GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

isepamicin   Click here for help

GtoPdb Ligand ID: 12136

Synonyms: HAPA-B | Sch 21420
Approved drug
isepamicin is an approved drug
Compound class: Synthetic organic
Comment: Isepamicin is a semisynthetic derivative of gentamicin B, with activity against Gram-negative bacteria [2]. It belongs to the aminoglycoside class of antibacterial compounds.
2D Structure
Click here for help

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.

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

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.

✖
Hydrogen bond acceptors 17
Hydrogen bond donors 12
Rotatable bonds 10
Topological polar surface area 297.72
Molecular weight 569.29
XLogP -5.87
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
Click here for help

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/)

✖
Canonical SMILES NC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)O)O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1O)O)O)O
Isomeric SMILES C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CN)O)O)O)N)NC(=O)[C@H](CN)O)O
InChI InChI=1S/C22H43N5O12/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-/m0/s1
InChI Key UDIIBEDMEYAVNG-ZKFPOVNWSA-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 Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
(2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxypropanamide
International Nonproprietary Names Click here for help
INN number INN
5849 isepamicin
Synonyms Click here for help
HAPA-B | Sch 21420
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Isepamicin
Other databases
CAS Registry No. 58152-03-7 (source: Scifinder)
ChEMBL Ligand CHEMBL272080
DrugBank Ligand DB13540
DrugCentral Ligand 1486
GtoPdb PubChem SID 472319258
PubChem CID 3037209
Search Google for chemical match using the InChIKey UDIIBEDMEYAVNG-ZKFPOVNWSA-N
Search Google for chemicals with the same backbone UDIIBEDMEYAVNG
Search PubMed clinical trials isepamicin
Search PubMed titles isepamicin
Search PubMed titles/abstracts isepamicin
UniChem Compound Search for chemical match using the InChIKey UDIIBEDMEYAVNG-ZKFPOVNWSA-N
UniChem Connectivity Search for chemical match using the InChIKey UDIIBEDMEYAVNG-ZKFPOVNWSA-N