1038713-54-0

Basic information

• Product Name: 3-chloro-2-hydroxy-5-phenylbenzoic acid
• Synonyms: 3-chloro-2-hydroxy-5-phenylbenzoic acid
• CAS NO: 1038713-54-0
• Molecular Formula: C13H9ClO3
• Molecular Weight: 248.66
• Mol File: 1038713-54-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-chloro-2-hydroxy-5-phenylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-2-hydroxy-5-phenylbenzoic acid(1038713-54-0)
• EPA Substance Registry System: 3-chloro-2-hydroxy-5-phenylbenzoic acid(1038713-54-0)

Safety Data

• Hazardous Substances Data: 1038713-54-0(Hazardous Substances Data)

Upstream product

• 1245532-94-8 methyl 5-chloro-4-methoxybiphenyl-3-carboxylate 

Relevant articles and documents

Structure-based optimization and biological evaluation of human 20α-hydroxysteroid dehydrogenase (AKR1C1) salicylic acid-based inhibitors

The tertiary structure of the Leu308Val mutant of human 20α-hydroxysteroid dehydrogenase (AKR1C1) in complex with the inhibitor 3,5-dichlorosalicylic acid (DCL) has been determined. Structures and kinetic properties of the wild-type and mutant enzymes indicate that Leu308 is a selectivity determinant for inhibitor binding. The Leu308Val mutation resulted in 13-fold and 3-fold reductions in the inhibitory potencies of DCL and 3-bromo-5-phenylsalicylic acid (BPSA), respectively. The replacement of Leu308 with an alanine resulted in 473-fold and 27-fold reductions in the potencies for DCL and BPSA, respectively. In our attempts to optimize inhibitor potency and selectivity we synthesized 5-substituted 3-chlorosalicylic acid derivatives, of which the most potent compound, 3-chloro-5-phenylsalicylic acid (Ki = 0.86 nM), was 24-fold more selective for AKR1C1 relative to the structurally similar 3α-hydroxysteroid dehydrogenase (AKR1C2). Furthermore, the compound inhibited the metabolism of progesterone in AKR1C1-overexpressed cells with an IC50 value equal to 100 nM.