3-2′-Oxopropyl-10,11-dimethoxy-16-epi-14,15-didehydrovincanmine






Names

    • 3-2′-Oxopropyl-10,11-dimethoxy-16-epi-14,15-didehydrovincanmine

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C24H28N2O4/c1-4-23-11-9-16(13-15(2)27)25-12-10-18-17-7-5-6-8-19(17)26(20(18)21(23)25)24(29,14-23)22(28)30-3/h5-9,11,16,21,29H,4,10,12-14H2,1-3H3/t16-,21-,23+,24-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.77000000000001
  • #RotBonds: 4
  • MW: 408.4980000000002
  • HBD: 1
  • HBA: 6
  • logP: 3.076200000000001
  • Chemical Formula: C24H28N2O4


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) -4.71
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.75
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.33
    Distribution Blood-Brain Barrier (Central Nervous System) -2.41
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.17
    Plasma Protein Binding 62.16
    Steady State Volume of Distribution 1.97
    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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.93
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.38
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.1
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.27
    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 Toxic
    T. Pyriformis -46.82
    Rat (Acute) 2.75
    Rat (Chronic Oral) 1.62
    Fathead Minnow 4.16
    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 457.07
    Hydration Free Energy -3.65
    Log(D) at pH=7.4 2.52
    Log(P) 2.49
    Log S -2.93
    Log(Vapor Pressure) -9.32
    Melting Point 184.92
    pKa Acid 7.58
    pKa Basic 5.33