PRD_000760
Summary
| Name: | THIOPEPTIDE THIOSTREPTON OXIDIZED AT CA-CB BOND OF RESIDUE 9 |
| Formula: | C69 H79 N18 O17 S5 |
| Fomular weight: | 1592.801 |
| Component type: | peptide-like |
| Polymer sequences: | QUA, ILE, ALA, DHA, ALA, SER, BB9, THR, DBU, BB9, TS9, BB9, THR, BB9, MH6, BB9, 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 MACROCYCLIC 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 HETEROCYCLIC THIOPEPTIDE, CONSISTING OF FOUR THIAZOLES ONE THIOZOLINE ONE PIPERIDEINE RINGS. A MODIFIED QUINOLINE LINKED TO MAIN-CHAIN RESIDUE 1 AND SIDE-CHAIN OF RESIDUE 12. IN THIS ENTRY RESIDUE 9 WAS CHEMICALLY MODIFIED: THE CA-CB BOND WAS OXIDIZED FROM SINGLE TO DOUBLE. RESIDUE 17 (HET DHA) WAS DELETED. |
| Families: | FAM_000096 |
| Program | Version | Name |
| ACDLabs | 12.01 | N-(3-amino-3-oxoprop-1-en-2-yl)-2-[(1R,8S,11Z,18S,25S,26R,35R,37S,40S,46S,53S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-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),14,19(62),21,29,31,33,51,54,57,60-tridecaen-51-yl]-1,3-thiazole-4-carboxamide (non-preferred name) |
Chemical Descriptors
| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | O=C(c1nc(sc1)C%10=NC6c2nc(sc2)C9NC(=O)c3nc(sc3)C(NC(=O)c4nc(sc4)C(=C/C)/NC(=O)C(NC(=O)c5nc(sc5)C6(NC(=O)C(NC(=O)C(=C)\NC(=O)C(NC(=O)C(NC8C=Cc7c(cc(nc7C8O)C(=O)OC9C)C(O)C)C(C)CC)C)C)CC%10)C(O)C)C(O)(C(O)C)C)NC(=C)/C(=O)N |
| InChI | InChI | 1.03 | InChI=1S/C69H80N18O17S5/c1-13-25(3)45-60(100)74-28(6)54(94)72-27(5)53(93)73-29(7)55(95)87-69-18-17-38(63-81-41(21-106-63)56(96)71-26(4)52(70)92)77-50(69)40-20-107-64(79-40)47(32(10)104-66(102)39-19-35(30(8)88)34-15-16-37(75-45)49(91)48(34)76-39)85-57(97)42-23-108-65(82-42)51(68(12,103)33(11)90)86-59(99)43-22-105-62(80-43)36(14-2)78-61(101)46(31(9)89)84-58(98)44-24-109-67(69)83-44/h14-16,19-25,28-33,37,45-47,49-51,75,88-91,103H,4-5,13,17-18H2,1-3,6-12H3,(H2,70,92)(H,71,96)(H,72,94)(H,73,93)(H,74,100)(H,78,101)(H,84,98)(H,85,97)(H,86,99)(H,87,95)/b36-14-/t25-,28-,29-,30-,31+,32+,33+,37+,45-,46-,47-,49-,50+,51+,68+,69+/m0/s1 |
| InChIKey | InChI | 1.03 | DKRYJPOZCOVFFS-NOCGNKOMSA-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)c6csc(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(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)c6csc(n6)C(NC(=O)[CH](NC(=O)c7csc(n7)[C]8(CCC(=N[C]8c9csc4n9)c%10scc(n%10)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)c8csc(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)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)N)C)C |
