235:
160:
24:
1255:
396:
708:
and visible spectrum, with peak absorption at 435 nm in methanol, giving the molecule a yellow color. The molecule spontaneously oxidizes in aerobic conditions or in some organic solvents such as
97:
409:
501:, respectively. Both groups independently discovered that the same compound was used in both luminescent systems. The molecule was named after the now-obsolete phylum
732:
To improve its biophysical properties, derivatives of coelenterazine have been synthesized by means of different procedures including multicomponent strategies.
281:
268:
InChI=1S/C26H21N3O3/c30-20-10-6-18(7-11-20)15-23-26(32)29-16-24(19-8-12-21(31)13-9-19)27-22(25(29)28-23)14-17-4-2-1-3-5-17/h1-13,16,27,30-31H,14-15H2
258:
InChI=1S/C26H21N3O3/c30-20-10-6-18(7-11-20)15-23-26(32)29-16-24(19-8-12-21(31)13-9-19)27-22(25(29)28-23)14-17-4-2-1-3-5-17/h1-13,16,27,30-31H,14-15H2
993:
799:
696:
also produce luciferases that use this compound, some of which are secreted into extracellular space, an unusual property for luciferases.
523:, it was later shown that they do not synthesize coelenterazine, but obtain it through their diet, largely from crustaceans and copepods.
1170:"Cloning and expression of cDNA for a luciferase from the marine copepod Metridia longa. A novel secreted bioluminescent reporter enzyme"
453:
249:
1060:"Occurrence of Isopenicillin-N-Synthase Homologs in Bioluminescent Ctenophores and Implications for Coelenterazine Biosynthesis"
1209:
Vece V, Vuocolo G (2015). "Multicomponent
Synthesis of Novel Coelenterazine Derivatives Substituted at the C-3 Position".
613:
374:
192:
787:
213:
416:
1285:
1259:
579:
1275:
596:
484:
Coelenterazine was simultaneously isolated and characterized by two groups studying the luminescent organisms
1280:
155:
590:
1117:
Tessler M, Gaffney JP, Crawford JM, Trautman E, Gujarati NA, Alatalo P, et al. (14 September 2018).
607:
1211:
665:
573:
36:
935:"Can coelenterates make coelenterazine? Dietary requirement for luciferin in cnidarian bioluminescence"
1071:
1010:
946:
887:
828:
1034:
230:
1300:
791:
642:
63:
704:
Coelenterazine can be crystallized into orange-yellow crystals. The molecule absorbs light in the
1026:
689:, and some researchers believe this comes in the form of a cyclized "Phe-Tyr-Tyr" (FYY) peptide.
562:
449:
751:
1191:
1150:
1099:
974:
915:
856:
795:
713:
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659:
556:
550:
519:
514:
497:
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1181:
1140:
1130:
1089:
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1001:
964:
954:
905:
895:
846:
836:
779:
650:
469:
304:
201:
73:
137:
780:
649:
The compound has also been isolated from organisms that are not luminescent, such as the
1240:
1075:
1014:
950:
891:
832:
234:
159:
1145:
1118:
1094:
1059:
746:
741:
510:
506:
387:
117:
910:
875:
851:
816:
181:
1269:
969:
934:
686:
628:
472:. All these proteins catalyze the oxidation of this substance, a reaction catalogued
359:
148:
1030:
502:
473:
461:
1084:
705:
632:
619:
535:
939:
Proceedings of the
National Academy of Sciences of the United States of America
880:
Proceedings of the
National Academy of Sciences of the United States of America
821:
Proceedings of the
National Academy of Sciences of the United States of America
1224:
1058:
Francis WR, Shaner NC, Christianson LM, Powers ML, Haddock SH (30 June 2015).
637:
540:
444:
369:
338:
128:
841:
721:
545:
493:
485:
432:
23:
1195:
1186:
1169:
1154:
1103:
978:
959:
900:
860:
1254:
919:
756:
717:
682:
465:
1135:
602:
168:
1168:
Markova SV, Golz S, Frank LA, Kalthof B, Vysotski ES (January 2004).
1022:
654:
585:
440:
436:
386:
Except where otherwise noted, data are given for materials in their
289:
C1=CC=C(C=C1)CC2=C3N=C(C(=O)N3C=C(N2)C4=CC=C(C=C4)O)CC5=CC=C(C=C5)O
568:
108:
96:
86:
624:
40:
6-(4-Hydroxyphenyl)-2--8-(phenylmethyl)-7H-imidazopyrazin-3-one
531:
Coelenterazine is widely found in marine organisms including:
876:"Chemical nature of bioluminescence systems in coelenterates"
218:
815:
Hori K, Charbonneau H, Hart RC, Cormier MJ (October 1977).
364:
175 to 178 °C (347 to 352 °F; 448 to 451 K)
404:
933:
Haddock SH, Rivers TJ, Robison BH (September 2001).
817:"Structure of native Renilla reinformis luciferin"
435:, a molecule that emits light after reaction with
782:Bioluminescence: Chemical Principles and Methods
773:
771:
180:
517:. While coelenterazine was first discovered in
439:, found in many aquatic organisms across eight
72:
8:
233:
158:
136:
15:
1185:
1144:
1134:
1093:
1083:
968:
958:
909:
899:
850:
840:
200:
767:
505:. Likewise, the two main metabolites –
286:
254:
229:
874:Shimomura O, Johnson FH (April 1975).
149:
261:Key: YHIPILPTUVMWQT-UHFFFAOYSA-N
116:
7:
728:Synthetic coelenterazine derivatives
513:– were named after their respective
1174:The Journal of Biological Chemistry
171:
677:Biosynthesis of coelenterazine in
14:
1253:
716:and is preferentially stored in
394:
322:
316:
22:
390:(at 25 °C , 100 kPa).
1243:showing major luciferin types.
994:"A bioluminescent chaetognath"
443:. It is the substrate of many
328:
310:
1:
992:Haddock SHD, Case JF (1994).
681:starts from two molecules of
1085:10.1371/journal.pone.0128742
788:World Scientific Publishing
1317:
692:Many members of the genus
1225:10.1016/j.tet.2015.09.048
597:Oplophorus gracilirostris
580:Vampyroteuthis infernalis
384:
297:
277:
245:
56:
45:
35:
30:
21:
842:10.1073/pnas.74.10.4285
460:luciferase (Gluc), and
380:= 9800 M cm (methanol)
354:Orange-yellow crystals
1187:10.1074/jbc.M309639200
960:10.1073/pnas.201329798
901:10.1073/pnas.72.4.1546
778:Shimomura, O. (2006).
574:Watasenia scintillans
1262:at Wikimedia Commons
1241:Bioluminescence Page
685:and one molecule of
591:Systellaspis debilis
1076:2015PLoSO..1028742F
1015:1994Natur.367..225H
951:2001PNAS...9811148H
892:1975PNAS...72.1546S
833:1977PNAS...74.4285H
643:Amphiura filiformis
608:Pleuromamma xiphias
346: g·mol
18:
1136:10.7717/peerj.5506
666:Pandalus platyuros
657:species including
563:Renilla reniformis
490:Renilla reniformis
450:Renilla reniformis
417:Infobox references
16:
1258:Media related to
1119:"Metridia lucens"
801:978-981-256-801-4
710:dimethylformamide
660:Pandalus borealis
557:Obelia geniculata
551:Aequorea victoria
520:Aequorea victoria
515:functional groups
498:Aequorea victoria
425:Chemical compound
423:
422:
214:CompTox Dashboard
98:Interactive image
1308:
1286:Imidazopyrazines
1257:
1229:
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1200:
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1189:
1165:
1159:
1158:
1148:
1138:
1114:
1108:
1107:
1097:
1087:
1055:
1049:
1048:
1046:
1045:
1039:
1033:. Archived from
1023:10.1038/367225a0
1009:(6460): 225–26.
998:
989:
983:
982:
972:
962:
945:(20): 11148–51.
930:
924:
923:
913:
903:
871:
865:
864:
854:
844:
812:
806:
805:
785:
775:
651:Atlantic herring
614:Gaussia princeps
407:
401:
398:
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345:
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305:Chemical formula
238:
237:
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100:
76:
26:
19:
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1309:
1307:
1306:
1305:
1276:Bioluminescence
1266:
1265:
1250:
1237:
1232:
1219:(46): 8781–85.
1208:
1207:
1203:
1167:
1166:
1162:
1116:
1115:
1111:
1070:(6): e0128742.
1057:
1056:
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1037:
996:
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990:
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932:
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927:
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872:
868:
814:
813:
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802:
777:
776:
769:
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738:
730:
702:
675:
627:including some
529:
482:
426:
419:
414:
413:
412: ?)
403:
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395:
391:
378:
343:
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187:
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143:
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103:
90:
79:
66:
52:
41:
17:Coelenterazine
12:
11:
5:
1314:
1312:
1304:
1303:
1298:
1293:
1288:
1283:
1281:Aminopyrazines
1278:
1268:
1267:
1264:
1263:
1260:Coelenterazine
1249:
1248:External links
1246:
1245:
1244:
1236:
1235:External links
1233:
1231:
1230:
1201:
1160:
1109:
1050:
984:
925:
866:
827:(10): 4285–7.
807:
800:
766:
764:
761:
760:
759:
754:
749:
747:Coelenteramine
744:
742:Coelenteramide
737:
734:
729:
726:
701:
698:
674:
671:
647:
646:
635:
622:
617:
600:
583:
566:
543:
538:
528:
525:
511:coelenteramine
507:coelenteramide
481:
478:
429:Coelenterazine
424:
421:
420:
415:
393:
392:
388:standard state
385:
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231:DTXSID80204342
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1188:
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1180:(5): 3212–7.
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1147:
1142:
1137:
1132:
1128:
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1040:on 2008-05-16
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886:(4): 1546–9.
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727:
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707:
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695:
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688:
687:phenylalanine
684:
680:
672:
670:
668:
667:
662:
661:
656:
652:
645:
644:
639:
636:
634:
630:
629:Neoscopelidae
626:
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516:
512:
508:
504:
500:
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495:
491:
487:
479:
477:
475:
471:
467:
463:
462:photoproteins
459:
455:
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438:
434:
430:
418:
411:
406:
389:
383:
379:
373:
371:
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361:
360:Melting point
358:
357:
353:
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342:
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309:
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154:
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150:ECHA InfoCard
147:
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119:
115:
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1216:
1210:
1204:
1177:
1173:
1163:
1126:
1122:
1112:
1067:
1063:
1053:
1042:. Retrieved
1035:the original
1006:
1000:
987:
942:
938:
928:
883:
879:
869:
824:
820:
810:
781:
731:
703:
693:
691:
678:
676:
673:Biosynthesis
664:
658:
653:and several
648:
641:
620:chaetognaths
612:
606:
595:
589:
578:
572:
561:
555:
549:
536:radiolarians
530:
518:
503:coelenterata
496:
489:
483:
474:EC 1.13.12.5
464:, including
457:
448:
428:
427:
57:Identifiers
48:
46:Other names
1212:Tetrahedron
790:. pp.
720:or with an
706:ultraviolet
638:echinoderms
633:Myctophidae
541:ctenophores
445:luciferases
351:Appearance
298:Properties
156:100.164.960
1301:Luciferins
1270:Categories
1044:2008-10-28
763:References
752:Furimazine
700:Properties
546:cnidarians
527:Occurrence
492:) and the
454:luciferase
370:Absorbance
339:Molar mass
202:3O1CB88RRD
129:ChemSpider
118:CHEBI:2311
85:3D model (
74:55779-48-1
64:CAS Number
37:IUPAC name
1129:: e5506.
722:inert gas
494:cnidarian
486:sea pansy
433:luciferin
182:135445694
51:luciferin
1196:14583604
1155:30233994
1104:26125183
1064:PLOS ONE
979:11572972
861:16592444
757:Vargulin
736:See also
718:methanol
694:Metridia
683:tyrosine
679:Metridia
640:such as
605:such as
603:copepods
588:such as
571:such as
548:such as
466:aequorin
456:(Rluc),
447:such as
1296:Phenols
1291:Lactams
1146:6140675
1095:4488382
1072:Bibcode
1031:4362422
1011:Bibcode
947:Bibcode
888:Bibcode
829:Bibcode
480:History
458:Gaussia
410:what is
408: (
344:423.472
169:PubChem
49:Renilla
1194:
1153:
1143:
1102:
1092:
1029:
1002:Nature
977:
967:
920:236561
918:
911:432574
908:
859:
852:431924
849:
798:
655:shrimp
586:shrimp
470:obelin
468:, and
437:oxygen
405:verify
402:
282:SMILES
31:Names
1123:PeerJ
1038:(PDF)
1027:S2CID
997:(PDF)
970:58698
794:–65.
569:squid
441:phyla
431:is a
250:InChI
109:ChEBI
87:JSmol
1192:PMID
1151:PMID
1100:PMID
975:PMID
916:PMID
857:PMID
796:ISBN
714:DMSO
712:and
663:and
631:and
625:fish
611:and
594:and
577:and
560:and
509:and
193:UNII
138:2728
1221:doi
1182:doi
1178:279
1141:PMC
1131:doi
1090:PMC
1080:doi
1019:doi
1007:367
965:PMC
955:doi
906:PMC
896:doi
847:PMC
837:doi
792:159
377:435
219:EPA
172:CID
1272::
1217:71
1215:.
1190:.
1176:.
1172:.
1149:.
1139:.
1125:.
1121:.
1098:.
1088:.
1078:.
1068:10
1066:.
1062:.
1025:.
1017:.
1005:.
999:.
973:.
963:.
953:.
943:98
941:.
937:.
914:.
904:.
894:.
884:72
882:.
878:.
855:.
845:.
835:.
825:74
823:.
819:.
786:.
770:^
724:.
669:.
554:,
476:.
320:21
314:26
1227:.
1223::
1198:.
1184::
1157:.
1133::
1127:6
1106:.
1082::
1074::
1047:.
1021::
1013::
981:.
957::
949::
922:.
898::
890::
863:.
839::
831::
804:.
488:(
400:N
375:ε
332:3
329:O
326:3
323:N
317:H
311:C
221:)
217:(
89:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
