apigenin   Click here for help

GtoPdb Ligand ID: 4136

PDB Ligand
Compound class: Natural product
Comment: Apigenin is a plant-derived flavonoid. It has been found in coriander, celery and chili peppers.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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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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Click here for structure editor
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/)
References
1. Amin F, Ibrahim MAA, Rizwan-Ul-Hasan S, Khaliq S, Gabr GA, Muhammad, Khan A, Sidhom PA, Tikmani P, Shawky AM et al.. (2022)
Interactions of Apigenin and Safranal with the 5HT1A and 5HT2A Receptors and Behavioral Effects in Depression and Anxiety: A Molecular Docking, Lipid-Mediated Molecular Dynamics, and In Vivo Analysis.
Molecules, 27 (24). [PMID:36557792]
2. Anand P, Singh B. (2013)
Flavonoids as lead compounds modulating the enzyme targets in Alzheimer’s disease.
Medicinal Chemistry Research, 22: 3061–3075. DOI: 10.1007/s00044-012-0353-y
3. Androutsopoulos VP, Papakyriakou A, Vourloumis D, Spandidos DA. (2011)
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
Bioorg Med Chem, 19 (9): 2842-9. [PMID:21482471]
4. Iakovleva I, Brännström K, Nilsson L, Gharibyan AL, Begum A, Anan I, Walfridsson M, Sauer-Eriksson AE, Olofsson A. (2015)
Enthalpic Forces Correlate with the Selectivity of Transthyretin-Stabilizing Ligands in Human Plasma.
J Med Chem, 58 (16): 6507-15. [PMID:26214366]
5. Siddique YH, Rahul, Ara G, Afzal M, Varshney H, Gaur K, Subhan I, Mantasha I, Shahid M. (2022)
Beneficial effects of apigenin on the transgenic Drosophila model of Alzheimer's disease.
Chem Biol Interact, 366: 110120. [PMID:36027948]
6. Verkman AS, Galietta LJ. (2009)
Chloride channels as drug targets.
Nat Rev Drug Discov, 8 (2): 153-71. [PMID:19153558]