14,15-Didehydro-10-hydroxy11-methoxy-16-epivincamine






Names

    • 14,15-Didehydro-10-hydroxy11-methoxy-16-epivincamine

Attributes

  • Canonical SMILES

    OC1=C(OC)C=C(N4C3=C2CCN5C3[C@](C=CC5)(CC)C[C@@]([C@](OC)=O)4O)C2=C1

  • InChI

    InChI=1S/C22H26N2O5/c1-4-21-7-5-8-23-9-6-13-14-10-16(25)17(28-2)11-15(14)24(18(13)19(21)23)22(27,12-21)20(26)29-3/h5,7,10-11,19,25,27H,4,6,8-9,12H2,1-3H3/t19?,21-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 84.16
  • #RotBonds: 3
  • MW: 398.4590000000002
  • HBD: 2
  • HBA: 7
  • logP: 2.4427000000000003
  • Chemical Formula: C22H26N2O5


Species

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

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -4.89
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.98
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.15
    Distribution Blood-Brain Barrier (Central Nervous System) -2.87
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 43.42
    Steady State Volume of Distribution 2.02
    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 Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 13.79
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.36
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.31
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.12
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -29.18
    Rat (Acute) 2.57
    Rat (Chronic Oral) 1.96
    Fathead Minnow 4.26
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 465.33
    Hydration Free Energy -5.1
    Log(D) at pH=7.4 2.2
    Log(P) 1.95
    Log S -2.81
    Log(Vapor Pressure) -8.74
    Melting Point 231.63
    pKa Acid 7.13
    pKa Basic 6.73