Fluorocarpamine






Names

    • CHEBI:229119
    • Fluorocarpamine
    • methyl (10R,12E)-12-ethylidene-2-oxo-9,14-diazapentacyclo[9.5.2.01,9.03,8.014,17]octadeca-3,5,7-triene-10-carboxylate

Attributes

  • Canonical SMILES

    C/C=C/1\C[NH+]2CC[C@@]34[C@@H]2C[C@@H]1[C@H](N3C5=CC=CC=C5C4=O)C(=O)OC

  • InChI

    InChI=1S/C20H22N2O3/c1-3-12-11-21-9-8-20-16(21)10-14(12)17(19(24)25-2)22(20)15-7-5-4-6-13(15)18(20)23/h3-7,14,16-17H,8-11H2,1-2H3/p+1/b12-3+/t14-,16-,17-,20-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 51.05
  • #RotBonds: 1
  • MW: 339.41500000000013
  • HBD: 1
  • HBA: 4
  • logP: 0.6067
  • Chemical Formula: C20H23N2O3+


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) -4.96
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.81
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.59
    Distribution Blood-Brain Barrier (Central Nervous System) -3.63
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 50.5
    Steady State Volume of Distribution 1.2
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.48
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.6
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.07
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.01
    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 -3.73
    Rat (Acute) 3.49
    Rat (Chronic Oral) 2.06
    Fathead Minnow 4.01
    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 442.1
    Hydration Free Energy -3.55
    Log(D) at pH=7.4 0.91
    Log(P) -0.12
    Log S -1.93
    Log(Vapor Pressure) -8.55
    Melting Point 264.98
    pKa Acid 5.72
    pKa Basic 5.28