Coelenteramine

Last updated
Coelenteramine
Coelenteramine.svg
Names
Preferred IUPAC name
3-Benzyl-5-(4-hydroxyphenyl)pyrazin-2-amine
Other names
Coelenteramine, 2-Amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H15N3O/c18-17-15(10-12-4-2-1-3-5-12)20-16(11-19-17)13-6-8-14(21)9-7-13/h1-9,11,21H,10H2,(H2,18,19) X mark.svgN
    Key: BWNPYAKFDUFNND-UHFFFAOYSA-N X mark.svgN
  • C1=CC=C(C=C1)CC2=NC(=CN=C2N)C3=CC=C(C=C3)O
Properties
C17H15N3O
Molar mass 277.327 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Coelenteramine is a metabolic product of the bioluminescent reactions in organisms that utilize coelenterazine. It was first isolated from Aequorea victoria along with coelenteramide after coelenterates were stimulated to emit light. [1]

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Coelenterazine Chemical compound

Coelenterazine is a luciferin, a molecule that emits light after reaction with oxygen, found in many aquatic organisms across eight phyla. It is the substrate of many luciferases such as Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), and photoproteins, including aequorin, and obelin. All these proteins catalyze the oxidation of this substance, a reaction catalogued EC 1.13.12.5.

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Coelenteramide Chemical compound

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References

  1. 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.