10-Methoxy-14,15-didehydroapovincanmine






Names

    • 10-Methoxy-14,15-didehydroapovincanmine

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C22H24N2O3/c1-4-22-9-5-10-23-11-8-15-16-12-14(26-2)6-7-17(16)24(19(15)20(22)23)18(13-22)21(25)27-3/h5-7,9,12-13,20H,4,8,10-11H2,1-3H3/t20-,22+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 43.7
  • #RotBonds: 3
  • MW: 364.44500000000016
  • HBD: 0
  • HBA: 5
  • logP: 3.5428000000000015
  • Chemical Formula: C22H24N2O3


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) -4.89
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.65
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.32
    Distribution Blood-Brain Barrier (Central Nervous System) -2.5
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.07
    Plasma Protein Binding 52.43
    Steady State Volume of Distribution 3.68
    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 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 8.08
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.94
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.04
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.34
    Micronucleos Toxic
    NR-AhR Toxic
    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 Toxic
    T. Pyriformis -12.39
    Rat (Acute) 2.88
    Rat (Chronic Oral) 1.71
    Fathead Minnow 4.41
    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 455.67
    Hydration Free Energy -5.81
    Log(D) at pH=7.4 3.78
    Log(P) 3.88
    Log S -3.31
    Log(Vapor Pressure) -7.61
    Melting Point 183.41
    pKa Acid 9.81
    pKa Basic 6.92