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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:41487
ChemSpider	20120243^Y
DrugBank	DB04049
KEGG	C15038
PubChem CID	448487
UNII	S5MSB8RF66
CompTox Dashboard (EPA)	DTXSID10416113
InChI 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
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/cm^3
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). N verify (what is ^YN ?) Infobox references

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

External links

• Media related to Coelenteramide at Wikimedia Commons