leinamycin   Click here for help

GtoPdb Ligand ID: 11041

Synonyms: DC-107 | DC107
Comment: Leinamycin is a macrolactam antibiotic (activity against Gram-positive and gram-negative bacteria) that also has potent anti-tumour activity [1,3-4]. It is produced by several species of Streptomyces atroolivaceus. Cytotoxicity against cancer cells hinges upon the compound's 1,3-dioxo-1,2-dithiolane moiety [2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 0
Topological polar surface area 206.41
Molecular weight 510.1
XLogP -1.05
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES C/C/1=C\[C@@H](O)C(=O)/C=C/C=C\c2nc([C@H](NC(=O)C[C@@]3(CC1)S(=O)SC(=O)[C@]3(C)O)C)sc2
Isomeric SMILES C/C/1=C\[C@@H](O)C(=O)/C=C/C=C\c2nc([C@H](NC(=O)C[C@@]3(CC1)S(=O)SC(=O)[C@]3(C)O)C)sc2
InChI InChI=1S/C22H26N2O6S3/c1-13-8-9-22(21(3,29)20(28)32-33(22)30)11-18(27)23-14(2)19-24-15(12-31-19)6-4-5-7-16(25)17(26)10-13/h4-7,10,12,14,17,26,29H,8-9,11H2,1-3H3,(H,23,27)/b6-4-,7-5+,13-10+/t14-,17-,21+,22-,33?/m1/s1
InChI Key ZHTRILQJTPJGNK-FYBAATNNSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(2R,4'R,6R,9E,11R,13E,15Z)-4',11-dihydroxy-2,4',9-trimethyl-1'-oxospiro[19-thia-3,20-diazabicyclo[15.2.1]icosa-1(20),9,13,15,17-pentaene-6,5'-dithiolane]-3',4,12-trione
Synonyms Click here for help
DC-107 | DC107
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 981
Other databases
ChEMBL Ligand CHEMBL360089
GtoPdb PubChem SID 405560482
PubChem CID 9849230
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