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Esperamicin

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InChI=1S/C59H80N4O22S4/c1-28(2)60-36-27-77-43(25-39(36)73-8)83-52-50(66)47(63-85-45-24-37(64)53(86-12)31(5)79-45)29(3)80-57(52)82-38-18-16-14-15-17-20-59(71)34(19-21-88-89-87-13)46(38)48(62-58(70)76-11)51(67)54(59)84-44-26-42(49(65)30(4)78-44)81-56(69)33-22-40(74-9)41(75-10)23-35(33)61-55(68)32(6)72-7/h14-15,19,22-23,28-31,36-39,42-45,47,49-50,52-54,57,60,63-66,71H,6,21,24-27H2,1-5,7-13H3,(H,61,68)(H,62,70)/b15-14-,34-19+
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InChI=1/C59H80N4O22S4/c1-28(2)60-36-27-77-43(25-39(36)73-8)83-52-50(66)47(63-85-45-24-37(64)53(86-12)31(5)79-45)29(3)80-57(52)82-38-18-16-14-15-17-20-59(71)34(19-21-88-89-87-13)46(38)48(62-58(70)76-11)51(67)54(59)84-44-26-42(49(65)30(4)78-44)81-56(69)33-22-40(74-9)41(75-10)23-35(33)61-55(68)32(6)72-7/h14-15,19,22-23,28-31,36-39,42-45,47,49-50,52-54,57,60,63-66,71H,6,21,24-27H2,1-5,7-13H3,(H,61,68)(H,62,70)/b15-14-,34-19+
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O=C(C(\OC)=C)Nc1cc(OC)c(OC)cc1C(=O)OC2CC(OC(C)C2O)OC7C(=O)C(\NC(=O)OC)=C6/C(=C\CSSSC)C7(O)C#C\C=C/C#CC6OC5OC(C)C(NOC3OC(C)C(SC)C(O)C3)C(O)C5OC4OCC(NC(C)C)C(OC)C4
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attacked (T greater than C greater than A greater than G) is different from that of calicheamicin (C much greater than T greater than A = G),
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of bacterial origin. Esperamicin A1 is the most well studied compound in this class. Esperamcin A1 and the related enediyne
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strand breakage by esperamicin, but the cleavage of DNA by esperamicin is greatly accelerated in the presence of
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are the two most potent antitumor agents known. The esperamicins are extremely toxic DNA splicing compounds.
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Sugiura, Y.; Uesawa, Y.; Takahashi, Y.; Kuwahara, J.; Golik, J.; Doyle, T. W. (1989).
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Calicheamicin and Esperamicin are the two most potent antitumor agents known to man
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Oxygen and active oxygen-radical scavengers have no significant influence upon
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Except where otherwise noted, data are given for materials in their
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compounds. The preferential cutting sites of esperamicin are at
477: 473: 313: 378:(T greater than A greater than C greater than G), or 542: 511: 382:(C greater than T greater than A greater than G). 144: 424:Proceedings of the National Academy of Sciences 55: 489: 8: 496: 482: 474: 119: 15: 453: 443: 164: 391: 219: 184: 191:Key: LJQQFQHBKUKHIS-WJHRIEJJSA-N 99: 7: 201:Key: LJQQFQHBKUKHIS-WJHRIEJJBF 135: 14: 303: 255: 249: 31: 22: 370:residues, and the frequency of 299:(at 25 °C , 100 kPa). 267: 261: 243: 1: 401:, Univ Of Georgia Chem 4500 405:September 21, 2008, at the 682: 293: 230: 210: 175: 39: 30: 21: 606:Isopropylamino compounds 445:10.1073/pnas.86.20.7672 349:antitumor antibiotics 436:1989PNAS...86.7672S 289: g·mol 18: 666:Ten-membered rings 641:Alkene derivatives 616:Secondary alcohols 326:Infobox references 16: 578: 577: 543:10 membered rings 430:(20): 7672–7676. 334:Chemical compound 332: 331: 81:Interactive image 673: 534:Neocarzinostatin 512:9 membered rings 498: 491: 484: 475: 468: 467: 457: 447: 415: 409: 396: 376:neocarzinostatin 316: 310: 307: 306: 288: 286: 269: 263: 257: 251: 245: 238:Chemical formula 168: 148: 137: 123: 103: 83: 59: 35: 26: 19: 681: 680: 676: 675: 674: 672: 671: 670: 651:Benzoate esters 596:Cancer research 581: 580: 579: 574: 570:Shishijimicin A 538: 507: 502: 472: 471: 417: 416: 412: 407:Wayback Machine 397: 393: 388: 335: 328: 323: 322: 321:  ?) 312: 308: 304: 300: 284: 282: 272: 266: 260: 254: 248: 240: 226: 223: 218: 217: 206: 203: 202: 199: 193: 192: 189: 183: 182: 171: 151: 138: 126: 106: 86: 73: 62: 49: 17:Esperamicin A1 12: 11: 5: 679: 677: 669: 668: 663: 658: 653: 648: 643: 638: 633: 628: 623: 618: 613: 608: 603: 598: 593: 583: 582: 576: 575: 573: 572: 567: 562: 557: 552: 546: 544: 540: 539: 537: 536: 531: 526: 521: 515: 513: 509: 508: 503: 501: 500: 493: 486: 478: 470: 469: 410: 390: 389: 387: 384: 333: 330: 329: 324: 302: 301: 297:standard state 294: 291: 290: 280: 274: 273: 270: 264: 258: 252: 246: 241: 236: 233: 232: 228: 227: 225: 224: 221: 213: 212: 211: 208: 207: 205: 204: 200: 197: 196: 194: 190: 187: 186: 178: 177: 176: 173: 172: 170: 169: 161: 159: 153: 152: 150: 149: 141: 139: 131: 128: 127: 125: 124: 116: 114: 108: 107: 105: 104: 96: 94: 88: 87: 85: 84: 76: 74: 67: 64: 63: 61: 60: 52: 50: 45: 42: 41: 37: 36: 28: 27: 13: 10: 9: 6: 4: 3: 2: 678: 667: 664: 662: 659: 657: 656:Methyl esters 654: 652: 649: 647: 644: 642: 639: 637: 634: 632: 629: 627: 626:Phenol ethers 624: 622: 619: 617: 614: 612: 609: 607: 604: 602: 599: 597: 594: 592: 589: 588: 586: 571: 568: 566: 563: 561: 558: 556: 553: 551: 550:Calicheamicin 548: 547: 545: 541: 535: 532: 530: 527: 525: 522: 520: 517: 516: 514: 510: 506: 499: 494: 492: 487: 485: 480: 479: 476: 465: 461: 456: 451: 446: 441: 437: 433: 429: 425: 421: 414: 411: 408: 404: 400: 395: 392: 385: 383: 381: 377: 373: 369: 365: 361: 356: 354: 353:calicheamicin 350: 347: 344: 343:chromoprotein 340: 327: 320: 315: 298: 292: 281: 279: 276: 275: 242: 239: 235: 234: 229: 220: 216: 209: 195: 185: 181: 174: 167: 163: 162: 160: 158: 155: 154: 147: 143: 142: 140: 134: 130: 129: 122: 118: 117: 115: 113: 110: 109: 102: 98: 97: 95: 93: 90: 89: 82: 78: 77: 75: 71: 66: 65: 58: 54: 53: 51: 48: 44: 43: 38: 34: 29: 25: 20: 565:Golfomycin A 559: 529:Maduropeptin 427: 423: 413: 394: 357: 339:esperamicins 338: 336: 101:ChEMBL449274 40:Identifiers 591:Antibiotics 560:Esperamicin 555:Dynemicin A 368:thymidylate 231:Properties 636:Thioethers 611:Carbamates 585:Categories 524:Kedarcidin 386:References 372:nucleobase 278:Molar mass 166:PLX8T21X8G 112:ChemSpider 68:3D model ( 57:99674-26-7 47:CAS Number 601:Enediynes 505:Enediynes 380:bleomycin 646:Anilides 403:Archived 346:enediyne 661:Ketones 464:2813351 432:Bibcode 319:what is 317: ( 146:6435576 133:PubChem 121:4940320 631:Ethers 621:Amines 519:C-1027 462:  455:298132 452:  314:verify 311:  215:SMILES 92:ChEMBL 364:thiol 180:InChI 70:JSmol 460:PMID 341:are 337:The 157:UNII 450:PMC 440:doi 360:DNA 287:.54 285:325 136:CID 587:: 458:. 448:. 438:. 428:86 426:. 422:. 265:22 253:80 247:59 497:e 490:t 483:v 466:. 442:: 434:: 309:N 283:1 271:4 268:S 262:O 259:4 256:N 250:H 244:C 72:)

Index

Structural formula of esperamicin A1
Ball-and-stick model of the Esperamicin A1 molecule
CAS Number
99674-26-7
JSmol
Interactive image
ChEMBL
ChEMBL449274
ChemSpider
4940320
PubChem
6435576
UNII
PLX8T21X8G
InChI
SMILES
Chemical formula
Molar mass
standard state
verify
what is
Infobox references
chromoprotein
enediyne
antitumor antibiotics
calicheamicin
DNA
thiol
thymidylate
nucleobase

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