Vincinine






Names

    • Vincinine
    • NS00093771

Attributes

  • Canonical SMILES

    CC(=O)[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=C(N4[C@](C2)(C(=O)OC)O)C=C(C=C5)OC

  • InChI

    InChI=1S/C22H26N2O5/c1-13(25)21-8-4-9-23-10-7-16-15-6-5-14(28-2)11-17(15)24(18(16)19(21)23)22(27,12-21)20(26)29-3/h5-6,11,19,27H,4,7-10,12H2,1-3H3/t19-,21+,22+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 81.00000000000001
  • #RotBonds: 3
  • MW: 398.4590000000001
  • HBD: 1
  • HBA: 7
  • logP: 2.1401000000000003
  • Chemical Formula: C22H26N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. cymosa Colombia 761066 JBC3243

External Databases


References

  • Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq. Molecules, 2021 (PMID 34205626).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Antiinflammatory
    • Antioxidant

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) -5.09
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.82
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.3
    Distribution Blood-Brain Barrier (Central Nervous System) -3.03
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.3
    Plasma Protein Binding 52.44
    Steady State Volume of Distribution 3.81
    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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.74
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.44
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.55
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 9.26
    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 -30.79
    Rat (Acute) 2.96
    Rat (Chronic Oral) 1.92
    Fathead Minnow 4.13
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 433.13
    Hydration Free Energy -5.34
    Log(D) at pH=7.4 2.03
    Log(P) 1.43
    Log S -3.02
    Log(Vapor Pressure) -8.62
    Melting Point 202.88
    pKa Acid 7.42
    pKa Basic 6.66