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Substrate Report for: Coelenterazine

Name Class
CoelenterazineTypeLuciferin
Natural
Other_Name (5)
Chemical_NomenclatureN-[2-benzyl-6-(4-oxocyclohexa-2,5-dien-1-ylidene)-1H-pyrazin-3-yl]-2-(4-hydroxyphenyl)acetamide
FormulaC26H21N3O3
MW423.46
PaperChaloupkova_2019_ACS.Catal_9_48103
Woo_2008_Protein.Sci_17_725
Loening_2007_J.Mol.Biol_374_1017
Gao_2023_ChemCatChem_15_e202300745
Comment Luciferase from Renilla reniformis (RLuc) catalyzes the degradation of coelenterazine in the presence of molecular oxygen, resulting in the product coelenteramide, carbon dioxide, and the desired photon of light (EC 1.13.12.5). This enzyme belongs to the Haloalkane dehalogenase family II with a different catalytic function (EC 3.8.1.5) Reconstruction of an ancestral enzyme shows it has both hydrolase and monooxygenase activities ( Chaloupkova et al.)
Gene_locusrenre-luc
9zzzz-AncHLDRLuc
CID2830
FamilyHaloalkane_dehalogenase-HLD2
InChIKeyYHIPILPTUVMWQT-UHFFFAOYSA-N
CanonicalSMILESC1=CC=C(C=C1)CC2=C(N=CC(=C3C=CC(=O)C=C3)N2)NC(=O)CC4=CC=C(C=C4)O
InChIInChI=1S/C25H21N3O3/c29-20-10-6-18(7-11-20)15-24(31)28-25-22(14-17-4-2-1-3-5-17)27-23(16-26-25)19-8-12-21(30)13-9-19/h1-13,16,27,29H,14-15H2,(H,28,31)
WikipediaCoelenterazine

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Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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