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Coelenteramide

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Coelenteramide
Names
Preferred IUPAC name N--2-(4-hydroxyphenyl)acetamide
Other names Coelenteramide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • C1=CC=C(C=C1)CC2=NC(=CN=C2NC(=O)CC3=CC=C(C=C3)O)C4=CC=C(C=C4)O
Properties
Chemical formula C25H21N3O3
Molar mass 411.461 g·mol
Density 1.26 g/cm
Absorbance ε332.5 = 15000 M cm (methanol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. Under basic conditions, the compound will break down further into coelenteramine and 4-hydroxyphenylacetic acid.

It is an aminopyrazine.

References

  1. Shimomura, Osamu (2012). Bioluminescence : chemical principles and methods. Singapore Hackensack, NJ: World Scientific Publishing Co. Pte. Ltd. ISBN 978-981-4366-08-3. OCLC 794263013.
  2. Shimomura O, Johnson FH (1975). "Chemical Nature of Bioluminescence Systems in Coelenterates". PNAS USA. 72 (4): 1546–1549. doi:10.1073/pnas.72.4.1546. PMC 432574. PMID 236561.
  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, doi:10.2174/1389557043403927

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