Compound ID | 860

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Cyclothialidine

Synonym(s): Ro 09-1437

Class: Natural product antibiotic

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: DNA synthesis inhibitor. DNA gyrase inhibitor
Description: Natural product from Streptomyces filipinensis; Goetschi E, Angehrn P, Gmuender H, et al. Cyclothialidine (Ro 09-1437) and its congeners; a new class of DNA gyrase inhibitors: synthesis and structure-activity relationships. 32nd-Intersci-Conf-Antimicrobial-Agents-Chemother 1992; 193
Institute where first reported: Hoffmann-La Roche Inc, Switzerland
Year first mentioned: 1992
Development status: Experimental
Chemical structure(s):
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Molecular weight: 641.65
Iso. SMILES: CC1=C2C(=C(C=C1O)O)CSC[C@H](NC(=O)[C@H](COC2=O)NC(=O)[C@@H]3[C@@H](CCN3C(=O)[C@H](CO)N)O)C(=O)N[C@@H](C)C(=O)O
InChI Key: HMHQWJDFNVJCHA-BTZKOOKSSA-N
Can. SMILES: CC1=C(C=C(C2=C1C(=O)OC[C@@H](C(=O)N[C@@H](CSC2)C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@@H]3[C@@H](CCN3C(=O)[C@H](CO)N)O)O)O
InChI: InChI=1S/C26H35N5O12S/c1-10-17(34)5-18(35)12-8-44-9-15(22(37)28-11(2)25(40)41)30-21(36)14(7-43-26(42)19(10)12)29-23(38)20-16(33)3-4-31(20)24(39)13(27)6-32/h5,11,13-16,20,32-35H,3-4,6-9,27H2,1-2H3,(H,28,37)(H,29,38)(H,30,36)(H,40,41)/t11-,13-,14-,15-,16+,20-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/164470
Guide to Pharmacology: cyclothialidine
Citation: https://doi.org/10.1016/0163-7258(93)90017-8

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