Katanosin B   Click here for help

GtoPdb Ligand ID: 10970

Synonyms: Lysobactin
Comment: Katanosins (lysobactins) are antibiotic compounds [2]. They have been isolated from Cytophaga [4] or the Gram-negative bacterium Lysobacter sp [5]. Katanosin B is also known as lysobactin. This can now be chemically synthesised [1,6]. Katanosins target bacterial cell wall biosynthesis [3] and they are potent against problematic Gram-positive hospital pathogens such as staphylococci and enterococci.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 32
Hydrogen bond donors 18
Rotatable bonds 25
Topological polar surface area 531.73
Molecular weight 1275.72
XLogP 5.16
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
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Canonical SMILES OCC1NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(OC1=O)c1ccccc1)NC(=O)C(NC(=O)C(CC(C)C)N)CC(C)C)C(C(C)C)O)CC(C)C)CCCN=C(N)N)C(CC)C)C(O)C)C(C(=O)N)O
Isomeric SMILES OCC1NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(OC1=O)c1ccccc1)NC(=O)C(NC(=O)C(CC(C)C)N)CC(C)C)C(C(C)C)O)CC(C)C)CCCN=C(N)N)C(CC)C)C(O)C)C(C(=O)N)O
InChI InChI=1S/C58H97N15O17/c1-12-30(10)39-53(85)71-40(31(11)75)52(84)64-24-38(76)69-42(45(78)47(60)79)55(87)68-37(25-74)57(89)90-46(32-17-14-13-15-18-32)43(73-51(83)36(23-28(6)7)66-48(80)33(59)21-26(2)3)56(88)72-41(44(77)29(8)9)54(86)67-35(22-27(4)5)50(82)65-34(49(81)70-39)19-16-20-63-58(61)62/h13-15,17-18,26-31,33-37,39-46,74-75,77-78H,12,16,19-25,59H2,1-11H3,(H2,60,79)(H,64,84)(H,65,82)(H,66,80)(H,67,86)(H,68,87)(H,69,76)(H,70,81)(H,71,85)(H,72,88)(H,73,83)(H4,61,62,63)
InChI Key KQMKBWMQSNKASI-UHFFFAOYSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
2-amino-N-[1-[[6-(2-amino-1-hydroxy-2-oxoethyl)-15-butan-2-yl-18-[3-(diaminomethylideneamino)propyl]-12-(1-hydroxyethyl)-3-(hydroxymethyl)-24-(1-hydroxy-2-methylpropyl)-21-(2-methylpropyl)-2,5,8,11,14,17,20,23,26-nonaoxo-28-phenyl-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide
Synonyms Click here for help
Lysobactin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 371
Other databases
CAS Registry No. 118374-47-3 (source: PubChem)
GtoPdb PubChem SID 405560411
PubChem CID 197270
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