10,11-Dimethoxy-16-epi-14,15-didehydrovincanmine N4-oxide






Names

    • 10,11-Dimethoxy-16-epi-14,15-didehydrovincanmine N4-oxide

Attributes

  • Canonical SMILES

    CC[C@@]12C=CC[N+]3([O-])[C@]1([H])C4=C(C5=C(C=C(C(OC)=C5)OC)N4[C@@](C(OC)=O)(C2)O)CC3

  • InChI

    InChI=1S/C23H28N2O6/c1-5-22-8-6-9-25(28)10-7-14-15-11-17(29-2)18(30-3)12-16(15)24(19(14)20(22)25)23(27,13-22)21(26)31-4/h6,8,11-12,20,27H,5,7,9-10,13H2,1-4H3/t20-,22+,23+,25?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 92.98
  • #RotBonds: 4
  • MW: 428.48500000000024
  • HBD: 1
  • HBA: 7
  • logP: 2.758300000000001
  • Chemical Formula: C23H28N2O6


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) -5.59
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.33
    Distribution Blood-Brain Barrier (Central Nervous System) -3.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.87
    Plasma Protein Binding 63.61
    Steady State Volume of Distribution 0.58
    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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 4.95
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.15
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.03
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.59
    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 -67.48
    Rat (Acute) 2.59
    Rat (Chronic Oral) 1.62
    Fathead Minnow 4.34
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 471.69
    Hydration Free Energy -3.26
    Log(D) at pH=7.4 1.5
    Log(P) 0.54
    Log S -1.35
    Log(Vapor Pressure) -8.95
    Melting Point 235.68
    pKa Acid 5.97
    pKa Basic 2.14