3-(2-Oxopropyl)coronaridine






Names

    • CHEMBL4645050
    • AKOS040734956
    • 39967-45-8
    • Methyl (1S,15S,17S,18S)-17-ethyl-14-(2-oxopropyl)-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
    • 3-(2-Oxopropyl)coronaridine

Attributes

  • Canonical SMILES

    O=C(OC)[C@]12C3=C(CC[N@@]([C@@H]4CC(C)=O)C1[C@@H](CC)C[C@H]4C2)C5=CC=CC=C5N3

  • InChI

    InChI=1S/C24H30N2O3/c1-4-15-12-16-13-24(23(28)29-3)21-18(17-7-5-6-8-19(17)25-21)9-10-26(22(15)24)20(16)11-14(2)27/h5-8,15-16,20,22,25H,4,9-13H2,1-3H3/t15-,16-,20+,22?,24+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.4
  • #RotBonds: 4
  • MW: 394.5150000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.6029000000000018
  • Chemical Formula: C24H30N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604
    T. officinalis China - Cai20120227
    T. pauciflora Malaysia 761086 -

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Analgesic components from bornean medicinal plants, Tabernaemontana pauciflora Blume and Tabernaemontana pandacaqui Poir. Chem Pharm Bull (Tokyo), 1992 (PMID 1423760).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Xanthine oxidase inhibitory
    • Analgesic
    • Antiinflammatory
    • Inhibitory
    • Cytotoxicity
    • Acetylcholinesterase inhibitory
    • Lysosomal acidification

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) -4.56
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.77
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.81
    Distribution Blood-Brain Barrier (Central Nervous System) -3.1
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.13
    Plasma Protein Binding 67.83
    Steady State Volume of Distribution 3.78
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.54
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.11
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.4
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.53
    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 -35.52
    Rat (Acute) 3.27
    Rat (Chronic Oral) 1.84
    Fathead Minnow 4.11
    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 443.18
    Hydration Free Energy -4.43
    Log(D) at pH=7.4 3.05
    Log(P) 2.8
    Log S -3.64
    Log(Vapor Pressure) -8.72
    Melting Point 198.66
    pKa Acid 9.01
    pKa Basic 6.59