BIRD-PRD_000221: Nosiheptide

基本情報

• 登録情報: データベース: 生物学的重要分子辞書 (BIRD) / ID: PRD_000221
• 状態: 状態: REF ONLY
• 名称: Nosiheptide

BIRD information

• タイプ: チオペプチド / 抗生剤

詳細

• Nosiheptide 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. The main characteristic of the nosiheptide structure is a general tendency to be more oxidized than the thiostrepton one. No thiazoline, or hydrogenated quinaldic precursor nor tetrahydropyridine rings are present in nosiheptide. All the corresponding rings are unsaturated. Nosiheptide possess an indolic acid ring system that is appended to the side chains of the Ser/Cys and a central 6-membered nitrogen heterocycle produced by cyclization between two corresponding dehydroalanine acids with incorporation of an adjacent carbonyl group. Thiazole formation is by nucleophilic addition of each Cys side chain to the proceeding carbonyl group followed by dehydration and dehydrogenation. HERE, NOSIHEPTIDE IS REPRESENTED BY GROUPING TOGETHER THE SEQUENCE (SEQRES) AND THE ONE LIGAND (HET) NO1.
• NOSIHEPTIDE IS A HETROCYCLIC THIOPEPTIDE, CONSISTING OF FIVE THIAZOLES AND ONE 3-HYDROXYPYRIDINE RINGS. A MODIFIED INDOLE RING NO1(14) IS LINKED VIA THE SIDE CHAINS OF 3-HYDROXY 3GL(6) AND CYS(8). THE OBSERVED C-TERMINAL AMINO GROUP NH2(13) IS LIKELY TO BE A POST-TRANSLATIONAL DECARBOXYLATED REMNANT OF A SER C-TERMINAL RESIDUE

• ダウンロード: Molecular definition / Chemical definition / Family definition

別称

• 260-138-4 (ChemSpider)
• Multhiomycin (PubChem, ChemSpider)
• Multiomycin (ChemSpider)
• N-[1-(Aminocarbonyl)ethenyl]-2-[(11S,14Z,21S,23S,29S)-14-ethylidene-9,10,11,12,13,14,19,20,21,22,23,24,26,33,35,36-hexadecahydro-3,23-dihydroxy-11-[(1R)-1-hydroxyethyl]-31-methyl-9,12,19,24,33,43-hexaoxo-30,32-imino-8,5:18,15:40,37-trinitrilo-21,36-([2,4]-endo-thiazolomethanimino)-5H,15H,37H-pyrido[3,2-w][2,11,21,27,31,7,14,17]benzoxatetrathiatriaza cyclohexatriacontin-2-yl]-4-thiazolecarboxamide (chemBlink)
• NOSIHEPTIDE (PDB)
• multiomycin (PubChem)
• nosiheptide (ChemSpider)

Annotation

• 分子機能: Thiopeptide antibiotic / 情報源: PubMed: 18406324

由来

• Streptomyces actuosus 40037 (NRRL 2954), KEGG: C12053
• Streptomyces actuosus (バクテリア), UniProt: C6FX52

External info

• EINECS: 260-138-4
• Merck: 14:6719
• ChemSpider: 16735938
• PubChem: 25080270
• CAS: 56377-79-8
• [KEGG_Compound_ID] KEGG: C12053
• [KEGG_Drug_ID] KEGG: D02392
• [MESH_Unique_ID] MESH: C014134

Family

Thiopeptides

Nosiheptide / THIOSTREPTON / GE2270a / THIOPEPTIDE THIOSTREPTON REDUCED AT N-CA BOND OF RESIDUE 14 / THIOPEPTIDE THIOSTREPTON WITH EPIMER FORM OF RESIDUE 9 / THIOPEPTIDE THIOSTREPTON OXIDIZED AT CA-CB BOND OF RESIDUE 9 / Thiocillin GE2270 analogue NVP-LFF571 / Thiocillin GE2270 analogue NVP-LDK733 / Thiocillin GE2270 analogue NVP-LDI028 / thiomuracin A derivative

Related structures

• Thiostrepton / CCDC: TSTREP / Reference
• Nosiheptide chloroform solvate / CCDC: NOSHEP10 / Reference

Chemical information

組成

組成式: C₅₁H₄₆N₁₃O₁₁S₆ / 化学式量: 1209.381

• その他: タイプ: peptide-like

履歴

• 外部リンク: UniChem / ChemSpider / Wikipedia search / Google search

詳細

SMILES

• CACTVS 3.370: CC=C1NC(=O)[CH](NC(=O)c2csc(n2)[CH]3CC[C](=[N]=[C]3c4csc(n4)[CH]5CSC(=O)c6[nH]c7cccc(COC(=O)[CH](O)C[CH](NC(=O)c8csc1n8)c9scc(n9)C(=O)N5)c7c6C)c%10scc(n%10)C(=O)NC(=C)C(N)=O)[CH](C)O
• OpenEye OEToolkits 1.7.6: CC=C1c2nc(cs2)C(=O)NC3CC(C(=O)OCc4cccc5c4c(c([nH]5)C(=O)SCC(c6nc(cs6)C7=[N]=C(CCC7c8nc(cs8)C(=O)NC(C(=O)N1)C(C)O)c9nc(cs9)C(=O)NC(=C)C(=O)N)NC(=O)c1csc3n1)C)O

SMILES CANONICAL

• CACTVS 3.370: C\C=C1/NC(=O)[C@@H](NC(=O)c2csc(n2)[C@H]3CC[C](=[N]=[C]3c4csc(n4)[C@@H]5CSC(=O)c6[nH]c7cccc(COC(=O)[C@@H](O)C[C@H](NC(=O)c8csc1n8)c9scc(n9)C(=O)N5)c7c6C)c%10scc(n%10)C(=O)NC(=C)C(N)=O)[C@@H](C)O
• OpenEye OEToolkits 1.7.6: C/C=C\1/c2nc(cs2)C(=O)N[C@H]3C[C@@H](C(=O)OCc4cccc5c4c(c([nH]5)C(=O)SC[C@@H](c6nc(cs6)C7=[N]=C(CC[C@H]7c8nc(cs8)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)c9nc(cs9)C(=O)NC(=C)C(=O)N)NC(=O)c1csc3n1)C)O

InChI

• InChI 1.03: InChI=1S/C51H46N13O11S6/c1-5-24-46-61-30(16-78-46)41(69)57-27-11-34(66)50(73)75-12-22-7-6-8-25-35(22)19(2)36(54-25)51(74)81-18-33(58-42(70)31-17-80-48(27)63-31)49-59-28(13-77-49)38-23(45-60-32(14-76-45)43(71)64-37(21(4)65)44(72)56-24)9-10-26(55-38)47-62-29(15-79-47)40(68)53-20(3)39(52)67/h5-8,13-17,21,23,27,33-34,37,54,65-66H,3,9-12,18H2,1-2,4H3,(H2,52,67)(H,53,68)(H,56,72)(H,57,69)(H,58,70)(H,64,71)

InChIKey

• InChI 1.03: YBIKXSCMCFEFTI-UHFFFAOYSA-N

PDBエントリ

全2件を表示しています

PDB-2zjp:
Thiopeptide antibiotic Nosiheptide bound to the large ribosomal subunit of Deinococcus radiodurans

PDB-2zjp:
Thiopeptide antibiotic Nosiheptide bound to the large ribosomal subunit of Deinococcus radiodurans