BNPP

Inhibitor of carboxylesterases (and also AADAC), substrate of metallo-beta-lactamase. hCE1b IC50 69.3 +/- 9.4

General

Type : Organophosphate, pNP

Chemical_Nomenclature : Bis(4-nitrophenyl)phosphate

Canonical SMILES : C1=CC(=CC=C1[N+](=O)[O-])OP(=O)(O)OC2=CC=C(C=C2)[N+](=O)[O-]

InChI : InChI=1S\/C12H9N2O8P\/c15-13(16)9-1-5-11(6-2-9)21-23(19,20)22-12-7-3-10(4-8-12)14(17)18\/h1-8H,(H,19,20)

InChIKey : MHSVUSZEHNVFKW-UHFFFAOYSA-N

Other name(s) : Bis(4-nitrophenyl)phosphate  ||  Bis(4-nitrophenyl) phosphate  ||  Bis(4-nitrophenyl) hydrogen phosphate  ||  Bis(p-nitrophenyl)phosphate  ||  bis-(p-nitrophenyl)phosphoric acid


MW : 340.18

Formula : C12H9N2O8P

CAS_number : 645-15-8

PubChem : 255

UniChem : MHSVUSZEHNVFKW-UHFFFAOYSA-N

Wikipedia : Bis_(p-nitrophenyl)phosphate

Target

Families : BNPP ligand of proteins in family
Carb_B_Chordata Arylacetamide_deacetylase

Protein :
human-CES2

References (11)

Title : Rationally Engineered hCES2A Near-Infrared Fluorogenic Substrate for Functional Imaging and High-Throughput Inhibitor Screening - Fan_2023_Anal.Chem_95_15665
Author(s) : Fan Y , Zhang T , Song Y , Sang Z , Zeng H , Liu P , Wang P , Ge G
Ref : Analytical Chemistry , 95 :15665-15672 , 2023
Abstract :
PubMedSearch : Fan_2023_Anal.Chem_95_15665
PubMedID: 37782032
Gene_locus related to this paper: human-CES2

Title : Deciphering the species differences in CES1A-mediated hydrolytic metabolism by using a bioluminescence substrate - Jin_2022_Chem.Biol.Interact_368_110197
Author(s) : Jin Q , Li Z , Zhang MJ , Liu WC , Zou LW , Sui H , Wang DD , Tang QF , Ge GB
Ref : Chemico-Biological Interactions , 368 :110197 , 2022
Abstract :
PubMedSearch : Jin_2022_Chem.Biol.Interact_368_110197
PubMedID: 36174736

Title : Optimal pH 8.5 to 9 for the Hydrolysis of Vixotrigine and Other Basic Substrates of Carboxylesterase-1 in Human Liver Microsomes - Johnson_2022_Xenobiotica_52_105
Author(s) : Johnson JL , Huang J , Rooney M , Gu C
Ref : Xenobiotica , 52 :105 , 2021
Abstract :
PubMedSearch : Johnson_2022_Xenobiotica_52_105
PubMedID: 34904522

Title : Inhibition of Human Liver Carboxylesterase (hCE1) by Organophosphate Ester Flame Retardants and Plasticizers: Implications for Pharmacotherapy - Phillips_2019_Toxicol.Sci_171_396
Author(s) : Phillips AL , Stapleton HM
Ref : Toxicol Sci , 171 :396 , 2019
Abstract :
PubMedSearch : Phillips_2019_Toxicol.Sci_171_396
PubMedID: 31268531

Title : Inhibition of human carboxylesterases hCE1 and hiCE by cholinesterase inhibitors - Tsurkan_2013_Chem.Biol.Interact_203_226
Author(s) : Tsurkan LG , Hatfield MJ , Edwards CC , Hyatt JL , Potter PM
Ref : Chemico-Biological Interactions , 203 :226 , 2013
Abstract :
PubMedSearch : Tsurkan_2013_Chem.Biol.Interact_203_226
PubMedID: 23123248

Title : Comparative study of the hydrolytic metabolism of methyl-, ethyl-, propyl-, butyl-, heptyl- and dodecylparaben by microsomes of various rat and human tissues - Ozaki_2013_Xenobiotica_43_1064
Author(s) : Ozaki H , Sugihara K , Watanabe Y , Fujino C , Uramaru N , Sone T , Ohta S , Kitamura S
Ref : Xenobiotica , 43 :1064 , 2013
Abstract :
PubMedSearch : Ozaki_2013_Xenobiotica_43_1064
PubMedID: 23742084

Title : Utility of the carboxylesterase inhibitor bis-para-nitrophenylphosphate (BNPP) in the plasma unbound fraction determination for a hydrolytically unstable amide derivative and agonist of the TGR5 receptor - Eng_2010_Xenobiotica_40_369
Author(s) : Eng H , Niosi M , McDonald TS , Wolford A , Chen Y , Simila ST , Bauman JN , Warmus J , Kalgutkar AS
Ref : Xenobiotica , 40 :369 , 2010
Abstract :
PubMedSearch : Eng_2010_Xenobiotica_40_369
PubMedID: 20297923

Title : Human arylacetamide deacetylase is a principal enzyme in flutamide hydrolysis - Watanabe_2009_Drug.Metab.Dispos_37_1513
Author(s) : Watanabe A , Fukami T , Nakajima M , Takamiya M , Aoki Y , Yokoi T
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 37 :1513 , 2009
Abstract :
PubMedSearch : Watanabe_2009_Drug.Metab.Dispos_37_1513
PubMedID: 19339378
Gene_locus related to this paper: human-AADAC

Title : Detection of a new N-oxidized metabolite of flutamide, N-[4-nitro-3-(trifluoromethyl)phenyl]hydroxylamine, in human liver microsomes and urine of prostate cancer patients - Goda_2006_Drug.Metab.Dispos_34_828
Author(s) : Goda R , Nagai D , Akiyama Y , Nishikawa K , Ikemoto I , Aizawa Y , Nagata K , Yamazoe Y
Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 34 :828 , 2006
Abstract :
PubMedSearch : Goda_2006_Drug.Metab.Dispos_34_828
PubMedID: 16507648

Title : Involvement of human blood arylesterases and liver microsomal carboxylesterases in nafamostat hydrolysis - Yamaori_2006_Drug.Metab.Pharmacokinet_21_147
Author(s) : Yamaori S , Fujiyama N , Kushihara M , Funahashi T , Kimura T , Yamamoto I , Sone T , Isobe M , Ohshima T , Matsumura K , Oda M , Watanabe K
Ref : Drug Metab Pharmacokinet , 21 :147 , 2006
Abstract :
PubMedSearch : Yamaori_2006_Drug.Metab.Pharmacokinet_21_147
PubMedID: 16702735

Title : [Phosphoric acid-bis-(p-nitro-phenylester), a new inhibitor of microsomal carboxylesterases] -
Author(s) : Heymann E , Krisch K
Ref : Hoppe-Seylers Zeitschrift fur physiologische Chemie , 348 :609 , 1967
PubMedID: 5613978