sisomicin   Click here for help

GtoPdb Ligand ID: 10858

Synonyms: Antibiotic 66-40 | Antibiotic 6640 | rickamicin | Sch-13475 | Sch13475 | sisomycin | Sissomicin
Approved drug PDB Ligand
sisomicin is an approved drug
Compound class: Natural product
Comment: Sisomicin is a naturally occurring aminoglycoside antibacterial that has activity against Gram-positive and Gram-negative bacteria [1-2]. It is produced by Micromonospora inyoensis. It is active against some microorganisms that are resistant to other aminoglycosides, and offers synergistic activity against enterococci, staphylocicci, Enterobacteriaceae, and nonfermentative gram-negative bacilli when combined with beta-lactam antibacterials.

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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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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 12
Hydrogen bond donors 8
Rotatable bonds 6
Topological polar surface area 213.72
Molecular weight 447.27
XLogP -3.63
No. Lipinski's rules broken 2

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 NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N
Isomeric SMILES NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N
InChI InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
InChI Key URWAJWIAIPFPJE-YFMIWBNJSA-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
Approved drug? Yes.
IUPAC Name Click here for help
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
International Nonproprietary Names Click here for help
INN number INN
3027 sisomicin
Synonyms Click here for help
Antibiotic 66-40 | Antibiotic 6640 | rickamicin | Sch-13475 | Sch13475 | sisomycin | Sissomicin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sisomicin
Other databases
CAS Registry No. 32385-11-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL221886
DrugBank Ligand DB12604
DrugCentral Ligand 2447
GtoPdb PubChem SID 405560299
PubChem CID 36119
RCSB PDB Ligand SIS
Search Google for chemical match using the InChIKey URWAJWIAIPFPJE-YFMIWBNJSA-N
Search Google for chemicals with the same backbone URWAJWIAIPFPJE
Search PubMed clinical trials sisomicin
Search PubMed titles sisomicin
Search PubMed titles/abstracts sisomicin
UniChem Compound Search for chemical match using the InChIKey URWAJWIAIPFPJE-YFMIWBNJSA-N
UniChem Connectivity Search for chemical match using the InChIKey URWAJWIAIPFPJE-YFMIWBNJSA-N

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MedChemExpress
Sisomicin (links to external site)
Cat. No. HY-B1222A