Compound ID | 247

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Thiazomycin

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, Streptococcus pneumoniae, and enterococci
Propensity to select resistant mutants: Yes, at 4x MIC
Description: Natural product from Amycolatopsis fastidiosa (previously Nocardia sp.); a thiazolyl peptide; shows efficacy when administered via subcutaneous route in mice infected with Staphylococcus aureus
Institute where first reported: Merck Research Laboratories, USA
Year first mentioned: 2007
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 1435.53
Iso. SMILES: C[C@H]1[C@@H]2[C@](C[C@@H](O1)O[C@H]3[C@@H]4[C@H]5C6=NC(=CS6)C(=O)N[C@@H](COC(=O)C7=C(CO4)C8=C(COC3=O)C=CC=C8N7O)C9=NC(=CS9)C%10=NC(=C(C=C%10C%11=NC(=CS%11)C(=O)N[C@H](C(=O)N/C(=C(\C)/OC)/C%12=NC(=CS%12)C(=O)N5)[C@@H](C)O)O)C%13=NC(=CS%13)C(=O)NC(=C)C(=O)N)(OCN2C)C
InChI Key: GYOHFSLEKIIJMU-UMNFMQIXSA-N
Can. SMILES: C=C(C(=O)N)NC(=O)C1=CSC(=N1)C2=C(C=C3C(=N2)C4=CSC(=N4)[C@@H]5COC(=O)C6=C7CO[C@@H]([C@@H](C8=NC(=CS8)C(=O)N5)NC(=O)C9=CSC(=N9)/C(=C(/C)\OC)/NC(=O)[C@H]([C@@H](C)O)NC(=O)C%10=CSC3=N%10)[C@@H](C(=O)OCC%11=CC=CC(=C%117)N6O)O[C@H]%12C[C@@]%13(C)[C@@H]([C@H](C)O%12)N(C)CO%13)O
InChI: InChI=1S/C61H58N14O18S5/c1-22(48(62)78)63-49(79)31-18-97-57(68-31)42-36(77)11-27-41(70-42)30-16-95-55(65-30)29-15-90-59(84)44-28-14-88-45(46(60(85)89-13-26-9-8-10-35(38(26)28)75(44)86)93-37-12-61(5)47(25(4)92-37)74(6)21-91-61)43(58-69-32(19-98-58)50(80)64-29)73-52(82)34-20-96-56(67-34)40(24(3)87-7)72-53(83)39(23(2)76)71-51(81)33-17-94-54(27)66-33/h8-11,16-20,23,25,29,37,39,43,45-47,76-77,86H,1,12-15,21H2,2-7H3,(H2,62,78)(H,63,79)(H,64,80)(H,71,81)(H,72,83)(H,73,82)/b40-24+/t23-,25+,29+,37+,39+,43+,45+,46+,47-,61+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16156566
Guide to Pharmacology: Thiazomycin A
Citations:
  • http://www.ncbi.nlm.nih.gov/pubmed/17917239
  • https://pubmed.ncbi.nlm.nih.gov/17917238/

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