14,15-Didehydroapovincanmine






Names

    • InChI=1/C21H22N2O2/c1-3-21-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(18(15)19(21)22)17(13-21)20(24)25-2/h4-8,10,13,19H,3,9,11-12H2,1-2H3/t19-,21+/m1/s
    • eburnamenine-14-carboxylic acid, 17,18-didehydro-, methyl ester, (3alpha,16alpha)-
    • methyl (3alpha,16alpha)-17,18-didehydroeburnamenine-14-carboxylate
    • 14,15-Didehydroapovincanmine

Attributes

  • Canonical SMILES

    CC[C@@]12C=CCN3[C@]1([H])C4=C(C5=CC=CC=C5N4C(C(OC)=O)=C2)CC3

  • InChI

    InChI=1S/C21H22N2O2/c1-3-21-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(18(15)19(21)22)17(13-21)20(24)25-2/h4-8,10,13,19H,3,9,11-12H2,1-2H3/t19-,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 34.47
  • #RotBonds: 2
  • MW: 334.41900000000015
  • HBD: 0
  • HBA: 4
  • logP: 3.534200000000002
  • Chemical Formula: C21H22N2O2


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) -4.8
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.63
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.38
    Distribution Blood-Brain Barrier (Central Nervous System) -2.09
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.22
    Plasma Protein Binding 57.06
    Steady State Volume of Distribution 3.83
    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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.0
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.07
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.11
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.71
    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 Safe
    T. Pyriformis -3.21
    Rat (Acute) 2.69
    Rat (Chronic Oral) 1.59
    Fathead Minnow 4.32
    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 433.17
    Hydration Free Energy -5.75
    Log(D) at pH=7.4 3.62
    Log(P) 3.77
    Log S -3.24
    Log(Vapor Pressure) -7.58
    Melting Point 179.36
    pKa Acid 9.65
    pKa Basic 6.63