Alstonerine






Names

    • Alstonerin
    • 1-(3,20-Dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8,16-pentaen-17-yl)ethanone
    • Alstophyllan-19-one, (all-.xi.)-', "Ethanone, 1-(1,4a,5,6,7,12,13,13a-octahydro-7,14-dimethyl-6,13-iminopyrano[3',4':5,6]cyclooct[1,2-b]indol-4-yl)-"
    • Alstophyllan-19-one
    • Alstophylline, demethoxy-
    • Alstonerine
    • PMIRJPWEIZTLEG-UHFFFAOYSA-N

Attributes

  • Canonical SMILES

    CC(C1=COC[C@@]2([H])[C@]1([H])C[C@]3([H])C4=C(C5=CC=CC=C5N4C)C[C@@]2([H])N3C)=O

  • InChI

    InChI=1S/C21H24N2O2/c1-12(24)16-10-25-11-17-14(16)8-20-21-15(9-19(17)22(20)2)13-6-4-5-7-18(13)23(21)3/h4-7,10,14,17,19-20H,8-9,11H2,1-3H3/t14-,17+,19-,20-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 34.47
  • #RotBonds: 1
  • MW: 336.4350000000001
  • HBD: 0
  • HBA: 4
  • logP: 3.2151000000000014
  • Chemical Formula: C21H24N2O2


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) -4.85
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.6
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.1
    Distribution Blood-Brain Barrier (Central Nervous System) -2.64
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.82
    Plasma Protein Binding 65.57
    Steady State Volume of Distribution 2.45
    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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.52
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.48
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.32
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.45
    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 -5.98
    Rat (Acute) 3.04
    Rat (Chronic Oral) 1.1
    Fathead Minnow 4.1
    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 419.9
    Hydration Free Energy -6.35
    Log(D) at pH=7.4 2.12
    Log(P) 2.39
    Log S -2.51
    Log(Vapor Pressure) -8.33
    Melting Point 193.17
    pKa Acid 9.87
    pKa Basic 6.61