Pandoline






Names

    • SCHEMBL10922682
    • Pandoline

Attributes

  • Canonical SMILES

    CC[C@]1(C[C@]2([H])CC(C(OC)=O)=C3NC4=C([C@]35CCN([C@]25[H])C1)C=CC=C4)O

  • InChI

    InChI=1S/C21H26N2O3/c1-3-20(25)11-13-10-14(19(24)26-2)17-21(8-9-23(12-20)18(13)21)15-6-4-5-7-16(15)22-17/h4-7,13,18,22,25H,3,8-12H2,1-2H3/t13-,18+,20+,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 61.8
  • #RotBonds: 2
  • MW: 354.45
  • HBD: 2
  • HBA: 5
  • logP: 2.416000000000001
  • Chemical Formula: C21H26N2O3


Species

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

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • [Determination of Structures by H NMR at 400 MHz: two new alkaloids from Tabernaemontana albiflora]. Planta Med, 1981 (PMID 17401839).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Inhibitory
    • 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) -5.09
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.97
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.78
    Distribution Blood-Brain Barrier (Central Nervous System) -2.62
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.75
    Plasma Protein Binding 46.1
    Steady State Volume of Distribution 4.41
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 5.17
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.47
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.72
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.71
    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 -10.69
    Rat (Acute) 3.28
    Rat (Chronic Oral) 2.22
    Fathead Minnow 4.1
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 395.71
    Hydration Free Energy -7.57
    Log(D) at pH=7.4 2.36
    Log(P) 2.74
    Log S -2.44
    Log(Vapor Pressure) -8.02
    Melting Point 182.94
    pKa Acid 6.92
    pKa Basic 7.03