apigenin   Click here for help

GtoPdb Ligand ID: 4136

PDB Ligand
Compound class: Natural product
Comment: Molecular docking studies show interactions with 5-HT1A and 5-HT2A receptors [1]. In vivo reductions in depressive and anxiety symptoms have been demonstrated in rodents.
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 1
Topological polar surface area 90.9
Molecular weight 270.05
XLogP 3.67
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 Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O
Isomeric SMILES Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O
InChI InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
InChI Key KZNIFHPLKGYRTM-UHFFFAOYSA-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
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Database Links Click here for help
BitterDB Ligand 859
CAS Registry No. 520-36-5 (source: Scifinder)
ChEBI CHEBI:18388
ChEMBL Ligand CHEMBL28
DrugBank Ligand DB07352
GtoPdb PubChem SID 178100958
LIPID MAPS LMPK12110005
PubChem CID 5280443
RCSB PDB Ligand AGI
Search Google for chemical match using the InChIKey KZNIFHPLKGYRTM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KZNIFHPLKGYRTM
UniChem Compound Search for chemical match using the InChIKey KZNIFHPLKGYRTM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KZNIFHPLKGYRTM-UHFFFAOYSA-N
Wikipedia Apigenin