Pseudoindoxyl coronaridine






Names

    • Pseudoindoxyl coronaridine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC34C(=O)C5=CC=CC=C5N4)C(=O)OC

  • InChI

    InChI=1S/C21H26N2O3/c1-3-14-10-13-11-20(19(25)26-2)17(14)23(12-13)9-8-21(20)18(24)15-6-4-5-7-16(15)22-21/h4-7,13-14,17,22H,3,8-12H2,1-2H3/t13-,14+,17+,20-,21?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 58.64
  • #RotBonds: 2
  • MW: 354.45000000000005
  • HBD: 1
  • HBA: 5
  • logP: 2.7171000000000003
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Taberdines L and M, two new alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2022 (PMID 34933610).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Inhibitory
    • Cytotoxicity
    • Xanthine oxidase inhibitory

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) -4.58
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.92
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.88
    Distribution Blood-Brain Barrier (Central Nervous System) -2.23
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.89
    Plasma Protein Binding 53.62
    Steady State Volume of Distribution 2.16
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 6.86
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -1.08
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose None
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.19
    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 -7.1
    Rat (Acute) 3.98
    Rat (Chronic Oral) 1.74
    Fathead Minnow 3.92
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 440.29
    Hydration Free Energy -3.32
    Log(D) at pH=7.4 2.32
    Log(P) 2.91
    Log S -3.15
    Log(Vapor Pressure) -8.15
    Melting Point 185.88
    pKa Acid 6.27
    pKa Basic 6.73