Vincophylline






Names

    • Methyl (1S,9S,11S,12E,18S)-12-ethylidene-18-(hydroxymethyl)-8,15-diazapentacyclo(9.6.1.0,.0,.0,)octadeca-2,4,6-triene-18-carboxylic acid
    • Methyl (1S,9S,11S,12E,18S)-12-ethylidene-18-(hydroxymethyl)-8,15-diazapentacyclo[9.6.1.0,.0,.0,]octadeca-2,4,6-triene-18-carboxylic acid
    • 958247-23-9
    • CHEMBL253985
    • Vincophylline
    • vincophylline

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CC[C@@]34[C@@]2(CC[C@H]1C3(CO)C(=O)OC)CC5=CC=CC=C45

  • InChI

    InChI=1S/C22H27NO3/c1-3-15-13-23-11-10-22-18-7-5-4-6-16(18)12-20(22,23)9-8-17(15)21(22,14-24)19(25)26-2/h3-7,17,24H,8-14H2,1-2H3/b15-3-/t17-,20-,21?,22-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 49.769999999999996
  • #RotBonds: 2
  • MW: 353.46200000000005
  • HBD: 1
  • HBA: 4
  • logP: 2.4466
  • Chemical Formula: C22H27NO3


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) -4.72
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.83
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.27
    Distribution Blood-Brain Barrier (Central Nervous System) -2.53
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.0
    Plasma Protein Binding 52.76
    Steady State Volume of Distribution 3.76
    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 Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-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 11.75
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.02
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.83
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.3
    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 -7.44
    Rat (Acute) 3.25
    Rat (Chronic Oral) 2.18
    Fathead Minnow 4.08
    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 419.43
    Hydration Free Energy -6.0
    Log(D) at pH=7.4 2.13
    Log(P) 2.49
    Log S -2.98
    Log(Vapor Pressure) -8.28
    Melting Point 183.82
    pKa Acid 9.77
    pKa Basic 6.86