Ethyl apovincaminate






Names

    • NCGC00016854-03
    • SCHEMBL160952
    • NCGC00021727-02
    • Tocris-0757
    • ETHYL(41R,13AR)-13A-ETHYL-2,3,41,5,6,13A-HEXAHYDRO-1H-INDOLO[3,2,1-DE]PYRIDO[3,2,1-IJ][1,5]NAPHTHYRIDINE-12-CARBOXYLATE
    • NCGC00016854-01
    • DTXSID10904848
    • Eburnamenine-14-carboxylic acid, ethyl ester
    • Ethyl apovincaminate
    • NCGC00018204-01
    • ETHYL (41R,13AR)-13A-ETHYL-2,3,41,5,6,13A-HEXAHYDRO-1H-INDOLO[3,2,1-DE]PYRIDO[3,2,1-IJ][1,5]NAPHTHYRIDINE-12-CARBOXYLATE
    • (-)-Vinpocetine
    • Lopac-V-6383
    • CHEMBL1360725
    • (-)-Ethyl apovincaminate
    • ethyl (15R,19R)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
    • (3R,16R)-Vinpocetine
    • NCGC00018204-03
    • 42971-12-0
    • (-)-Apovincaminic acid ethyl ester
    • NCGC00018204-02
    • CAS-42971-09-5
    • NCGC00016085-01

Attributes

  • Canonical SMILES

    CC[C@]12CCCN3[C@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC

  • InChI

    InChI=1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 34.47
  • #RotBonds: 3
  • MW: 350.46200000000016
  • HBD: 0
  • HBA: 4
  • logP: 4.148300000000003
  • Chemical Formula: C22H26N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res, 2022 (PMID 35075954).

Compound-Protein Relationships


Compound Activities

    • Antiproliferative

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) -4.78
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.68
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor 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) 1.01
    Plasma Protein Binding 65.29
    Steady State Volume of Distribution 6.38
    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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.79
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.82
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.29
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.69
    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 Safe
    T. Pyriformis -7.25
    Rat (Acute) 2.81
    Rat (Chronic Oral) 1.84
    Fathead Minnow 4.26
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 434.72
    Hydration Free Energy -5.19
    Log(D) at pH=7.4 3.86
    Log(P) 4.23
    Log S -3.22
    Log(Vapor Pressure) -7.4
    Melting Point 157.73
    pKa Acid 9.9
    pKa Basic 7.84