5-Bromo-4-hydroxy-3-biphenylcarboxylic acid

Modify Date: 2025-08-25 11:02:07

5-Bromo-4-hydroxy-3-biphenylcarboxylic acid Structure
5-Bromo-4-hydroxy-3-biphenylcarboxylic acid structure
Common Name 5-Bromo-4-hydroxy-3-biphenylcarboxylic acid
CAS Number 4906-68-7 Molecular Weight 293.113
Density 1.6±0.0 g/cm3 Boiling Point 439.2±0.0 °C at 760 mmHg
Molecular Formula C13H9BrO3 Melting Point N/A
MSDS N/A Flash Point 219.4±0.0 °C

 Use of 5-Bromo-4-hydroxy-3-biphenylcarboxylic acid


AKR1C1-IN-1 is a potent and selective inhibitor of human 20α-hydroxysteroid dehydrogenase (AKR1C1), with a Ki value of 4 nM for AKR1C1[1].

 Names

Name 3-bromo-2-hydroxy-5-phenylbenzoic acid
Synonym More Synonyms

  Biological Activity

Description AKR1C1-IN-1 is a potent and selective inhibitor of human 20α-hydroxysteroid dehydrogenase (AKR1C1), with a Ki value of 4 nM for AKR1C1[1].
Related Catalog
Target

Ki: 4 nM (AKR1C1), 87 nM (AKR1C2), 4.2 μM (AKR1C3), 18.2 μM (AKR1C4)[1]

In Vitro AKR1C1-IN-1 potently inhibits the metabolism of progesterone in AKR1C1-overexpressed BAECs, and with an IC50 of 460 nM[1].
References

[1]. El-Kabbani O, et al. Structure-guided design, synthesis, and evaluation of salicylic acid-based inhibitors targeting a selectivity pocket in the active site of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1). J Med Chem. 2009 May 28;52(10):3259-64.

 Chemical & Physical Properties

Density 1.6±0.0 g/cm3
Boiling Point 439.2±0.0 °C at 760 mmHg
Molecular Formula C13H9BrO3
Molecular Weight 293.113
Flash Point 219.4±0.0 °C
Exact Mass 291.974000
PSA 57.53000
LogP 4.43
Vapour Pressure 0.0±0.0 mmHg at 25°C
Index of Refraction 1.663
InChIKey XVZSXNULHSIRCQ-UHFFFAOYSA-N
SMILES O=C(O)c1cc(-c2ccccc2)cc(Br)c1O

 Synthetic Route

~%

5-Bromo-4-hydroxy-3-biphenylcarboxylic acid Structure

5-Bromo-4-hydro...

CAS#:4906-68-7

Literature: Dow Chem. Co. Patent: US2779785 , 1952 ;

 Precursor & DownStream

Precursor  1

DownStream  0

 Bioassay

View more

Name: Inhibition of human recombinant 20-alpha HSD expressed in BAEC assessed as inhibition...
Source: ChEMBL
Target: Aldo-keto reductase family 1 member C1
External Id: CHEMBL968789
Name: Selectivity ratio of Ki for human type 3 3-alpha-HSD to Ki for human 20-alpha HSD
Source: ChEMBL
Target: N/A
External Id: CHEMBL980738
Name: Inhibition of PTP1B
Source: ChEMBL
Target: Tyrosine-protein phosphatase non-receptor type 1
External Id: CHEMBL905766
Name: Selectivity ratio of Ki for human type 1 3-alpha-HSD to Ki for human 20-alpha HSD
Source: ChEMBL
Target: N/A
External Id: CHEMBL968788
Name: Selectivity ratio of Ki for human type 2 3-alpha-HSD to Ki for human 20-alpha HSD
Source: ChEMBL
Target: N/A
External Id: CHEMBL968787
Name: Selectivity ratio of Ki for human AKR1C1 Leu308Val mutant to Ki for human wild type A...
Source: ChEMBL
Target: N/A
External Id: CHEMBL1285649
Name: Selectivity ratio of Ki for human AKR1C1 Leu308Ala mutant to Ki for human wild type A...
Source: ChEMBL
Target: N/A
External Id: CHEMBL1285650
Name: Inhibition of human AKR1C2 dehydrogenase activity by fluorometric assay
Source: ChEMBL
Target: Aldo-keto reductase family 1 member C2
External Id: CHEMBL1285651
Name: Selectivity ratio of IC50 of human recombinant AKR1C3 to IC50 of human recombinant AK...
Source: ChEMBL
Target: N/A
External Id: CHEMBL2175573
Name: Selectivity ratio of Ki for human AKR1C2 to Ki for human AKR1C1
Source: ChEMBL
Target: N/A
External Id: CHEMBL1285652
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 Synonyms

5-Brom-4-hydroxy-biphenyl-3-carbonsaeure
5-bromo-4-hydroxy-biphenyl-3-carboxylic acid
3-bromo-5-phenylsalicylic acid
3-Bromo-5-phenylsalicylc acid
5-Bromo-4-hydroxy-3-biphenylcarboxylic acid
3'-Bromo-4-hydroxy-3-biphenylcarboxylic acid
[1,1'-biphenyl]-3-carboxylic acid,5-bromo-4-hydroxy
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