O-Acetylvallesamine






Names

    • O-Acetylvallesamine

Attributes

  • Canonical SMILES

    C/C=C(CC1)\[C@](C2(COC(C)=O)C(OC)=O)([H])CN1CC3=C2NC4=C3C=CC=C4

  • InChI

    InChI=1S/C22H26N2O4/c1-4-15-9-10-24-11-17-16-7-5-6-8-19(16)23-20(17)22(18(15)12-24,21(26)27-3)13-28-14(2)25/h4-8,18,23H,9-13H2,1-3H3/b15-4-/t18-,22?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.63
  • #RotBonds: 3
  • MW: 382.4600000000001
  • HBD: 1
  • HBA: 5
  • logP: 2.9236000000000013
  • Chemical Formula: C22H26N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Characterization of a Suspension Culture of Tabernaemontana elegans on Growth, Nutrient Uptake, and Accumulation of Indole Alkaloids*. Planta Med, 1989 (PMID 17262332).
  • Comparison of terpenoid indole alkaloid production and degradation in two cell lines of Tabernaemontana divaricata. Plant Cell Rep, 1993 (PMID 24196295).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Xanthine oxidase inhibitory
    • Convulsive
    • Spasmolytic
    • Inhibitory
    • Cytotoxicity

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) -4.81
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.89
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.18
    Distribution Blood-Brain Barrier (Central Nervous System) -2.45
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.04
    Plasma Protein Binding 47.12
    Steady State Volume of Distribution 6.35
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.07
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor 0.45
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.9
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.91
    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 -14.96
    Rat (Acute) 2.71
    Rat (Chronic Oral) 2.01
    Fathead Minnow 4.47
    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 428.46
    Hydration Free Energy -5.84
    Log(D) at pH=7.4 2.76
    Log(P) 2.56
    Log S -3.61
    Log(Vapor Pressure) -8.41
    Melting Point 168.12
    pKa Acid 9.7
    pKa Basic 6.72