Knowledge (XXG)

Oligomycin

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InChI=1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1
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InChI=1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1
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Nakata M, Ishiyama T, Akamatsu S, Hirose Y, Maruoka H, Suzuki R, Tatsuta K (1995). "Synthetic studies on oligomycins. Synthesis of the oligomycin B spiroketal and polypropionate portions".
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of ATP synthase. In oxidative phosphorylation research, it is used to prevent stage 3 (phosphorylating) respiration. Oligomycin A inhibits ATP synthase by blocking its proton channel (F
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Administering oligomycin to rats can result in very high levels of lactate accumulating in the blood and urine.
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Kramar R, Hohenegger M, Srour AN, Khanakah G (December 1984). "Oligomycin toxicity in intact rats".
1179: 381: 166: 134:)-22-ethyl-7,11,14,15-tetrahydroxy-6'--5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3 1118: 647: 1110: 1075: 1026: 508: 240: 1145: 1102: 1065: 1057: 1016: 1006: 605: 465: 450:
C(C)(O)C1O2(CC1C)O3CC(CC)/C=C\C=C\C(C)(O)(C)(O)C(=O)(C)(O)(C)C(=O)(C)(O)(C)/C=C/C(=O)O(2C)3C
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Mackieh R, Al-Bakkar N, Kfoury M, Roufayel R, Sabatier JM, Fajloun Z (March 2023).
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Jastroch M, Divakaruni AS, Mookerjee S, Treberg JR, Brand MD (2010).
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Except where otherwise noted, data are given for materials in their
327: 211: 199: 189: 655: 995:"Inhibitors of ATP Synthase as New Antibacterial Candidates" 369: 663: 146:-spirononacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione 540: 577:that are strong antibacterial agents but are often 315: 175: 8: 384: 261: 239: 29: 1138:Bulletin of the Chemical Society of Japan 1069: 1046:"Mitochondrial proton and electron leaks" 1020: 1010: 351: 982: 447: 405: 380: 293: 581:to other organisms, including humans. 252: 429:Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N 412:Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N 219: 7: 988: 986: 422:Key: QBAMBSAJEFIQBK-GJHUHQBXBC 306: 25: 612:subunit), which is necessary for 672: 530: 477: 36: 526:(at 25 °C , 100 kPa). 483: 471: 1: 1012:10.3390/antibiotics12040650 498:791.062 g/mol 27:Group of chemical compounds 1201: 638:. This process is due to 671: 614:oxidative phosphorylation 520: 502: 458: 438: 396: 159: 151: 49: 44: 35: 635:mitochondrial uncoupling 626:electron transport chain 589:Oligomycins have use as 1185:ATP synthase inhibitors 1050:Essays in Biochemistry 1170:Macrolide antibiotics 640:facilitated diffusion 644:mitochondrial matrix 642:of protons into the 1150:10.1246/bcsj.68.967 944:44-Homooligomycin B 912:44-Homooligomycin A 668: 604:Oligomycin A is an 32: 1107:10.1007/BF01966788 1095:Agents and Actions 1062:10.1042/bse0470053 664: 648:uncoupling protein 553:Infobox references 30: 974: 973: 561:Chemical compound 559: 558: 515:MSDS at Fermentek 509:Safety data sheet 365:CompTox Dashboard 201:Interactive image 16:(Redirected from 1192: 1154: 1153: 1133: 1127: 1126: 1101:(5–6): 660–663. 1090: 1084: 1083: 1073: 1041: 1035: 1034: 1024: 1014: 990: 676: 669: 543: 537: 534: 533: 485: 479: 473: 466:Chemical formula 389: 388: 373: 371: 355: 319: 308: 297: 273: 265: 254: 243: 223: 203: 179: 40: 33: 21: 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571:created by 565:Oligomycins 459:Properties 295:Oligomycins 259:100.014.334 221:CHEBI:28285 18:Oligomycins 1180:Triketones 1164:Categories 1005:(4): 650. 977:References 569:macrolides 494:Molar mass 353:14JVM0OHLV 232:ChemSpider 188:3D model ( 167:CAS Number 154:Oligomycin 51:IUPAC name 606:inhibitor 579:poisonous 335:RK3325000 280:215-767-9 272:EC Number 177:1404-19-9 1080:20533900 1031:37107012 1022:10135114 650:such as 585:Function 503:Hazards 241:21106358 1123:7837164 1115:6532186 1071:3122475 681:  546:what is 544: ( 317:6450197 304:PubChem 1121:  1113:  1078:  1068:  1029:  1019:  541:verify 538:  511:(SDS) 443:SMILES 45:Names 1119:S2CID 654:, or 401:InChI 212:ChEBI 190:JSmol 1111:PMID 1076:PMID 1027:PMID 932:H,H 900:H,H 871:H,H 815:H,H 784:H,H 728:H,H 656:UCP1 597:and 567:are 344:UNII 289:MeSH 1146:doi 1103:doi 1066:PMC 1058:doi 1017:PMC 1007:doi 961:OH 929:OH 868:OH 840:OH 837:OH 812:OH 753:OH 725:OH 632:or 622:ATP 620:to 618:ADP 616:of 370:EPA 307:CID 142:,13 130:,29 126:,28 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Index

Oligomycins

IUPAC name
CAS Number
1404-19-9
JSmol
Interactive image
ChEBI
CHEBI:28285
ChemSpider
21106358
ECHA InfoCard
100.014.334
Edit this at Wikidata
EC Number
MeSH
Oligomycins
PubChem
6450197
RTECS number
UNII
14JVM0OHLV
CompTox Dashboard
DTXSID7040570
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Safety data sheet

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