Dehydrovoachalotine






Names

    • Dehydrovoachalotine

Attributes

  • Canonical SMILES

    C/C=C1C[N@@]2[C@H]3C[C@@H]/1[C@@]4(C(OC)=O)[C@@H]2[C@H](OC4)C5=C3N(C)C6=C5C=CC=C6

  • InChI

    InChI=1S/C22H24N2O3/c1-4-12-10-24-16-9-14(12)22(21(25)26-3)11-27-19(20(22)24)17-13-7-5-6-8-15(13)23(2)18(16)17/h4-8,14,16,19-20H,9-11H2,1-3H3/b12-4-/t14-,16-,19+,20-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 43.699999999999996
  • #RotBonds: 1
  • MW: 364.44500000000005
  • HBD: 0
  • HBA: 5
  • logP: 3.1141000000000014
  • Chemical Formula: C22H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. laeta Brazil 761076 WAG

External Databases


References

  • Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc, 2008 (PMID 18797794).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Acetylbutyrylcholinesterase 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) -4.68
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.66
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.42
    Distribution Blood-Brain Barrier (Central Nervous System) -2.93
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.97
    Plasma Protein Binding 66.1
    Steady State Volume of Distribution 6.29
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.48
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -0.04
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.41
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.75
    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 -19.07
    Rat (Acute) 3.69
    Rat (Chronic Oral) 1.74
    Fathead Minnow 4.44
    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 477.65
    Hydration Free Energy -5.7
    Log(D) at pH=7.4 2.78
    Log(P) 2.87
    Log S -3.46
    Log(Vapor Pressure) -8.66
    Melting Point 232.26
    pKa Acid 8.53
    pKa Basic 7.23