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
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
Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors.	2001 Jun	11408161
Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations.	2002 Aug 15	12166940
New class of HIV integrase inhibitors that block viral replication in cell culture.	2002 Jul 23	12176326
Diketo acid inhibitor mechanism and HIV-1 integrase: implications for metal binding in the active site of phosphotransferase enzymes.	2002 May 14	11997448
The total synthesis of fukiic acid, an HIV-1 integrase inhibitor.	2008 Oct	18243421
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)