-34(51-4)13-12-26-27-14-15-47-20-23-16-28(22(2)48)40(47)43(19-23,42(50)53-6)39(27)45-38(26)36/h7-13,23,28-29,31,33,35,40,44-45H,14-21H2,1-6H3/b24-7-/t23-,28-,29+,31-,33+,35+,40+,43-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 116.96000000000001
  • #RotBonds: 5
  • MW: 718.895
  • HBD: 2
  • HBA: 8
  • logP: 5.667900000000006
  • Chemical Formula: C43H50N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. holstii Kenya - -

External Databases


References

  • Plant anticancer agents III: Isolation of indole and bisindole alkaloids from Tabernaemontana holstii roots. J Pharm Sci, 1977 (PMID 561182).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Reproducible
    • Antiinflammatory
    • Inhibitory
    • Cytotoxicity
    • Acetylcholinesterase 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) -5.93
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 27.71
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4390.46
    Distribution Blood-Brain Barrier (Central Nervous System) -3.58
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.2
    Plasma Protein Binding 87.77
    Steady State Volume of Distribution 4.44
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate 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 Inhibitor
    Excretion Clearance 9.91
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -107.04
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.28
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.82
    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 Safe
    T. Pyriformis -7966073.45
    Rat (Acute) 2.89
    Rat (Chronic Oral) 2.3
    Fathead Minnow 10057.9
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 891999.89
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.05
    Log(P) 4.04
    Log S -5.38
    Log(Vapor Pressure) -29315.47
    Melting Point 302.1
    pKa Acid -172.73
    pKa Basic 5.23