HOPDA
General
Type : Ketone
Chemical_Nomenclature : (3E,5E)-6-hydroxy-2-oxo-6-phenylhexa-3,5-dienoic acid
Canonical SMILES : C1=CC=C(C=C1)C(=CC=CC(=O)C(=O)O)O || C1=CC=C(C=C1)C(=O)CC=CC(=O)C(=O)O || C1=CC=C(C=C1)C(=O)CC=CC(=O)C(=O)[O-]
InChI : InChI=1S\/C12H10O4\/c13-10(9-5-2-1-3-6-9)7-4-8-11(14)12(15)16\/h1-8,13H,(H,15,16)\/b8-4+,10-7+ || InChI=1S\/C12H10O4\/c13-10(9-5-2-1-3-6-9)7-4-8-11(14)12(15)16\/h1-6,8H,7H2,(H,15,16)\/b8-4+ || InChI=1S\/C12H10O4\/c13-10(9-5-2-1-3-6-9)7-4-8-11(14)12(15)16\/h1-6,8H,7H2,(H,15,16)\/p-1\/b8-4+
InChIKey : YOVXRIACERVBAG-AJQRHIRFSA-N || QPGAZPBFRAAJBD-XBXARRHUSA-N || QPGAZPBFRAAJBD-XBXARRHUSA-M || YOVXRIACERVBAG-UHFFFAOYSA-N
Other name(s) : HDPA, 2-Hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid, AC1NUSYI, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate, 2,6-dioxo-6-phenylhexa-3-enoic acid, AC1NUHL4, SCHEMBL638183, CHEBI:64687, (E)-2,6-dioxo-6-phenylhex-3-enoic acid, (3E)-2,6-dioxo-6-phenylhex-3-enoic acid, HPK, DB07911, CHEBI:64675, 2,6-dioxo-6-phenylhexa-3-enoate(1-), 6-Hydroxy-2-oxo-6-phenylhexa-3,5-dienoic acid, HPDA, AC1L19J4, CTK7I2713, (2Z,4E)-2-Hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid
Target
Families : Carbon-carbon_bond_hydrolase
References (19)
| Title : Characterization of an extradiol dioxygenase involved in the catabolism of lignin-derived biphenyl - Kuatsjah_2017_FEBS.Lett_591_1001 |
| Author(s) : Kuatsjah E , Chen HM , Withers SG , Eltis LD |
| Ref : FEBS Letters , 591 :1001 , 2017 |
| Abstract : Kuatsjah_2017_FEBS.Lett_591_1001 |
| ESTHER : Kuatsjah_2017_FEBS.Lett_591_1001 |
| PubMedSearch : Kuatsjah_2017_FEBS.Lett_591_1001 |
| PubMedID: 28247503 |
| Title : Mechanism-based inhibition of HsaD: a C-C bond hydrolase essential for survival of Mycobacterium tuberculosis in macrophage - Ryan_2014_FEMS.Microbiol.Lett_350_42 |
| Author(s) : Ryan A , Keany S , Eleftheriadou O , Ballet R , Cheng HY , Sim E |
| Ref : FEMS Microbiology Letters , 350 :42 , 2014 |
| Abstract : Ryan_2014_FEMS.Microbiol.Lett_350_42 |
| ESTHER : Ryan_2014_FEMS.Microbiol.Lett_350_42 |
| PubMedSearch : Ryan_2014_FEMS.Microbiol.Lett_350_42 |
| PubMedID: 24164668 |
| Title : The Lid Domain of the MCP Hydrolase DxnB2 Contributes to the Reactivity toward Recalcitrant PCB Metabolites - Ruzzini_2013_Biochemistry_52_5685 |
| Author(s) : Ruzzini AC , Bhowmik S , Yam KC , Ghosh S , Bolin JT , Eltis LD |
| Ref : Biochemistry , 52 :5685 , 2013 |
| Abstract : Ruzzini_2013_Biochemistry_52_5685 |
| ESTHER : Ruzzini_2013_Biochemistry_52_5685 |
| PubMedSearch : Ruzzini_2013_Biochemistry_52_5685 |
| PubMedID: 23879719 |
| Gene_locus related to this paper: sphww-a5j2a5 |
| Title : The key role of a non-active-site residue Met148 on the catalytic efficiency of meta-cleavage product hydrolase BphD - Zhou_2013_Appl.Microbiol.Biotechnol_97_10399 |
| Author(s) : Zhou H , Qu Y , Kong C , Shen E , Wang J , Zhang X , Ma Q , Zhou J |
| Ref : Applied Microbiology & Biotechnology , 97 :10399 , 2013 |
| Abstract : Zhou_2013_Appl.Microbiol.Biotechnol_97_10399 |
| ESTHER : Zhou_2013_Appl.Microbiol.Biotechnol_97_10399 |
| PubMedSearch : Zhou_2013_Appl.Microbiol.Biotechnol_97_10399 |
| PubMedID: 23494625 |
| Title : Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism - Lack_2010_J.Biol.Chem_285_434 |
| Author(s) : Lack NA , Yam KC , Lowe ED , Horsman GP , Owen RL , Sim E , Eltis LD |
| Ref : Journal of Biological Chemistry , 285 :434 , 2010 |
| Abstract : Lack_2010_J.Biol.Chem_285_434 |
| ESTHER : Lack_2010_J.Biol.Chem_285_434 |
| PubMedSearch : Lack_2010_J.Biol.Chem_285_434 |
| PubMedID: 19875455 |
| Gene_locus related to this paper: myctu-Rv3569c |
| Title : Characterization of a C-C bond hydrolase from Sphingomonas wittichii RW1 with novel specificities towards polychlorinated biphenyl metabolites - Seah_2007_J.Bacteriol_189_4038 |
| Author(s) : Seah SY , Ke J , Denis G , Horsman GP , Fortin PD , Whiting CJ , Eltis LD |
| Ref : Journal of Bacteriology , 189 :4038 , 2007 |
| Abstract : Seah_2007_J.Bacteriol_189_4038 |
| ESTHER : Seah_2007_J.Bacteriol_189_4038 |
| PubMedSearch : Seah_2007_J.Bacteriol_189_4038 |
| PubMedID: 17416660 |
| Gene_locus related to this paper: sphww-a5j2a5 |
| Title : Temperature-dependent biotransformation of 2,4'-dichlorobiphenyl by psychrotolerant Hydrogenophaga strain IA3-A: higher temperatures prevent excess accumulation of problematic meta-cleavage products - Lambo_2007_Lett.Appl.Microbiol_44_447 |
| Author(s) : Lambo AJ , Patel TR |
| Ref : Lett Appl Microbiol , 44 :447 , 2007 |
| Abstract : Lambo_2007_Lett.Appl.Microbiol_44_447 |
| ESTHER : Lambo_2007_Lett.Appl.Microbiol_44_447 |
| PubMedSearch : Lambo_2007_Lett.Appl.Microbiol_44_447 |
| PubMedID: 17397486 |
| Title : The molecular basis for inhibition of BphD, a C-C bond hydrolase involved in polychlorinated biphenyls degradation: large 3-substituents prevent tautomerization - Bhowmik_2007_J.Biol.Chem_282_36377 |
| Author(s) : Bhowmik S , Horsman GP , Bolin JT , Eltis LD |
| Ref : Journal of Biological Chemistry , 282 :36377 , 2007 |
| Abstract : Bhowmik_2007_J.Biol.Chem_282_36377 |
| ESTHER : Bhowmik_2007_J.Biol.Chem_282_36377 |
| PubMedSearch : Bhowmik_2007_J.Biol.Chem_282_36377 |
| PubMedID: 17932031 |
| Gene_locus related to this paper: burxl-bphD |
| Title : The tautomeric half-reaction of BphD, a C-C bond hydrolase. Kinetic and structural evidence supporting a key role for histidine 265 of the catalytic triad - Horsman_2007_J.Biol.Chem_282_19894 |
| Author(s) : Horsman GP , Bhowmik S , Seah SY , Kumar P , Bolin JT , Eltis LD |
| Ref : Journal of Biological Chemistry , 282 :19894 , 2007 |
| Abstract : Horsman_2007_J.Biol.Chem_282_19894 |
| ESTHER : Horsman_2007_J.Biol.Chem_282_19894 |
| PubMedSearch : Horsman_2007_J.Biol.Chem_282_19894 |
| PubMedID: 17442675 |
| Gene_locus related to this paper: burxl-bphD |
| Title : Expression and homology modeling of 2-aminobiphenyl-2,3-diol-1,2-dioxygenase from Pseudomonas stutzeri carbazole degradation pathway - Larentis_2006_Cell.Biochem.Biophys_44_530 |
| Author(s) : Larentis AL , Almeida RV , Rossle SC , Cardoso AM , Almeida WI , Bisch PM , Alves TL , Martins OB |
| Ref : Cell Biochem Biophys , 44 :530 , 2006 |
| Abstract : Larentis_2006_Cell.Biochem.Biophys_44_530 |
| ESTHER : Larentis_2006_Cell.Biochem.Biophys_44_530 |
| PubMedSearch : Larentis_2006_Cell.Biochem.Biophys_44_530 |
| PubMedID: 16679541 |
| Title : A glutathione S-transferase catalyzes the dehalogenation of inhibitory metabolites of polychlorinated biphenyls - Fortin_2006_J.Bacteriol_188_4424 |
| Author(s) : Fortin PD , Horsman GP , Yang HM , Eltis LD |
| Ref : Journal of Bacteriology , 188 :4424 , 2006 |
| Abstract : Fortin_2006_J.Bacteriol_188_4424 |
| ESTHER : Fortin_2006_J.Bacteriol_188_4424 |
| PubMedSearch : Fortin_2006_J.Bacteriol_188_4424 |
| PubMedID: 16740949 |
| Title : Structures of ternary complexes of BphK, a bacterial glutathione S-transferase that reductively dechlorinates polychlorinated biphenyl metabolites - Tocheva_2006_J.Biol.Chem_281_30933 |
| Author(s) : Tocheva EI , Fortin PD , Eltis LD , Murphy ME |
| Ref : Journal of Biological Chemistry , 281 :30933 , 2006 |
| Abstract : Tocheva_2006_J.Biol.Chem_281_30933 |
| ESTHER : Tocheva_2006_J.Biol.Chem_281_30933 |
| PubMedSearch : Tocheva_2006_J.Biol.Chem_281_30933 |
| PubMedID: 16920719 |
| Title : Kinetic and structural insight into the mechanism of BphD, a C-C bond hydrolase from the biphenyl degradation pathway - Horsman_2006_Biochemistry_45_11071 |
| Author(s) : Horsman GP , Ke J , Dai S , Seah SY , Bolin JT , Eltis LD |
| Ref : Biochemistry , 45 :11071 , 2006 |
| Abstract : Horsman_2006_Biochemistry_45_11071 |
| ESTHER : Horsman_2006_Biochemistry_45_11071 |
| PubMedSearch : Horsman_2006_Biochemistry_45_11071 |
| PubMedID: 16964968 |
| Gene_locus related to this paper: burxl-bphD |
| Title : Comparative specificities of two evolutionarily divergent hydrolases involved in microbial degradation of polychlorinated biphenyls - Seah_2001_J.Bacteriol_183_1511 |
| Author(s) : Seah SY , Labbe G , Kaschabek SR , Reifenrath F , Reineke W , Eltis LD |
| Ref : Journal of Bacteriology , 183 :1511 , 2001 |
| Abstract : Seah_2001_J.Bacteriol_183_1511 |
| ESTHER : Seah_2001_J.Bacteriol_183_1511 |
| PubMedSearch : Seah_2001_J.Bacteriol_183_1511 |
| PubMedID: 11160080 |
| Title : Expression of the bph genes involved in biphenyl\/PCB degradation in Pseudomonas sp. KKS102 induced by the biphenyl degradation intermediate, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid - Ohtsubo_2000_Gene_256_223 |
| Author(s) : Ohtsubo Y , Nagata Y , Kimbara K , Takagi M , Ohta A |
| Ref : Gene , 256 :223 , 2000 |
| Abstract : Ohtsubo_2000_Gene_256_223 |
| ESTHER : Ohtsubo_2000_Gene_256_223 |
| PubMedSearch : Ohtsubo_2000_Gene_256_223 |
| PubMedID: 11054551 |
| Title : Identification of a serine hydrolase as a key determinant in the microbial degradation of polychlorinated biphenyls - Seah_2000_J.Biol.Chem_275_15701 |
| Author(s) : Seah SY , Labbe G , Nerdinger S , Johnson MR , Snieckus V , Eltis LD |
| Ref : Journal of Biological Chemistry , 275 :15701 , 2000 |
| Abstract : Seah_2000_J.Biol.Chem_275_15701 |
| ESTHER : Seah_2000_J.Biol.Chem_275_15701 |
| PubMedSearch : Seah_2000_J.Biol.Chem_275_15701 |
| PubMedID: 10821847 |
| Gene_locus related to this paper: burxl-bphD |
| Title : Degradation of anaerobic reductive dechlorination products of Aroclor 1242 by four aerobic bacteria - Maltseva_1999_Biodegradation_10_363 |
| Author(s) : Maltseva OV , Tsoi TV , Quensen JF, 3rd , Fukuda M , Tiedje JM |
| Ref : Biodegradation , 10 :363 , 1999 |
| Abstract : Maltseva_1999_Biodegradation_10_363 |
| ESTHER : Maltseva_1999_Biodegradation_10_363 |
| PubMedSearch : Maltseva_1999_Biodegradation_10_363 |
| PubMedID: 10870552 |
| Title : Location and sequence analysis of a 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase-encoding gene (bpdF) of the biphenyl\/polychlorinated biphenyl degradation pathway in Rhodococcus sp. M5 - Lau_1996_Gene_171_53 |
| Author(s) : Lau PC , Garnon J , Labbe D , Wang Y |
| Ref : Gene , 171 :53 , 1996 |
| Abstract : Lau_1996_Gene_171_53 |
| ESTHER : Lau_1996_Gene_171_53 |
| PubMedSearch : Lau_1996_Gene_171_53 |
| PubMedID: 8675030 |
| Gene_locus related to this paper: rhosp-bpdF |
| Title : Purification of two isofunctional hydrolases (EC 3.7.1.8) in the degradative pathway for dibenzofuran in Sphingomonas sp. strain RW1 - Bunz_1993_Biodegradation_4_171 |
| Author(s) : Bunz PV , Falchetto R , Cook AM |
| Ref : Biodegradation , 4 :171 , 1993 |
| Abstract : Bunz_1993_Biodegradation_4_171 |
| ESTHER : Bunz_1993_Biodegradation_4_171 |
| PubMedSearch : Bunz_1993_Biodegradation_4_171 |
| PubMedID: 7764304 |