Lirioresinol B






Names

    • DA-59414
    • DL-Syringaresinol
    • DTXSID901316029
    • Syringaresinol, (-)-
    • CHEMBL402653
    • ()-Syringaresinol;
    • 6216-81-5
    • XS164035
    • minus Syringaresinol
    • Syringaresinol - 93%
    • KOWMJRJXZMEZLD-WRMVBYCNSA-N
    • CS-0090357
    • Q27121535', "4,4'-(1R,3aS,4R,6aS)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)", '4-[(3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxy-phenol
    • (-)-syringaresinol
    • MS-27314
    • SCHEMBL16562875
    • HY-126066
    • CHEBI:49212
    • AKOS030231411
    • (-)-Lirioresinol B
    • 4-((3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2,6-dimethoxyphenol
    • QD6NNG8CM5
    • Lirioresinol B
    • UNII-QD6NNG8CM5', "4,4'-((1R,3aS,4R,6aS)-Tetrahydro-1H,3H-furo(3,4-C)furan-1,4-diyl)bis(2,6-dimethoxyphenol)", "Phenol, 4,4'-((1R,3aS,4R,6aS)-tetrahydro-1H,3H-furo(3,4-C)furan-1,4-diyl)bis(2,6-dimethoxy-", '4-[(3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol', "(7beta,7'beta,8beta,8'beta)-3,3',5,5'-tetramethoxy-7,9':7',9-diepoxylignane-4,4'-diol", "Phenol, 4,4'-(tetrahydro-1H,3H-furo(3,4-C)furan-1,4-diyl)bis(2,6-dimethoxy-, (1R-(1alpha,3aalpha,4alpha,6aalpha))-", "PHENOL, 4,4'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2,6-DIMETHOXY-, (1R-(1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.))-", 'Lirioresinol b

Attributes

  • Canonical SMILES

    C[C@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5([C@@H](C[C@@H](C6)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)C)O)O)O)C)C)C)OC1

  • InChI

    InChI=1S/C39H62O12/c1-17-9-12-39(46-16-17)18(2)28-26(51-39)15-25-23-8-7-21-13-22(49-35-33(44)31(42)29(40)19(3)47-35)14-27(38(21,6)24(23)10-11-37(25,28)5)50-36-34(45)32(43)30(41)20(4)48-36/h7,17-20,22-36,40-45H,8-16H2,1-6H3/t17-,18-,19-,20+,22+,23+,24-,25-,26-,27+,28-,29-,30-,31+,32-,33+,34+,35-,36-,37-,38-,39+/m0/s1

  • Molecule Class: Minor compounds
  • TPSA: 176.76
  • #RotBonds: 4
  • MW: 722.9130000000002
  • HBD: 6
  • HBA: 12
  • logP: 2.388300000000001
  • Chemical Formula: C39H62O12


Species

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

External Databases


References

  • Chemical Constituents from Tabernaemontana bufalina Lour. Chem Biodivers, 2019 (PMID 30411487).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 0.09
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability 718.81
    Distribution Blood-Brain Barrier (Central Nervous System) -3.81
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.84
    Plasma Protein Binding 98.14
    Steady State Volume of Distribution 0.67
    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 Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 1.06
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -15.17
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.29
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.49
    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 -1306515.33
    Rat (Acute) 3.71
    Rat (Chronic Oral) 3.46
    Fathead Minnow 1655.3
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 144604.78
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 3.97
    Log(P) 2.9
    Log S -3.91
    Log(Vapor Pressure) -4647.61
    Melting Point 230.51
    pKa Acid -2.81
    pKa Basic 4.92