METHYL CHLOROGENATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H20O9
Molecular Weight	368.3353
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@@H](C1)OC(=O)\C=C\C2=CC(O)=C(O)C=C2

InChI

InChIKey=MZNIJRAPCCELQX-AWOKGZDASA-N

InChI=1S/C17H20O9/c1-25-16(23)17(24)7-12(20)15(22)13(8-17)26-14(21)5-3-9-2-4-10(18)11(19)6-9/h2-6,12-13,15,18-20,22,24H,7-8H2,1H3/b5-3+/t12-,13-,15-,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C17H20O9
Molecular Weight	368.3353
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27013795 | https://www.ncbi.nlm.nih.gov/pubmed/10901160 | https://www.ncbi.nlm.nih.gov/pubmed/10230515

Methyl chlorogenate, an antioxidant flavonoid, exhibited strong activity against HDAC8 and the high affinity to trichostatin A binding site. Methyl chlorogenate showed specific cytotoxicity against certain types of tested cancer cell lines such as Hep2 and MCF7. Methyl chlorogenate may inhibit NFkappaB activation, exhibiting its ability to downregulate the NFkappaB-dependent gene expression. Thus, it can be expected that Methyl chlorogenate may have potential for therapeutic intervention on various NFkappaB-dependent pathological conditions such as inflammatory or possibly mutagenic processes. Methyl chlorogenate has demonstrated antioxidant activity.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histone deacetylase 8 17 Target ID: CHEMBL3192 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27013795	Inhibitor 8297	8.22 µM [IC50]
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10901160	Inhibitor 8297
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10230515	Inhibitor 8297	840.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27013795	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters.	2013 Aug-Sep	23684728
In vitro neuroprotective activities of compounds from Angelica shikokiana Makino.	2015 Mar 16	25786165

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Neuro-2A cells were treated with different concentrations (6.25, 12.5, 25, 50, 100 uM) of Methyl chlorogenate. Methyl chlorogenate showed dose-dependent neuroprotection, and, at 100 uM, resulted in significant increase in cell viability of 12% ± 2.6%. Methyl chlorogenate at concentrations of 50 and 100 uM could significantly decrease the fluorescence intensity of DFF, indicating their ability to scavenge intracellular ROS and decrease oxidative stress.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:44:33 GMT 2023` Edited by `admin` on `Sat Dec 16 10:44:33 GMT 2023`
Record UNII	E6GC3KV7JK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYL CHLOROGENATE

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4,5-TRIHYDROXY-, METHYL ESTER, (1S,3R,4R,5R)-

Systematic Name

English

METHYL 5-O-CAFFEOYLQUINATE

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, METHYL ESTER, (1S-(1.ALPHA.,3.BETA.,4.ALPHA.,5.ALPHA.))-

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4,5-TRIHYDROXY-, METHYL ESTER, (1S,3R,4R,5R)-

Systematic Name

English

CHLOROGENIC ACID, METHYL ESTER

Common Name

English

Code System Code Type Description

FDA UNII

E6GC3KV7JK