1-CAFFEOYLQUINIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18O9
Molecular Weight	354.3087
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=GWTUHAXUUFROTF-JUHZACGLSA-N

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-16(15(23)24)6-11(19)14(22)12(20)7-16/h1-5,11-12,14,17-20,22H,6-7H2,(H,23,24)/b4-2+/t11-,12-,14-,16+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23661994 | https://www.ncbi.nlm.nih.gov/pubmed/24151872 | https://www.ncbi.nlm.nih.gov/pubmed/24228586

1-caffeoylquinic acid was extracted from Tetrastigma hemsleyanum leafs and identified in Ixeris sonchifolia. This dietary phytochemical is found in Quince, also. In silico study revealed that 1-caffeoylquinic acid effectively binds in the RH domain of NF-κB and might be a potent inhibitor of NF-κB pathway in cure and prevention of breast cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nuclear factor NF-kappa-B p105 subunit 4 Target ID: CHEMBL3251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23661994	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23661994	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Artichoke (Cynara cardunculus L. var. scolymus) waste as a natural source of carbonyl trapping and antiglycative agents.	2017-10	28873750
Qualitative and quantitative analysis of phenolics in Tetrastigma hemsleyanum and their antioxidant and antiproliferative activities.	2013-11-06	24151872
[Identification of chemical component from Ixeris sonchifolia and its injection by HPLC-ESI-MS(n)].	2013-08	24228586
Dietary phytochemicals as potent chemotherapeutic agents against breast cancer: Inhibition of NF-κB pathway via molecular interactions in rel homology domain of its precursor protein p105.	2013-01	23661994
Polyphenols are intensively metabolized in the human gastrointestinal tract after apple juice consumption.	2007-12-26	18047284
Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS(n).	2005-05-18	15884803

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

1-CAFFEOYLQUINIC ACID

Common Name

English

NPLC-0528

Preferred Name

English

1-O-CAFFEOYLQUINIC ACID

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 1-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-

Systematic Name

English

CYCLOHEXANECARBOXYLIC ACID, 1,3,4,5-TETRAHYDROXY-, (-)-, 1-(3,4-DIHYDROXYCINNAMATE)

Systematic Name

English

CYCLOHEXANECARBOXYLIC ACID, 1-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-

Systematic Name

English

TRANS-1-O-CAFFEOYLQUINIC ACID

Common Name

English

1-CQA

Common Name

English

Code System Code Type Description

CHEBI

136555