L-Chicoric acid

Category	HIV Integrase
CAS	70831-56-0
Description	Cichoric acid, that can be isolated from the herbs of Echinacea purpurea, has been shown to inhibit hyaluronidase and HIV-1 integrase, and to possess phagoeytosis stimulatory activity in vitro and in vivo and antiviral acitivy. Chicoric acid may reduce acute alcohol-induced steatosis in mice through interfering with the induction of iNOS and iNOS-dependent signaling cascades in the liver. Chicoric acid also inhibited cell viability and induced apoptosis in 3T3-L1 preadipocytes which was characterized by chromatin condensation and poly ADP-ribose-polymerase (PARP) cleavage.

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Product Information

Synonyms	(2r,3r)-2,3-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid; (2R,3R)-2,3-BIS[[(2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL]OXY]-BUTANE DIOIC ACID; CHICHORIC ACID; CICHORIC ACID; CICHORINIC ACID; DICAFFEOYL TARTARIC ACID; L-CHICORIC ACID; Cichoric Acid (Chicoric acid)
IUPAC Name	(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
Molecular Weight	474.37
Molecular Formula	C22H18O12
Canonical SMILES	C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O
InChI	1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
InChIKey	YDDGKXBLOXEEMN-IABMMNSOSA-N
Boiling Point	785.0±60.0 °C at 760 mmHg
Flash Point	272.9±26.4 °C
Purity	>98%
Density	1.6±0.1 g/cm3
Solubility	Soluble in DMSO
Appearance	White powder
Application	Anti-inflammatory
Shelf Life	As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Storage	Store at -20 °C
Complexity	740
Exact Mass	474.07982601
Index Of Refraction	1.726
In Vitro	L-Chicoric Acid inhibits integration at concentrations from 500 nM to 10 μM but also inhibits entry at concentrations above 1 μM. L-Chicoric Acid clearly affects viral entry at concentrations of 5 μM and higher. L-Chicoric Acid also inhibits integration as indicated both by an increased ratio of two LTR circle DNA to cDNA and an accompanying decrease in integrated provirus. The EC50 of L-Chicoric Acid against HIV is approximately 500 nM, a concentration that does not inhibit HIV entry in H9 cells. The ED50 of L-Chicoric Acid against HIVNL4-3 control virus is 400 nM, while HIVNL4-3 passaged in the presence of 8 μM L-Chicoric Acid is completely resistant to the compound.
PSA	208.12000
Target	IC50: ~100 nM (HIV-1 integrase) HIV-1
Vapor Pressure	0.0±2.9 mmHg at 25°C
XLogP3-AA	2