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- BIRD-PRD_000221: Nosiheptide -

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Basic information

EntryDatabase: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000221
StatusStatus: REF ONLY
NameNosiheptide
WikipediaWikipedia - Nosiheptide: Nosiheptide is a thiopeptide antibiotic produced by the bacterium Streptomyces actuosus.

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BIRD information

TypeThiopeptide / Antibiotic
Details
  • 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
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • 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
Source
External info
FamilyThiopeptides

Nosiheptide / THIOSTREPTON / GE2270a ...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

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Chemical information

Composition
Formula: C51H46N13O11S6 / Formula weight: 1209.381
OthersType: peptide-like
History
External linksUniChem / ChemSpider / Wikipedia search / Google search

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Structure visualization

Structure viewerMolecule:
MolmilJmol/JSmol

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Details

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SMILES

CACTVS 3.370CC=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 1.7.6CC=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

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SMILES CANONICAL

CACTVS 3.370C\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 1.7.6C/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

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InChI

InChI 1.03InChI=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)

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InChIKey

InChI 1.03YBIKXSCMCFEFTI-UHFFFAOYSA-N

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PDB entries

Showing all 2 items

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

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