Nb-Methylvoachalotine






Names

    • (4R,19E)-16-(hydroxymethyl)-12,17-dimethoxy-1,4-dimethyl-17-oxosarpagan-4-ium
    • 12-methoxy-Nb-methylvoachalotine
    • Nb-Methylvoachalotine
    • 85O

Attributes

  • Canonical SMILES

    C/C=C1C[N@@+]2(C)[C@H]3C[C@@H]/1[C@@](CO)(C(OC)=O)[C@@H]2CC4=C3N(C)C5=C4C=CC=C5

  • InChI

    InChI=1S/C23H29N2O3/c1-5-14-12-25(3)19-11-17(14)23(13-26,22(27)28-4)20(25)10-16-15-8-6-7-9-18(15)24(2)21(16)19/h5-9,17,19-20,26H,10-13H2,1-4H3/q+1/b14-5-/t17-,19-,20-,23+,25-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 51.46
  • #RotBonds: 2
  • MW: 381.4960000000001
  • HBD: 1
  • HBA: 4
  • logP: 2.722200000000001
  • Chemical Formula: C23H29N2O3+


Species

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

External Databases


References

  • A new natural auaternary indole alkaloid isolated from Tabernaemontana laeta Mart. (Apocynaceae) Journal of the Brazilian Chemical Society, 2001 (DOI).
  • 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) -4.97
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.74
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.46
    Distribution Blood-Brain Barrier (Central Nervous System) -3.51
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.91
    Plasma Protein Binding 61.99
    Steady State Volume of Distribution 3.17
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-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 6.33
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.63
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.18
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.23
    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 -15.77
    Rat (Acute) 3.36
    Rat (Chronic Oral) 1.76
    Fathead Minnow 4.41
    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 490.85
    Hydration Free Energy -6.05
    Log(D) at pH=7.4 1.88
    Log(P) -0.1
    Log S -1.76
    Log(Vapor Pressure) -10.42
    Melting Point 242.68
    pKa Acid 6.82
    pKa Basic 5.19