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- BIRD-PRD_000223: THIOSTREPTON -

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Basic information

EntryDatabase: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000223
StatusStatus: REF ONLY
NameTHIOSTREPTON

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BIRD information

TypeThiopeptide / Antibiotic
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)
  • 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.
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • A 8506 (PubChem)
  • A-8506 (ChemSpider)
  • Alaninamide (UniProt)
  • Antibiotic 6761-31 (ChemSpider, ChemBank)
  • Antibiotic A 8506 (ChemBank)
  • Antibiotic X 146 (ChemSpider)
  • Antibiotic X-146 (ChemBank)
  • BSPBio_002468 (PubChem)
  • Bryamycin (SciFinder, UniProt, ChemBank)
  • Bryamycin (BMS) (Merck)
  • EINCES 215-734-9 (ChemSpider)
  • EINECS 215-734-9 (PubChem)
  • Gargon (SciFinder, UniProt)
  • LS-153388 (PubChem)
  • NCGC00096010-01 (PubChem)
  • NSC 170365 (SciFinder, PubChem)
  • NSC 81722 (SciFinder, PubChem)
  • NSC-170365 (ChemBank)
  • NSC-81722 (ChemBank)
  • NSC170365 (ChemSpider)
  • NSC81722 (ChemSpider)
  • SPECTRUM 1505111 (PubChem)
  • THIOSTREPTON (PDB)
  • Thiactin (SciFinder, Merck, UniProt, ChemSpider, ChemBank)
  • Thiostrepton (SciFinder, KEGG, UniProt, PubChem, ChemSpider, ChemBank)
  • Thiostrepton A (SciFinder)
  • X146 (ChemSpider)
  • alaninamide (PubChem)
  • antibiotic a 8506 (PubChem)
  • antibiotic x 146 (PubChem)
  • bryamycin (PubChem)
  • gargon (PubChem)
  • iostrepton (Merck)
  • prestwick2_0005222 (PubChem)
  • thiactin (PubChem)
  • x146 (PubChem)
Annotation
  • Function: Antibacterial (veterinary) / Info source: KEGG
  • Function: Has bacteriocidal activity. Inhibits bacterial protein biosynthesis by acting on the elongation factor Tu (EF-Tu) / Info source: UniProt
  • Function: active against gram-positive bacteria / Info source: PubChem
  • Function: Verterinary uses include mastitis and dermatological disorders / Info source: PubChem
  • Function: antibacterial / Info source: PubChem
  • Therapeutic category: Thiostrepton is used as a reagent for both positive and negative selection of genes involved in nucleotide metabolism. Thiostrepton is highly active against gram-positive bacteria. .In its crude form, Thiostrepton is used in veterinary medicine, in mastitis caused by gram-negative organisms and in dermatologic disorders. / Info source: WikiPedia
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: C72H84N19O18S5 / Formula weight: 1663.879
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

ACDLabs 12.01O=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
CACTVS 3.370CC[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
OpenEye OEToolkits 1.7.6CCC(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

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SMILES CANONICAL

CACTVS 3.370CC[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
OpenEye OEToolkits 1.7.6CC[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

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InChI

InChI 1.03InChI=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

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InChIKey

InChI 1.03NSFFHOGKXHRQEW-RKZUCAFPSA-N

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SYSTEMATIC NAME

ACDLabs 12.01N-{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) #

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