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leinamycin   Click here for help

GtoPdb Ligand ID: 11041

Synonyms: DC-107 | DC107
Compound class: Natural product
Comment: Leinamycin is a macrolactam antibacterial (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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
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 Leinamycin, DC107
Other databases
ChEMBL Ligand CHEMBL360089
GtoPdb PubChem SID 405560482
PubChem CID 9849230
Search Google for chemical match using the InChIKey ZHTRILQJTPJGNK-FYBAATNNSA-N
Search Google for chemicals with the same backbone ZHTRILQJTPJGNK
UniChem Compound Search for chemical match using the InChIKey ZHTRILQJTPJGNK-FYBAATNNSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZHTRILQJTPJGNK-FYBAATNNSA-N