369:
296:
94:
680:
431:
InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)
800:
Gramicidins can be used as topical antibiotic medications in low doses, even though they are potentially lethal for human cells. Bacteria die at lower gramicidin concentrations than human cells. Gramicidins are not used internally, as their significant intake may cause
411:
C(C(=O)N(CC(C)C)C(=O)N(C)C(=O)N(C(C)C)C(=O)N(C(C)C)C(=O)N(C(C)C)C(=O)N(CC1=CNC2=CC=CC=C21)C(=O)N(CC(C)C)C(=O)N(CC3=CNC4=CC=CC=C43)C(=O)N(CC(C)C)C(=O)N(CC5=CNC6=CC=CC=C65)C(=O)N(CC(C)C)C(=O)N(CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)CNC(=O)(C(C)C)NC=O
962:"Efficacy and safety of a triple active sore throat lozenge in the treatment of patients with acute pharyngitis: Results of a multi-centre, randomised, placebo-controlled, double-blind, parallel-group trial (DoriPha)"
3658:
1837:
3132:
695:. 2 gramicidins can also form antiparallel or parallel double helices, especially in organic solvents. Dimers are long enough to span cellular lipid bilayers and thus function as
2851:
109:
447:
691:
Gramicidins form helices. The alternating pattern of D- and L-amino acids is important for the formation of these structures. Helices occur most often as head-to-head
3566:
1319:"Exploring the structural relationship between encapsulated antimicrobial peptides and the bilayer membrane mimetic lipidic cubic phase: studies with gramicidin A′"
589:. These were the first antibiotics to be manufactured commercially. Letter "D" in gramicidin D is short for "Dubos", and was invented to differentiate the mix from
3626:
1830:
71:
59:
3644:
1593:
875:"The linear pentadecapeptide gramicidin is assembled by four multimodular nonribosomal peptide synthetases that comprise 16 modules with 56 catalytic domains"
569:. Multiple antibiotics increase efficiency against various strains of bacteria. Such eye-drops are also used to treat eye infections of animals, like horses.
403:
3125:
3362:
3357:
1823:
3110:
3118:
3076:
1249:
3721:
3668:
3651:
3329:
683:
Gramicidin helices. Antiparallel (left) and parallel double helices and the helix dimer present in lipid bilayers. C and N are C- and
24:
1586:
1067:
423:
3716:
1011:"The efficacy and safety of topical polymyxin B, neomycin and gramicidin for treatment of presumed bacterial corneal ulceration"
3726:
1998:
1938:
1927:
917:
Wang F, Qin L, Pace CJ, Wong P, Malonis R, Gao J (January 2012). "Solubilized gramicidin A as potential systemic antibiotics".
2995:
3334:
2881:
844:
549:
for sore throat and in topical medicines to treat infected wounds. Gramicidins are often mixed with other antibiotics like
2047:
1579:
224:
3093:
2906:
2826:
1953:
1887:
1085:"Studies on a bactericidal agent extracted from a soil bacillus: I. Preparation of the agent. Its activity in vitro"
3317:
1682:
1466:"N-terminally glutamate-substituted analogue of gramicidin A as protonophore and selective mitochondrial uncoupler"
1815:
2831:
1958:
1854:
1662:
2760:
3598:
3081:
2896:
2856:
1963:
1871:
706:
Gramicidin mixture is a crystalline solid. Its solubility in water is minimal, 6 mg/L, and it may form
291:
2920:
2871:
2861:
794:
1277:
Sarges R, Bernhard W (1964). "gramicidin A. IV. Primary sequence of valine and isoleucine gramicidin A".
273:
3322:
3149:
2901:
2886:
2866:
1702:
1643:
1638:
676:– in natural gramicidin mixes of A, B and C, about 5% of the total gramicidins are isoleucine isoforms.
532:
3349:
3305:
3199:
2985:
2891:
2836:
1656:
1477:
1430:
1371:
1330:
1197:
623:
496:
1464:
Sorochkina AI, Plotnikov EY, Rokitskaya TI, Kovalchuk SI, Kotova EA, Sychev SV, et al. (2012).
1186:"Exchange of gramicidin between lipid bilayers: implications for the mechanism of channel formation"
3731:
3339:
2876:
2846:
2695:
2657:
1652:
763:
711:
139:
93:
1707:
942:
3636:
2411:
2117:
1892:
1557:
1505:
1446:
1399:
1294:
1231:
1213:
1166:
1114:
1063:
1040:
991:
934:
896:
850:
840:
751:
692:
526:
3545:
3540:
3485:
3475:
3470:
3460:
3455:
3450:
3430:
213:
3571:
3400:
3380:
3287:
3282:
3277:
3272:
3267:
3262:
3252:
3242:
3237:
3227:
3222:
3145:
2999:
2150:
1948:
1765:
1547:
1539:
1495:
1485:
1438:
1389:
1379:
1338:
1286:
1221:
1205:
1156:
1148:
1104:
1096:
1030:
1022:
981:
973:
926:
886:
810:
596:
In 1964, the sequence of gramicidin A was determined by
Reinhard Sarges and Bernhad Witkop.
390:
308:
3257:
3232:
789:, between membranes thereby killing the cell via various effects. For example, ion leak in
233:
3184:
3179:
2787:
2231:
2058:
1717:
1697:
1418:
611:
148:
561:
for bacterial eye infections. In drops, they are often mixed with other antibiotics like
1481:
1434:
1375:
1334:
1201:
295:
3087:
2017:
1672:
1633:
1552:
1527:
1500:
1465:
1226:
1185:
1161:
1136:
1109:
1084:
1035:
1010:
986:
961:
770:
759:
599:
In 1971, the dimeric head-to-head structure of gramicidins was proposed by D. W. Urry.
546:
494:, so the mix has 6 different types of gramicidin molecules. They can be extracted from
1394:
1359:
64:
3710:
2981:
2840:
2649:
2616:
2481:
2455:
2388:
2300:
2283:
2195:
2189:
2135:
2131:
2101:
2096:
2091:
2086:
2076:
2012:
1983:
1973:
1727:
1667:
657:
607:
578:
521:
380:
284:
173:
1419:"High-resolution conformation of gramicidin A in a lipid bilayer by solid-state NMR"
3685:
3157:
2750:
2667:
2510:
2368:
2353:
2159:
1988:
1862:
1858:
1804:
1606:
946:
790:
786:
735:
731:
646:
590:
509:
122:
117:
679:
76:
1490:
52:
3695:
3510:
3372:
3062:
3040:
3009:
3003:
2929:
2809:
2799:
2685:
2677:
2662:
2576:
2546:
2541:
2536:
2531:
2526:
2505:
2494:
2466:
2460:
2416:
2378:
2358:
2343:
2291:
2169:
2126:
2067:
2033:
2008:
1978:
1968:
1846:
1755:
1740:
1677:
1648:
1623:
755:
715:
696:
582:
562:
554:
505:
475:
1364:
Proceedings of the
National Academy of Sciences of the United States of America
3593:
3576:
3174:
3050:
3013:
2989:
2960:
2938:
2804:
2777:
2727:
2708:
2639:
2629:
2591:
2581:
2571:
2556:
2551:
2499:
2470:
2436:
2426:
2406:
2363:
2333:
2328:
2318:
2287:
2213:
2185:
2164:
2140:
2081:
2072:
1913:
1773:
1735:
1692:
1687:
1615:
1209:
684:
673:
653:
586:
550:
341:
204:
1298:
1217:
3603:
3057:
2943:
2794:
2772:
2745:
2740:
2735:
2713:
2703:
2634:
2605:
2596:
2566:
2521:
2445:
2440:
2431:
2421:
2401:
2373:
2348:
2338:
2323:
2313:
2308:
2268:
2263:
2256:
2245:
2235:
2226:
2107:
2028:
2023:
1850:
1788:
1783:
1571:
1543:
1442:
854:
802:
782:
774:
767:
747:
700:
558:
490:, which make up about 80%, 5%, and 15% of the mix, respectively. Each has 2
472:
1561:
1509:
1235:
1170:
1118:
1044:
995:
960:
Palm J, Fuchs K, Stammer H, Schumacher-Stimpfl A, Milde J (December 2018).
938:
930:
900:
891:
874:
85:
1450:
1403:
1384:
873:
Kessler N, Schuhmann H, Morneweg S, Linne U, Marahiel MA (February 2004).
23:
3690:
3561:
3166:
3033:
2624:
2600:
2586:
2561:
2516:
2489:
2450:
2396:
2251:
2240:
1750:
1628:
1009:
Bosscha MI, van Dissel JT, Kuijper EJ, Swart W, Jager MJ (January 2004).
806:
719:
661:
630:. They consist of 15 L- and D-amino acids. Their amino acid sequence is:
603:
566:
491:
184:
2937:
Insert into bacterial cell wall causing perforation and depolarization:
1290:
1152:
1026:
193:
3535:
3530:
3490:
3480:
3465:
3445:
3440:
3435:
3425:
3141:
1778:
1343:
1318:
1100:
977:
727:
723:
707:
665:
538:
501:
159:
3420:
3415:
3410:
3405:
3395:
3390:
3385:
3297:
3153:
2783:
2279:
1712:
1602:
837:
The Merck index: an encyclopedia of chemicals, drugs, and biologicals
778:
669:
634:
264:
253:
3586:
3581:
3495:
3247:
3217:
3212:
2768:
2217:
1917:
1360:"The gramicidin A transmembrane channel: a proposed pi(L,D) helix"
678:
368:
359:
3613:
3608:
3525:
3515:
3505:
3500:
3310:
3207:
3189:
627:
244:
47:
3640:
3114:
1819:
1575:
602:
In 1993, the structure of the gramicidin head-to-head dimer in
3520:
785:. This destroys vital ion concentration differences, i.e.
641:-Gly-L-Ala-D-Leu-L-Ala-D-Val-L-Val-D-Val-L-Trp-D-Leu-L-
454:
1062:(2nd ed.). Elsevier Saunders. pp. 111, 190.
98:
Structure of gramicidin A, B, and C (click to enlarge)
2852:
Benzathine benzylpenicillin/procaine benzylpenicillin
1317:
Meikle TG, Conn CE, Separovic F, Drummond CJ (2016).
585:. Later this was shown to be a mix of gramicidin and
1250:"Gramicidin from Bacillus brevis product No. G 5002"
3554:
3371:
3348:
3296:
3198:
3165:
3023:
2973:
2952:
2928:
2919:
2819:
2759:
2726:
2694:
2676:
2648:
2615:
2480:
2387:
2299:
2278:
2212:
2178:
2149:
2116:
2057:
2046:
1997:
1937:
1926:
1912:
1870:
1797:
1764:
1726:
1614:
1528:"Gramicidin A: A New Mission for an Old Antibiotic"
389:
379:
357:
340:
307:
302:
283:
263:
243:
223:
203:
183:
158:
138:
133:
108:
103:
70:
58:
46:
38:
33:
781:(Na), can travel through these pores freely via
172:
3567:LDL-receptor-related protein-associated protein
536:, but not well against gram-negative ones like
147:
3652:
3126:
1831:
1587:
1417:Ketchem RR, Hu W, Cross TA (September 1993).
8:
84:
3659:
3645:
3637:
3133:
3119:
3111:
2925:
2296:
2054:
1934:
1923:
1909:
1838:
1824:
1816:
1594:
1580:
1572:
966:International Journal of Clinical Practice
294:
212:
3363:Pulmonary surfactant-associated protein C
3358:Pulmonary surfactant-associated protein B
2959:Inhibits PG elongation and crosslinking:
1551:
1499:
1489:
1393:
1383:
1342:
1225:
1160:
1108:
1034:
985:
890:
232:
1279:Journal of the American Chemical Society
520:Gramicidins work as antibiotics against
385:229 to 230 °C (444 to 446 °F)
822:
797:production in cells with mitochondria.
428:
408:
192:
3667:Non-ribosomally synthesized channels (
500:soil bacteria. Gramicidins are linear
285:
83:
18:
3627:other cell membrane protein disorders
1521:
1519:
1312:
1310:
1308:
839:(12th ed.). Merck. p. 712.
272:
7:
1141:The Journal of Experimental Medicine
1137:"René Dubos: unearthing antibiotics"
1130:
1128:
1089:The Journal of Experimental Medicine
1015:The British Journal of Ophthalmology
912:
910:
868:
866:
864:
830:
828:
826:
710:suspensions. It is soluble in small
121:
3330:Myelin oligodendrocyte glycoprotein
879:The Journal of Biological Chemistry
805:and be toxic to the liver, kidney,
508:. This is in contrast to unrelated
252:
163:
545:Gramicidins are used in medicinal
14:
2984:subunit synthesis and transport:
1526:David JM, Rajasekaran AK (2015).
1532:Journal of Kidney Cancer and VHL
325:
319:
92:
22:
1058:Gilger BC, Allbaugh RA (2011).
730:, and practically insoluble in
610:was determined by solution and
557:. Gramicidins are also used in
436:Key:IUAYMJGZBVDSGL-UHFFFAOYSA-N
28:Gramicidin A head-to-head dimer
3599:Phospholipid transfer proteins
3335:Myelin-associated glycoprotein
2882:Imipenem/cilastatin/relebactam
766:of bacteria and animal cells.
331:
313:
1:
1135:Van Epps HL (February 2006).
512:, which is a cyclic peptide.
16:Mix of ionophoric antibiotics
1491:10.1371/journal.pone.0041919
2907:Ticarcillin/clavulanic acid
2827:Amoxicillin/clavulanic acid
1964:Phenoxymethylpenicillin (V)
1954:Benzathine benzylpenicillin
622:Gramicidins A, B and C are
3748:
3722:Integral membrane proteins
3318:Myelin proteolipid protein
303:Chemical and physical data
3676:
3622:
3071:
2832:Ampicillin/flucloxacillin
1959:Procaine benzylpenicillin
1210:10.1016/j.bpj.2017.08.049
645:-D-Leu-L-Trp-D-Leu-L-Trp-
444:
419:
399:
91:
21:
3717:Polypeptide antibiotics
2897:Piperacillin/tazobactam
2857:Cefepime/enmetazobactam
1544:10.15586/jkcvhl.2015.21
1443:10.1126/science.7690158
618:Structure and chemistry
581:isolated the substance
3727:Antimicrobial peptides
2988:synthesis inhibition (
2872:Ceftolozane/tazobactam
2862:Cefoperazone/sulbactam
2761:β-lactamase inhibitors
1683:Dichlorobenzyl alcohol
1624:Acriflavinium chloride
1358:Urry DW (March 1971).
1083:Dubos RJ (June 1939).
931:10.1002/cbic.201100671
892:10.1074/jbc.M309658200
742:Pharmacological effect
688:
3150:Cell surface receptor
2902:Sulbactam/durlobactam
2887:Meropenem/vaborbactam
2867:Ceftazidime/avibactam
1999:β-lactamase resistant
1939:β-lactamase sensitive
1703:Myristyl-benzalkonium
1385:10.1073/pnas.68.3.672
813:among other effects.
682:
624:nonribosomal peptides
533:Staphylococcus aureus
3350:Pulmonary surfactant
3306:Myelin basic protein
3200:Membrane-spanning 4A
2892:Panipenem/betamipron
2837:Ampicillin/sulbactam
1949:Benzylpenicillin (G)
1883:cell wall by binding
1060:Equine ophthalmology
793:halts mitochondrial
722:, poorly soluble in
626:, thus they have no
497:Brevibacillus brevis
3340:Myelin protein zero
2877:Imipenem/cilastatin
2847:Aztreonam/avibactam
2658:Ceftaroline fosamil
1482:2012PLoSO...741919S
1435:1993Sci...261.1457K
1376:1971PNAS...68..672U
1335:2016RSCAd...668685M
1329:(73): 68685–68694.
1291:10.1021/ja01063a049
1202:2017BpJ...113.1757L
1190:Biophysical Journal
1153:10.1084/jem.2032fta
1027:10.1136/bjo.88.1.25
835:Budavari S (1996).
764:cellular organelles
664:in C. X determines
656:in gramicidin A, L-
391:Solubility in water
88:
3098:Never to phase III
3030:Hydrolyze NAM-NAG
2118:Carboxypenicillins
1881:layer of bacterial
1877:(inhibit synthesis
1344:10.1039/C6RA13658C
1101:10.1084/jem.70.1.1
978:10.1111/ijcp.13272
689:
3704:
3703:
3634:
3633:
3146:membrane proteins
3108:
3107:
2969:
2968:
2915:
2914:
2722:
2721:
2504:Antipseudomonal (
2412:Cefuroxime axetil
2208:
2207:
2204:
2203:
2151:Ureidopenicillins
2042:
2041:
1906:
1899:
1895:
1885:to and inhibiting
1813:
1812:
1766:Local anesthetics
1429:(5127): 1457–60.
527:Bacillus subtilis
462:
461:
370:Interactive image
82:
81:
3739:
3661:
3654:
3647:
3638:
3135:
3128:
3121:
3112:
2926:
2297:
2153:(4th generation)
2120:(4th generation)
2061:(3rd generation)
2059:Aminopenicillins
2055:
2002:(2nd generation)
1942:(1st generation)
1935:
1924:
1910:
1905:
1897:
1893:
1879:of peptidoglycan
1875:
1840:
1833:
1826:
1817:
1596:
1589:
1582:
1573:
1566:
1565:
1555:
1523:
1514:
1513:
1503:
1493:
1461:
1455:
1454:
1414:
1408:
1407:
1397:
1387:
1355:
1349:
1348:
1346:
1314:
1303:
1302:
1285:(9): 1862–1863.
1274:
1268:
1267:
1265:
1264:
1257:sigmaaldrich.com
1254:
1246:
1240:
1239:
1229:
1196:(8): 1757–1767.
1181:
1175:
1174:
1164:
1132:
1123:
1122:
1112:
1080:
1074:
1073:
1055:
1049:
1048:
1038:
1006:
1000:
999:
989:
957:
951:
950:
914:
905:
904:
894:
870:
859:
858:
832:
811:olfactory system
746:Gramicidins are
458:
457:
450:
372:
352:
350:
333:
327:
321:
315:
298:
287:
276:
256:
236:
216:
196:
176:
166:
165:
151:
125:
96:
89:
87:
26:
19:
3747:
3746:
3742:
3741:
3740:
3738:
3737:
3736:
3707:
3706:
3705:
3700:
3672:
3665:
3635:
3630:
3618:
3572:Neurofibromin 2
3555:Other/ungrouped
3550:
3367:
3344:
3292:
3194:
3161:
3139:
3109:
3104:
3103:
3088:Clinical trials
3067:
3019:
2965:
2948:
2911:
2815:
2788:Clavulanic acid
2755:
2718:
2690:
2672:
2644:
2611:
2476:
2383:
2290:
2286:
2282:
2274:
2232:Antipseudomonal
2200:
2174:
2145:
2112:
2049:
2038:
2001:
1993:
1941:
1929:
1902:transpeptidases
1901:
1891:
1886:
1884:
1882:
1880:
1878:
1876:
1874:
1866:
1844:
1814:
1809:
1793:
1760:
1722:
1718:Povidone-iodine
1698:Hexylresorcinol
1663:Cetylpyridinium
1610:
1600:
1570:
1569:
1525:
1524:
1517:
1463:
1462:
1458:
1416:
1415:
1411:
1357:
1356:
1352:
1316:
1315:
1306:
1276:
1275:
1271:
1262:
1260:
1252:
1248:
1247:
1243:
1183:
1182:
1178:
1134:
1133:
1126:
1082:
1081:
1077:
1070:
1057:
1056:
1052:
1008:
1007:
1003:
959:
958:
954:
916:
915:
908:
872:
871:
862:
847:
834:
833:
824:
819:
771:monovalent ions
758:-like pores in
744:
620:
612:solid-state NMR
575:
518:
453:
451:
448:(what is this?)
445:
440:
437:
432:
427:
426:
415:
412:
407:
406:
395:0.006 mg/L
375:
348:
346:
336:
330:
324:
318:
279:
259:
239:
219:
199:
179:
162:
154:
129:
99:
60:OPM superfamily
29:
17:
12:
11:
5:
3745:
3743:
3735:
3734:
3729:
3724:
3719:
3709:
3708:
3702:
3701:
3699:
3698:
3693:
3688:
3683:
3677:
3674:
3673:
3666:
3664:
3663:
3656:
3649:
3641:
3632:
3631:
3623:
3620:
3619:
3617:
3616:
3611:
3606:
3601:
3596:
3591:
3590:
3589:
3584:
3574:
3569:
3564:
3558:
3556:
3552:
3551:
3549:
3548:
3543:
3538:
3533:
3528:
3523:
3518:
3513:
3508:
3503:
3498:
3493:
3488:
3483:
3478:
3473:
3468:
3463:
3458:
3453:
3448:
3443:
3438:
3433:
3428:
3423:
3418:
3413:
3408:
3403:
3398:
3393:
3388:
3383:
3377:
3375:
3369:
3368:
3366:
3365:
3360:
3354:
3352:
3346:
3345:
3343:
3342:
3337:
3332:
3327:
3326:
3325:
3315:
3314:
3313:
3302:
3300:
3294:
3293:
3291:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3250:
3245:
3240:
3235:
3230:
3225:
3220:
3215:
3210:
3204:
3202:
3196:
3195:
3193:
3192:
3187:
3182:
3177:
3171:
3169:
3163:
3162:
3140:
3138:
3137:
3130:
3123:
3115:
3106:
3105:
3102:
3101:
3100:
3099:
3096:
3085:
3079:
3073:
3072:
3069:
3068:
3066:
3065:
3060:
3055:
3054:
3053:
3048:
3038:
3037:
3036:
3027:
3025:
3021:
3020:
3018:
3017:
3007:
2993:
2977:
2975:
2971:
2970:
2967:
2966:
2964:
2963:
2956:
2954:
2950:
2949:
2947:
2946:
2941:
2934:
2932:
2923:
2917:
2916:
2913:
2912:
2910:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2834:
2829:
2823:
2821:
2817:
2816:
2814:
2813:
2807:
2802:
2797:
2793:non-β-lactam (
2791:
2781:
2775:
2765:
2763:
2757:
2756:
2754:
2753:
2748:
2743:
2738:
2732:
2730:
2724:
2723:
2720:
2719:
2717:
2716:
2711:
2706:
2700:
2698:
2692:
2691:
2689:
2688:
2682:
2680:
2674:
2673:
2671:
2670:
2665:
2660:
2654:
2652:
2650:5th generation
2646:
2645:
2643:
2642:
2637:
2632:
2627:
2621:
2619:
2617:4th generation
2613:
2612:
2610:
2609:
2603:
2594:
2589:
2584:
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2508:
2502:
2497:
2492:
2486:
2484:
2482:3rd generation
2478:
2477:
2475:
2474:
2464:
2458:
2453:
2448:
2443:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2393:
2391:
2389:2nd generation
2385:
2384:
2382:
2381:
2376:
2371:
2366:
2361:
2356:
2351:
2346:
2341:
2336:
2331:
2326:
2321:
2316:
2311:
2305:
2303:
2301:1st generation
2294:
2284:Cephalosporins
2276:
2275:
2273:
2272:
2266:
2260:
2254:
2249:
2243:
2238:
2229:
2222:
2220:
2210:
2209:
2206:
2205:
2202:
2201:
2199:
2198:
2193:
2182:
2180:
2176:
2175:
2173:
2172:
2167:
2162:
2156:
2154:
2147:
2146:
2144:
2143:
2138:
2129:
2123:
2121:
2114:
2113:
2111:
2110:
2105:
2099:
2094:
2089:
2084:
2079:
2070:
2064:
2062:
2052:
2044:
2043:
2040:
2039:
2037:
2036:
2031:
2026:
2021:
2018:Flucloxacillin
2015:
2005:
2003:
1995:
1994:
1992:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1951:
1945:
1943:
1932:
1921:
1907:
1868:
1867:
1849:active on the
1847:Antibacterials
1845:
1843:
1842:
1835:
1828:
1820:
1811:
1810:
1808:
1807:
1801:
1799:
1795:
1794:
1792:
1791:
1786:
1781:
1776:
1770:
1768:
1762:
1761:
1759:
1758:
1753:
1748:
1743:
1738:
1732:
1730:
1724:
1723:
1721:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1673:Chlorquinaldol
1670:
1665:
1660:
1646:
1641:
1636:
1634:Amylmetacresol
1631:
1626:
1620:
1618:
1612:
1611:
1605:preparations (
1601:
1599:
1598:
1591:
1584:
1576:
1568:
1567:
1515:
1456:
1409:
1350:
1304:
1269:
1241:
1184:Lum K (2017).
1176:
1124:
1075:
1068:
1050:
1001:
972:(12): e13272.
952:
906:
860:
845:
821:
820:
818:
815:
760:cell membranes
743:
740:
650:
649:
619:
616:
608:lipid bilayers
574:
571:
524:bacteria like
517:
514:
471:, is a mix of
467:, also called
460:
459:
442:
441:
439:
438:
435:
433:
430:
422:
421:
420:
417:
416:
414:
413:
410:
402:
401:
400:
397:
396:
393:
387:
386:
383:
377:
376:
374:
373:
365:
363:
355:
354:
344:
338:
337:
334:
328:
322:
316:
311:
305:
304:
300:
299:
289:
281:
280:
278:
277:
269:
267:
261:
260:
258:
257:
249:
247:
241:
240:
238:
237:
229:
227:
221:
220:
218:
217:
209:
207:
201:
200:
198:
197:
189:
187:
181:
180:
178:
177:
169:
167:
156:
155:
153:
152:
144:
142:
136:
135:
131:
130:
128:
127:
114:
112:
106:
105:
101:
100:
97:
80:
79:
74:
68:
67:
62:
56:
55:
50:
44:
43:
40:
36:
35:
31:
30:
27:
15:
13:
10:
9:
6:
4:
3:
2:
3744:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3714:
3712:
3697:
3694:
3692:
3689:
3687:
3684:
3682:
3679:
3678:
3675:
3670:
3662:
3657:
3655:
3650:
3648:
3643:
3642:
3639:
3629:
3628:
3621:
3615:
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3588:
3585:
3583:
3580:
3579:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3559:
3557:
3553:
3547:
3544:
3542:
3539:
3537:
3534:
3532:
3529:
3527:
3524:
3522:
3519:
3517:
3514:
3512:
3509:
3507:
3504:
3502:
3499:
3497:
3494:
3492:
3489:
3487:
3484:
3482:
3479:
3477:
3474:
3472:
3469:
3467:
3464:
3462:
3459:
3457:
3454:
3452:
3449:
3447:
3444:
3442:
3439:
3437:
3434:
3432:
3429:
3427:
3424:
3422:
3419:
3417:
3414:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3394:
3392:
3389:
3387:
3384:
3382:
3379:
3378:
3376:
3374:
3370:
3364:
3361:
3359:
3356:
3355:
3353:
3351:
3347:
3341:
3338:
3336:
3333:
3331:
3328:
3324:
3321:
3320:
3319:
3316:
3312:
3309:
3308:
3307:
3304:
3303:
3301:
3299:
3295:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3251:
3249:
3246:
3244:
3241:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3205:
3203:
3201:
3197:
3191:
3188:
3186:
3183:
3181:
3178:
3176:
3173:
3172:
3170:
3168:
3164:
3159:
3155:
3151:
3147:
3143:
3136:
3131:
3129:
3124:
3122:
3117:
3116:
3113:
3097:
3095:
3092:
3091:
3089:
3086:
3083:
3080:
3078:
3075:
3074:
3070:
3064:
3061:
3059:
3056:
3052:
3049:
3047:
3044:
3043:
3042:
3039:
3035:
3032:
3031:
3029:
3028:
3026:
3022:
3015:
3011:
3008:
3005:
3001:
2997:
2994:
2991:
2987:
2983:
2979:
2978:
2976:
2974:Intracellular
2972:
2962:
2958:
2957:
2955:
2951:
2945:
2942:
2940:
2936:
2935:
2933:
2931:
2927:
2924:
2922:
2918:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2842:
2841:Sultamicillin
2838:
2835:
2833:
2830:
2828:
2825:
2824:
2822:
2818:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2792:
2789:
2785:
2782:
2779:
2776:
2774:
2770:
2767:
2766:
2764:
2762:
2758:
2752:
2749:
2747:
2744:
2742:
2739:
2737:
2734:
2733:
2731:
2729:
2725:
2715:
2712:
2710:
2707:
2705:
2702:
2701:
2699:
2697:
2693:
2687:
2684:
2683:
2681:
2679:
2675:
2669:
2666:
2664:
2661:
2659:
2656:
2655:
2653:
2651:
2647:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2622:
2620:
2618:
2614:
2607:
2604:
2602:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2512:
2509:
2507:
2503:
2501:
2498:
2496:
2493:
2491:
2488:
2487:
2485:
2483:
2479:
2472:
2468:
2465:
2462:
2459:
2457:
2456:Cefbuperazone
2454:
2452:
2449:
2447:
2444:
2442:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2394:
2392:
2390:
2386:
2380:
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2350:
2347:
2345:
2342:
2340:
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2312:
2310:
2307:
2306:
2304:
2302:
2298:
2295:
2293:
2289:
2285:
2281:
2277:
2270:
2267:
2265:
2261:
2258:
2255:
2253:
2250:
2247:
2244:
2242:
2239:
2237:
2233:
2230:
2228:
2225:Carbapenems (
2224:
2223:
2221:
2219:
2215:
2211:
2197:
2196:Sulbenicillin
2194:
2191:
2190:Pivmecillinam
2187:
2184:
2183:
2181:
2177:
2171:
2168:
2166:
2163:
2161:
2158:
2157:
2155:
2152:
2148:
2142:
2139:
2137:
2136:Carindacillin
2133:
2132:Carbenicillin
2130:
2128:
2125:
2124:
2122:
2119:
2115:
2109:
2106:
2103:
2102:Talampicillin
2100:
2098:
2097:Metampicillin
2095:
2093:
2092:Lenampicillin
2090:
2088:
2087:Bacampicillin
2085:
2083:
2080:
2078:
2077:Pivampicillin
2074:
2071:
2069:
2066:
2065:
2063:
2060:
2056:
2053:
2051:
2045:
2035:
2032:
2030:
2027:
2025:
2022:
2019:
2016:
2014:
2013:Dicloxacillin
2010:
2007:
2006:
2004:
2000:
1996:
1990:
1987:
1985:
1984:Clometocillin
1982:
1980:
1977:
1975:
1974:Pheneticillin
1972:
1970:
1967:
1965:
1962:
1960:
1957:
1955:
1952:
1950:
1947:
1946:
1944:
1940:
1936:
1933:
1931:
1925:
1922:
1919:
1915:
1911:
1908:
1903:
1889:
1873:
1869:
1864:
1860:
1856:
1852:
1848:
1841:
1836:
1834:
1829:
1827:
1822:
1821:
1818:
1806:
1803:
1802:
1800:
1796:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1771:
1769:
1767:
1763:
1757:
1754:
1752:
1749:
1747:
1744:
1742:
1739:
1737:
1734:
1733:
1731:
1729:
1725:
1719:
1716:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1671:
1669:
1668:Chlorhexidine
1666:
1664:
1661:
1658:
1654:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1622:
1621:
1619:
1617:
1613:
1608:
1604:
1597:
1592:
1590:
1585:
1583:
1578:
1577:
1574:
1563:
1559:
1554:
1549:
1545:
1541:
1537:
1533:
1529:
1522:
1520:
1516:
1511:
1507:
1502:
1497:
1492:
1487:
1483:
1479:
1476:(7): e41919.
1475:
1471:
1467:
1460:
1457:
1452:
1448:
1444:
1440:
1436:
1432:
1428:
1424:
1420:
1413:
1410:
1405:
1401:
1396:
1391:
1386:
1381:
1377:
1373:
1369:
1365:
1361:
1354:
1351:
1345:
1340:
1336:
1332:
1328:
1324:
1320:
1313:
1311:
1309:
1305:
1300:
1296:
1292:
1288:
1284:
1280:
1273:
1270:
1258:
1251:
1245:
1242:
1237:
1233:
1228:
1223:
1219:
1215:
1211:
1207:
1203:
1199:
1195:
1191:
1187:
1180:
1177:
1172:
1168:
1163:
1158:
1154:
1150:
1146:
1142:
1138:
1131:
1129:
1125:
1120:
1116:
1111:
1106:
1102:
1098:
1094:
1090:
1086:
1079:
1076:
1071:
1069:9781437708462
1065:
1061:
1054:
1051:
1046:
1042:
1037:
1032:
1028:
1024:
1020:
1016:
1012:
1005:
1002:
997:
993:
988:
983:
979:
975:
971:
967:
963:
956:
953:
948:
944:
940:
936:
932:
928:
924:
920:
913:
911:
907:
902:
898:
893:
888:
885:(9): 7413–9.
884:
880:
876:
869:
867:
865:
861:
856:
852:
848:
842:
838:
831:
829:
827:
823:
816:
814:
812:
808:
804:
798:
796:
792:
788:
787:ion gradients
784:
780:
776:
772:
769:
765:
761:
757:
753:
749:
741:
739:
737:
733:
729:
725:
721:
717:
713:
709:
704:
702:
698:
694:
686:
681:
677:
675:
671:
667:
663:
659:
658:phenylalanine
655:
648:
644:
640:
636:
633:
632:
631:
629:
625:
617:
615:
613:
609:
605:
600:
597:
594:
592:
588:
584:
580:
572:
570:
568:
564:
560:
556:
552:
548:
543:
541:
540:
535:
534:
529:
528:
523:
522:gram-positive
515:
513:
511:
507:
503:
499:
498:
493:
489:
485:
481:
477:
474:
470:
466:
456:
449:
443:
434:
429:
425:
418:
409:
405:
398:
394:
392:
388:
384:
382:
381:Melting point
378:
371:
367:
366:
364:
361:
356:
345:
343:
339:
312:
310:
306:
301:
297:
293:
290:
288:
286:ECHA InfoCard
282:
275:
271:
270:
268:
266:
262:
255:
251:
250:
248:
246:
242:
235:
231:
230:
228:
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215:
211:
210:
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202:
195:
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186:
182:
175:
171:
170:
168:
161:
157:
150:
146:
145:
143:
141:
137:
132:
124:
119:
116:
115:
113:
111:
107:
104:Clinical data
102:
95:
90:
78:
75:
73:
69:
66:
63:
61:
57:
54:
51:
49:
45:
41:
37:
32:
25:
20:
3686:Syringomycin
3680:
3624:
3158:cytoskeleton
3148:(other than
3045:
3012:inhibitors (
3002:inhibitors (
2930:Lipopeptides
2921:Polypeptides
2820:Combinations
2751:Nocardicin A
2668:Ceftobiprole
2511:Cefoperazone
2369:Cefaloridine
2354:Cefaloglycin
2292:Carbacephems
2160:Piperacillin
1989:Penamecillin
1890:, a group of
1805:Flurbiprofen
1745:
1708:Oxyquinoline
1644:Benzethonium
1639:Benzalkonium
1538:(1): 15–24.
1535:
1531:
1473:
1469:
1459:
1426:
1422:
1412:
1370:(3): 672–6.
1367:
1363:
1353:
1326:
1323:RSC Advances
1322:
1282:
1278:
1272:
1261:. Retrieved
1259:. 1997-09-06
1256:
1244:
1193:
1189:
1179:
1144:
1140:
1092:
1088:
1078:
1059:
1053:
1018:
1014:
1004:
969:
965:
955:
922:
918:
882:
878:
836:
799:
791:mitochondria
745:
736:hydrocarbons
732:diethylether
705:
690:
651:
647:ethanolamine
642:
638:
621:
601:
598:
595:
591:gramicidin S
576:
544:
537:
531:
525:
519:
516:Medical uses
510:gramicidin S
495:
487:
483:
480:gramicidin A
479:
469:gramicidin D
468:
464:
463:
452:
446:
274:ChEMBL557217
3696:Alamethicin
3373:Tetraspanin
3084:from market
3063:Teixobactin
3041:Tyrothricin
3010:bactoprenol
3004:Cycloserine
2810:Vaborbactam
2800:Durlobactam
2728:Monobactams
2686:Cefiderocol
2678:Siderophore
2663:Ceftolozane
2577:Cefpimizole
2547:Cefpodoxime
2542:Cefpiramide
2537:Cefmenoxime
2532:Ceftizoxime
2527:Cefdaloxime
2506:Ceftazidime
2495:Ceftriaxone
2467:Carbacephem
2461:Cefmetazole
2417:Cefamandole
2379:Cefatrizine
2359:Cefacetrile
2344:Cefroxadine
2288:Cephamycins
2214:Carbapenems
2170:Mezlocillin
2127:Ticarcillin
2068:Amoxicillin
2034:Methicillin
2009:Cloxacillin
1979:Azidocillin
1969:Propicillin
1914:Penicillins
1756:Tyrothricin
1741:Fusafungine
1728:Antibiotics
1678:Dequalinium
1649:Cetrimonium
1616:Antiseptics
1095:(1): 1–10.
1021:(1): 25–8.
925:(1): 51–5.
919:ChemBioChem
756:ion channel
716:acetic acid
697:ion channel
685:N-terminals
660:in B and L-
583:tyrothricin
563:polymyxin B
555:antiseptics
506:amino acids
476:antibiotics
353: g·mol
292:100.014.355
134:Identifiers
72:OPM protein
34:Identifiers
3732:Formamides
3711:Categories
3681:Gramicidin
3577:Presenilin
3051:Tyrocidine
3046:Gramicidin
3014:Bacitracin
2990:Fosfomycin
2961:Ramoplanin
2939:Daptomycin
2805:Relebactam
2778:Tazobactam
2709:Cefquinome
2696:Veterinary
2640:Cefquinome
2630:Cefozopran
2592:Ceftiolene
2582:Cefsulodin
2572:Cefodizime
2557:Cefditoren
2552:Ceftibuten
2500:Cefotaxime
2471:Loracarbef
2437:Cephamycin
2427:Ceforanide
2407:Cefuroxime
2364:Cefalonium
2334:Cefazaflur
2329:Cefazedone
2319:Cefadroxil
2186:Mecillinam
2165:Azlocillin
2141:Temocillin
2082:Hetacillin
2073:Ampicillin
1774:Benzocaine
1746:Gramicidin
1736:Bacitracin
1693:Hexetidine
1688:Hexamidine
1263:2019-10-03
1147:(2): 259.
846:0911910123
817:References
773:, such as
748:ionophores
701:ionophores
674:isoleucine
654:tryptophan
587:tyrocidine
579:René Dubos
551:tyrocidine
473:ionophoric
465:Gramicidin
358:3D model (
342:Molar mass
234:5IE62321P4
205:ChemSpider
140:CAS Number
86:Gramicidin
3625:see also
3604:Dysferlin
3094:Phase III
3082:Withdrawn
3058:Isoniazid
2944:Surfactin
2795:Avibactam
2773:Sulbactam
2746:Carumonam
2741:Tigemonam
2736:Aztreonam
2714:Cefovecin
2704:Ceftiofur
2635:Cefpirome
2606:Latamoxef
2597:Oxacephem
2567:Cefetamet
2522:Cefcapene
2446:Cefotetan
2441:Cefoxitin
2432:Cefuzonam
2422:Cefonicid
2402:Cefprozil
2374:Cefalotin
2349:Ceftezole
2339:Cefradine
2324:Cefapirin
2314:Cefalexin
2309:Cefazolin
2269:Ritipenem
2264:Faropenem
2257:Panipenem
2246:Meropenem
2236:Doripenem
2227:Ertapenem
2108:Epicillin
2029:Nafcillin
2024:Oxacillin
1872:β-lactams
1851:cell wall
1789:Lidocaine
1784:Dyclonine
1299:0002-7863
1218:0006-3495
803:hemolysis
783:diffusion
775:potassium
768:Inorganic
708:colloidal
699:-type of
668:. X is L-
577:In 1939,
559:eye drops
149:1405-97-6
3691:Tolaasin
3562:Calnexin
3167:Arrestin
3034:lysozyme
2980:Inhibit
2625:Cefepime
2601:Flomoxef
2587:Cefteram
2562:Cefotiam
2517:Cefdinir
2490:Cefixime
2451:Cefminox
2397:Cefaclor
2262:Penems (
2252:Biapenem
2241:Imipenem
2050:spectrum
2048:Extended
1930:spectrum
1900:-alanine
1896:-alanyl-
1855:envelope
1751:Neomycin
1657:chloride
1629:Ambazone
1562:28326255
1510:22911866
1470:PLOS ONE
1236:29045870
1171:16528813
1119:19870884
1045:14693766
996:30329199
939:22113881
901:14670971
855:34552962
807:meninges
777:(K) and
750:. Their
720:pyridine
712:alcohols
662:tyrosine
604:micelles
567:neomycin
547:lozenges
504:with 15
502:peptides
492:isoforms
455:(verify)
185:DrugBank
174:16130140
110:ATC code
3546:TSPAN34
3541:TSPAN33
3536:TSPAN32
3531:TSPAN31
3526:TSPAN30
3521:TSPAN29
3516:TSPAN28
3511:TSPAN27
3506:TSPAN26
3501:TSPAN25
3496:TSPAN24
3491:TSPAN23
3486:TSPAN22
3481:TSPAN21
3476:TSPAN20
3471:TSPAN19
3466:TSPAN18
3461:TSPAN17
3456:TSPAN16
3451:TSPAN15
3446:TSPAN14
3441:TSPAN13
3436:TSPAN12
3431:TSPAN11
3426:TSPAN10
3154:enzymes
3144:: cell
3142:Protein
2280:Cephems
1779:Cocaine
1653:bromide
1553:5345515
1501:3404012
1478:Bibcode
1451:7690158
1431:Bibcode
1423:Science
1404:5276779
1372:Bibcode
1331:Bibcode
1227:5647621
1198:Bibcode
1162:2118194
1110:2133784
1036:1771930
987:6282512
947:4906040
728:dioxane
724:acetone
666:isoform
652:Y is L-
573:History
539:E. coli
309:Formula
214:3076403
194:DB00027
160:PubChem
126:)
120: (
118:R02AB30
3421:TSPAN9
3416:TSPAN8
3411:TSPAN7
3406:TSPAN6
3401:TSPAN5
3396:TSPAN4
3391:TSPAN3
3386:TSPAN2
3381:TSPAN1
3298:Myelin
3288:MS4A18
3283:MS4A15
3278:MS4A14
3273:MS4A13
3268:MS4A12
3263:MS4A10
3253:MS4A8B
3243:MS4A6E
3238:MS4A6A
3228:MS4A4E
3223:MS4A4A
3156:, and
3077:WHO-EM
2784:Clavam
2218:Penems
1928:Narrow
1918:Penams
1713:Phenol
1603:Throat
1560:
1550:
1508:
1498:
1449:
1402:
1395:389014
1392:
1297:
1234:
1224:
1216:
1169:
1159:
1117:
1107:
1066:
1043:
1033:
994:
984:
945:
937:
899:
853:
843:
779:sodium
752:dimers
693:dimers
670:valine
635:formyl
404:SMILES
265:ChEMBL
254:D04369
39:Symbol
3669:TC 1D
3587:PSEN2
3582:PSEN1
3258:MS4A9
3248:MS4A7
3233:MS4A5
3218:MS4A3
3213:MS4A2
3208:MS4A1
3185:ARRB2
3180:ARRB1
3024:Other
2996:DADAL
2953:Other
2769:Penam
2179:Other
1798:Other
1253:(PDF)
943:S2CID
754:form
672:or L-
628:genes
424:InChI
360:JSmol
53:1.D.1
3614:OTOF
3609:STRC
3323:PLP1
3311:PMP2
3190:ARR3
1888:PBPs
1863:J01D
1859:J01C
1853:and
1558:PMID
1506:PMID
1447:PMID
1400:PMID
1295:ISSN
1232:PMID
1214:ISSN
1167:PMID
1115:PMID
1064:ISBN
1041:PMID
992:PMID
935:PMID
897:PMID
851:OCLC
841:ISBN
809:and
762:and
734:and
726:and
606:and
553:and
530:and
486:and
351:.332
245:KEGG
225:UNII
77:1grm
48:TCDB
3594:HFE
3175:SAG
2986:NAM
1607:R02
1548:PMC
1540:doi
1496:PMC
1486:doi
1439:doi
1427:261
1390:PMC
1380:doi
1339:doi
1287:doi
1222:PMC
1206:doi
1194:113
1157:PMC
1149:doi
1145:203
1105:PMC
1097:doi
1031:PMC
1023:doi
982:PMC
974:doi
927:doi
887:doi
883:279
795:ATP
637:-L-
565:or
349:882
323:140
164:CID
123:WHO
42:N/A
3713::
3152:,
3090::
3000:AR
2982:PG
2216:/
2134:/
1556:.
1546:.
1534:.
1530:.
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1504:.
1494:.
1484:.
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1445:.
1437:.
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1366:.
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1113:.
1103:.
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1039:.
1029:.
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1013:.
990:.
980:.
970:72
968:.
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895:.
881:.
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863:^
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714:,
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478:,
335:17
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2786:(
2780:)
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2234:(
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2011:(
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1374::
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1266:.
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1173:.
1151::
1121:.
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1072:.
1047:.
1025::
998:.
976::
949:.
929::
903:.
889::
857:.
687:.
643:Y
639:X
488:C
484:B
362:)
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332:O
326:N
320:H
314:C
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