5-CAFFEOYLSHIKIMIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H16O8
Molecular Weight	336.2934
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QMPHZIPNNJOWQI-GDDAOPKQSA-N

InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H16O8
Molecular Weight	336.2934
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24962011 | https://www.ncbi.nlm.nih.gov/pubmed/28702078

5-O-Caffeoylshikimic acid is a characteristic phenolic compound mainly found in the Palmae family. 5-O-Caffeoylshikimic acid was isolated from such plants as Vaccinium corymbosum, Livistona chinensis to name a few. The drug demonstrated the antiproliferative activity against different cancer cell lines. 5-O-Caffeoylshikimic acid could promote cancer cell apoptosis and block cancer cell adhesion, invasion and migration by inhibiting transforming growth factor beta 1 (TGF-beta1) signaling pathway.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
TGF-beta signaling pathway 8 Target ID: map04350 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28702078	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28702078	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor.	1982 Sep	6926750
Macrophage biospecific extraction and HPLC-ESI-MSn analysis for screening immunological active components in Smilacis Glabrae Rhizoma.	2013 Apr 15	23384550
5-O-caffeoylshikimic acid from Solanum somalense leaves: advantage of centrifugal partition chromatography over conventional column chromatography.	2014 Sep	24962011
Sarsaparilla (Smilax Glabra Rhizome) extract inhibits migration and invasion of cancer cells by suppressing TGF-β1 pathway.	2015	25742000
Anticancer activities and mechanisms of heat-clearing and detoxicating traditional Chinese herbal medicine.	2017	28702078

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

In a macrophages migration and adhesion assay, HUVEC were cultured in DMEM supplemented with 10% FBS, 1% penicillin-streptomycin, at 37C in a 5% CO2 incubator. Then HUVEC were seeded on the coverslips in 24-well plates at 80–90% confluence, starved and incubated with 5-O-Caffeoylshikimic acid (5 uM; 500 nM; 50 nM) + advanced glycation end-products (200 ug/mL) for 24 h.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:14:05 UTC 2023` Edited by `admin` on `Fri Dec 15 19:14:05 UTC 2023`
Record UNII	5U399BD0RZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-CAFFEOYLSHIKIMIC ACID

Common Name

English

TRANS-5-O-CAFFEOYLSHIKIMIC ACID

Common Name

English

1-CYCLOHEXENE-1-CARBOXYLIC ACID, 5-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (3R,4R,5R)-

Common Name

English

5-CSA

Common Name

English

TRANS-CAFFEIC ACID 5-O-SHIKIMATE

Common Name

English

1-CYCLOHEXENE-1-CARBOXYLIC ACID, 3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-4,5-DIHYDROXY-, (3R,4R,5R)-

Systematic Name

English

DACTYLIFRIC ACID

Common Name

English

5-O-CAFFEOYLSHIKIMIC ACID

Common Name

English

Code System Code Type Description

PUBCHEM

5281762