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    Pterostilbene

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 537-42-8, Trans-pterostilbene, 4-(3,5-dimethoxystyryl)phenol, (e)-4-(3,5-dimethoxystyryl)phenol, 4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol, 18259-15-9
    Molecular Formula
    C16H16O3
    Molecular Weight
    256.30  g/mol
    InChI Key
    VLEUZFDZJKSGMX-ONEGZZNKSA-N
    FDA UNII
    26R60S6A5I
    Pterostilbene is a naturally-derived stilbenoid structurally related to resveratrol, with potential antioxidant, anti-inflammatory, pro-apoptotic, antineoplastic and cytoprotective activities. Upon administration, pterostilbene exerts its anti-oxidant activity by scavenging reactive oxygen species (ROS), thereby preventing oxidative stress and ROS-induced cell damage. It may also activate the nuclear factor erythroid 2-related factor 2 (Nrf2)-mediated pathway and increase the expression of various antioxidant enzymes, such as superoxide dismutase (SOD). In addition, pterostilbene is able to inhibit inflammation by reducing the expression of various inflammatory mediators, such as interleukin (IL) 1beta, tumor necrosis factor alpha (TNF-a), inducible nitric oxide synthase (iNOS), cyclooxygenases (COX), and nuclear factor kappa B (NF-kB). It also inhibits or prevents the activation of many signaling pathways involved in carcinogenesis, and increases expression of various tumor suppressor genes while decreasing expression of certain tumor promoting genes. It also directly induces apoptosis in tumor cells.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
    2.1.2 InChI
    InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+
    2.1.3 InChI Key
    VLEUZFDZJKSGMX-ONEGZZNKSA-N
    2.1.4 Canonical SMILES
    COC1=CC(=CC(=C1)C=CC2=CC=C(C=C2)O)OC
    2.1.5 Isomeric SMILES
    COC1=CC(=CC(=C1)/C=C/C2=CC=C(C=C2)O)OC
    2.2 Other Identifiers
    2.2.1 UNII
    26R60S6A5I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3',5'-dimethoxy-4e-stilbenol

    2. 3',5'-dimethoxy-4trans-stilbenol

    3. 3',5'-dimethoxy-resveratrol

    4. 3,5-dimethoxy-4'-hydroxy-trans-stilbene

    5. 4-((e)-2-(3,5-dimethoxyphenyl)ethenyl)phenol

    6. 4trans-(2-(3,5-dimethoxyphenyl)ethenyl)phenol

    7. Phenol, 4-((1e)-2-(3,5-dimethoxyphenyl)ethenyl)-

    8. Pterostilbene, (e)-

    9. Trans-3,5-dimethoxy-4'-hydroxystilbene

    10. Trans-pterostilbene

    2.3.2 Depositor-Supplied Synonyms

    1. 537-42-8

    2. Trans-pterostilbene

    3. 4-(3,5-dimethoxystyryl)phenol

    4. (e)-4-(3,5-dimethoxystyryl)phenol

    5. 4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

    6. 18259-15-9

    7. 3',5'-dimethoxy-4-stilbenol

    8. 4-[(e)-2-(3,5-dimethoxyphenyl)vinyl]phenol

    9. Pterostilbene, (e)-

    10. Pterostilben

    11. 3,5-dimethoxy-4'-hydroxy-trans-stilbene

    12. Trans-3,5-dimethoxy-4'-hydroxystilbene

    13. Phenol, 4-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-

    14. Chembl83527

    15. Chebi:8630

    16. 4-((e)-2-(3,5-dimethoxyphenyl)ethenyl)phenol

    17. 26r60s6a5i

    18. 4-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

    19. 3,5-dimethoxy-4'-hydroxystilbene

    20. Phenol, 4-[2-(3,5-dimethoxyphenyl)ethenyl]-

    21. Phenol, 4-((1e)-2-(3,5-dimethoxyphenyl)ethenyl)-

    22. Mfcd00238710

    23. Smr000440694

    24. Pterostilbene, Pterocarpus Marsupium

    25. 4-((1e)-2-(3,5-dimethoxyphenyl)ethenyl)phenol

    26. Pteropure

    27. Unii-26r60s6a5i

    28. Tero-still-bean

    29. 4'-hydroxy-3,5-dimethoxy-trans-stilbene

    30. Cpd000440694

    31. 4-stilbenol, 3',5'-dimethoxy-, (e)-

    32. Phenol, 4-[(1z)-2-(3,5-dimethoxyphenyl)ethenyl]-

    33. 3,5-di-o-methylresveratrol

    34. Schembl20063

    35. Mls000759434

    36. Mls000863581

    37. Mls001424135

    38. Schembl563218

    39. Pterostilbene [who-dd]

    40. Gtpl2681

    41. Megxp0_000345

    42. Dtxsid9041106

    43. Acon1_000305

    44. 4'-hydroxy-3,5-dimethoxystilbene

    45. Hms2051b10

    46. Hms2270j16

    47. Trans-1-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)ethylene

    48. Zinc899213

    49. Act03896

    50. Albb-013778

    51. Amy24840

    52. Bcp22675

    53. Hy-n0828

    54. (e)-3',5'-dimethoxy-4-stilbenol

    55. Bdbm50131688

    56. Lmpk13090015

    57. Nsc613735

    58. S3937

    59. 4''-hydroxy-3,5-dimethoxy Stilbene

    60. Akos000277651

    61. Akos025310510

    62. Ac-5283

    63. Ccg-101015

    64. Cs-w008773

    65. Eh-301 Component Pterostilbene

    66. Nc00265

    67. Nsc-613735

    68. (e)-4'-hydroxy-3,5-dimethoxystilbene

    69. Pterostilbene, >=97% (hplc), Solid

    70. Ncgc00180691-01

    71. As-13710

    72. Ls-14484

    73. 3,5-dimethoxy-4''-hydroxyl-trans-stilbene

    74. Bb 0262300

    75. N2126

    76. P1924

    77. 4-[2-(3,5-dimethoxy-phenyl)-vinyl]-phenol

    78. Phenol,4-[2-(3,5-dmethoxyphenyl)ethenyl]-

    79. (e)-1-hydroxy-4-(3,5-dimethoxy)styrylbenzene

    80. E 4-[2-(3,5-dimethoxy-phenyl)-vinyl]-phenol

    81. 259p159

    82. 4-[(e)-2-(3,5-dimethoxy-phenyl)-vinyl]-phenol

    83. A829757

    84. J-523927

    85. Phenol, 4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]-

    86. Q2908011

    87. W-203025

    88. Phenol, 4-(2-(3,5-dimethoxyphenyl)ethenyl)-, (e)-

    89. 4-[(e)-2-(3,5-dimethoxyphenyl)vinyl]phenol;pterostilbene

    90. Ncgc00180691-03!4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 256.30 g/mol
    Molecular Formula C16H16O3
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass256.109944368 g/mol
    Monoisotopic Mass256.109944368 g/mol
    Topological Polar Surface Area38.7 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity270
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Metabolism/Metabolites

    Pterostilbene has known human metabolites that include (2S,3S,4S,5R)-6-[4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560