Benzoylecgonine
Benzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases (Brzezinski et al. 1994). It is excreted in the urine of cocaine users after processing in the liver. It is hydrolyzed by BCHE mutants (Chen et al. 2016)
General
Type : Drug, Not AlphaBeta Hydrolase target, Alkaloid, Azabicyclo
Chemical_Nomenclature : (1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid
Canonical SMILES : CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)O
InChI : InChI=1S\/C16H19NO4\/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10\/h2-6,11-14H,7-9H2,1H3,(H,18,19)\/t11-,12+,13-,14+\/m0\/s1
InChIKey : GVGYEFKIHJTNQZ-RFQIPJPRSA-N
Other name(s) : O-Benzoylecgonine || (-)-Benzoylecgonine || O-Benzoyl-(-)-ecgonine || Benzoylecgonine solution
MW : 289.32
Formula : C16H19NO4
CAS_number : 519-09-5
PubChem : 448223
UniChem : GVGYEFKIHJTNQZ-RFQIPJPRSA-N
Target
Structures : No structure
Families : BCHE, Cocaine_esterase
References (9)
| Title : Substrate Specificity and In Vivo Efficacy of Engineered Cocaine Esterases toward Cocaine and its Toxic Metabolites - Li_2026_Chem.Biol.Interact__112088 |
| Author(s) : Li Z , Hu Q , Deng X , Chen C , Ren Z , Mo N , Huang Z , Wang B , Fang L , Wang J , Hou S , Chen X |
| Ref : Chemico-Biological Interactions , :112088 , 2026 |
| Abstract : |
| PubMedSearch : Li_2026_Chem.Biol.Interact__112088 |
| PubMedID: 42000102 |
| Gene_locus related to this paper: human-BCHE , rhosm-cocE |
| Title : Catalytic mechanism, computational design, and crystal structure of a highly specific and efficient benzoylecgonine hydrolase - Chen_2024_Int.J.Biol.Macromol__137767 |
| Author(s) : Chen X , Zhang Y , Tong J , Ouyang P , Deng X , Zhang J , Liu H , Hu Y , Yao W , Wang J , Wang X , Hou S , Yao J |
| Ref : Int J Biol Macromol , :137767 , 2024 |
| Abstract : |
| PubMedSearch : Chen_2024_Int.J.Biol.Macromol__137767 |
| PubMedID: 39561846 |
| Gene_locus related to this paper: rhosm-cocE |
| Title : Computational Design and Crystal Structure of a Highly Efficient Benzoylecgonine Hydrolase - Chen_2021_Angew.Chem.Int.Ed.Engl_60_21959 |
| Author(s) : Chen X , Deng X , Zhang Y , Wu Y , Yang K , Li Q , Wang J , Yao W , Tong J , Xie T , Hou S , Yao J |
| Ref : Angew Chem Int Ed Engl , 60 :21959 , 2021 |
| Abstract : |
| PubMedSearch : Chen_2021_Angew.Chem.Int.Ed.Engl_60_21959 |
| PubMedID: 34351032 |
| Gene_locus related to this paper: rhosm-cocE |
| Title : Metabolic Enzymes of Cocaine Metabolite Benzoylecgonine - Chen_2016_ACS.Chem.Biol_11_2186 |
| Author(s) : Chen X , Zheng X , Zhan M , Zhou Z , Zhan CG , Zheng F |
| Ref : ACS Chemical Biology , 11 :2186 , 2016 |
| Abstract : |
| PubMedSearch : Chen_2016_ACS.Chem.Biol_11_2186 |
| PubMedID: 27224254 |
| Title : Simultaneous analysis of cocaine and its metabolites in urine by capillary electrophoresis-electrospray mass spectrometry using a pressurized liquid junction nanoflow interface - Hezinova_2012_Electrophoresis_33_653 |
| Author(s) : Hezinova V , Aturki Z , Kleparnik K , D'Orazio G , Foret F , Fanali S |
| Ref : Electrophoresis , 33 :653 , 2012 |
| Abstract : |
| PubMedSearch : Hezinova_2012_Electrophoresis_33_653 |
| PubMedID: 22451058 |
| Title : The ability of bacterial cocaine esterase to hydrolyze cocaine metabolites and their simultaneous quantification using high-performance liquid chromatography-tandem mass spectrometry - Brim_2011_Mol.Pharmacol_80_1119 |
| Author(s) : Brim RL , Noon KR , Collins GT , Nichols J , Narasimhan D , Sunahara RK , Woods JH |
| Ref : Molecular Pharmacology , 80 :1119 , 2011 |
| Abstract : |
| PubMedSearch : Brim_2011_Mol.Pharmacol_80_1119 |
| PubMedID: 21885621 |
| Gene_locus related to this paper: rhosm-cocE |
| Title : Major and minor metabolites of cocaine in human plasma following controlled subcutaneous cocaine administration - Kolbrich_2006_J.Anal.Toxicol_30_501 |
| Author(s) : Kolbrich EA , Barnes AJ , Gorelick DA , Boyd SJ , Cone EJ , Huestis MA |
| Ref : J Anal Toxicol , 30 :501 , 2006 |
| Abstract : |
| PubMedSearch : Kolbrich_2006_J.Anal.Toxicol_30_501 |
| PubMedID: 17132243 |
| Title : Purification and characterization of a human liver cocaine carboxylesterase that catalyzes the production of benzoylecgonine and the formation of cocaethylene from alcohol and cocaine - Brzezinski_1994_Biochem.Pharmacol_48_1747 |
| Author(s) : Brzezinski MR , Abraham TL , Stone CL , Dean RA , Bosron WF |
| Ref : Biochemical Pharmacology , 48 :1747 , 1994 |
| Abstract : |
| PubMedSearch : Brzezinski_1994_Biochem.Pharmacol_48_1747 |
| PubMedID: 7980644 |
| Gene_locus related to this paper: human-CES1 |
| Title : Analysis of cocaine, benzoylecgonine, ecgonine methyl ester, ethylcocaine and norcocaine in human urine using HPLC with post-column ion-pair extraction and fluorescence detection - Roy_1992_J.Pharm.Biomed.Anal_10_943 |
| Author(s) : Roy IM , Jefferies TM , Threadgill MD , Dewar GH |
| Ref : J Pharm Biomed Anal , 10 :943 , 1992 |
| Abstract : |
| PubMedSearch : Roy_1992_J.Pharm.Biomed.Anal_10_943 |
| PubMedID: 1298401 |