| Identification | Back Directory | [Name]
3-bromo-5-phenyl Salicylic Acid | [CAS]
4906-68-7 | [Synonyms]
AKR1C1-IN-1
XVZSXNULHSIRCQ-UHFFFAOYSA-N
3-bromo-5-phenyl Salicylic Acid
3-bromo-5-phenyl Salicylic Acid Exclusive
[1,1'-Biphenyl]-3-carboxylic acid, 5-bromo-4-hydroxy- | [EINECS(EC#)]
225-535-9 | [Molecular Formula]
C13H9BrO3 | [MDL Number]
MFCD16495825 | [MOL File]
4906-68-7.mol | [Molecular Weight]
293.11 |
| Chemical Properties | Back Directory | [Melting point ]
212-214 °C | [Boiling point ]
401.2±45.0 °C(Predicted) | [density ]
1.611±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMF: 15 mg/ml; DMF:PBS (pH 7.2) (1:9): 0.1 mg/ml; DMSO: 12.5 mg/ml; Ethanol: 0.1 mg/ml | [form ]
A crystalline solid | [pka]
2.45±0.14(Predicted) | [color ]
White to pink | [InChI]
1S/C13H9BrO3/c14-11-7-9(8-4-2-1-3-5-8)6-10(12(11)15)13(16)17/h1-7,15H,(H,16,17) | [InChIKey]
XVZSXNULHSIRCQ-UHFFFAOYSA-N | [SMILES]
OC1=C(C(O)=O)C=C(C2=CC=CC=C2)C=C1Br |
| Hazard Information | Back Directory | [Description]
The aldo-keto reductase (AKR) enzymes constitute a family of related NADPH-dependent oxidoreductases. The 1C subfamily (AKR1C) includes four human hydroxysteroid dehydrogenases, with AKR1C1 being a 20α-HSD and the other three being 3α-HSDs. AKR1C1 metabolizes progesterone to an inactive progestin, 20α-hydroxy progesterone. In addition, AKR1C1 actions have been implicated in cancer and in the processing of neuroactive steroids involved in brain function. 3-bromo-5-phenyl Salicylic acid selectively inhibits AKR1C1 (Ki = 4 nM) over AKR1C2 (Ki = 87 nM), AKR1C3 (Ki = 4.2 μM), and AKR1C4 (Ki = 18.2 μM). Moreover, it potently inhibits the metabolism of progesterone by bovine aortic endothelial cells overexpressing AKR1C1 (IC50 = 460 nM). | [Uses]
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]. | [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. DOI:10.1021/jm9001633 |
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