Oenothein B

Category	Hepatitis C Virus (HCV)
CAS	104987-36-2
Description	Oenothein B is a dimeric macrocyclic ellagitannin with a wide range of pharmacological activities, including antioxidant, anti-inflammatory, anti-fungal, anti-HCV and anti-tumor properties. It is an effective and specific inhibitor of poly(ADP-ribose) glycohydrolase.

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Product Information

Synonyms	D-Glucose, Cyclic 4,6-[(1S)-4-(6-carboxy-2,3,4-trihydroxyphenoxy)-4',5,5',6,6'-pentahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate] 2-[2-[[(1S)-6,6'-dicarboxy-2,2',3,3',4'-pentahydroxy[1,1'-biphenyl]-4-yl]oxy]-3,4,5-trihydroxybenzoate] 3-(3,4,5-trihydroxybenzoate), Cyclic Ester with D-Glucose 3-(3,4,5-trihydroxybenzoate)
IUPAC Name	[(11R,12R,14R,15R,37R,38R,40R,57R,58S,64S)-4,5,6,12,20,21,22,25,26,30,31,32,38,46,47,48,51,52-octadecahydroxy-9,17,35,43,55,61-hexaoxo-64-(3,4,5-trihydroxybenzoyl)oxy-2,10,13,16,28,36,39,42,56,62-decaoxaundecacyclo[35.15.6.514,27.111,15.03,8.018,23.029,34.040,57.044,49.050,54.024,60]tetrahexaconta-1(52),3,5,7,18,20,22,24,26,29,31,33,44,46,48,50,53,59-octadecaen-58-yl] 3,4,5-trihydroxybenzoate
Molecular Weight	1569.08
Molecular Formula	C68H48O44
Canonical SMILES	C1C2C3C(C(C(O2)O)OC(=O)C4=CC(=C(C(=C4OC5=C(C(=C6C(=C5)C(=O)OCC7C(C(C(C(O7)O)OC(=O)C8=CC(=C(C(=C8OC9=C(C(=C(C(=C9)C(=O)O3)C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)O)O)O)OC(=O)C1=CC(=C(C(=C16)O)O)O)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)O)O)O
InChI	InChI=1S/C68H48O44/c69-21-1-13(2-22(70)37(21)77)59(91)109-55-53-32-12-102-62(94)17-9-29(43(83)47(87)35(17)34-16(63(95)107-53)6-26(74)40(80)46(34)86)103-51-19(7-27(75)41(81)49(51)89)65(97)112-58-56(110-60(92)14-3-23(71)38(78)24(72)4-14)54-31(105-68(58)100)11-101-61(93)15-5-25(73)39(79)45(85)33(15)36-18(64(96)108-54)10-30(44(84)48(36)88)104-52-20(8-28(76)42(82)50(52)90)66(98)111-57(55)67(99)106-32/h1-10,31-32,53-58,67-90,99-100H,11-12H2/t31-,32-,53-,54-,55+,56+,57-,58-,67-,68-/m1/s1
InChIKey	YSLFLCIPPPJEHH-REWRZFNASA-N
Purity	≥95%
Density	2.20±0.1 g/cm3 (Predicted)
Solubility	In vitro: 10 mM in DMSO
Appearance	Solid powder
Storage	Store at 2-8°C
Complexity	3400
Exact Mass	1568.1518448
In Vitro	Oenothein B (15-45 µM; 12-72 hours) has a dose- and time-dependent inhibition rate effect on A549 cells in the range of 12 hours, 24 hours, 36 hours, 48 hours, 60 hours and 72 hours of exposure. Oenothein B (15-45 µM; 24 hours) effectively inhibits the proliferation of A549 cells by inducing Apoptosis and arresting cells at G1 stage. Oenothein B (15-45 µM; 24 hours) not only increases the level of intracellular reactive oxygen species (ROS), but also induces the upregulation of intracellular apoptotic triggers (cleavage Caspase-3, PARP, cytochrome c level in the cytosol, Bax). Cell Viability Assay Cell Line: A549 cells Concentration: 15 µM, 30 µM and 45 Incubation Time: 12 hours, 24 hours, 36 hours, 48 hours, 60 hours and 72 hours Result: Effectively inhibited the proliferation of A549 cells.
In Vivo	Oenothein B (100-300 mg/kg; p.o.) has the ability to reduce neuroinflammation in the brain during systemic inflammation in ICR mice.
PSA	732.84000
Target	HCV; Bacterial; Apoptosis; Fungal
XLogP3-AA	2.4