3S-(24S-Hydroxyethyl)coronaridine






Names

    • 3S-(24S-Hydroxyethyl)coronaridine
    • 3S-(24S-hydroxyethyl)-coronaridine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N([C@@H]2[C@H](C)O)CCC4=C3NC5=CC=CC=C45)C(=O)OC

  • InChI

    InChI=1S/C23H30N2O3/c1-4-14-11-15-12-23(22(27)28-3)20-17(16-7-5-6-8-18(16)24-20)9-10-25(21(14)23)19(15)13(2)26/h5-8,13-15,19,21,24,26H,4,9-12H2,1-3H3/t13-,14-,15+,19+,21-,23+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 65.56
  • #RotBonds: 3
  • MW: 382.50400000000013
  • HBD: 2
  • HBA: 4
  • logP: 3.0046000000000017
  • Chemical Formula: C23H30N2O3


Species

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

External Databases


References

  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • α-glucosidase inhibitory
    • Butyrylcholinesterase
    • Antimicrobial

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) -4.78
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.94
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.98
    Distribution Blood-Brain Barrier (Central Nervous System) -3.15
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.9
    Plasma Protein Binding 62.52
    Steady State Volume of Distribution 4.63
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.05
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.07
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.61
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.24
    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 -23.41
    Rat (Acute) 3.39
    Rat (Chronic Oral) 1.85
    Fathead Minnow 4.1
    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 433.68
    Hydration Free Energy -5.56
    Log(D) at pH=7.4 3.04
    Log(P) 2.87
    Log S -3.27
    Log(Vapor Pressure) -9.04
    Melting Point 199.57
    pKa Acid 8.65
    pKa Basic 7.48