N-Demethylconodurine






Names

    • N-Demethylconodurine
    • NSC289067
    • NSC-289067
    • N-DEMETHYLCONODURINE B640928K297

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](NC/C7=C\C)CC8=C6NC9=CC=CC=C89)C2

  • InChI

    InChI=1S/C42H50N4O5/c1-6-23-16-22-19-42(41(48)51-5)38-27(14-15-46(21-22)39(23)42)26-12-13-33(49-3)35(37(26)45-38)30-17-28-24(7-2)20-43-32(34(28)40(47)50-4)18-29-25-10-8-9-11-31(25)44-36(29)30/h7-13,22-23,28,30,32,34,39,43-45H,6,14-21H2,1-5H3/b24-7+/t22-,23+,28+,30-,32+,34+,39-,42-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 108.68
  • #RotBonds: 5
  • MW: 690.885
  • HBD: 3
  • HBA: 7
  • logP: 6.146700000000005
  • Chemical Formula: C42H50N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. van heurkii Moretti - 1455

External Databases


References

  • Isolation of bis-indole alkaloids with antileishmanial and antibacterial activities from Peschiera van heurkii (syn. Tabernaemontana van heurkii). Planta Med, 1994 (PMID 7997477).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antibacterial
    • Antileishmanial

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) -5.99
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 10.54
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 2136.24
    Distribution Blood-Brain Barrier (Central Nervous System) -3.3
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.44
    Plasma Protein Binding 89.75
    Steady State Volume of Distribution 4.46
    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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 10.24
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -52.23
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.18
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.96
    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 -3876071.75
    Rat (Acute) 2.78
    Rat (Chronic Oral) 2.52
    Fathead Minnow 4894.76
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 432284.18
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.62
    Log(P) 5.44
    Log S -5.61
    Log(Vapor Pressure) -14169.63
    Melting Point 316.01
    pKa Acid -66.63
    pKa Basic 5.63