Epidehydrovincamine






Names

    • 17,18-Dehydroepivincamine
    • CHEMBL4787172
    • Dehydroepivincamine
    • 17,18-Dehydro-14-epivincamine
    • Epidehydrovincamine
    • 14-Epivincamine, 17,18-didehydro-
    • Eburnamenine-14-carboxylic acid, 17,18-didehydro-14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14alpha,16alpha)-
    • Methyl 14-hydroxy-17,18-didehydro-14,15-dihydroeburnamenine-14-carboxylate
    • 32790-10-6
    • DTXSID00954453

Attributes

  • Canonical SMILES

    CC[C@@]3(C=CC5)C(N5CC4)C2=C4C1=CC=CC=C1N2[C@](O)(OC(C)=O)C3

  • InChI

    InChI=1S/C21H24N2O3/c1-3-20-10-6-11-22-12-9-16-15-7-4-5-8-17(15)23(18(16)19(20)22)21(25,13-20)26-14(2)24/h4-8,10,19,25H,3,9,11-13H2,1-2H3/t19?,20-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.699999999999996
  • #RotBonds: 2
  • MW: 352.43400000000014
  • HBD: 1
  • HBA: 5
  • logP: 3.076100000000001
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Xanthine oxidase inhibitory

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) -4.77
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.68
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.37
    Distribution Blood-Brain Barrier (Central Nervous System) -2.29
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.18
    Plasma Protein Binding 50.75
    Steady State Volume of Distribution 2.63
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.64
    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 0.05
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.67
    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 -6.98
    Rat (Acute) 2.9
    Rat (Chronic Oral) 1.57
    Fathead Minnow 4.18
    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 429.71
    Hydration Free Energy -6.66
    Log(D) at pH=7.4 1.99
    Log(P) 2.76
    Log S -2.94
    Log(Vapor Pressure) -8.5
    Melting Point 182.39
    pKa Acid 9.2
    pKa Basic 6.27