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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 of 5-CAFFEOYLSHIKIMIC ACID

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

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Sarsaparilla (Smilax Glabra Rhizome) extract inhibits migration and invasion of cancer cells by suppressing TGF-β1 pathway.
2015

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 GMT 2023
Edited
by admin
on Fri Dec 15 19:14:05 GMT 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
Created by admin on Fri Dec 15 19:14:05 GMT 2023 , Edited by admin on Fri Dec 15 19:14:05 GMT 2023
PRIMARY
CAS
73263-62-4
Created by admin on Fri Dec 15 19:14:05 GMT 2023 , Edited by admin on Fri Dec 15 19:14:05 GMT 2023
PRIMARY
WIKIPEDIA
Dactylifric acid
Created by admin on Fri Dec 15 19:14:05 GMT 2023 , Edited by admin on Fri Dec 15 19:14:05 GMT 2023
PRIMARY
FDA UNII
5U399BD0RZ
Created by admin on Fri Dec 15 19:14:05 GMT 2023 , Edited by admin on Fri Dec 15 19:14:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID501312675
Created by admin on Fri Dec 15 19:14:05 GMT 2023 , Edited by admin on Fri Dec 15 19:14:05 GMT 2023
PRIMARY
CAS
1656981-79-1
Created by admin on Fri Dec 15 19:14:05 GMT 2023 , Edited by admin on Fri Dec 15 19:14:05 GMT 2023
ALTERNATIVE
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Methanol extracts of stevia dry leaves were directly used for LC-MS analysis. Efficient separation and resolution were achieved with diphenyl packing and acetonitrile/water as solvent in the HPLC method. Negative ion mode was used for all MS measurements.