CHICORIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H18O12
Molecular Weight	474.3711
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)=O

InChI

InChIKey=YDDGKXBLOXEEMN-IABMMNSOSA-N

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

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.	1996 Jun 25	8692814
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.	1996 Oct	8863829
L-chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of Zidovudine plus a protease inhibitor (AG1350).	1998 Aug	9806487
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.	1998 Jan	9449274
Human immunodeficiency virus type 1 cDNA integration: new aromatic hydroxylated inhibitors and studies of the inhibition mechanism.	1998 Sep	9736543
Chicoric acid analogues as HIV-1 integrase inhibitors.	1999 Apr 22	10212126
Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.	1999 Feb 11	9986720
Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides.	2000 Aug 21	10969990
Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters.	2000 Sep	10953059
HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum.	2001 Aug	11534758
Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations.	2002 Aug 15	12166940
Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors.	2003 Aug 15	12901903
Catechol-substituted L-chicoric acid analogues as HIV integrase inhibitors.	2003 Dec 15	14643320
Human immunodeficiency virus type-1 integrase containing a glycine to serine mutation at position 140 is attenuated for catalysis and resistant to integrase inhibitors.	2003 Feb 1	12620807
A new anti-HIV flavonoid glucuronide from Chrysanthemum morifolium.	2003 Sep	14598216
Design, synthesis, and biological evaluation of novel hybrid dicaffeoyltartaric/diketo acid and tetrazole-substituted L-chicoric acid analogue inhibitors of human immunodeficiency virus type 1 integrase.	2010 Nov 25	20977258

Patents

Name

Type

Language

CHICORIC ACID

Common Name

English

NSC-699173

Code

English

CICHORIC ACID

Common Name

English

DICAFFEOYLTARTARIC ACID

Common Name

English

BUTANEDIOIC ACID, 2,3-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (2R,3R)-

Systematic Name

English

CHICORIC ACID, (-)-

Common Name

English

(-)-L-CHICORIC ACID

Common Name

English

TRANS-CAFFEOYLTARTARIC ACID

Common Name

English

L-CHICORIC ACID

Common Name

English

(-)-CHICORIC ACID

Common Name

English

CHICORIC ACID (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS) [DSC]

Common Name

English

CHICORIC ACID [USP-RS]

Common Name

English

TARTARIC ACID, BIS(3,4-DIHYDROXYCINNAMATE)

Common Name

English

NSC-99173

Code

English

Classification Tree Code System Code

DSLD

4390 (Number of products:2)