Δ14-Vincine






Names

    • Δ14-Vincine

Attributes

  • Canonical SMILES

    CC[C@]1([C@]2([H])N3CCC4=C2N([C@@](C(OC)=O)(C1)O)C5=C4C=CC(OC)=C5)C=CC3=O

  • InChI

    InChI=1S/C22H24N2O5/c1-4-21-9-7-17(25)23-10-8-15-14-6-5-13(28-2)11-16(14)24(18(15)19(21)23)22(27,12-21)20(26)29-3/h5-7,9,11,19,27H,4,8,10,12H2,1-3H3/t19-,21+,22+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 81.0
  • #RotBonds: 3
  • MW: 396.4430000000001
  • HBD: 1
  • HBA: 6
  • logP: 2.2637
  • Chemical Formula: C22H24N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bovina China, Vietnam 3036760 Cai20150423

External Databases


References

  • Vincan- and eburnan-type alkaloids from Tabernaemontana bovina and their hypoglycemic activity. Phytochemistry, 2021 (PMID 34218044).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Hypoglycemic

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) -4.79
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.72
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.89
    Distribution Blood-Brain Barrier (Central Nervous System) -2.69
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.92
    Plasma Protein Binding 58.14
    Steady State Volume of Distribution 1.6
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.71
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.23
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.17
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.36
    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 -30.32
    Rat (Acute) 2.79
    Rat (Chronic Oral) 1.9
    Fathead Minnow 4.16
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 472.26
    Hydration Free Energy -4.72
    Log(D) at pH=7.4 2.37
    Log(P) 2.24
    Log S -2.8
    Log(Vapor Pressure) -8.72
    Melting Point 230.46
    pKa Acid 8.69
    pKa Basic 5.79