10,11,12-Trimethoxy14,15-didehydrovincanmine






Names

    • 10,11,12-Trimethoxy14,15-didehydrovincanmine

Attributes

  • Canonical SMILES

    CC[C@@]12C=CC([H])N3[C@]1([H])C4=C(C5=C(C(OC)=C(C(OC)=C5)OC)N4[C@@](C(OC)=O)(C2)O)CC3

  • InChI

    InChI=1S/C24H30N2O6/c1-6-23-9-7-10-25-11-8-14-15-12-16(29-2)19(30-3)20(31-4)17(15)26(18(14)21(23)25)24(28,13-23)22(27)32-5/h7,9,12,21,28H,6,8,10-11,13H2,1-5H3/t21-,23+,24+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 82.39
  • #RotBonds: 5
  • MW: 442.5120000000002
  • HBD: 1
  • HBA: 8
  • logP: 2.7543000000000006
  • Chemical Formula: C24H30N2O6


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) -4.75
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.89
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.21
    Distribution Blood-Brain Barrier (Central Nervous System) -3.3
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.81
    Plasma Protein Binding 50.95
    Steady State Volume of Distribution 1.37
    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 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 5.17
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    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 -0.34
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.84
    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 -131.41
    Rat (Acute) 3.08
    Rat (Chronic Oral) 1.92
    Fathead Minnow 4.52
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 462.94
    Hydration Free Energy -2.89
    Log(D) at pH=7.4 2.15
    Log(P) 2.17
    Log S -2.43
    Log(Vapor Pressure) -8.33
    Melting Point 186.77
    pKa Acid 7.85
    pKa Basic 6.53