hesperetin   Click here for help

GtoPdb Ligand ID: 10953

Synonyms: 3',5,7-Trihydroxy-4'-methoxyflavanone | NP-13 | NSC-57654
PDB Ligand
Compound class: Natural product
Comment: Hesperetin is a natural flavonoid. It has antibacterial activity against Gram-negative H. pylori [1].

hesperetin is commercially available from our sponsors

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 1
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 96.22
Molecular weight 302.08
XLogP 1.68
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 COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
Isomeric SMILES COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
InChI InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
InChI Key AIONOLUJZLIMTK-AWEZNQCLSA-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)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms Click here for help
3',5,7-Trihydroxy-4'-methoxyflavanone | NP-13 | NSC-57654
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Hesperetin
Other databases
BindingDB Ligand 23418
CAS Registry No. 520-33-2 (source: PubChem)
ChEBI CHEBI:28230
ChEMBL Ligand CHEMBL399121
DrugBank Ligand DB01094
DrugCentral Ligand 1362
GtoPdb PubChem SID 405560394
LIPID MAPS LMPK12140003
PubChem CID 72281
RCSB PDB Ligand 6JP
Search Google for chemical match using the InChIKey AIONOLUJZLIMTK-AWEZNQCLSA-N
Search Google for chemicals with the same backbone AIONOLUJZLIMTK
UniChem Compound Search for chemical match using the InChIKey AIONOLUJZLIMTK-AWEZNQCLSA-N
UniChem Connectivity Search for chemical match using the InChIKey AIONOLUJZLIMTK-AWEZNQCLSA-N

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MedChemExpress
Hesperetin (links to external site)
Cat. No. HY-N0168