780:(in this case, biliverdin), and successful imaging of the first bacteriophytochrome-based probe required addition of the exogenous biliverdin. Recent studies demonstrated that bacteriophytochrome-based fluorescent proteins with high affinity to biliverdin can be imaged in vivo utilizing endogenous ligand only and, thus, with the same ease as the conventional fluorescent proteins. Advent of the second and further generations of the biliverdin-binding bacteriophytochrome-based probes should broaden the possibilities for the non-invasive in vivo imaging.
301:
212:
47:
545:
38:
477:
129:
459:
324:
InChI=1S/C33H34N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-,28-15-
334:
InChI=1/C33H34N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-,28-15-
680:, the wings of moth and butterfly, the serum and eggs of frogs, and the placenta of dogs. With dogs this can lead, in extremely rare cases, to the birth of puppies with green fur; however, the green color fades out soon after birth. In the
668:
Research has shown that the biliverdin of egg shells is produced from the shell gland, rather than from the breakdown of erythrocytes in the blood stream, although there is no evidence that the sources of the material are neither
616:
Bile pigments such as biliverdin possess significant anti-mutagenic and antioxidant properties and therefore, may fulfil a useful physiological function. Biliverdin and bilirubin have been shown to be potent scavengers of
737:
713:. It is uncertain whether this presence of biliverdin is an ecological or physiological adaptation of any kind. It has been suggested that accumulation of biliverdin might deter harmful infection by
1350:
Lee
Grismer, L.; Thy, Neang; Chav, Thou; Holden, Jeremy (2007). "A New Species of Chiromantis Peters 1854 (Anura: Rhacophoridae) from Phnom Samkos in the Northwestern Cardamom Mountains, Cambodia".
613:
While typically regarded as a mere waste product of heme breakdown, evidence that suggests that biliverdin β and other bile pigments β has a physiological role in humans has been mounting.
1622:
490:
736:
1182:
Halepas, Steven; Hamchand, Randy; Lindeyer, Samuel E. D.; BrΓΌckner, Christian (2017). "Isolation of
Biliverdin IXΞ±, as its Dimethyl Ester, from Emu Eggshells".
676:
Along with its presence in avian egg shells, other studies have also shown that biliverdin is present in the blue-green blood of many marine fish, the blood of
653:
though further research is needed to confirm these results. There are currently no practical implications for using biliverdin in the treatment of any disease.
350:
1615:
1903:
1608:
665:
egg shells, especially blue and green shells. Blue egg shells have a significantly higher concentration of biliverdin than brown egg shells.
637:. Some studies have found that people with higher concentration levels of bilirubin and biliverdin in their bodies have a lower frequency of
1500:
Rodriguez, Erik A.; Tran, Geraldine N.; Gross, Larry A.; Crisp, Jessica L.; Shu, Xiaokun; Lin, John Y.; Tsien, Roger Y. (2016-08-01).
1305:"Parasites in a biodiversity hotspot: a survey of hematozoa and a molecular phyolgenetic analysis of plasmodium in New Guinea skinks"
958:
646:
315:
740:
Fluorescent proteins visualize the cell cycle progression. IFP2.0-hGem(1/110) fluorescence is shown in green and highlights the S/G
589:
Biliverdin is seen briefly in some bruises as a green color. In bruises, its breakdown into bilirubin leads to a yellowish color.
1595:
622:
953:
Boron W, Boulpaep E. Medical
Physiology: a cellular and molecular approach, 2005. 984β986. Elsevier Saunders, United States.
769:
601:
is caused by the accumulation of biliverdin or bilirubin (or both) in the circulatory system and tissues. Jaundiced skin and
434:
873:
497:
2383:
258:
1896:
1448:
GSFilonov; Piatkevich, Kiryl D; Ting, Li-Min; Zhang, Jinghang; Kim, Kami; Verkhusha, Vladislav V; et al. (2011).
279:
1050:
Bulmer, A. C.; Ried, K.; Blanchfield, J. T.; Wagner, K. H. (2008). "The anti-mutagenic properties of bile pigments".
645:. It has been suggested that biliverdin β as well as many other tetrapyrrolic pigments β may function as an HIV-1
1135:"Bile pigments as HIV-1 protease inhibitors and their effects on HIV-1 viral maturation and infectivity in vitro"
793:
219:
2117:
1363:
1820:
724:
207:
2388:
2211:
1889:
1696:
1634:
642:
225:
169:
2310:
2289:
2217:
1815:
1716:
73:
59:
722:
parasites, although no statistically significant correlation has been established. The
Cambodian frog,
688:) and related species, the bones are bright green because of biliverdin. The green coloration of many
46:
2207:
2197:
2015:
1921:
1691:
1401:
1191:
579:
2142:
296:
2203:
2158:
2132:
1686:
1661:
1018:
Seyfried, H; Klicpera, M; Leithner, C; Penner, E (1976). "Bilirubin metabolism (author's transl)".
885:
784:
765:
358:
CC\1=C(/C(=C/C2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/N/C1=C\C4=NC(=O)C(=C4C)C=C)CCC(=O)O
95:
2281:
1252:
2323:
2193:
1367:
1332:
1000:
764:, biliverdin has been employed as an IR-emitting chromophore for in vivo imaging. In contrast to
626:
1970:
1390:"Mammalian expression of infrared fluorescent proteins engineered from a bacterial phytochrome"
2122:
2050:
2000:
1721:
1574:
1539:
1521:
1479:
1427:
1324:
1234:
1164:
1133:
McPhee, F.; Caldera, P. S.; Bemis, G. W.; McDonagh, A. F.; Kuntz, I. D.; Craik, C. S. (1996).
1115:
1094:"Transient relief of asthma symptoms during jaundice: a possible beneficial role of bilirubin"
1067:
1027:
992:
954:
861:
845:
773:
453:
189:
2346:
597:
Biliverdin has been found in excess in the blood of humans suffering from hepatic diseases.
2336:
2245:
2239:
2189:
1982:
1566:
1529:
1513:
1469:
1461:
1417:
1409:
1359:
1316:
1278:
1226:
1199:
1154:
1146:
1105:
1059:
984:
798:
677:
373:
267:
2302:
2060:
2005:
1945:
1840:
1681:
802:
105:
1405:
1195:
300:
211:
149:
2235:
2079:
2055:
1534:
1501:
1474:
1449:
1422:
1389:
1159:
1134:
975:
Mosqueda, L; Burnight, K; Liao, S (2005). "The Life Cycle of
Bruises in Older Adults".
468:
82:-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-1(2),4(5),6(7)-triene-3,5-diyl)dipropanoic acid
2377:
2354:
2263:
2257:
2181:
2150:
2010:
1570:
1230:
988:
877:
841:
788:
699:
Biliverdin is also present in the green blood, muscles, bones, and mucosal lining of
418:
200:
1371:
1004:
2275:
1955:
1913:
1850:
1336:
924:
705:
693:
689:
670:
618:
563:
2253:
1950:
1845:
1304:
1203:
1063:
919:
865:
849:
817:
761:
575:
247:
1600:
2271:
2127:
2033:
1992:
1502:"A far-red fluorescent protein evolved from a cyanobacterial phycobiliprotein"
715:
710:
567:
559:
527:
400:
180:
63:
3,3β²-(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-19,21,22,24-tetrahydro-1
1525:
1267:
2070:
2042:
1935:
1791:
1771:
1642:
1413:
909:
829:
813:
583:
571:
544:
1543:
1483:
1431:
1328:
1119:
1071:
996:
17:
1578:
1450:"Bright and stable near infra-red fluorescent protein for in vivo imaging"
1282:
1238:
1168:
2331:
1960:
1881:
1866:
1217:
Fang, LS; Bada, JL (1990). "The blue-green blood plasma of marine fish".
1110:
1093:
1031:
929:
598:
37:
2227:
1795:
1517:
821:
719:
681:
634:
630:
530:. It is the pigment responsible for a greenish color sometimes seen in
520:
234:
78:
3,3β²-(-1,7-Diethenyl-1,3,5,7-tetramethyl-1,7-dioxo-1,1,7,7-tetrahydro-3
1320:
1150:
2109:
2103:
2097:
2091:
1465:
893:
869:
857:
853:
837:
810:
806:
777:
745:
700:
650:
638:
602:
531:
160:
467:
Except where otherwise noted, data are given for materials in their
1092:
Ohrui, T.; Yasuda, H.; Yamaya, M.; Matsui, T.; Sasaki, H. (2003).
889:
833:
825:
543:
513:
140:
128:
118:
2087:
1763:
1735:
1631:
914:
881:
748:-hCdtI(30/120) fluorescence is shown in red and highlights the G
728:, also exhibits this characteristic along with turquoise bones.
662:
574:
erythrocytes and break the heme down into biliverdin along with
555:
524:
517:
1885:
1604:
1557:
Tsien, Roger Y. (1998-01-01). "The Green
Fluorescent Protein".
897:
880:(0.20), which makes it comparable biophysical brightness to
284:
605:(whites of the eyes) are characteristic of liver failure.
1364:
10.1655/0018-0831(2007)63[392:ANSOCP]2.0.CO;2
485:
621:. They have also been shown to inhibit the effects of
413:
Dark green plates or prisms with violet surface color
2345:
2322:
2301:
2226:
2180:
2171:
2141:
2078:
2069:
2041:
2032:
1991:
1969:
1920:
1859:
1833:
1804:
1780:
1752:
1745:
1734:
1705:
1670:
1650:
1641:
1266:Shamim, G; Ranjan, S; Pandey, D; Ramani, R (2014).
896:spectral properties are similar to the organic dye
884:and about 2-fold brighter than most red or far-red
1268:"Biochemistry and biosynthesis of insect pigments"
805:, and named small ultra red fluorescent protein (
661:Biliverdin is an important pigment component in
246:
104:
1897:
1616:
554:Biliverdin results from the breakdown of the
8:
1443:
1441:
1098:The Tohoku Journal of Experimental Medicine
820:biliverdin without the need of an external
2177:
2075:
2038:
1975:
1928:
1904:
1890:
1882:
1749:
1742:
1647:
1623:
1609:
1601:
977:Journal of the American Geriatrics Society
299:
210:
188:
29:
1533:
1473:
1421:
1219:Comparative Biochemistry and Physiology B
1158:
1109:
760:In a complex with reengineered bacterial
516:for green bile) is a green tetrapyrrolic
266:
1383:
1381:
1253:"These Puppies Were Born with Green Fur"
735:
649:as well as having beneficial effects in
949:
947:
945:
941:
355:
320:
295:
224:
836:-derived fluorescent proteins require
201:
1596:Explaining jaundice in newborn at NHS
1495:
1493:
1045:
1043:
1041:
970:
968:
966:
768:which form their chromophore through
673:nor free haem from the blood plasma.
327:Key: QBUVFDKTZJNUPP-BBROENKCSA-N
168:
148:
7:
1087:
1085:
1083:
1081:
337:Key: QBUVFDKTZJNUPP-BBROENKCBK
237:
696:larvae is also due to biliverdin.
67:-biline-8,12-diyl)dipropanoic acid
25:
1571:10.1146/annurev.biochem.67.1.509
989:10.1111/j.1532-5415.2005.53406.x
876:(180,000 M cm) and has a modest
776:, phytochromes bind an external
623:polycyclic aromatic hydrocarbons
475:
45:
36:
770:posttranslational modifications
578:, in which biliverdin normally
471:(at 25 Β°C , 100 kPa).
1303:Austin, C; Perkins, S (2006).
1275:European Journal of Entomology
1020:Wiener Klinische Wochenschrift
435:Occupational safety and health
1:
1834:Intestine, excretion in feces
1559:Annual Review of Biochemistry
1184:Journal of Chemical Education
1388:X. Shu; et al. (2009).
1231:10.1016/0305-0491(90)90174-R
609:Role in treatment of disease
1204:10.1021/acs.jchemed.7b00449
1064:10.1016/j.mrrev.2007.05.001
2405:
1860:Kidney, excretion in urine
1978:
1931:
465:
432:
427:
366:
346:
311:
88:
72:
58:
53:
44:
35:
2118:Magnesium protoporphyrin
794:Trichodesmium erythraeum
1821:Bilirubin diglucuronide
1635:metabolic intermediates
1414:10.1126/science.1168683
1309:Journal of Parasitology
1139:The Biochemical Journal
732:In fluorescence imaging
725:Chiromantis samkosensis
1697:Coproporphyrinogen III
1643:Porphyrin biosynthesis
874:extinction coefficient
816:self-incorporates the
757:
643:cardiovascular disease
549:
523:, and is a product of
2218:Protoporphyrinogen IX
1816:Bilirubin glucuronide
1717:Protoporphyrinogen IX
1662:D-Aminolevulinic acid
1283:10.14411/eje.2014.021
739:
619:hydroperoxyl radicals
547:
405:582.646
74:Systematic IUPAC name
2311:Bacteriochlorophyll
2290:Bacteriochlorophyll
1692:Uroporphyrinogen III
1653:early mitochondrial:
1111:10.1620/tjem.199.193
886:fluorescent proteins
766:fluorescent proteins
657:In non-human animals
2384:Biological pigments
2324:Isobacteriochlorins
2159:Protochlorophyllide
2133:Zinc protoporphyrin
1708:late mitochondrial:
1687:Hydroxymethylbilane
1406:2009Sci...324..804S
1196:2017JChEd..94.1533H
787:was evolved from a
785:fluorescent protein
633:β all of which are
627:heterocyclic amines
32:
2204:Coproporphyrinogen
1518:10.1038/nmeth.3935
758:
647:protease inhibitor
550:
498:Infobox references
30:
27:Green bile pigment
2371:
2370:
2367:
2366:
2363:
2362:
2167:
2166:
2123:Protoporphyrin IX
2051:Adenosylcobalamin
2028:
2027:
2024:
2023:
2001:Phycoerythrobilin
1879:
1878:
1875:
1874:
1829:
1828:
1746:Breakdown of heme
1730:
1729:
1722:Protoporphyrin IX
1400:(5928): 804β807.
1321:10.1645/GE-693R.1
1190:(10): 1533β1537.
1151:10.1042/bj3200681
1145:(Pt 2): 681β686.
1052:Mutation Research
862:hydrogen peroxide
856:does not require
846:hydrogen peroxide
814:autocatalytically
774:polypeptide chain
506:Chemical compound
504:
503:
454:Safety data sheet
280:CompTox Dashboard
130:Interactive image
16:(Redirected from
2396:
2337:Sirohydrochlorin
2303:Bacteriochlorins
2190:Uroporphyrinogen
2178:
2076:
2039:
1983:Phytochromobilin
1976:
1929:
1906:
1899:
1892:
1883:
1809:
1785:
1757:
1750:
1743:
1736:Heme degradation
1710:
1675:
1655:
1648:
1625:
1618:
1611:
1602:
1583:
1582:
1554:
1548:
1547:
1537:
1497:
1488:
1487:
1477:
1466:10.1038/nbt.1918
1445:
1436:
1435:
1425:
1385:
1376:
1375:
1347:
1341:
1340:
1300:
1294:
1293:
1291:
1289:
1272:
1263:
1257:
1256:
1249:
1243:
1242:
1214:
1208:
1207:
1179:
1173:
1172:
1162:
1130:
1124:
1123:
1113:
1089:
1076:
1075:
1047:
1036:
1035:
1015:
1009:
1008:
983:(8): 1339β1343.
972:
961:
951:
799:phycobiliprotein
678:tobacco hornworm
488:
482:
479:
478:
374:Chemical formula
304:
303:
288:
286:
270:
250:
239:
228:
214:
203:
192:
172:
152:
132:
108:
49:
40:
33:
21:
2404:
2403:
2399:
2398:
2397:
2395:
2394:
2393:
2374:
2373:
2372:
2359:
2341:
2318:
2297:
2222:
2173:
2163:
2143:Phytoporphyrins
2137:
2080:Protoporphyrins
2065:
2061:Methylcobalamin
2020:
2016:Phycoviolobilin
2006:Phycocyanobilin
1987:
1965:
1946:Stercobilinogen
1924:
1916:
1910:
1880:
1871:
1855:
1841:Stercobilinogen
1825:
1805:
1800:
1781:
1776:
1753:
1738:
1726:
1706:
1701:
1682:Porphobilinogen
1671:
1666:
1651:
1637:
1629:
1592:
1587:
1586:
1556:
1555:
1551:
1499:
1498:
1491:
1447:
1446:
1439:
1387:
1386:
1379:
1349:
1348:
1344:
1302:
1301:
1297:
1287:
1285:
1277:. 111(2): 155.
1270:
1265:
1264:
1260:
1251:
1250:
1246:
1216:
1215:
1211:
1181:
1180:
1176:
1132:
1131:
1127:
1091:
1090:
1079:
1049:
1048:
1039:
1017:
1016:
1012:
974:
973:
964:
952:
943:
938:
906:
803:allophycocyanin
783:A new class of
755:
751:
743:
734:
659:
611:
595:
593:Role in disease
580:rapidly reduces
552:
551:
548:Heme metabolism
540:
507:
500:
495:
494:
493: ?)
484:
480:
476:
472:
445:
394:
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386:
382:
376:
362:
359:
354:
353:
342:
339:
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240:
195:
175:
155:
135:
122:
111:
98:
84:
83:
68:
28:
23:
22:
15:
12:
11:
5:
2402:
2400:
2392:
2391:
2386:
2376:
2375:
2369:
2368:
2365:
2364:
2361:
2360:
2358:
2357:
2351:
2349:
2343:
2342:
2340:
2339:
2334:
2328:
2326:
2320:
2319:
2317:
2316:
2307:
2305:
2299:
2298:
2296:
2295:
2287:
2269:
2251:
2236:Chlorophyllide
2232:
2230:
2224:
2223:
2221:
2220:
2215:
2201:
2186:
2184:
2182:Porphyrinogens
2175:
2169:
2168:
2165:
2164:
2162:
2161:
2156:
2147:
2145:
2139:
2138:
2136:
2135:
2130:
2125:
2120:
2115:
2084:
2082:
2073:
2067:
2066:
2064:
2063:
2058:
2056:Cyanocobalamin
2053:
2047:
2045:
2036:
2030:
2029:
2026:
2025:
2022:
2021:
2019:
2018:
2013:
2008:
2003:
1997:
1995:
1989:
1988:
1986:
1985:
1979:
1973:
1967:
1966:
1964:
1963:
1958:
1953:
1948:
1943:
1938:
1932:
1926:
1918:
1917:
1911:
1909:
1908:
1901:
1894:
1886:
1877:
1876:
1873:
1872:
1870:
1869:
1863:
1861:
1857:
1856:
1854:
1853:
1848:
1843:
1837:
1835:
1831:
1830:
1827:
1826:
1824:
1823:
1818:
1812:
1810:
1802:
1801:
1799:
1798:
1788:
1786:
1778:
1777:
1775:
1774:
1760:
1758:
1747:
1740:
1732:
1731:
1728:
1727:
1725:
1724:
1719:
1713:
1711:
1703:
1702:
1700:
1699:
1694:
1689:
1684:
1678:
1676:
1668:
1667:
1665:
1664:
1658:
1656:
1645:
1639:
1638:
1630:
1628:
1627:
1620:
1613:
1605:
1599:
1598:
1591:
1590:External links
1588:
1585:
1584:
1565:(1): 509β544.
1549:
1506:Nature Methods
1489:
1460:(8): 757β761.
1454:Nat Biotechnol
1437:
1377:
1358:(3): 392β400.
1342:
1315:(4): 770β777.
1295:
1258:
1244:
1209:
1174:
1125:
1104:(3): 193β196.
1077:
1058:(1β2): 28β41.
1037:
1026:(15): 477β82.
1010:
962:
940:
939:
937:
934:
933:
932:
927:
922:
917:
912:
905:
902:
842:stoichiometric
840:and produce a
789:cyanobacterial
753:
749:
741:
733:
730:
658:
655:
610:
607:
594:
591:
542:
541:
539:
536:
505:
502:
501:
496:
474:
473:
469:standard state
466:
463:
462:
457:
450:
449:
446:
443:
440:
439:
430:
429:
425:
424:
421:
415:
414:
411:
407:
406:
403:
397:
396:
392:
388:
384:
380:
377:
372:
369:
368:
364:
363:
361:
360:
357:
349:
348:
347:
344:
343:
341:
340:
336:
333:
332:
330:
326:
323:
322:
314:
313:
312:
309:
308:
306:
305:
297:DTXSID70883307
292:
290:
278:
275:
274:
272:
271:
263:
261:
255:
254:
252:
251:
243:
241:
233:
230:
229:
222:
216:
215:
205:
197:
196:
194:
193:
185:
183:
177:
176:
174:
173:
165:
163:
157:
156:
154:
153:
145:
143:
137:
136:
134:
133:
125:
123:
116:
113:
112:
110:
109:
101:
99:
94:
91:
90:
86:
85:
77:
76:
70:
69:
62:
56:
55:
51:
50:
42:
41:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2401:
2390:
2389:Tetrapyrroles
2387:
2385:
2382:
2381:
2379:
2356:
2355:Cofactor F430
2353:
2352:
2350:
2348:
2344:
2338:
2335:
2333:
2330:
2329:
2327:
2325:
2321:
2315:
2314:
2309:
2308:
2306:
2304:
2300:
2294:
2293:
2288:
2285:
2284:
2279:
2278:
2273:
2270:
2267:
2266:
2261:
2260:
2255:
2252:
2249:
2248:
2243:
2242:
2237:
2234:
2233:
2231:
2229:
2225:
2219:
2216:
2213:
2209:
2205:
2202:
2199:
2195:
2191:
2188:
2187:
2185:
2183:
2179:
2176:
2170:
2160:
2157:
2155:
2154:
2149:
2148:
2146:
2144:
2140:
2134:
2131:
2129:
2126:
2124:
2121:
2119:
2116:
2113:
2112:
2107:
2106:
2101:
2100:
2095:
2094:
2089:
2086:
2085:
2083:
2081:
2077:
2074:
2072:
2068:
2062:
2059:
2057:
2054:
2052:
2049:
2048:
2046:
2044:
2040:
2037:
2035:
2031:
2017:
2014:
2012:
2011:Phycourobilin
2009:
2007:
2004:
2002:
1999:
1998:
1996:
1994:
1990:
1984:
1981:
1980:
1977:
1974:
1972:
1968:
1962:
1959:
1957:
1954:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1933:
1930:
1927:
1923:
1919:
1915:
1914:tetrapyrroles
1907:
1902:
1900:
1895:
1893:
1888:
1887:
1884:
1868:
1865:
1864:
1862:
1858:
1852:
1849:
1847:
1844:
1842:
1839:
1838:
1836:
1832:
1822:
1819:
1817:
1814:
1813:
1811:
1808:
1803:
1797:
1793:
1790:
1789:
1787:
1784:
1779:
1773:
1769:
1765:
1762:
1761:
1759:
1756:
1751:
1748:
1744:
1741:
1739:and excretion
1737:
1733:
1723:
1720:
1718:
1715:
1714:
1712:
1709:
1704:
1698:
1695:
1693:
1690:
1688:
1685:
1683:
1680:
1679:
1677:
1674:
1669:
1663:
1660:
1659:
1657:
1654:
1649:
1646:
1644:
1640:
1636:
1633:
1626:
1621:
1619:
1614:
1612:
1607:
1606:
1603:
1597:
1594:
1593:
1589:
1580:
1576:
1572:
1568:
1564:
1560:
1553:
1550:
1545:
1541:
1536:
1531:
1527:
1523:
1519:
1515:
1511:
1507:
1503:
1496:
1494:
1490:
1485:
1481:
1476:
1471:
1467:
1463:
1459:
1455:
1451:
1444:
1442:
1438:
1433:
1429:
1424:
1419:
1415:
1411:
1407:
1403:
1399:
1395:
1391:
1384:
1382:
1378:
1373:
1369:
1365:
1361:
1357:
1353:
1352:Herpetologica
1346:
1343:
1338:
1334:
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1299:
1296:
1284:
1280:
1276:
1269:
1262:
1259:
1254:
1248:
1245:
1240:
1236:
1232:
1228:
1224:
1220:
1213:
1210:
1205:
1201:
1197:
1193:
1189:
1185:
1178:
1175:
1170:
1166:
1161:
1156:
1152:
1148:
1144:
1140:
1136:
1129:
1126:
1121:
1117:
1112:
1107:
1103:
1099:
1095:
1088:
1086:
1084:
1082:
1078:
1073:
1069:
1065:
1061:
1057:
1053:
1046:
1044:
1042:
1038:
1033:
1029:
1025:
1021:
1014:
1011:
1006:
1002:
998:
994:
990:
986:
982:
978:
971:
969:
967:
963:
960:
959:1-4160-2328-3
956:
950:
948:
946:
942:
935:
931:
928:
926:
923:
921:
918:
916:
913:
911:
908:
907:
903:
901:
899:
895:
891:
888:derived from
887:
883:
879:
878:quantum yield
875:
871:
867:
864:and uses the
863:
859:
855:
851:
847:
843:
839:
835:
831:
827:
824:, known as a
823:
819:
815:
812:
808:
804:
800:
796:
795:
790:
786:
781:
779:
775:
771:
767:
763:
747:
738:
731:
729:
727:
726:
721:
718:
717:
712:
708:
707:
703:of the genus
702:
697:
695:
691:
687:
686:Belone belone
683:
679:
674:
672:
671:tetrapyrroles
666:
664:
656:
654:
652:
648:
644:
640:
636:
632:
628:
624:
620:
614:
608:
606:
604:
600:
592:
590:
587:
585:
581:
577:
573:
569:
565:
561:
557:
546:
537:
535:
533:
529:
526:
522:
519:
515:
511:
499:
492:
487:
470:
464:
461:
460:Sigma-Aldrich
458:
455:
452:
451:
447:
442:
441:
437:
436:
431:
426:
422:
420:
419:Melting point
417:
416:
412:
409:
408:
404:
402:
399:
398:
378:
375:
371:
370:
365:
356:
352:
345:
331:
321:
317:
310:
302:
298:
294:
293:
291:
281:
277:
276:
269:
265:
264:
262:
260:
257:
256:
249:
245:
244:
242:
236:
232:
231:
227:
223:
221:
218:
217:
213:
209:
206:
204:
202:ECHA InfoCard
199:
198:
191:
187:
186:
184:
182:
179:
178:
171:
167:
166:
164:
162:
159:
158:
151:
147:
146:
144:
142:
139:
138:
131:
127:
126:
124:
120:
115:
114:
107:
103:
102:
100:
97:
93:
92:
87:
81:
75:
71:
66:
61:
57:
52:
48:
43:
39:
34:
19:
2312:
2291:
2282:
2276:
2264:
2258:
2246:
2240:
2152:
2151:Chlorophyll
2110:
2104:
2098:
2092:
1956:Urobilinogen
1940:
1851:Urobilinogen
1806:
1782:
1767:
1754:
1707:
1672:
1652:
1562:
1558:
1552:
1512:(9): 763β9.
1509:
1505:
1457:
1453:
1397:
1393:
1355:
1351:
1345:
1312:
1308:
1298:
1286:. Retrieved
1274:
1261:
1247:
1225:(1): 37β45.
1222:
1218:
1212:
1187:
1183:
1177:
1142:
1138:
1128:
1101:
1097:
1055:
1051:
1023:
1019:
1013:
980:
976:
925:Tetrapyrrole
872:has a large
868:biliverdin.
792:
782:
759:
723:
714:
706:Prasinohaema
704:
698:
694:lepidopteran
690:grasshoppers
685:
675:
667:
660:
615:
612:
596:
588:
564:erythrocytes
553:
509:
508:
444:Main hazards
433:
423:> 300 Β°C
170:ChEMBL455477
89:Identifiers
79:
64:
2254:Chlorophyll
1993:Phycobilins
1971:Phytobilins
1951:Stercobilin
1846:Stercobilin
920:Stercobilin
866:chromophore
860:or produce
852:formation.
850:chromophore
818:chromophore
809:) in 2016.
762:phytochrome
744:/M phases.
709:, found in
576:hemosiderin
570:break down
568:Macrophages
438:(OHS/OSH):
410:Appearance
367:Properties
208:100.003.675
150:CHEBI:17033
31:Biliverdin
18:Biliverdine
2378:Categories
2272:Pheophytin
2174:porphyrins
2128:Pterobilin
2071:Porphyrins
2043:Corrinoids
2034:Macrocycle
1941:Biliverdin
1768:Biliverdin
1673:cytosolic:
936:References
844:amount of
716:Plasmodium
711:New Guinea
560:hemoglobin
558:moiety of
538:Metabolism
528:catabolism
512:(from the
510:Biliverdin
401:Molar mass
268:O9MIA842K9
226:Biliverdin
181:ChemSpider
117:3D model (
96:CAS Number
60:IUPAC name
1936:Bilirubin
1912:Types of
1792:Bilirubin
1772:Bilirubin
1526:1548-7105
910:Bilirubin
830:Jellyfish
584:bilirubin
572:senescent
448:Irritant
2347:Corphins
2332:Siroheme
2228:Chlorins
1961:Urobilin
1925:(Linear)
1867:Urobilin
1544:27479328
1484:21765402
1432:19423828
1372:84472376
1329:16995395
1120:12703664
1072:17602853
1005:12394659
997:16078959
930:Urobilin
904:See also
635:mutagens
631:oxidants
599:Jaundice
582:to free
428:Hazards
190:10628548
106:114-25-0
2172:Reduced
1922:Bilanes
1796:Albumin
1755:spleen:
1579:9759496
1535:5007177
1475:3152693
1423:2763207
1402:Bibcode
1394:Science
1337:1937837
1288:25 June
1239:2253479
1192:Bibcode
1169:8973584
1160:1217983
822:protein
772:of the
756:phases.
720:malaria
682:garfish
532:bruises
521:pigment
491:what is
489: (
395:
235:PubChem
1807:liver:
1783:blood:
1577:
1542:
1532:
1524:
1482:
1472:
1430:
1420:
1370:
1335:
1327:
1237:
1167:
1157:
1118:
1070:
1032:793184
1030:
1003:
995:
957:
894:smURFP
870:smURFP
858:oxygen
854:smURFP
838:oxygen
832:- and
811:smURFP
807:smURFP
778:ligand
746:smURFP
701:skinks
651:asthma
639:cancer
629:, and
603:sclera
486:verify
483:
456:(SDS)
351:SMILES
161:ChEMBL
54:Names
1368:S2CID
1333:S2CID
1271:(PDF)
1001:S2CID
890:coral
848:upon
834:coral
826:lyase
663:avian
514:Latin
316:InChI
141:ChEBI
119:JSmol
2088:Heme
1764:Heme
1632:Heme
1575:PMID
1540:PMID
1522:ISSN
1480:PMID
1428:PMID
1325:PMID
1290:2023
1235:PMID
1165:PMID
1116:PMID
1068:PMID
1028:PMID
993:PMID
955:ISBN
915:Heme
882:eGFP
801:, Ξ±-
692:and
641:and
556:heme
525:heme
518:bile
259:UNII
220:MeSH
2212:III
2198:III
1567:doi
1530:PMC
1514:doi
1470:PMC
1462:doi
1418:PMC
1410:doi
1398:324
1360:doi
1317:doi
1279:doi
1227:doi
1200:doi
1155:PMC
1147:doi
1143:320
1106:doi
1102:199
1060:doi
1056:658
985:doi
898:Cy5
562:in
285:EPA
248:251
238:CID
2380::
2280:,
2262:,
2244:,
2210:,
2196:,
2108:,
2102:,
2096:,
1770:β
1766:β
1573:.
1563:67
1561:.
1538:.
1528:.
1520:.
1510:13
1508:.
1504:.
1492:^
1478:.
1468:.
1458:29
1456:.
1452:.
1440:^
1426:.
1416:.
1408:.
1396:.
1392:.
1380:^
1366:.
1356:63
1354:.
1331:.
1323:.
1313:92
1311:.
1307:.
1273:.
1233:.
1223:97
1221:.
1198:.
1188:94
1186:.
1163:.
1153:.
1141:.
1137:.
1114:.
1100:.
1096:.
1080:^
1066:.
1054:.
1040:^
1024:88
1022:.
999:.
991:.
981:53
979:.
965:^
944:^
900:.
892:.
828:.
797:)
752:/G
625:,
586:.
566:.
534:.
385:34
381:33
2313:a
2292:c
2286:)
2283:b
2277:a
2274:(
2268:)
2265:b
2259:a
2256:(
2250:)
2247:b
2241:a
2238:(
2214:)
2208:I
2206:(
2200:)
2194:I
2192:(
2153:c
2114:)
2111:o
2105:a
2099:c
2093:b
2090:(
1905:e
1898:t
1891:v
1794:+
1624:e
1617:t
1610:v
1581:.
1569::
1546:.
1516::
1486:.
1464::
1434:.
1412::
1404::
1374:.
1362::
1339:.
1319::
1292:.
1281::
1255:.
1241:.
1229::
1206:.
1202::
1194::
1171:.
1149::
1122:.
1108::
1074:.
1062::
1034:.
1007:.
987::
791:(
754:1
750:0
742:2
684:(
481:Y
393:6
391:O
389:4
387:N
383:H
379:C
287:)
283:(
121:)
80:H
65:H
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
