Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H24O2 |
Molecular Weight | 332.4355 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)CCC(C)(C)C2=C1C=CC(=C2)C#CC3=CC=C(C=C3)C(O)=O
InChI
InChIKey=OQVLOWLEEHYBJH-UHFFFAOYSA-N
InChI=1S/C23H24O2/c1-22(2)13-14-23(3,4)20-15-17(9-12-19(20)22)6-5-16-7-10-18(11-8-16)21(24)25/h7-12,15H,13-14H2,1-4H3,(H,24,25)
EC23, also known as AGN 190205, is photostable synthetic analog of All-trans retinoic acid (ATRA). EC23 is an agonist of retinoic acid receptors: alpha, beta and gamma, while having no appreciable activity for retinoid X receptors and weakly activates aryl hydrocarbon receptor. It was shown, that EC23 induced neural differentiation in human pluripotent embryonic stem cells.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363069 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30108774 |
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Target ID: CHEMBL2003 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11809858 |
0.4 nM [EC50] | ||
Target ID: CHEMBL2008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11809858 |
0.5 nM [EC50] | ||
Target ID: CHEMBL2055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11809858 |
41.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19082150
Curator's Comment: When exposed to cultured human pluripotent stem cells, synthetic retinoid 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid, 4a (para-isomer/EC 23), induces neural differentiation similarly to All-trans-retinoic acid.
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104561-41-3
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admin on Fri Dec 15 15:47:45 GMT 2023 , Edited by admin on Fri Dec 15 15:47:45 GMT 2023
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10314719
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AGN-190205
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admin on Fri Dec 15 15:47:45 GMT 2023 , Edited by admin on Fri Dec 15 15:47:45 GMT 2023
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PRIMARY | All-trans retinoic acid (ATRA, Item No. 11017) is frequently used in cell culture to induce stem cell differentiation or enhance the growth, differentiation, and maintenance of neural cell types. Unfortunately, ATRA is readily susceptible to isomerisation and degradation upon exposure to light or other factors such as temperature and oxidation, which presents confounding issues for cell culture. EC 23 is a photostable synthetic analog of ATRA that induces differentiation in human pluripotent embryonic stem cells when used within the range of 100 nM-10 uM. | ||
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DTXSID40438025
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VSDTYDJDJJ
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admin on Fri Dec 15 15:47:45 GMT 2023 , Edited by admin on Fri Dec 15 15:47:45 GMT 2023
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EC23
Created by
admin on Fri Dec 15 15:47:45 GMT 2023 , Edited by admin on Fri Dec 15 15:47:45 GMT 2023
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PRIMARY | EC23 is a retinoic acid receptor (RAR) agonist with pan-RAR activity (EC50: RAR.ALPHA. 41 nM, RAR.BETA. 0.5 nM, RAR.GAMMA. 0.4 nM), while having no appreciable activity for retinoid X receptors (RXR; EC50 > 10.MU.M for all; Gambone et al.). It is a photostable synthetic analog of all-trans retinoic acid (ATRA; Christie et al. 2008). EC23 also weakly activates aryl hydrocarbon receptor (Gambone et al.). |
ACTIVE MOIETY