3S-(24R-Hydroxyethyl)coronaridine






Names

    • 3S-(24R-Hydroxyethyl)coronaridine

Attributes

  • Canonical SMILES

    [H][C@]12C[C@]3(C(OC)=O)C4=C(CCN([C@]2([H])C(O)C)[C@@]3([H])[C@@H](CC)C1)C5=CC(OC)=CC=C5N4

  • InChI

    InChI=1S/C24H32N2O4/c1-5-14-10-15-12-24(23(28)30-4)21-17(8-9-26(22(14)24)20(15)13(2)27)18-11-16(29-3)6-7-19(18)25-21/h6-7,11,13-15,20,22,25,27H,5,8-10,12H2,1-4H3/t13?,14-,15+,20+,22-,24-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 74.78999999999999
  • #RotBonds: 4
  • MW: 412.5300000000002
  • HBD: 2
  • HBA: 5
  • logP: 3.013200000000001
  • Chemical Formula: C24H32N2O4


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) -4.88
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.93
    Distribution Blood-Brain Barrier (Central Nervous System) -3.25
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 53.6
    Steady State Volume of Distribution 4.48
    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 9.71
    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 -1.39
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.59
    Micronucleos Toxic
    NR-AhR Toxic
    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 -52.98
    Rat (Acute) 3.19
    Rat (Chronic Oral) 1.83
    Fathead Minnow 4.12
    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 454.23
    Hydration Free Energy -3.66
    Log(D) at pH=7.4 3.01
    Log(P) 2.97
    Log S -3.36
    Log(Vapor Pressure) -9.31
    Melting Point 202.01
    pKa Acid 8.95
    pKa Basic 7.53