10,11-Dimethoxy-14,15-didehydroapovincanmine






Names

    • 10,11-Dimethoxy-14,15-didehydroapovincanmine

Attributes

  • Canonical SMILES

    CC[C@@]12C=CCN3[C@]1([H])C4=C(C5=C(C=C(C(OC)=C5)OC)N4C(C(OC)=O)=C2)CC3

  • InChI

    InChI=1S/C23H26N2O4/c1-5-23-8-6-9-24-10-7-14-15-11-18(27-2)19(28-3)12-16(15)25(20(14)21(23)24)17(13-23)22(26)29-4/h6,8,11-13,21H,5,7,9-10H2,1-4H3/t21-,23+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 52.93
  • #RotBonds: 4
  • MW: 394.4710000000002
  • HBD: 0
  • HBA: 6
  • logP: 3.551400000000002
  • Chemical Formula: C23H26N2O4


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) -4.82
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.73
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.41
    Distribution Blood-Brain Barrier (Central Nervous System) -2.72
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.0
    Plasma Protein Binding 48.43
    Steady State Volume of Distribution 2.42
    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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.49
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.01
    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 6.59
    Micronucleos Toxic
    NR-AhR Toxic
    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 -35.48
    Rat (Acute) 3.29
    Rat (Chronic Oral) 1.75
    Fathead Minnow 4.55
    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 469.71
    Hydration Free Energy -4.45
    Log(D) at pH=7.4 3.53
    Log(P) 3.17
    Log S -3.19
    Log(Vapor Pressure) -7.66
    Melting Point 191.97
    pKa Acid 9.16
    pKa Basic 6.88