Brand  (β version)

PDB ID: 5W58

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Ligands
Code Name Style Show Link
FF8 (2s)-2-{2-fluoro-3'-[(hexylcarbamoyl)oxy][1,1'-biphenyl]-4-yl}propanoic acid PoSSuM
HEM Protoporphyrin ix containing Fe PoSSuM
BOG Octyl beta-D-glucopyranoside PoSSuM
Non-standard Residues
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Glycosylation
Code Name Emphasize
NAG 2-acetamido-2-deoxy-beta-D-glucopyranose
Modification
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Structure summary

Code : 5W58   PDBj   RCSB PDB   PDBe
Header : OXIDOREDUCTASE/INHIBITOR
Title : Crystal Complex of Cyclooxygenase-2: (S)-ARN-2508 (a dual COX and FAAH inhibitor)
Release Data : 2018-01-31
Compound :
mol_id molecule chains synonym
1 Prostaglandin G/H synthase 2 A Cyclooxygenase-2,COX-2,Glucocorticoid-regulated inflammatory cyclooxygenase,Gripghs,Macrophage activation-associated marker protein P71/73,PES-2,PHS II,Prostaglandin H2 synthase 2,PGHS-2,Prostaglandin-endoperoxide synthase 2,TIS10 protein
ec: 1.14.99.1
Source :
mol_id organism_scientific organism_common expression_system
1 Mus musculus  (taxid:10090) Mouse Spodoptera frugiperda  (taxid:7108)
gene: Ptgs2, Cox-2, Cox2, Pghs-b, Tis10
expression_system_plasmid: pVL-1393-COX-2
Authors : Xu, S., Goodman, M.C., Banerjee, S., Piomelli, D., Marnett, L.J.
Keywords : cyclooxygenase, protein-inhibitor complex, prostaglandin, FAAH-COX dual inhibition, OXIDOREDUCTASE, OXIDOREDUCTASE-INHIBITOR complex
Exp. method : X-RAY DIFFRACTION ( 2.267 Å )
Citation :

Dual cyclooxygenase-fatty acid amide hydrolase inhibitor exploits novel binding interactions in the cyclooxygenase active site.

Goodman, M.C.,Xu, S.,Rouzer, C.A.  et al.
(2018)  J. Biol. Chem.  293 : 3028 - 3038

PubMed: 29326169
DOI: 10.1074/jbc.M117.802058

Reaction

Chain : A
UniProt : Q05769 (PGH2_MOUSE)
Reaction: EC: Evidence:
Physiological Direction:
(5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = A + H2O + prostaglandin H2 1.14.99.1 PubMed:12925531, PubMed:20463020, PubMed:20810665, PubMed:21489986, PubMed:22942274
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = prostaglandin G2 - PubMed:12244105, PubMed:22942274
left-to-right PubMed:12244105, PubMed:22942274
AH2 + prostaglandin G2 = A + H2O + prostaglandin H2 - PubMed:12244105, PubMed:22942274
left-to-right
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + 2 O2 = prostaglandin G3 - UniProtKB:P35354
left-to-right
AH2 + prostaglandin G3 = A + H2O + prostaglandin H3 - UniProtKB:P35354
left-to-right
(8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1 - UniProtKB:P35354
left-to-right
AH2 + prostaglandin G1 = A + H2O + prostaglandin H1 - UniProtKB:P35354
left-to-right
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3- phosphoethanolamine + 2 O2 = 2-(prostaglandin G2)-sn-glycero-3- phosphoethanolamine - UniProtKB:P35354
left-to-right
2-(prostaglandin G2)-sn-glycero-3-phosphoethanolamine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamine + A + H2O - UniProtKB:P35354
left-to-right
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + 2 O2 = 2-(prostaglandin G2)-sn-glycero-3-phosphocholine - UniProtKB:P35354
left-to-right
2-(prostaglandin G2)-sn-glycero-3-phosphocholine + AH2 = 2- (prostaglandin H2)-sn-glycero-3-phosphocholine + A + H2O - UniProtKB:P35354
left-to-right
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + AH2 = (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O - UniProtKB:P35354
left-to-right
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn- glycero-3-phosphocholine + A + H2O - UniProtKB:P35354
left-to-right
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn- glycero-3-phosphocholine + A + H2O - UniProtKB:P35354
left-to-right
2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn- glycero-3-phosphocholine + A + H2O - UniProtKB:P35354
left-to-right
(9Z,12Z)-octadecadienoate + AH2 + O2 = 9-hydroxy-(10E,12Z)- octadecadienoate + A + H2O - UniProtKB:P35354
left-to-right
(9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)- octadecadienoate + A + H2O - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy- (5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy- (5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)- hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18S)- hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)- hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)- hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15S)- hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O - UniProtKB:P35354
left-to-right
(7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R- hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O - UniProtKB:P35354
left-to-right
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13- hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O - UniProtKB:P35354
left-to-right
(5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O - UniProtKB:P35354
left-to-right
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R- hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O - UniProtKB:P35354
left-to-right
(5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O - UniProtKB:P35354
left-to-right
(5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O - UniProtKB:P35354
left-to-right
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 2 O2 = 2- glyceryl-prostaglandin G2 - PubMed:12244105, PubMed:22942274
left-to-right
2-glyceryl-prostaglandin G2 + AH2 = 2-glyceryl-prostaglandin H2 + A + H2O - PubMed:12244105, PubMed:22942274
left-to-right PubMed:12244105, PubMed:22942274
(5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy- (5Z,8Z,11Z,13E)-eicosatetraenoate - UniProtKB:P35354
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 11R-hydroperoxy- (5Z,8Z,12E,14Z)-eicosatetraenoate - UniProtKB:P35354
left-to-right
(9Z,12Z)-octadecadienoate + AH2 + O2 = (9R)-hydroxy-(10E,12Z)- octadecadienoate + A + H2O - UniProtKB:P79208
left-to-right
(9Z,12Z)-octadecadienoate + AH2 + O2 = (9S)-hydroxy-(10E,12Z)- octadecadienoate + A + H2O - UniProtKB:P79208
left-to-right
(9Z,12Z)-octadecadienoate + AH2 + O2 = (13S)-hydroxy-(9Z,11E)- octadecadienoate + A + H2O - UniProtKB:P79208
left-to-right
(9Z,12Z)-octadecadienoate + AH2 + O2 = (13R)-hydroxy-(9Z,11E)- octadecadienoate + A + H2O - UniProtKB:P79208
left-to-right