3-Oxocoronaridine






Names

    • 3-Oxocoronaridine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2=O)CCC4=C3NC5=CC=CC=C45)C(=O)OC

  • InChI

    InChI=1S/C21H24N2O3/c1-3-12-10-13-11-21(20(25)26-2)17-15(8-9-23(18(12)21)19(13)24)14-6-4-5-7-16(14)22-17/h4-7,12-13,18,22H,3,8-11H2,1-2H3/t12-,13-,18-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.400000000000006
  • #RotBonds: 2
  • MW: 352.4340000000001
  • HBD: 1
  • HBA: 3
  • logP: 2.7818000000000014
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604
    T. cymosa Colombia 761066 JBC3243
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227
    T. peduncularis Thailand 761087 WU 0099055
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).
  • Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq. Molecules, 2021 (PMID 34205626).
  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Antiproliferative
    • Xanthine oxidase inhibitory
    • Antiinflammatory
    • Inhibitory
    • α-glucosidase inhibitory
    • Antimicrobial
    • Antioxidant
    • Cytotoxicity
    • Butyrylcholinesterase

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) -4.68
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.75
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -0.97
    Distribution Blood-Brain Barrier (Central Nervous System) -2.62
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.02
    Plasma Protein Binding 62.51
    Steady State Volume of Distribution 5.61
    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 Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.26
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.19
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.5
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.65
    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 -8.08
    Rat (Acute) 3.18
    Rat (Chronic Oral) 2.33
    Fathead Minnow 4.0
    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 453.51
    Hydration Free Energy -5.6
    Log(D) at pH=7.4 2.77
    Log(P) 2.6
    Log S -4.07
    Log(Vapor Pressure) -8.54
    Melting Point 229.01
    pKa Acid 10.17
    pKa Basic 7.1