2-coumaroylquinic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-coumaroylquinic acid: precursor of chlorogenic acid & metabolite of cinnamic acid in Cestrum Poep gii, a plant; RN in Chemline for (5beta)-isomer: 1899-30-5; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-p-coumaroylquinic acid : A cinnamate ester obtained by formal condensation of the carboxy group of 4-coumaric acid with the 5-hydroxy group of (-)-quinic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

trans-5-O-(4-coumaroyl)-D-quinic acid : The 5-O-(4-coumaroyl) derivative of (-)-quinic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Flora	Rank	Flora Definition	Family	Family Definition
Cestrum	genus	A plant genus of the family SOLANACEAE. Members contain steroidal saponins and cause CALCINOSIS in grazing livestock due to high levels of 1 ALPHA,25-DIHYDROXYVITAMIN D3.[MeSH]	Solanaceae	A plant family of the order SOLANALES, class MAGNOLIOPSIDA. Among the most noted are POTATOES; TOMATOES; CAPSICUM (green and red peppers); TOBACCO; and BELLADONNA.[MeSH]

Cross-References

ID Source	ID
PubMed CID	6441280
CHEMBL ID	284243
CHEBI ID	15937
CHEBI ID	75500
SCHEMBL ID	10307372
MeSH ID	M0050145

Synonyms (34)

Synonym
CHEBI:15937 ,
(1s,3r,4r,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexanecarboxylic acid
trans-5-o-(4-coumaroyl)-d-quinic acid
p-coumaroyl quinic acid
o-coumaroylquinic acid
CHEMBL284243
(1s,3r,4r,5r)-1,3,4-trihydroxy-5-[(e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-((3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (1s-(1alpha,3alpha,4alpha,5beta))-
p-coumaroylquinic acid
1899-30-5
cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-((3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (1s-(1alpha,3alpha,4alpha,5beta(e)))-
2-coumaroylquinic acid
5746-55-4
unii-4c4bu5688g
4c4bu5688g ,
(1s,3r,4r,5r)-1,3,4-trihydroxy-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid
5-p-coumaroylquinic acid
CHEBI:75500
SCHEMBL10307372
5-p-coumaroylquinic acid, (e)-
5-p-coqa
cinnamic acid, p-hydroxy-, 5-ester with 1,3,4,5-tetrahydroxycyclohexanecarboxylic acid, (e)-
5-p-trans-coumaroylquinic acid
trans-p-coumaric acid 5-o-d-quinate
21600yp321
cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-(((2e)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (1s,3r,4r,5r)-
cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-((3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (1s-(1.alpha.,3.alpha.,4.alpha.,5.beta.(e)))-
cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-(((2e)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (1s,3r,4r,5r)-
coumaroylquinic acid
Q27098307
(1s,3r,4r,5r)-1,3,4-trihydroxy-5-(((e)-3-(4-hydroxyphenyl)acryloyl)oxy)cyclohexanecarboxylic acid
HY-N10543
CS-0610713
5-o-(e)-p-coumaroylquinic acid

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
quinic acid	A cyclitol carboxylic acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

Pathway	Proteins	Compounds
Flavonoid Biosynthesis	11	50

Bioassays (3)

Assay ID	Title	Year	Journal	Article
AID75271	Inhibition glucose-6-phosphate hydrolysis in highly intact microsomal preparations obtained from livers of 20-h fasted rats.	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Chlorogenic acid and synthetic chlorogenic acid derivatives: novel inhibitors of hepatic glucose-6-phosphate translocase.
AID311973	Hepatoprotective activity against HBV in human HepG2.2.15 cells	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Isolation of quinic acid derivatives and flavonoids from the aerial parts of Lactuca indica L. and their hepatoprotective activity in vitro.
AID311974	Antiviral activity against hepatitis B virus assessed as inhibition of viral particle production	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Isolation of quinic acid derivatives and flavonoids from the aerial parts of Lactuca indica L. and their hepatoprotective activity in vitro.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (14.29)	18.7374
1990's	1 (14.29)	18.2507
2000's	1 (14.29)	29.6817
2010's	3 (42.86)	24.3611
2020's	1 (14.29)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.91

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	12.91 (24.57)
Research Supply Index	2.08 (2.92)
Research Growth Index	4.99 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.91)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	7 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.17	1	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	3.15	5
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.17	1	catechin	antioxidant; plant metabolite
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	2.17	1	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	3.18	5	cinnamate ester; tannin	food component; plant metabolite
4-coumaroylshikimic acid [no description available]	1.99	1	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid
5'-o-caffeoylquinic acid trans-5-O-caffeoyl-D-quinic acid : A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid.	2.03	1	cinnamate ester; cyclitol carboxylic acid	plant metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	2.03	1	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
3,4-di-o-caffeoylquinic acid 3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis	2.03	1	quinic acid
4,5-di-O-caffeoylquinic acid [no description available]	2.03	1	quinic acid
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	2.03	1
methyl chlorogenate methyl chlorogenate: from Eriobotrya japonica; structure in first source	1.99	1	quinic acid

Condition	Indicated	Relationship Strength	Studies	Trials
Liver Dysfunction [description not available]	0	2.03	1	0
Liver Diseases Pathological processes of the LIVER.	0	2.03	1	0

chemdatabank.com