Coelenteramide

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Coelenteramide
File:Coelenteramide.svg
Names
Preferred IUPAC name
N-[3-Benzyl-5-(4-hydroxyphenyl)pyrazin-2-yl]-2-(4-hydroxyphenyl)acetamide
Other names
Coelenteramide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=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)
    Key: CJIIERPDFZUYPI-UHFFFAOYSA-N
  • C1=CC=C(C=C1)CC2=NC(=CN=C2NC(=O)CC3=CC=C(C=C3)O)C4=CC=C(C=C4)O
Properties
C25H21N3O3
Molar mass 411.461 g·mol−1
Density 1.26 g/cm3
Absorbance ε332.5 = 15000 M−1 cm−1 (methanol)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coelenteramide is the oxidized product, or oxyluciferin, of the bioluminescent reactions in many marine organisms that use coelenterazine. It was first isolated as a blue fluorescent protein from Aequorea victoria after the animals were stimulated to emit light.[2] Under basic conditions, the compound will break down further into coelenteramine and 4-hydroxyphenylacetic acid.

It is an aminopyrazine.[3]

References

[edit | edit source]
  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Discovery and Validation of a New Family of Antioxidants: The Aminopyrazine Derivatives. M. L. N. Dubuisson, J.-F. Rees and J. Marchand-Brynaert, Mini-Reviews in Medicinal Chemistry, 2004, 4, 159-165, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
[edit | edit source]
  • Error creating thumbnail: File missing Media related to Lua error in Module:Commons_link at line 62: attempt to index field 'wikibase' (a nil value). at Wikimedia Commons