Voachalotine oxindole






Names

    • Voachalotine oxindole
    • XFZSKHOXTFALFI-YIXHJXPBSA-N', "Spiro[3H-indole-3,1'(5'H)-[3,7]methanoindolizine]-9'-carboxylic acid, 6'-ethylidene-1,2,2',3',6',7',8',8'a-octahydro-9'-(hydroxymethyl)-1-methyl-2-oxo-, methyl ester, [1'S-(1'.alpha.,3'.beta.,6'E,7'.beta.,8'a.alpha.,9'S)]-", "Spiro[3H-indole-3,1'(5'H)-[3,7]methanoindolizine]-9'-carboxylic acid, 6'-ethylidene-1,2,2',3',6',7',8',8'a-octahydro-9'-(hydroxymethyl)-1-methyl-2-oxo-, methyl ester, [1'S-(1'.alpha.,3'.beta.,6'E,7'.beta.,8'a.alpha.,9'S*)]-", "Spiro[3H-indole-3,1'(5'H)-[3,7]methanoindolizine]-9'-carboxylic acid, 6'-ethylidene-1,2,2',3',6',7',8',8'a-octahydro-9'-(hydroxymethyl)-1-methyl-2-oxo-, methyl ester, [3S-(3.alpha.,3'.beta.,6'E,7'.beta.,8'a.alpha.,9'S*)]-", "Spiro[indoline-3,1'(5'H)-[3,7]methanoindolizine]-9'-carboxylic acid, 6'-ethylidene-1,2,2',3',6',7',8',8'a-octahydro-9'-(hydroxymethyl)-1-methyl-2-oxo-, methyl ester, [3S-(3.alpha.,3'.beta.,6'E,7'.beta.,8'a.alpha.,9'S*)]-"

Attributes

  • Canonical SMILES

    C/C=C1CN2[C@H]3C[C@@H]\1C(O)(C(OC)=O)[C@@H]2C[C@]34C5=CC=CC=C5N(C)C4=O

  • InChI

    InChI=1S/C21H24N2O4/c1-4-12-11-23-16-9-14(12)21(26,19(25)27-3)17(23)10-20(16)13-7-5-6-8-15(13)22(2)18(20)24/h4-8,14,16-17,26H,9-11H2,1-3H3/b12-4+/t14-,16-,17-,20-,21?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 70.08000000000001
  • #RotBonds: 1
  • MW: 368.43300000000005
  • HBD: 1
  • HBA: 5
  • logP: 1.2275999999999994
  • Chemical Formula: C21H24N2O4


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) -4.85
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.81
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.71
    Distribution Blood-Brain Barrier (Central Nervous System) -2.3
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.63
    Plasma Protein Binding 48.04
    Steady State Volume of Distribution 3.12
    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 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 5.35
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -0.5
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.24
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.29
    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 -12.15
    Rat (Acute) 3.54
    Rat (Chronic Oral) 1.6
    Fathead Minnow 4.05
    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 448.12
    Hydration Free Energy -4.73
    Log(D) at pH=7.4 1.22
    Log(P) 1.01
    Log S -2.98
    Log(Vapor Pressure) -9.65
    Melting Point 208.85
    pKa Acid 5.53
    pKa Basic 6.72