cyclothialidine   

GtoPdb Ligand ID: 10988

Synonyms: Ro 09-1437
Comment: Cyclothialidine is a potent DNA gyrase inhibitor, isolated from Streptomyces filipinensis following microbial broth screening [3]. It belongs to a novel class of antibacterial compounds, containing a unique 12-membered lactone ring that is partly integrated into a pentapeptide chain, that exhibit broad-spectrum in vitro activity against Gram-positive bacteria. Further development of cyclothialidine has been precluded due to low growth-inhibitory activity against intact bacterial cells but analogues with improved in vivo efficacy have been synthesized [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 15
Hydrogen bond donors 9
Rotatable bonds 10
Topological polar surface area 303.45
Molecular weight 641.2
XLogP -4.34
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES OCC(C(=O)N1CC[C@H]([C@H]1C(=O)N[C@H]1COC(=O)c2c(C)c(O)cc(c2CSC[C@H](NC1=O)C(=O)N[C@H](C(=O)O)C)O)O)N
Isomeric SMILES OCC(C(=O)N1CC[C@H]([C@H]1C(=O)N[C@H]1COC(=O)c2c(C)c(O)cc(c2CSC[C@H](NC1=O)C(=O)N[C@H](C(=O)O)C)O)O)N
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
InChI Key HMHQWJDFNVJCHA-ZPGBQQFCSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(2S)-2-[[(5S,8R)-5-[[(2S,3R)-1-(2-amino-3-hydroxypropanoyl)-3-hydroxypyrrolidine-2-carbonyl]amino]-13,15-dihydroxy-16-methyl-2,6-dioxo3-oxa-10-thia-7-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-8-carbonyl]amino]propanoic acid
Synonyms
Ro 09-1437
Database Links
Specialist databases
AntibioticDB 704
Other databases
CAS Registry No. 147214-63-9 (source: Scifinder)
ChEBI CHEBI:29566
ChEMBL Ligand CHEMBL4286501
GtoPdb PubChem SID 405560429
PubChem CID 443601
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