1370:{{cite journal | year=1975 | title=Heme A of Cytochrome c Oxidase | journal=] | volume=250 | issue=19 | pages=7602–7622 | author1=Caughey, W.S. | author2=Smythe, G.A. | author3=O'Keefe, D.H. | author4=Maskasky, J.E. | author5=Smith, M.L. | doi=10.1016/S0021-9258(19)40860-0 | pmid=170266 | doi-access=free }}</ref> The structure was confirmed by synthesis of the dimethyl ester of the iron-free form.<ref>{{cite journal |doi=10.1039/P19850000135 |title=Isolation, crystallisation, and synthesis of the dimethyl ester of porphyrin a, the iron-free prosthetic group of cytochrome c oxidase |year=1985 |last1=Battersby |first1=Alan R. |last2=McDonald |first2=Edward |last3=Thompson |first3=Mervyn |last4=Chaudhry |first4=Irshad A. |last5=Clezy |first5=Peter S. |last6=Fookes |first6=Christopher J. R. |last7=Hai |first7=Ton That |journal=Journal of the Chemical Society, Perkin Transactions 1 |pages=135 }}</ref>
494:| InChI = 1/C49H59N4O6.Fe/c1-9-34-31(6)39-25-45-49(46(55)18-12-17-30(5)16-11-15-29(4)14-10-13-28(2)3)33(8)40(52-45)24-44-37(27-54)36(20-22-48(58)59)43(53-44)26-42-35(19-21-47(56)57)32(7)38(51-42)23-41(34)50-39;/h9,13,15,17,23-27,43,46,55H,1,10-12,14,16,18-22H2,2-8H3,(H4-,50,51,52,53,56,57,58,59);/q-1;+2/p-2/b29-15+,30-17+,42-26-;/rC49H57FeN4O6/c1-9-34-31(6)39-25-45-49(46(56)18-12-17-30(5)16-11-15-29(4)14-10-13-28(2)3)33(8)40-24-44-37(27-55)36(20-22-48(59)60)43-26-42-35(19-21-47(57)58)32(7)38-23-41(34)51(39)50(52(38)42,53(40)45)54(43)44/h9,13,15,17,23-27,43,46,56H,1,10-12,14,16,18-22H2,2-8H3,(H,57,58)(H,59,60)/q-1/b29-15+,30-17+
487:| InChI = 1/C49H59N4O6.Fe/c1-9-34-31(6)39-25-45-49(46(55)18-12-17-30(5)16-11-15-29(4)14-10-13-28(2)3)33(8)40(52-45)24-44-37(27-54)36(20-22-48(58)59)43(53-44)26-42-35(19-21-47(56)57)32(7)38(51-42)23-41(34)50-39;/h9,13,15,17,23-27,43,46,55H,1,10-12,14,16,18-22H2,2-8H3,(H4-,50,51,52,53,56,57,58,59);/q-1;+2/p-2/b29-15+,30-17+,42-26-;/rC49H57FeN4O6/c1-9-34-31(6)39-25-45-49(46(56)18-12-17-30(5)16-11-15-29(4)14-10-13-28(2)3)33(8)40-24-44-37(27-55)36(20-22-48(59)60)43-26-42-35(19-21-47(57)58)32(7)38-23-41(34)51(39)50(52(38)42,53(40)45)54(43)44/h9,13,15,17,23-27,43,46,56H,1,10-12,14,16,18-22H2,2-8H3,(H,57,58)(H,59,60)/q-1/b29-15+,30-17+
2084:
first1 = S. | last1 = Yoshikawa | first2 = K. | last2 = Shinzawa-Itoh | first3 = R. | last3 = Nakashima | first4 = R. | last4 = Yaono | first5 = E. | last5 = Yamashita | first6 = N. | last6 = Inoue | first7 = M. | last7 = Yao | first8 = M. J. | last8 = Fei | first9 = C. | last10 = Mizushima | first10 = T | last11 = Yamaguchi | first11 = H | last12 = Tomizaki | first12 = T | last13 = Tsukihara | first13 = T | last9 = Peters Libeu | pmid=9624044 | issue=5370 |doi= 10.1126/science.280.5370.1723 |s2cid=37147458 |display-authors=3 }}
2029:|vauthors=Tsukihara T, Shimokata K, Katayama Y, Shimada H, Muramoto K, Aoyama H, Mochizuki M, Shinzawa-Itoh K, Yamashita E, Yao M, Ishimura Y, Yoshikawa S | year=2003 | title=The low-spin heme of cytochrome c oxidase as the driving element of the proton-pumping process |journal=] |volume=100 |pages=15304–15309 |doi=10.1073/pnas.2635097100 |pmid=14673090 |issue=26 |pmc=307562 |bibcode=2003PNAS..10015304T |doi-access=free |display-authors=3 }}</ref> Histidine is a common ligand for many ] including ] and ].
2343:{{cite journal | vauthors=Shimokata K, Katayama Y, Murayama H, Suematsu M, Tsukihara T, Muramoto K, Aoyama H, Yoshikawa S, Shimada H |year=2007 |title=The proton pumping pathway of bovine heart cytochrome c oxidase |journal=] |volume=104 |pages=4200–4205 |doi =10.1073/pnas.0611627104 |pmid=17360500 |issue=10 |pmc=1820732 |bibcode=2007PNAS..104.4200S | doi-access=free |display-authors=3 }}</ref>
537:| StdInChI = 1S/C49H59N4O6.Fe/c1-9-34-31(6)39-25-45-49(46(55)18-12-17-30(5)16-11-15-29(4)14-10-13-28(2)3)33(8)40(52-45)24-44-37(27-54)36(20-22-48(58)59)43(53-44)26-42-35(19-21-47(56)57)32(7)38(51-42)23-41(34)50-39;/h9,13,15,17,23-27,43,46,55H,1,10-12,14,16,18-22H2,2-8H3,(H4-,50,51,52,53,56,57,58,59);/q-1;+2/p-2/b29-15+,30-17+,42-26-;
530:| StdInChI = 1S/C49H59N4O6.Fe/c1-9-34-31(6)39-25-45-49(46(55)18-12-17-30(5)16-11-15-29(4)14-10-13-28(2)3)33(8)40(52-45)24-44-37(27-54)36(20-22-48(58)59)43(53-44)26-42-35(19-21-47(56)57)32(7)38(51-42)23-41(34)50-39;/h9,13,15,17,23-27,43,46,55H,1,10-12,14,16,18-22H2,2-8H3,(H4-,50,51,52,53,56,57,58,59);/q-1;+2/p-2/b29-15+,30-17+,42-26-;
1580:}}</ref>. Heme A is similar to ], in that both have this farnesyl addition at position 3 but heme O does not have the ] group at position 8, still containing the methyl group. The correct structure of heme A, based upon NMR and IR experiments of the reduced, Fe(II), form of the heme, was published in 1975<ref>
2083:
Heme A in the cytochrome a portion of cytochrome c oxidase, bound by two ] residues (shown in pink)<ref name="Yoshikawa-1998">{{ cite journal | journal = ] | year = 1998 | volume = 280 | pages = 1723–1729 | title = Redox-Coupled
Crystal Structural Changes in Bovine Heart Cytochrome c Oxidase |
2028:
Like heme B, heme A is often attached to the apoprotein through a coordinate bond between the heme iron and a conserved amino acid side-chain. In the important respiratory protein ] (CCO) this ligand 5 for the heme A at the oxygen reaction center is a histidyl group.<ref>{{cite journal
1109:'''Heme A''' (or '''haem A''') is a ], a ] consisting of a ] ligand called a ], ] an iron atom. Heme A is a ] and is produced naturally by many organisms. Heme A, often appears a dichroic green/red when in solution, is a structural relative of ], a component of ], the red pigment in blood.
2197:}}</ref>. In addition, this enzyme binds 3 copper, magnesium, zinc, and several potassium and sodium ions. The two heme A groups in CCO are thought to readily exchange electrons between each other, the copper ions and the closely associated protein cytochrome c.
1828:
Like heme B, heme A is often attached to the apoprotein through a coordinate bond between the heme iron and a conserved amino acid side-chain. In the important respiratory protein ] (CCO) this ligand 5 for the heme A at the oxygen reaction center is a histidyl
2253:
In addition, this enzyme binds 3 copper, magnesium, zinc, and several potassium and sodium ions. The two heme A groups in CCO are thought to readily exchange electrons between each other, the copper ions and the closely associated protein cytochrome
229:
2312:
Both the ] group and the ] side chain are thought to play important roles in conservation of the energy of oxygen reduction by ]. CCO is thought to be responsible for conserving the energy of dioxygen reduction by pumping protons into the
2269:
Both the ] group and the ] side chain are thought to play important roles in conservation of the energy of oxygen reduction by ]. CCO is thought to be responsible for conserving the energy of dioxygen reduction by pumping protons into the
78:
35:
2043:
An example of a metalloprotein that contains heme A is cytochrome c oxidase. This very complicated protein contains heme A at two different sites, each with a different function. The iron of the heme A of cytochrome a is
2274:
mitochondrial space. Both the formyl and hydroxyethylfarnesyl groups of heme A are thought to play important roles in this critical process, as published by the influential group of S. Yoshikawa<ref>
2227:
An example of a metalloprotein that contains heme A is cytochrome c oxidase. This very complicated protein contains heme A at two different sites, each with a different function. The iron of the heme A of
1742:| title=Absolute configuration of the hydroxyfarnesylethyl group of heme A, determined by X-ray structural analysis of bovine heart cytochrome c oxidase using methods applicable at 2.8 Angstrom resolution
86:
1892:
title=Absolute configuration of the hydroxyfarnesylethyl group of heme A, determined by X-ray structural analysis of bovine heart cytochrome c oxidase using methods applicable at 2.8 Angstrom resolution
92:
49:
2317:
mitochondrial space. Both the formyl and hydroxyethylfarnesyl groups of heme A are thought to play important roles in this critical process, as published by the influential group of S. Yoshikawa
11:
43:
2048:, that is bound with 6 other atoms. The iron of the heme A of cytochrome a3 is sometimes bound by 5 other atoms leaving the sixth site available to bind dioxygen(molecular ])<ref>
57:
1847:
The final structural question of the exact geometric configuration about the first carbon at ring position 3 of ring I, the carbon bound to the hydroxyl group, has been
1694:
The final structural question of the exact geometric configuration about the first carbon at ring position 3 of ring I, the carbon bound to the hydroxyl group, has been
1401:
Heme A was first isolated by the German biochemist ] in 1951 and shown by him to be the active component of the integral membrane ] cytochrome c oxidase.<ref>
2093:| author=Yoshikawa S, Shinzawa-Itoh K, Nakashima R, Yaono R, Yamashita E, Inoue N, Yao M, Fei MJ, Libeu CP, Mizushima T, Yamaguchi H, Tomizaki T, Tsukihara T.
100:
1904:| author=Tsukihara T, Shimokata K, Katayama Y, Shimada H, Muramoto K, Aoyama H, Mochizuki M, Shinzawa-Itoh K, Yamashita E, Yao M, Ishimura Y, Yoshikawa S.
212:
205:
1894:|journal=] |volume=61 |issue=10 |pages=1373–1377 |doi=10.1107/S0907444905023358 |pmid=16204889 |doi-access=free |display-authors=3 }}</ref>
116:
24:
254:
247:
2330:| author=Shimokata K, Katayama Y, Murayama H, Suematsu M, Tsukihara T, Muramoto K, Aoyama H, Yoshikawa S, Shimada H.
847:| Formula = C<sub>49</sub>H<sub>56</sub>O<sub>6</sub>N<sub>4</sub>Fe
161:
840:
Formula = C<sub>49</sub>H<sub>56</sub>O<sub>6</sub>N<sub>4</sub>Fe
236:
179:
186:
1890:
vauthors=Yamashita E, Aoyama H, Yao M, Muramoto K, Shinzawa-Itoh K, Yoshikawa S, Tsukihara T |year=2005 |
168:
87:
1926:| title=The low-spin heme of cytochrome c oxidase as the driving element of the proton-pumping process
1590:
220:
58:
2437:
2304:
2261:
2219:
2103:
2035:
1880:
1839:
1783:
1734:
1683:
1512:
1473:
1264:
1135:
190:
157:
44:
243:
224:
1715:| author=Yamashita E, Aoyama H, Yao M, Muramoto K, Shinzawa-Itoh K, Yoshikawa S, Tsukihara T.
101:
8:
204:
Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the
175:
1272:
Heme A differs from ] in that a ] ] at ring position 8 is oxidized to a ] group and a
2240:
is sometimes bound by 5 other atoms leaving the sixth site available to bind dioxygen
2131:| title=Redox-coupled crystal structural changes in bovine heart cytochrome c oxidase
12:
1150:
differs from ] in that a ] ] at ring position 8 is oxidized to a ] group and a
132:
1338:
group. The correct structure of heme A, based upon NMR and IR experiments
1154:
group, an ] chain, has been attached to the ] side chain at ring position
2363:| title=The proton pumping pathway of bovine heart cytochrome c oxidase
2003:}}</ref>. This is a common ligand 5 for many ] including ] and ].
1276:, an ] chain, has been attached to the ] side chain at ring position
377:| ImageFileR1 = Haem-a-in-cyctochrome-c-oxidase-PDB-1OCR-3D-SF-A.png
112:
111:
2236:, that is bound with 6 other atoms. The iron of the heme A of
459:| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
1300:
both have this farnesyl addition at position 2 but heme
548:| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
139:
521:| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
1704:
the chiral S configuration<ref>{{cite journal
275:(64 intermediate revisions by 40 users not shown)
208:- Updated: InChI1->InChI StdInChI StdInChIKey.
221:Latest revision as of 08:03, 10 November 2023
564:| StdInChIKey = RRRJRRNGYOECDS-ZHOBENDVSA-L
557:| StdInChIKey = RRRJRRNGYOECDS-ZHOBENDVSA-L
1789:
293:{{short description|Chemical compound}}
2443:
2310:
2267:
2225:
2109:
2041:
1886:
1845:
1740:
1689:
1642:| title=Heme A of Cytochrome c Oxidase
1596:
1518:
1479:
1270:
1141:
510:| InChIKey = RRRJRRNGYOECDS-DRKRPJRXBB
503:| InChIKey = RRRJRRNGYOECDS-DRKRPJRXBB
422:Iron cytoporphyrin IX, formilporphyrin
158:Revision as of 10:59, 2 December 2010
77:
34:
268:so text won't be offset so much
148:
131:
1280:of the iron tetrapyrrole ]. Heme A
1158:of the iron tetrapyrrole ]. Heme A
274:
266:
235:
218:
211:
202:
167:
155:
9:
2164:|doi=10.1126/science.280.5370.1723
120:
2647:
95:
81:
52:
38:
1948:| volume=100 | pages=15304–15309
1482:| title=Cytohämin aus Herzmuskel
2153:| volume=280 | pages= 1723–1729
1256:==Relationship to other hemes==
1118:{{Lead missing|date=June 2010}}
448:|Section1={{Chembox Identifiers
206:Chem/Drugbox validation project
2396:| doi =10.1073/pnas.0611627104
2385:| volume=104 | pages=4200–4205
1664:| volume=250 | pages=7602–7622
828:|Section2={{Chembox Properties
1:
2600:
2525:
2518:
2425:
2414:
2403:
2392:
2381:
2370:
2359:
2348:
2339:
2326:
2290:
2283:
2193:
2182:
2171:
2160:
2149:
2138:
2127:
2116:
2089:
2079:
2066:
2061::] residues (shown in pink)]]
2057:
2024:
1999:
1988:
1977:
1966:
1959:| doi=10.1073/pnas.2635097100
1955:
1944:
1933:
1922:
1911:
1900:
1866:
1824:
1815:
1771:
1764:| volume=61 | pages=1373–1377
1760:
1749:
1722:
1711:
1671:
1660:
1649:
1638:
1627:
1620:| author=Caughey, W.S. et al.
1616:
1605:
1576:
1567:
1553:
1546:
1537:
1527:
1502:
1489:
1437:
1422:
1397:
1386:
1377:
1366:
1252:
1127:
1114:
1105:
1060:
1047:
1036:
1023:
1012:
999:
988:
979:
963:
938:
928:
919:
909:
900:
890:
881:
871:
862:
852:
843:
833:
824:
808:
783:
773:
701:
604:
595:
585:
544:
517:
474:
464:
455:
444:
428:
416:
409:
384:
373:
362:
349:
336:
325:
316:
289:
1357:heme, was published in 1975.
14:Browse history interactively
7:
983:|Section3={{Chembox Hazards
320:| verifiedrevid = 400103417
2652:
1857:the chiral S configuration
1559:10.1515/bchm2.1951.288.1.1
2598:
2565:
2562:
2454:
2432:
2421:
2410:
2399:
2388:
2377:
2366:
2355:
2337:
2333:
2301:
2297:
2281:
2277:
2216:
2200:
2189:
2178:
2167:
2156:
2145:
2134:
2123:
2100:
2096:
2077:
2073:
2055:
2051:
2022:
2006:
1995:
1984:
1973:
1962:
1951:
1940:
1929:
1918:
1907:
1877:
1873:
1861:<ref>{{cite journal
1836:
1832:
1813:
1797:
1778:
1767:
1756:
1745:
1729:
1718:
1707:
1678:
1667:
1656:
1645:
1634:
1623:
1612:
1587:
1583:
1565:
1523:
1500:
1496:
1470:
1395:
1384:
1375:
1364:
1261:
1250:
1246:
1125:
1121:
1103:
1067:
542:
515:
478:| ChemSpiderID = 21106444
453:
382:
371:
360:
356:
314:
287:
282:
279:
217:
154:
255:Extended confirmed users
2249:name="Yoshikawa-1998" /
471:ChemSpiderID = 21106444
153:
2604:{{DEFAULTSORT:Heme A}}
2529:* ] (Complex IV of ])
2522:* ] (Complex IV of ])
1506:| volume=288 |issue=1
866:| MolarMass = 852.837
441:{{Chembox Identifiers
388:| ImageSizeR1 = 100px
366:| ImageSizeL1 = 170px
2581:{{Enzyme cofactors}}
2574:{{Enzyme cofactors}}
821:{{Chembox Properties
580:| CASNo = 18535-39-2
573:| CASNo = 18535-39-2
187:Edit filter managers
109:
66:
1819:==Stereochemistry==
859:MolarMass = 852.837
787:| MeSHName = Heme+a
599:| PubChem = 5288529
69:
26:
1064:| Autoignition =
233:
165:
74:
31:
2640:
976:{{Chembox Hazards
780:MeSHName = Heme+a
592:PubChem = 5288529
219:
156:
97:
83:
70:
54:
40:
27:
2643:
2046:hexa-coordinated
1829:group<ref>
1692:}}</ref>.
1331:still containing
697:n2(/3=4)(N56)N78
269:
261:
251:
232:
227:
209:
197:
183:
164:
145:
144:
142:
137:
135:
127:
124:
113:
98:
84:
73:
55:
41:
30:
17:
15:
2651:
2650:
2646:
2645:
2644:
2642:
2641:
2637:
2630:
2621:
2614:
2605:
2594:
2589:
2582:
2575:
2558:
2551:
2542:
2537:
2530:
2523:
2514:
2507:
2498:
2491:
2482:
2475:
2466:
2461:
2452:
2451:
2447:
2430:
2419:
2408:
2407:| pmid=17360500
2397:
2386:
2375:
2364:
2353:
2344:
2331:
2322:
2320:
2316:
2295:
2286:
2275:
2273:
2256:
2255:
2250:
2246:
2242:
2239:
2235:
2234:hexacoordinated
2231:
2212:
2207:
2198:
2187:
2176:
2165:
2154:
2143:
2132:
2121:
2112:
2094:
2085:
2071:
2062:
2049:
2047:
2030:
2018:
2013:
2004:
1993:
1982:
1971:
1970:| pmid=14673090
1960:
1949:
1938:
1927:
1916:
1905:
1896:
1895:
1891:
1871:
1862:
1860:
1856:
1853:
1850:
1830:
1820:
1809:
1804:
1795:
1794:
1776:
1765:
1754:
1743:
1727:
1716:
1705:
1703:
1700:
1697:
1693:
1676:
1665:
1654:
1643:
1632:
1621:
1610:
1601:
1599:
1581:
1572:
1561:
1560:
1551:
1542:
1535:
1533:
1521:
1507:
1494:
1485:
1483:
1466:
1459:
1450:
1448:
1444:
1435:
1433:
1429:
1418:
1411:
1402:
1391:
1380:
1371:
1360:
1358:
1355:
1352:
1349:
1346:
1343:
1339:
1336:
1332:
1329:
1326:
1323:
1320:
1317:
1314:
1311:
1308:
1305:
1301:
1298:
1295:
1292:
1289:
1286:
1283:
1279:
1275:
1257:
1244:
1242:
1239:
1236:
1233:
1230:
1227:
1223:
1220:
1216:
1213:
1210:
1207:
1204:
1201:
1198:
1195:
1192:
1189:
1186:
1182:
1179:
1176:
1173:
1170:
1167:
1164:
1161:
1157:
1153:
1149:
1145:
1130:
1119:
1110:
1099:
1092:
1083:
1076:
1065:
1056:
1054:
1045:
1043:
1032:
1030:
1021:
1019:
1008:
1006:
997:
995:
984:
977:
975:
972:
969:
959:
952:
943:
936:
934:
924:
917:
915:
905:
898:
896:
886:
879:
877:
867:
860:
858:
848:
841:
839:
829:
822:
820:
817:
814:
804:
797:
788:
781:
779:
769:
768:
764:
760:
756:
752:
748:
744:
740:
736:
732:
728:
724:
720:
716:
712:
708:
699:
698:
694:
690:
686:
682:
678:
677:\C5C(\CCC(O)=O)
674:
670:
666:
662:
658:
654:
650:
646:
642:
638:
634:
630:
626:
622:
618:
614:
610:
600:
593:
591:
581:
574:
565:
558:
549:
538:
531:
522:
511:
504:
495:
488:
479:
472:
470:
460:
449:
442:
440:
437:
434:
424:
423:
414:
405:
398:
389:
378:
367:
354:
345:
343:
334:
332:
321:
310:
303:
294:
270:
267:
265:
264:
263:
259:
257:
241:
239:
234:
228:
223:
215:
213:← Previous edit
210:
203:
201:
200:
199:
195:
193:
173:
171:
166:
160:
152:
151:
150:
149:
147:
146:
140:
138:
133:
130:
128:
125:
123:Content deleted
122:
119:
117:← Previous edit
114:
110:
108:
107:
106:
105:
104:
103:
102:
94:
91:
90:
89:
88:
80:
71:
67:
65:
64:
63:
62:
61:
60:
59:
51:
48:
47:
46:
45:
37:
28:
22:
21:
20:
13:
5:
2649:
2639:
2638:
2635:
2633:
2631:
2628:
2626:
2623:
2622:
2619:
2617:
2615:
2612:
2610:
2607:
2606:
2603:
2601:
2599:
2596:
2595:
2592:
2590:
2587:
2584:
2583:
2580:
2578:
2576:
2573:
2571:
2568:
2567:
2564:
2560:
2559:
2557:==References==
2556:
2554:
2552:
2550:==References==
2549:
2547:
2544:
2543:
2540:
2538:
2535:
2532:
2531:
2528:
2526:
2524:
2521:
2519:
2516:
2515:
2512:
2510:
2508:
2505:
2503:
2500:
2499:
2496:
2494:
2492:
2489:
2487:
2484:
2483:
2480:
2478:
2476:
2473:
2471:
2468:
2467:
2464:
2462:
2459:
2456:
2455:
2453:
2449:
2445:
2442:
2440:
2434:
2433:
2431:
2428:
2426:
2423:
2422:
2420:
2417:
2415:
2412:
2411:
2409:
2406:
2404:
2401:
2400:
2398:
2395:
2393:
2390:
2389:
2387:
2384:
2382:
2379:
2378:
2376:
2373:
2371:
2368:
2367:
2365:
2362:
2360:
2357:
2356:
2354:
2351:
2349:
2346:
2345:
2342:
2340:
2338:
2335:
2334:
2332:
2329:
2327:
2324:
2323:
2318:
2315:inter-membrane
2314:
2309:
2307:
2302:
2299:
2298:
2296:
2294:{{cite journal
2293:
2291:
2288:
2287:
2284:
2282:
2279:
2278:
2276:
2271:
2266:
2264:
2258:
2257:
2252:
2248:
2244:
2241:
2237:
2233:
2229:
2224:
2222:
2217:
2214:
2213:
2210:
2208:
2205:
2202:
2201:
2199:
2196:
2194:
2191:
2190:
2188:
2185:
2183:
2180:
2179:
2177:
2175:| pmid=9624044
2174:
2172:
2169:
2168:
2166:
2163:
2161:
2158:
2157:
2155:
2152:
2150:
2147:
2146:
2144:
2141:
2139:
2136:
2135:
2133:
2130:
2128:
2125:
2124:
2122:
2119:
2117:
2114:
2113:
2108:
2106:
2101:
2098:
2097:
2095:
2092:
2090:
2087:
2086:
2082:
2080:
2078:
2075:
2074:
2072:
2070:{{cite journal
2069:
2067:
2064:
2063:
2060:
2058:
2056:
2053:
2052:
2050:
2045:
2040:
2038:
2032:
2031:
2027:
2025:
2023:
2020:
2019:
2016:
2014:
2011:
2008:
2007:
2005:
2002:
2000:
1997:
1996:
1994:
1991:
1989:
1986:
1985:
1983:
1980:
1978:
1975:
1974:
1972:
1969:
1967:
1964:
1963:
1961:
1958:
1956:
1953:
1952:
1950:
1947:
1945:
1942:
1941:
1939:
1936:
1934:
1931:
1930:
1928:
1925:
1923:
1920:
1919:
1917:
1914:
1912:
1909:
1908:
1906:
1903:
1901:
1898:
1897:
1893:
1889:
1885:
1883:
1878:
1875:
1874:
1872:
1870:{{cite journal
1869:
1867:
1864:
1863:
1858:
1854:
1851:
1848:
1844:
1842:
1837:
1834:
1833:
1831:
1827:
1825:
1822:
1821:
1818:
1816:
1814:
1811:
1810:
1807:
1805:
1802:
1799:
1798:
1796:
1792:
1791:}}</ref>
1788:
1786:
1780:
1779:
1777:
1774:
1772:
1769:
1768:
1766:
1763:
1761:
1758:
1757:
1755:
1752:
1750:
1747:
1746:
1744:
1739:
1737:
1731:
1730:
1728:
1725:
1723:
1720:
1719:
1717:
1714:
1712:
1709:
1708:
1706:
1701:
1698:
1695:
1691:
1688:
1686:
1680:
1679:
1677:
1674:
1672:
1669:
1668:
1666:
1663:
1661:
1658:
1657:
1655:
1652:
1650:
1647:
1646:
1644:
1641:
1639:
1636:
1635:
1633:
1630:
1628:
1625:
1624:
1622:
1619:
1617:
1614:
1613:
1611:
1609:{{cite journal
1608:
1606:
1603:
1602:
1600:}}</ref>
1598:
1595:
1593:
1588:
1585:
1584:
1582:
1579:
1577:
1574:
1573:
1571:|pmid=14860765
1570:
1568:
1566:
1563:
1562:
1558:
1556:
1554:
1552:
1549:
1547:
1544:
1543:
1540:
1538:
1536:
1531:
1530:
1528:
1525:
1524:
1522:
1517:
1515:
1509:
1508:
1505:
1503:
1501:
1498:
1497:
1495:
1492:
1490:
1487:
1486:
1481:
1478:
1476:
1471:
1468:
1467:
1464:
1462:
1460:
1457:
1455:
1452:
1451:
1446:
1442:
1440:
1438:
1436:
1431:
1427:
1425:
1423:
1420:
1419:
1417:{{cite journal
1416:
1414:
1412:
1410:{{cite journal
1409:
1407:
1404:
1403:
1400:
1398:
1396:
1393:
1392:
1389:
1387:
1385:
1382:
1381:
1378:
1376:
1373:
1372:
1369:
1367:
1365:
1362:
1361:
1356:
1353:
1350:
1347:
1344:
1341:
1337:
1334:
1330:
1327:
1324:
1321:
1318:
1315:
1312:
1309:
1306:
1303:
1299:
1296:
1293:
1290:
1287:
1284:
1281:
1277:
1273:
1269:
1267:
1262:
1259:
1258:
1255:
1253:
1251:
1248:
1247:
1245:
1240:
1237:
1234:
1231:
1228:
1225:
1221:
1218:
1214:
1211:
1208:
1205:
1202:
1199:
1196:
1193:
1190:
1187:
1184:
1180:
1177:
1174:
1171:
1168:
1165:
1162:
1159:
1155:
1151:
1147:
1143:
1140:
1138:
1132:
1131:
1128:
1126:
1123:
1122:
1120:
1117:
1115:
1112:
1111:
1108:
1106:
1104:
1101:
1100:
1097:
1095:
1093:
1090:
1088:
1085:
1084:
1081:
1079:
1077:
1074:
1072:
1069:
1068:
1066:
1063:
1061:
1058:
1057:
1053:AutoignitionPt
1052:
1050:
1048:
1046:
1041:
1039:
1037:
1034:
1033:
1028:
1026:
1024:
1022:
1017:
1015:
1013:
1010:
1009:
1004:
1002:
1000:
998:
993:
991:
989:
986:
985:
982:
980:
978:
974:
971:
968:
966:
964:
961:
960:
957:
955:
953:
950:
948:
945:
944:
941:
939:
937:
933:
931:
929:
926:
925:
922:
920:
918:
914:
912:
910:
907:
906:
903:
901:
899:
895:
893:
891:
888:
887:
885:| Appearance =
884:
882:
880:
876:
874:
872:
869:
868:
865:
863:
861:
857:
855:
853:
850:
849:
846:
844:
842:
838:
836:
834:
831:
830:
827:
825:
823:
819:
816:
813:
811:
809:
806:
805:
802:
800:
798:
795:
793:
790:
789:
786:
784:
782:
778:
776:
774:
771:
770:
766:
762:
758:
754:
750:
746:
742:
738:
734:
730:
726:
722:
718:
714:
710:
706:
704:
702:
700:
696:
692:
688:
684:
680:
676:
672:
668:
664:
660:
656:
652:
648:
644:
640:
636:
632:
628:
624:
620:
616:
612:
609:
607:
605:
602:
601:
598:
596:
594:
590:
588:
586:
583:
582:
579:
577:
575:
572:
570:
567:
566:
563:
561:
559:
556:
554:
551:
550:
547:
545:
543:
540:
539:
536:
534:
532:
529:
527:
524:
523:
520:
518:
516:
513:
512:
509:
507:
505:
502:
500:
497:
496:
493:
491:
489:
486:
484:
481:
480:
477:
475:
473:
469:
467:
465:
462:
461:
458:
456:
454:
451:
450:
447:
445:
443:
439:
436:
433:
431:
429:
426:
425:
421:
420:| OtherNames =
419:
417:
415:
413:| OtherNames =
412:
410:
407:
406:
403:
401:
399:
396:
394:
391:
390:
387:
385:
383:
380:
379:
376:
374:
372:
369:
368:
365:
363:
361:
358:
357:
355:
352:
350:
347:
346:
341:
339:
337:
335:
330:
328:
326:
323:
322:
319:
317:
315:
312:
311:
308:
306:
304:
301:
299:
296:
295:
292:
290:
288:
285:
284:
281:
277:
276:
272:
271:
258:
253:
252:
237:
216:
194:
191:Administrators
185:
184:
169:
129:
121:
115:
99:
93:
85:
79:
76:
75:
68:
56:
50:
42:
36:
33:
32:
25:
23:
19:
18:
10:
6:
4:
3:
2:
2648:
2634:
2632:
2627:
2625:
2624:
2618:
2616:
2611:
2609:
2608:
2602:
2597:
2593:
2591:
2588:
2586:
2585:
2579:
2577:
2572:
2570:
2569:
2561:
2555:
2553:
2548:
2546:
2545:
2541:
2539:
2536:
2534:
2533:
2527:
2520:
2517:
2511:
2509:
2504:
2502:
2501:
2495:
2493:
2488:
2486:
2485:
2479:
2477:
2472:
2470:
2469:
2465:
2463:
2460:
2458:
2457:
2444:
2441:
2439:
2436:
2435:
2429:| pmc=1820732
2427:
2424:
2416:
2413:
2405:
2402:
2394:
2391:
2383:
2380:
2372:
2369:
2361:
2358:
2350:
2347:
2341:
2336:
2328:
2325:
2311:
2308:
2306:
2303:
2300:
2292:
2289:
2285:
2280:
2268:
2265:
2263:
2260:
2259:
2243:(molecular ])
2226:
2223:
2221:
2218:
2215:
2211:
2209:
2206:
2204:
2203:
2195:
2192:
2184:
2181:
2173:
2170:
2162:
2159:
2151:
2148:
2140:
2137:
2129:
2126:
2118:
2115:
2110:
2107:
2105:
2102:
2099:
2091:
2088:
2081:
2076:
2068:
2065:
2059:
2054:
2042:
2039:
2037:
2034:
2033:
2026:
2021:
2017:
2015:
2012:
2010:
2009:
2001:
1998:
1990:
1987:
1979:
1976:
1968:
1965:
1957:
1954:
1946:
1943:
1935:
1932:
1924:
1921:
1913:
1910:
1902:
1899:
1887:
1884:
1882:
1879:
1876:
1868:
1865:
1846:
1843:
1841:
1838:
1835:
1826:
1823:
1817:
1812:
1808:
1806:
1803:
1801:
1800:
1790:
1787:
1785:
1782:
1781:
1773:
1770:
1762:
1759:
1751:
1748:
1741:
1738:
1736:
1733:
1732:
1724:
1721:
1713:
1710:
1690:
1687:
1685:
1682:
1681:
1673:
1670:
1662:
1659:
1651:
1648:
1640:
1637:
1629:
1626:
1618:
1615:
1607:
1604:
1597:
1594:
1592:
1589:
1586:
1578:
1575:
1569:
1564:
1555:
1548:
1545:
1539:
1532:| volume=288
1529:
1526:
1519:
1516:
1514:
1511:
1510:
1504:
1499:
1491:
1488:
1480:
1477:
1475:
1472:
1469:
1463:
1461:
1456:
1454:
1453:
1445:=Warburg, O
1439:
1424:
1421:
1415:
1413:
1408:
1406:
1405:
1399:
1394:
1388:
1383:
1379:
1374:
1368:
1363:
1271:
1268:
1266:
1263:
1260:
1254:
1249:
1142:
1139:
1137:
1134:
1133:
1129:
1124:
1116:
1113:
1107:
1102:
1096:
1094:
1089:
1087:
1086:
1080:
1078:
1073:
1071:
1070:
1062:
1059:
1049:
1038:
1035:
1025:
1014:
1011:
1001:
990:
987:
981:
965:
962:
956:
954:
949:
947:
946:
942:| BoilingPt =
940:
930:
927:
923:| MeltingPt =
921:
911:
908:
902:
892:
889:
883:
873:
870:
864:
854:
851:
845:
835:
832:
826:
810:
807:
801:
799:
794:
792:
791:
785:
775:
772:
703:
606:
603:
597:
587:
584:
578:
576:
571:
569:
568:
562:
560:
555:
553:
552:
546:
541:
535:
533:
528:
526:
525:
519:
514:
508:
506:
501:
499:
498:
492:
490:
485:
483:
482:
476:
466:
463:
457:
452:
446:
430:
427:
418:
411:
408:
404:| IUPACName =
402:
400:
397:| IUPACName =
395:
393:
392:
386:
381:
375:
370:
364:
359:
353:| ImageSize =
351:
348:
338:
327:
324:
318:
313:
307:
305:
300:
298:
297:
291:
286:
278:
273:
256:
249:
245:
240:
231:
226:
222:
214:
207:
192:
188:
181:
177:
172:
163:
159:
143:
136:
126:Content added
118:
16:
2481:==See also==
2474:==See also==
2448:</ref>
2186:| issue=5370
2111:</ref>
1992:| pmc=307562
1430:=Warburg, O
878:Appearance =
719:c3n7c6cc2c(/
344:= Heme a.svg
333:= Heme a.svg
238:Alfa-ketosav
2374:| journal=]
2352:| year=2007
2321:<ref>
2142:| journal=]
2120:| year=1998
1937:| journal=]
1915:| year=2003
1753:| journal=]
1726:| year=2005
1653:| journal=]
1631:| year=1975
1541:| pages=1–4
1534:| pages=1–4
1520:| journal=]
1484:| journal=]
1465:| year=1951
1458:| year=1951
1449:Gewitz H S.
1434:Gewitz H S.
1390:==History==
1359:<ref>
1243:<ref>
1018:MainHazards
1005:MainHazards
935:BoilingPt =
916:MeltingPt =
904:| Density =
705:| SMILES =
342:ImageFileL1
2418:| issue=10
1981:| issue=26
1235:cytochrome
1181:biochemist
994:Solubility
765:\C=C(C)/C)
735:cc4n(78n12
731:O)c1cc5n8c
96:Revision 2
53:Revision 1
2563:Line 104:
1699:published
1447:|author2=
1222:component
897:Density =
667:C(/C)=C(/
611:SMILES =
331:ImageFile
309:{{chembox
302:{{chembox
2566:Line 78:
2438:⚫
2305:⚫
2262:⚫
2220:⚫
2104:⚫
2036:⚫
1881:⚫
1840:⚫
1784:⚫
1735:⚫
1696:recently
1684:⚫
1591:⚫
1513:⚫
1493:| title=
1474:⚫
1342:reduced,
1325:position
1265:⚫
1229:membrane
1226:integral
1166:isolated
1152:farnesyl
1136:⚫
970:Section3
815:Section2
669:CCC(O)=O
435:Section1
248:contribs
180:contribs
170:Beetstra
141:Wikitext
2247:<ref
1443:author1
1340:of the
1285:similar
1241:oxidase
1224:of the
1191:Warburg
1042:FlashPt
1029:FlashPt
753:C=C(/C)
747:c4c)c(\
283:Line 1:
280:Line 1:
196:171,922
1775:| doi=
1675:| doi=
1557:| doi=
1550:| doi=
1428:author
1345:Fe(II)
1335:methyl
1219:active
1178:German
1146:Heme A
751:(O)CC\
715:CC/c6c
693:/c(c1C
633:C\CCC(
621:=C\CCC
134:Visual
82:Page 2
72:Page 2
39:Page 1
29:Page 1
2272:inner
1849:shown
1319:group
1203:shown
1175:great
1163:first
745:(C=C)
262:edits
260:1,965
198:edits
2251:>
1348:form
1333:the
1310:have
1304:does
1297:that
1217:the
1197:1951
767:c5\C
757:=C(/
755:CC\C
725:)=O)
721:CCC(
717:(\C)
655:C=C)
641:C\3C
637:c1c2
627:CCC(
623:(\C)
244:talk
230:undo
225:edit
176:talk
162:edit
2513:* ]
2506:* ]
2497:* ]
2490:* ]
2232:is
1432:and
1354:the
1313:the
1307:not
1209:him
1200:and
1188:von
1172:the
1160:was
1148:'''
1144:'''
743:3)c
739:c(c
729:/C=
689:C6=
679:=C(
673:C7=
665:C8/
661:=4/
639:/C=
625:=C\
613:C/C
2446:}}
2254:c.
1888:|
1855:be
1852:to
1702:as
1351:of
1328:8,
1322:at
1302:O
1294:in
1291:],
1288:to
1282:is
1215:be
1212:to
1206:by
1194:in
1169:by
1098:}}
1091:}}
1082:}}
1075:}}
1051:|
1040:|
1027:|
1016:|
1003:|
992:|
958:}}
951:}}
803:}}
796:}}
763:CC
727:c(
711:=O
707:OC
687:)/
685:=O
671:)\
663:C=
647:)=
645:\C
635:O)
631:)=
629:\C
340:|
329:|
246:|
189:,
178:|
2636:]
2629:]
2620:]
2613:]
2450:.
2319:.
2245:.
2238:]
2230:]
1859:.
1793:.
1441:|
1426:|
1316:]
1278:2
1274:]
1238:c
1232:]
1185:.
1183:O
1156:3
1055:=
1044:=
1031:=
1020:=
1007:=
996:=
973:=
967:|
932:|
913:|
894:|
875:|
856:|
837:|
818:=
812:|
777:|
761:)
759:C
749:C
741:=
737:)
733:(
723:O
713:)
709:(
695:)
691:C
683:C
681:\
675:C
659:C
657:/
653:\
651:(
649:C
643:(
619:)
617:C
615:(
608:|
589:|
468:|
438:=
432:|
250:)
242:(
182:)
174:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.