(3S)-3-Cyanocoronaridine






Names

    • (3S)-3-Cyanocoronaridine
    • CHEMBL360591

Attributes

  • Canonical SMILES

    O=C(OC)[C@]12C3=C(CCN(C4C#N)[C@@]1([H])[C@](CC)([H])C[C@@]4([H])C2)C5=CC=CC=C5N3

  • InChI

    InChI=1S/C22H25N3O2/c1-3-13-10-14-11-22(21(26)27-2)19-16(15-6-4-5-7-17(15)24-19)8-9-25(20(13)22)18(14)12-23/h4-7,13-14,18,20,24H,3,8-11H2,1-2H3/t13-,14-,18?,20-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 69.12
  • #RotBonds: 2
  • MW: 363.46100000000007
  • HBD: 1
  • HBA: 4
  • logP: 3.147380000000001
  • Chemical Formula: C22H25N3O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

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) -4.82
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.8
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.5
    Distribution Blood-Brain Barrier (Central Nervous System) -2.87
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.83
    Plasma Protein Binding 61.33
    Steady State Volume of Distribution 3.52
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.89
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.42
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.63
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.67
    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 -15.55
    Rat (Acute) 3.17
    Rat (Chronic Oral) 1.82
    Fathead Minnow 4.13
    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 441.5
    Hydration Free Energy -5.55
    Log(D) at pH=7.4 3.05
    Log(P) 2.9
    Log S -3.67
    Log(Vapor Pressure) -8.81
    Melting Point 211.41
    pKa Acid 8.25
    pKa Basic 6.52