3,4-DICAFFEOYLQUINIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H24O12
Molecular Weight	516.4509
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H]1OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)=O

InChI

InChIKey=UFCLZKMFXSILNL-RVXRWRFUSA-N

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21876716 | https://www.ncbi.nlm.nih.gov/pubmed/19752164 | https://www.ncbi.nlm.nih.gov/pubmed/9449274

3,4-Dicaffeoylquinic acid is a component of Brazilian green propolis water extract, green coffee beans and other plants. It was reported to have antivirus activity against Influenza A Virus. The compound was also shown to inhibit AngII-induced rVSMC proliferation and migration, probably through downregulating the Akt, JNK and part of the ERK1/2 pathways, in which the anti-oxidant property plays an important role. 3,4-Dicaffeoylquinic acid possesses a high binding affinity to plasma proteins, making it less preferable as a drug candidate as this characteristic would affect diffusion or transport across cell membranes, limiting pharmacological actions. 3,4-Dicaffeoylquinic acid is also a selective inhibitor of human immunodeficiency virus type 1 integrase.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 integrase 19 Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9449274	Inhibitor 8297		0.71 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Influenza A virus infection 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21876716	Primary	Preclinical	Unknown Approved Use Unknown
Liver diseases 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16176146	Primary	Preclinical	Unknown Approved Use Unknown
HIV-1 infection 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9449274	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cell cycle arrest and apoptosis induced by methyl 3,5-dicaffeoyl quinate in human colon cancer cells: Involvement of the PI3K/Akt and MAP kinase pathways.	2011 Oct 15	21872580
Anti-hepatitis B virus effect and possible mechanism of action of 3,4-o-dicaffeoylquinic Acid in vitro and in vivo.	2012	22701506

Patents

Sample Use Guides

In Vivo Use Guide

In a preclinical study, mice infected with influenza A virus were given 3,4-dicaffeoylquinic acid at a dose of 50 mg twice/kg/day. In a model of liver disease, mice received 5 and 10 mg/kg orally.

Route of Administration: Oral

In Vitro Use Guide

In an anti-influenza virus assay, MDCK cells (2*10(5)/well) were cultured in MEM that contained 10% fetal bovine serum, 60 U/mL of penicillin, and 60 ug/mL of streptomycin for 24 hrs on 96-well plates, washed with PBS, and infected with 20 to 200 TCID50 A/WSN/33 virus in the presence of 0, 10, 30, 100, 300 ug/ml of 3,4-dicaffeoylquinic acid. The compound was added almost simultaneously in an assay medium, MEM that was supplemented with 1% BSA, 1% DMSO, and 6.25 ug/mL trypsin. Cell cultures were maintained without medium exchange at 37 degrees Celsius, 5% CO2 for 48 hrs.

Name

Type

Language

3,4-DICAFFEOYLQUINIC ACID

Common Name

English

3,4-DI-O-CAFFEOYLQUINIC ACID

Common Name

English

3,4-DICQA

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 3,4-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,5-DIHYDROXY-, (1R,3R,4S,5R)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID601312292