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    Paeoniflorin

    ACTIVE PHARMA INGREDIENTS

    REF. STANDARDS & IMPURITIES

    ANALYTICAL

    PharmaCompass
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    2D Structure
    Also known as: 23180-57-6, Peoniflorin, Paeonia moutan, Paeony root, Nsc 178886, 21aiq4ev64
    Molecular Formula
    C23H28O11
    Molecular Weight
    480.5  g/mol
    InChI Key
    YKRGDOXKVOZESV-WRJNSLSBSA-N
    FDA UNII
    21AIQ4EV64
    paeoniflorin is a natural product found in Paeonia, Paeonia tenuifolia, and other organisms with data available.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
    2.1.2 InChI
    InChI=1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1
    2.1.3 InChI Key
    YKRGDOXKVOZESV-WRJNSLSBSA-N
    2.1.4 Canonical SMILES
    CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)CO)O)O)O)O
    2.1.5 Isomeric SMILES
    C[C@]12C[C@@]3([C@@H]4C[C@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    21AIQ4EV64
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Peoniflorin

    2. Peoniflorin Sulfonate

    2.3.2 Depositor-Supplied Synonyms

    1. 23180-57-6

    2. Peoniflorin

    3. Paeonia Moutan

    4. Paeony Root

    5. Nsc 178886

    6. 21aiq4ev64

    7. ((2s,2ar,2a1s,3ar,4r,5ar)-4-hydroxy-2-methyl-2a-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)hexahydro-2h-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methyl Benzoate

    8. Unii-21aiq4ev64

    9. Ccris 6494

    10. Nsc178886

    11. Nsc-178886

    12. .beta.-d-glucopyranoside, (1ar,2s,3ar,5r,5ar,5bs)-5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta(cd)pentalen-1a(2h)-yl

    13. .beta.-d-glucopyranoside, (1ar,2s,3ar,5r,5ar,5bs)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta[cd]pentalen-1a(2h)-yl

    14. Einecs 245-476-2

    15. Mfcd00869331

    16. Peoniflorin [inci]

    17. Paeoniflorin [usp-rs]

    18. Schembl549033

    19. Chebi:7889

    20. Chembl4303209

    21. Dtxsid2042648

    22. Paeoniflorin, Analytical Standard

    23. Paeoniflorin, >=98% (hplc)

    24. Hms3884d17

    25. Hy-n0293

    26. Zinc8234328

    27. S2410

    28. Akos025311455

    29. Ccg-269549

    30. As-12193

    31. Beta-d-glucopyranoside, (1as,2r,3ar,5r,5ar,5bs)-5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta(cd)pentalen-1a(2h)-yl

    32. C09959

    33. Ab01566855_01

    34. 180p576

    35. Q-100296

    36. Q7124104

    37. ((2s,2ar,2a1s,3ar,4r,5ar)-4-hydroxy-2-methyl-2a-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)hexahydro-2h-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methylbenzoate

    38. .beta.-d-glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta(cd)pentalen-1a(2h)-yl, (1ar-(1a.alpha.,2.beta.,3a.alpha.,5.alpha.,5a.alpha.,5b.alpha.))-

    39. [(1r,2s,3r,5r,6r,8s)-6-hydroxy-8-methyl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl Benzoate

    40. [hydroxy-methyl-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]yl]methyl Benzoate

    41. 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lh-3,4-dioxacyclobuta(cd)pentalen-1a(2h)-yl-beta-d-glucopyranoside

    42. B-d-glucopyranoside,(1ar,2s,3ar,5r,5ar,5bs)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta[cd]pentalen-1a(2h)-yl

    43. Beta-d-glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta(cd)pentalen-1a(2h)-yl, (1ar-(1a-alpha,2-beta,3a-alpha,5-alpha,5a-alpha,5b-alpha))-

    44. Beta-d-glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1h-3,4-dioxacyclobuta(cd)pentalen-1a(2h)-yl, (1ar-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 480.5 g/mol
    Molecular Formula C23H28O11
    XLogP3-1
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count7
    Exact Mass480.16316171 g/mol
    Monoisotopic Mass480.16316171 g/mol
    Topological Polar Surface Area164 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity849
    Isotope Atom Count0
    Defined Atom Stereocenter Count11
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)