Coelenteramide

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Coelenteramide
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
KEGG
PubChem CID
UNII
  • 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).
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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

  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. Bibcode:1975PNAS...72.1546S. 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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