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23180-57-6 molecular structure
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[(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

ChemBase ID: 73275
Molecular Formular: C23H28O11
Molecular Mass: 480.46182
Monoisotopic Mass: 480.16316172
SMILES and InChIs

SMILES:
[C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)O[C@]12[C@@]3([C@@H]4O[C@@]1(C)C[C@]([C@@H]3C2)(O4)O)COC(=O)c1ccccc1)O)O)O)CO
Canonical SMILES:
OC[C@H]1O[C@@H](O[C@@]23C[C@@H]4[C@@]3(COC(=O)c3ccccc3)[C@@H]3O[C@@]2(C)C[C@]4(O3)O)[C@@H]([C@H]([C@@H]1O)O)O
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
InChIKey:
YKRGDOXKVOZESV-BZXJDTEKSA-N

Cite this record

CBID:73275 http://www.chembase.cn/molecule-73275.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl benzoate
IUPAC Traditional name
paeoniflorin
Synonyms
Paeoniflorin
CAS Number
23180-57-6
PubChem SID
162038195
PubChem CID
442534

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S2410 external link Add to cart Please log in.
Data Source Data ID
PubChem 442534 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.543816  H Acceptors 10 
H Donor LogD (pH = 5.5) -0.38655037 
LogD (pH = 7.4) -0.38658112  Log P -0.38654998 
Molar Refractivity 109.3037 cm3 Polarizability 44.8915 Å3
Polar Surface Area 164.37 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2410 external link
Research Area: Neurological Disease
Biological Activity:
Paeoniflorin is a herbal constituent extracted from the root of Paeonia albiflora Pall. Paeoniflorin has broad pharmacological effects, such as analgesic, anti-diuretic,anti-inflammatory,anti-convulsant, vasodilatic, and etc. In a study, paeoniflorin effectively alleviated the symptoms of oxazolone-induced colitis through regulating the expression of HBD-2, IL-6 and IL-10. Paeoniflorin is used as Chinese traditional medicine for its spasmolytic and pain-relieving properties. Paeoniflorin exhibits anticoagulant, neuromuscular blocking, cognition-enhancing, immunoregulating, and antihyperglycemic effects. [1][2][3]References on Paeoniflorin[1] Yao Xue Xue Bao., 2010 Jan, 45(1):37-42[2] Int Immunopharmacol., 2011 Feb, 11(2):172-8[3] Phytother Res., 2011 May, 25(5):681-5

REFERENCES

REFERENCES

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  • • Mao QQ et al. Phytother Res. 2011 May; 25(5):681-5.
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PATENTS

PATENTS

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INTERNET

INTERNET

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