1012306-94-3

Basic information

• Product Name: 3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• Synonyms: 3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• CAS NO: 1012306-94-3
• Molecular Weight: 446.411
• Mol File: 1012306-94-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one(1012306-94-3)
• EPA Substance Registry System: 3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one(1012306-94-3)

Safety Data

• Hazardous Substances Data: 1012306-94-3(Hazardous Substances Data)

Upstream product

• 1417412-05-5 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one 
• 23405-70-1 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 
• 1268341-13-4 C₁₂H₁₈O₅ 

Relevant articles and documents

Improving the affinity of SL0101 for RSK using structure-based design

Enhanced activity of the Ser/Thr protein kinase, RSK, is associated with transformation and metastasis, which suggests that RSK is an attractive drug target. The natural product SL0101 (kaempferol 3-O-(3″,4″-di-O- acetyl-α-L-rhamnopyranoside)) has been shown to be an RSK selective inhibitor. However, the Ki for SL0101 is 1 μM with a half-life of less than 30 min in vivo. To identify analogues with improved efficacy we designed a set of analogues based on the crystallographic model of SL0101 in complex with the RSK2 N-terminal kinase domain. We identified an analogue with a 5″-n-propyl group on the rhamnose that has >40-fold improved affinity for RSK relative to SL0101 in an in vitro kinase assay. This analogue preferentially inhibited the proliferation of the human breast cancer line, MCF-7, versus the normal untransformed breast line, MCF-10A, which is consistent with results using SL0101. However, the efficacy of the 5″-n-propyl analogue to inhibit MCF-7 proliferation was only 2-fold better than for SL0101, which we hypothesize is due to limited membrane permeability. The improved affinity of the 5″-n-propyl analogue for RSK will aid in the design of future compounds for in vivo use.