PRD_000223
Summary
| Name: | THIOSTREPTON |
| Formula: | C72 H84 N19 O18 S5 |
| Fomular weight: | 1663.879 |
| Component type: | peptide-like |
| Polymer sequences: | QUA, ILE, ALA, DHA, ALA, SER, BB9, THR, DBU, DCY, TS9, BB9, THR, BB9, MH6, BB9, DHA, DHA, NH2 |
| Non-polymer components: | |
| BIRD class: | Antibiotic |
| Represented as: | polymer |
| Compound Details: | 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) |
| Description: | 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 |
| Program | Version | Name |
| 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) |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| 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 |
