PRD_000223
概要
| 名称: | THIOSTREPTON |
| 組成式: | C72 H84 N19 O18 S5 |
| 化学式量: | 1663.879 |
| 分子種別: | peptide-like |
| ポリマー配列: | QUA, ILE, ALA, DHA, ALA, SER, BB9, THR, DBU, DCY, TS9, BB9, THR, BB9, MH6, BB9, DHA, DHA, NH2 |
| 非ポリマー要素: | |
| BIRDクラス: | Antibiotic |
| PDB中の表現: | polymer |
| 化合物の詳細: | THIOSTREPTON IS A MEMBER OF A SULPHUR-RICH HETEROCYCLIC PEPTIDES CLASS. ALL SHARE A MACROCYLIC CORE, CONSISTING OF A NITROGEN CONTAINING, SIX-MEMBERED RING CENTRAL TO DEHYDROAMINO ACIDS AND A SUBSET OF FIVE MEMBER RING STRUCTURES INCLUDING THIAZOLES, THIAZOLINES AND OXAZOLES. HERE, THIOSTREPTON IS REPRESENTED BY THE SEQUENCE (SEQRES) |
| 表記: | Thiostrepton is a hetrocyclic thiopeptide belonging to the thiocillin family, consisting of four thiazole, one thiozoline and one piperideine rings. A modified quinoline linked to main-chain residue 1 and side-chain of residue 12. Post translational maturation of thiazole and oxazole containing antibiotics involves the enzymic condensation of a Cys or Ser with the alpha-carbonyl of the preceding amino acid to form a thioether or ether bond, then dehydration to form a double bond with the alpha-amino nitrogen. Thiazoline or oxazoline ring are dehydrogenated to form thiazole or oxazole rings. the pyridinyl involves the cross-linking of a Ser and a Cys-Ser pair usually separated by 7 or 8 residues along the peptide chain. The Ser residues are dehydrated to didehydroalanines, then bonded between their beta carbons. The alpha carbonyl of the Cys condenses with alpha carbon of the first Ser to form a pyridinyl ring. The ring may be mutiply dehydrogenated to form a pyridine ring with loss of the amino nitrogen of the first Ser. The amidation of Ser-17 probably does not occur by the same mechanism, oxidative cleavage of glycine, as in eukaryotes. |
| Families: | FAM_000096 |
| プログラム | バージョン | 表記 |
| ACDLabs | 12.01 | N-{3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl}-2-[(1R,8S,11Z,15R,18R,25R,26R,35S,37R,40R,46R,53S,59R)-37-[(2R)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8,31-bis[(1R)-1-hydroxyethyl]-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecaazanonacyclo[23.23.9.3~29,35~.1~2,5~.1~12,15~.1~19,22~.1~54,57~.0~1,53~.0~32,60~]tetrahexaconta-2(64),4,12(63),19(62),21,29,31,33,51,54,57,60-dodecaen-51-yl]-1,3-thiazole-4-carboxamide (non-preferred name) |
化合物記述子（線形表記）
| 種別 | プログラム | バージョン | 表記 |
| SMILES | ACDLabs | 12.01 | O=C8NC6c1nc(cs1)C3N=C(c2nc(cs2)C(=O)NC(=C)\C(=O)NC(=C)\C(=O)N)CCC3(NC(=O)C(NC(=O)C(=C)/NC(=O)C(NC(=O)C(NC5C=Cc4c(cc(nc4C5O)C(=O)OC6C)C(O)C)C(C)CC)C)C)c7scc(n7)C(=O)NC(C(=O)N/C(=C/C)C%10=NC(C(=O)NC(c9nc8cs9)C(O)(C)C(O)C)CS%10)C(O)C |
| InChI | InChI | 1.03 | InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15+/t26-,30?,31-,32+,33-,34-,35-,39+,45-,47-,48+,49?,51-,52-,53+,71-,72-/m1/s1 |
| InChIKey | InChI | 1.03 | NSFFHOGKXHRQEW-RKZUCAFPSA-N |
| SMILES_CANONICAL | CACTVS | 3.370 | CC[C@H](C)[C@@H]1N[C@@H]2C=Cc3c(cc(nc3[C@H]2O)C(=O)O[C@H](C)[C@@H]4NC(=O)c5csc(n5)[C@@H](NC(=O)[C@H]6CSC(=N6)C(/NC(=O)[C@@H](NC(=O)c7csc(n7)[C@]8(CCC(=N[C]8c9csc4n9)c%10scc(n%10)C(=O)NC(=C)C(=O)NC(=C)C(N)=O)NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC1=O)[C@@H](C)O)=C/C)[C@](C)(O)[C@@H](C)O)[C@H](C)O |
| SMILES | CACTVS | 3.370 | CC[CH](C)[CH]1N[CH]2C=Cc3c(cc(nc3[CH]2O)C(=O)O[CH](C)[CH]4NC(=O)c5csc(n5)[CH](NC(=O)[CH]6CSC(=N6)C(NC(=O)[CH](NC(=O)c7csc(n7)[C]8(CCC(=N[C]8c9csc4n9)c%10scc(n%10)C(=O)NC(=C)C(=O)NC(=C)C(N)=O)NC(=O)[CH](C)NC(=O)C(=C)NC(=O)[CH](C)NC1=O)[CH](C)O)=CC)[C](C)(O)[CH](C)O)[CH](C)O |
| SMILES_CANONICAL | OpenEye OEToolkits | 1.7.6 | CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)NC(=C)C(=O)N[C@H](C(=O)N[C@]23CCC(=N[C]2c4csc(n4)[C@H]([C@H](OC(=O)c5cc(c6c(n5)[C@H](C(N1)C=C6)O)[C@H](C)O)C)NC(=O)c7csc(n7)[C@@H](NC(=O)[C@H]8CSC(=N8)/C(=C/C)/NC(=O)[C@@H](NC(=O)c9csc3n9)[C@@H](C)O)[C@@](C)([C@@H](C)O)O)c1nc(cs1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C |
| SMILES | OpenEye OEToolkits | 1.7.6 | CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=N[C]2c4csc(n4)C(C(OC(=O)c5cc(c6c(n5)C(C(N1)C=C6)O)C(C)O)C)NC(=O)c7csc(n7)C(NC(=O)C8CSC(=N8)C(=CC)NC(=O)C(NC(=O)c9csc3n9)C(C)O)C(C)(C(C)O)O)c1nc(cs1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C |
