PMP-MeCyC

Soman analogue. Fluorogenic organophosphate diesters that produce fluorescence emission upon hydrolysis. The first ester is ethyl (E), isopropyl (I), cyclohexyl (C) or pinacoyl (P) analogous to the structure of VX, Sarin, Cyclosarin, and Somen respectively. The fluorescent ester is 3-cyano-4-methyl-7-hydroxy coumarin (MeCyC) or 1,3-dichloro-7-hydroxy-9,9-dimethyl-9H-acridin-2-one (DDAO)

General

Type : Organophosphate, Flu-OP, Nerve Agent G-series, Surrogate OP, Coumarin, Derivative of Soman, Chromen, Cyanide

Chemical_Nomenclature : 7-[3,3-dimethylbutan-2-yloxy(methyl)phosphoryl]oxy-4-methyl-2-oxochromene-3-carbonitrile

Canonical SMILES : CC1=C(C(=O)OC2=C1C=CC(=C2)OP(=O)(C)OC(C)C(C)(C)C)C#N

InChI : InChI=1S\/C18H22NO5P\/c1-11-14-8-7-13(9-16(14)22-17(20)15(11)10-19)24-25(6,21)23-12(2)18(3,4)5\/h7-9,12H,1-6H3

InChIKey : FHPKBNXJPLMRFC-UHFFFAOYSA-N

Other name(s) : methylphosphonic acid 3-cyano-7-hydroxy-4-mehtyl-2oxo-2H-coumarin-7-yl ester pinacoyl ester  ||  PMP-Coumarin  ||  3-Cyano-4-methyl-2-oxo-2H-chromen-7-yl 3,3-dimethyl-2-butanyl methylphosphonate  ||  Phosphonic acid, P-methyl-, 3-cyano-4-methyl-2-oxo-2H-1-benzopyran-7-yl 1,2,2-trimethylpropyl ester  ||  3-Cyano-4-methyl-2-oxo-2H-coumarin-7-ylpinacolyl methylphosphonate


MW : 363.34

Formula : C18H22NO5P

CAS_number :

PubChem : 49795037

UniChem : FHPKBNXJPLMRFC-UHFFFAOYSA-N

Target

Families : PMP-MeCyC ligand of proteins in family
ACHE

References (4)

Title : Evolved stereoselective hydrolases for broad-spectrum G-type nerve agent detoxification - Goldsmith_2012_Chem.Biol_19_456
Author(s) : Goldsmith M , Ashani Y , Simo Y , Ben-David M , Leader H , Silman I , Sussman JL , Tawfik DS
Ref : Chemical Biology , 19 :456 , 2012
Abstract :
PubMedSearch : Goldsmith_2012_Chem.Biol_19_456
PubMedID: 22520752

Title : Directed evolution of hydrolases for prevention of G-type nerve agent intoxication - Gupta_2011_Nat.Chem.Biol_7_120
Author(s) : Gupta RD , Goldsmith M , Ashani Y , Simo Y , Mullokandov G , Bar H , Ben-David M , Leader H , Margalit R , Silman I , Sussman JL , Tawfik DS
Ref : Nat Chemical Biology , 7 :120 , 2011
Abstract :
PubMedSearch : Gupta_2011_Nat.Chem.Biol_7_120
PubMedID: 21217689

Title : Asymmetric fluorogenic organophosphates for the development of active organophosphate hydrolases with reversed stereoselectivity - Amitai_2007_Toxicology_233_187
Author(s) : Amitai G , Adani R , Yacov G , Yishay S , Teitlboim S , Tveria L , Limanovich O , Kushnir M , Meshulam H
Ref : Toxicology , 233 :187 , 2007
Abstract :
PubMedSearch : Amitai_2007_Toxicology_233_187
PubMedID: 17129656

Title : Enhanced stereoselective hydrolysis of toxic organophosphates by directly evolved variants of mammalian serum paraoxonase - Amitai_2006_FEBS.J_273_1906
Author(s) : Amitai G , Gaidukov L , Adani R , Yishay S , Yacov G , Kushnir M , Teitlboim S , Lindenbaum M , Bel P , Khersonsky O , Tawfik DS , Meshulam H
Ref : Febs J , 273 :1906 , 2006
Abstract :
PubMedSearch : Amitai_2006_FEBS.J_273_1906
PubMedID: 16640555