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monensin   Click here for help

GtoPdb Ligand ID: 14126

Synonyms: monensic acid
Compound class: Natural product
Comment: Monensin is an antibacterial originally isolated from Streptomyces cinnamonensis [1]. It is used in veterinary medicine.
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 11
Hydrogen bond donors 4
Rotatable bonds 10
Topological polar surface area 153.37
Molecular weight 670.87
XLogP 3.37
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 CC[C@]1(CC[C@H]([C@]2(C)CC[C@]3(C[C@@H]([C@@H](C)[C@@H]([C@@H](C)[C@H]([C@H](C)C(=O)O)OC)O3)O)O2)O1)[C@H]4[C@@H](C)C[C@H]([C@@H]5[C@@H](C)C[C@@H](C)[C@@](CO)(O)O5)O4
Isomeric SMILES CC[C@]1(CC[C@@H](O1)[C@@]2(CC[C@@]3(O2)C[C@@H]([C@H]([C@H](O3)[C@@H](C)[C@H]([C@H](C)C(=O)O)OC)C)O)C)[C@H]4[C@H](C[C@@H](O4)[C@@H]5[C@H](C[C@H]([C@@](O5)(CO)O)C)C)C
InChI InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1
InChI Key GAOZTHIDHYLHMS-KEOBGNEYSA-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
(2S,3R,4S)-4-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-ethyl-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid
International Nonproprietary Names Click here for help
INN number INN
2501 monensin
Synonyms Click here for help
monensic acid
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Monensin
Other databases
CAS Registry No. 17090-79-8 (source: Scifinder)
ChEBI CHEBI:27617
ChEMBL Ligand CHEMBL256105
DrugBank Ligand DB11430
DrugCentral Ligand 5580
PubChem CID 441145
Search Google for chemical match using the InChIKey GAOZTHIDHYLHMS-KEOBGNEYSA-N
Search Google for chemicals with the same backbone GAOZTHIDHYLHMS
Search PubMed clinical trials monensin
Search PubMed titles monensin
Search PubMed titles/abstracts monensin
UniChem Compound Search for chemical match using the InChIKey GAOZTHIDHYLHMS-KEOBGNEYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GAOZTHIDHYLHMS-KEOBGNEYSA-N