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Inhibitor Report for: Coelenteramide

Name Class
CoelenteramideTypeNatural
Luciferin
Other_Name (5)
Chemical_NomenclatureN-[3-benzyl-5-(4-hydroxyphenyl)pyrazin-2-yl]-2-(4-hydroxyphenyl)acetamide
FormulaC25H21N3O3
CAS_number50611-86-4
MW411.5
PaperSchenkmayerova_2023_Nat.Catal_6_23
Schenkmayerova_2020_ChemRxiv__
Loening_2007_J.Mol.Biol_374_1017
Gao_2023_ChemCatChem_15_e202300745
Structure6YN2
7QXQ
7OMR
2PSJ
CommentDerives from an Oplophorus luciferin. The postcatalytic enzyme-product.
The most common marine luciferin. 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
CID5326781
448487
FamilyHaloalkane_dehalogenase-HLD2
InChIKeyCJIIERPDFZUYPI-UHFFFAOYSA-N
CanonicalSMILESC1=CC=C(C=C1)CC2=NC(=CN=C2NC(=O)CC3=CC=C(C=C3)O)C4=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/h1-13,16,29-30H,14-15H2,(H,26,28,31)

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Mail to: Nicolas Lenfant, Thierry Hotelier, Yves Bourne, Pascale Marchot and Arnaud Chatonnet.
Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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