Alstonal






Names

    • Alstonisine
    • SCHEMBL21832078', "(1S,2R,7R,9S,10S)-6-acetyl-1'-methylspiro[4-oxa-12-azatricyclo[7.2.1.02,7]dodec-5-ene-10,3'-indole]-2'-one"
    • CHEMBL592449
    • Alstonal

Attributes

  • Canonical SMILES

    CC1=C(C=O)[C@@H]2C[C@@H]3N[C@@H](C[C@@]34C(=O)N(C)C3CCCCC34)[C@@H]2CO1

  • InChI

    InChI=1S/C20H28N2O3/c1-11-13(9-23)12-7-18-20(8-16(21-18)14(12)10-25-11)15-5-3-4-6-17(15)22(2)19(20)24/h9,12,14-18,21H,3-8,10H2,1-2H3/t12-,14+,15?,16-,17?,18-,20-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 58.64
  • #RotBonds: 1
  • MW: 344.45500000000015
  • HBD: 1
  • HBA: 4
  • logP: 1.8732999999999993
  • Chemical Formula: C20H28N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. dichotoma Sri Lanka, Malaysia - -

External Databases


References

  • Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med, 2013 (PMID 22350216).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Vasorelaxant

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 -4.94
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.18
    Distribution Blood-Brain Barrier (Central Nervous System) -2.99
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.25
    Plasma Protein Binding 41.55
    Steady State Volume of Distribution 1.88
    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 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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 15.43
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.57
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.75
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 7.26
    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 -3.51
    Rat (Acute) 3.64
    Rat (Chronic Oral) 0.92
    Fathead Minnow 3.75
    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 434.72
    Hydration Free Energy -4.44
    Log(D) at pH=7.4 1.52
    Log(P) 1.39
    Log S -2.87
    Log(Vapor Pressure) -8.64
    Melting Point 171.84
    pKa Acid 7.79
    pKa Basic 8.13