(-)-Medioresinol






Names

    • AKOS040760549
    • C22585
    • Medioresil
    • G14091
    • 40957-99-1
    • (-)-medioresinol
    • Medioresinol, (+)-
    • SCHEMBL3486411
    • DTXSID50961334
    • (-)-Medioresinol
    • Phenol, 2,6-dimethoxy-4-[tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]-, [1S-(1alpha,3aalpha,4alpha,6aalpha)]-
    • Phenol, 2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]-
    • J74JLA8FFA
    • DA-65316
    • HY-N3307
    • (+)-Mediaresinol
    • 2,6-Dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenol
    • 4-[4-(4-Hydroxy-3-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2,6-dimethoxyphenol
    • 4-[(3S,3aR,6S,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenol
    • 4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2,6-dimethoxyphenol
    • Q27136115
    • MS-26440
    • (+)-Medioresinol
    • MEDIORESINOL
    • CS-0023864
    • 2,6-Dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenol; (+)-Mediaresinol
    • CHEMBL376507
    • CHEBI:67644

Attributes

  • Canonical SMILES

    COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O)OC

  • InChI

    InChI=1S/C21H24O7/c1-24-16-6-11(4-5-15(16)22)20-13-9-28-21(14(13)10-27-20)12-7-17(25-2)19(23)18(8-12)26-3/h4-8,13-14,20-23H,9-10H2,1-3H3/t13-,14-,20+,21+/m0/s1

  • Molecule Class: Minor compounds
  • TPSA: 86.61000000000001
  • #RotBonds: 5
  • MW: 388.4160000000001
  • HBD: 2
  • HBA: 7
  • logP: 3.198800000000001
  • Chemical Formula: C21H24O7


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


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) -4.7
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.91
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.18
    Distribution Blood-Brain Barrier (Central Nervous System) -3.31
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.02
    Plasma Protein Binding 75.07
    Steady State Volume of Distribution 0.89
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.52
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.53
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.73
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.92
    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 Toxic
    T. Pyriformis -17.79
    Rat (Acute) 2.12
    Rat (Chronic Oral) 2.34
    Fathead Minnow 4.08
    Respiratory Disease Safe
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 443.51
    Hydration Free Energy -5.68
    Log(D) at pH=7.4 2.93
    Log(P) 1.64
    Log S -4.57
    Log(Vapor Pressure) -8.46
    Melting Point 166.77
    pKa Acid 8.41
    pKa Basic 3.22