Coelenteramide

Coelenteramide
Names

Preferred IUPAC name N-[3-Benzyl-5-(4-hydroxyphenyl)pyrazin-2-yl]-2-(4-hydroxyphenyl)acetamide
Other names Coelenteramide
Identifiers
CAS Number	50611-86-4 ^checkY
3D model (JSmol)	Interactive image
ChemSpider	20120243 ^checkY
PubChem CID	448487
CompTox Dashboard (EPA)	DTXSID10416113 Edit this at Wikidata
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⁻¹
Density	1.26 g/cm³
Absorbance	ε_332.5 = 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). ☒N verify (what is ^checkY☒N ?) 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.^[2] Under basic conditions, the compound will break down further into coelenteramine and 4-hydroxyphenylacetic acid.

References

^ Shimomura, Osamu (2012). Bioluminescence : chemical principles and methods. Singapore Hackensack, NJ: World Scientific Publishing Co. Pte. Ltd. ISBN 978-981-4366年08月3日. OCLC 794263013.
^ 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.
^ 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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