3-2′-Oxopropyl-16-epi-14,15-didehydrovincanmine






Names

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

Attributes

  • Canonical SMILES

    CC[C@]1([C@]2([H])N3CCC4=C2N([C@](C(OC)=O)(C1)O)C5=C4C=C(OC)C(OC)=C5)C=C[C@@H]3CC(C)=O

  • InChI

    InChI=1S/C26H32N2O6/c1-6-25-9-7-16(11-15(2)29)27-10-8-17-18-12-20(32-3)21(33-4)13-19(18)28(22(17)23(25)27)26(31,14-25)24(30)34-5/h7,9,12-13,16,23,31H,6,8,10-11,14H2,1-5H3/t16-,23-,25+,26-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 90.23000000000002
  • #RotBonds: 6
  • MW: 468.55000000000024
  • HBD: 1
  • HBA: 8
  • logP: 3.0934000000000017
  • Chemical Formula: C26H32N2O6


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) -4.69
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.84
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.98
    Distribution Blood-Brain Barrier (Central Nervous System) -2.99
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.81
    Plasma Protein Binding 61.03
    Steady State Volume of Distribution 1.46
    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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.4
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.36
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.02
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.21
    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 Toxic
    T. Pyriformis -289.09
    Rat (Acute) 2.58
    Rat (Chronic Oral) 1.66
    Fathead Minnow 4.77
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 485.64
    Hydration Free Energy -2.85
    Log(D) at pH=7.4 2.31
    Log(P) 1.93
    Log S -2.5
    Log(Vapor Pressure) -9.11
    Melting Point 196.06
    pKa Acid 7.63
    pKa Basic 5.42