Antirhine






Names

    • (betaR,2S,12bS)-beta-Ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine-2-ethanol
    • Rhazinine
    • Antirhine
    • (betaR,2S,12bS)-beta-Ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-2-ethanol
    • Indolo[2,3-a]quinolizine-2-ethanol, beta-ethenyl-1,2,3,4,6,7,12,12b-octahydro-, (betaR,2S,12bS)-
    • (2R)-2-[(2S,12bS)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]but-3-en-1-ol
    • Q27105810
    • (2R)-2-[(2S,12BS)-1H,2H,3H,4H,6H,7H,12H,12BH-INDOLO[2,3-A]QUINOLIZIN-2-YL]BUT-3-EN-1-OL
    • C09033
    • CHEBI:2764
    • 2-(1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)but-3-en-1-ol
    • Anthirine
    • AKOS032948973
    • (2S,betaR)-beta-Vinyl-1,2,3,4,6,7,12,12bbeta-octahydroindolo[2,3-a]quinolizine-2-ethanol
    • 16049-28-8
    • DTXSID40936319

Attributes

  • Canonical SMILES

    C=C[C@@H](CO)[C@H]1CCN2CCC3=C([C@@H]2C1)NC4=CC=CC=C34

  • InChI

    InChI=1S/C19H24N2O/c1-2-13(12-22)14-7-9-21-10-8-16-15-5-3-4-6-17(15)20-19(16)18(21)11-14/h2-6,13-14,18,20,22H,1,7-12H2/t13-,14-,18-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.26
  • #RotBonds: 3
  • MW: 296.414
  • HBD: 2
  • HBA: 2
  • logP: 3.271600000000001
  • Chemical Formula: C19H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships


Compound Activities

    • Xanthine oxidase 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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -5.04
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.57
    Distribution Blood-Brain Barrier (Central Nervous System) -2.55
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.48
    Plasma Protein Binding 63.17
    Steady State Volume of Distribution 3.4
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 14.68
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor 1.0
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.18
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.17
    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 0.78
    Rat (Acute) 2.8
    Rat (Chronic Oral) 1.86
    Fathead Minnow 3.96
    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 394.23
    Hydration Free Energy -8.25
    Log(D) at pH=7.4 2.65
    Log(P) 3.31
    Log S -2.97
    Log(Vapor Pressure) -8.24
    Melting Point 156.12
    pKa Acid 12.05
    pKa Basic 7.72