Compound: Paeoniflorin
SMILES: O=C(OC[C@]12[C@@]3(O[C@@H]4O[C@@H]([C@@H](O)[C@@H]([C@H]4O)O)CO)[C@@]5(C[C@@]([C@@H]1C3)(O)O[C@H]2O5)C)c6ccccc6
InChIKey: YKRGDOXKVOZESV-WRJNSLSBSA-N
Synonyms: Paeoniflorin, Peoniflorin, 23180-57-6, NSC-178886, 21AIQ4EV64, DTXSID2042648, [(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, ((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, RefChem:45627, DTXCID401478399, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd) pentalen-1a(2H)-yl-beta-D-glucopyranoside, 245-476-2, Paeonia moutan, ((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, 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, Paeoniflorin (>80%), MFCD00869331, NSC 178886, paeonilflorin, UNII-21AIQ4EV64, CCRIS 6494, NSC178886, s2410, Paeoniflorin CRS, YKRGDOXKVOZESV-WRJNSLSBSA-N, .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, .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, EINECS 245-476-2, Paeoniflorin (Standard), PAEONIFLORIN [USP-RS], SCHEMBL549033, CHEBI:7889, orb1306020, orb3140604, CHEMBL4303209, HY-N0293R, Paeoniflorin, analytical standard, Paeoniflorin, >=98% (HPLC), GLXC-13167, HMS3884D17, HY-N0293, MSK157242, AKOS025311455, CCG-269549, EBC-461042, MP08290, AS-12193, 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, NS00027374, C09959, AB01566855_01, Q7124104, BRD-K83631119-001-02-1, ((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, .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.))-, [(1aR,2S,3aR,5R,5aR,5bS)-1a-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-methyltetrahydro-1H-2,5-methano-3,4-dioxacyclobuta[cd]pentalen-5b(3aH)-yl]methyl benzoate, [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate, [(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[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl benzoate, [hydroxy-methyl-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]yl]methyl benzoate, 5b-((Benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl-beta-D-glucopyranoside, 9[(Benzoyioxy)methyl]-1-(?-D-glucopyranosyloxy)-4,8-epoxy-6-methyl-7-oxaticyclo[4,3,0,0]nonane, 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))-, 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))-
Theoretical properties:
molecular_formula: C23H28O11
molecular_weight: 480.5 g/mol
exact_mass: 480.16316171 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 7
heavy_atom_count: 34
topological_polar_surface_area: 164 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Paeoniflorin is a terpene glycoside.
chembl: PAEONIFLORIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Paeoniflorin is a chemical compound which is one of the major constituents of an herbal medicine derived from Paeonia lactiflora. It can also be isolated from the fresh water fern Salvinia molesta.
In Paeonia, it can form new compounds with addition of phenolic substituents. In a study in female rats, paeoniflorin was found to inhibit the production of testosterone within the ovaries, however does not significantly affect the production of estradiol.
In mice, paeoniflorin was shown to protect against neuroinflammation and depression-like behavior induced by FN alpha.