Compound ID | 2766

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Thiopeptin

Class: Antimicrobial peptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Active against Staphylococcus aureus, Corynebacterium xerosis, and Mycoplasma sp.
Description: Natural product from Streptomyces tateyamensis; developed as animal feed-additive; a thiopeptide
Institute where first reported: Fujisawa Pharmaceutical Co. Ltd., Osaka, Japan
Year first mentioned: 1972
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1530.83
Iso. SMILES: C/C=C\1/C2=NC(CS2)C(=O)NC(C3=NC(=CS3)C(=S)NC4C(OC(=O)C5=NC6=C(C=CC(C6O)NC(C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC7(CCC(NC7C8=CSC4=N8)C9=NC(=CS9)C(=O)N)C%10=NC(=CS%10)C(=O)NC(C(=O)N1)C(C)O)C)C)C(C)C)C(=C5)C(C)O)C)C(C)(C(C)O)O
InChI Key: SRTDKHGZQCTGBY-OHSLDDHESA-N
Can. SMILES: C/C=C\1/C2=NC(CS2)C(=O)NC(C3=NC(=CS3)C(=S)NC4C(C)OC(=O)C5=NC6=C(C=CC(C6O)NC(C(C)C)C(=O)NC(C)C(=O)NC(=C)C(=O)NC(C)C(=O)NC7(CCC(C8=NC(=CS8)C(=O)N)NC7C9=CSC4=N9)C%10=NC(=CS%10)C(=O)NC(C(C)O)C(=O)N1)C(=C5)C(C)O)C(C)(C(C)O)O
InChI: InChI=1S/C65H79N17O15S6/c1-12-33-58-76-39(20-100-58)54(92)81-48(64(11,96)30(10)85)61-77-41(22-102-61)57(98)80-44-29(9)97-62(95)36-17-32(27(7)83)31-13-14-34(46(86)45(31)71-36)70-42(23(2)3)55(93)69-25(5)51(89)67-24(4)50(88)68-26(6)52(90)82-65(63-78-40(21-103-63)53(91)79-43(28(8)84)56(94)73-33)16-15-35(59-75-38(19-99-59)49(66)87)72-47(65)37-18-101-60(44)74-37/h12-14,17-19,21-23,25-30,34-35,39,42-44,46-48,70,72,83-86,96H,4,15-16,20H2,1-3,5-11H3,(H2,66,87)(H,67,89)(H,68,88)(H,69,93)(H,73,94)(H,79,91)(H,80,98)(H,81,92)(H,82,90)/b33-12-
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/25200027
Citations:
  • https://journals.asm.org/doi/10.1128/aac.1.6.496?url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&rfr_dat=cr_pub++0pubmed
  • https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=2ahUKEwiLw82C4K-EAxUSTkEAHQedAXMQFnoECBYQAQ&url=https%3A%2F%2Fwww.jstage.jst.go.jp%2Farticle%2Fmandi1957%2F20%2F3%2F20_3_233%2F_pdf%2F-char%2Fja&usg=AOvVaw0Vp6C_UChIAfC7ZBw3ATov&opi=89978449
  • https://journals.asm.org/doi/epdf/10.1128/aac.1.3.192

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