phenylbutyrate   Click here for help

GtoPdb Ligand ID: 8480

Synonyms: 4-phenylbutanoic acid | Ammonaps® | Buphenyl® | gamma-phenylbutyric acid | triButyrate
Approved drug PDB Ligand
phenylbutyrate is an approved drug (FDA (1996), EMA (1999))
Compound class: Synthetic organic
Comment: The salt, sodium phenylbutyrate (PubChem CID 5258) is an inhibitor of histone deacetylase (HDAC) activity [2-3].
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 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 37.3
Molecular weight 164.08
XLogP 2.19
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 OC(=O)CCCc1ccccc1
Isomeric SMILES OC(=O)CCCc1ccccc1
InChI InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)
InChI Key OBKXEAXTFZPCHS-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 Synthetic organic
Approved drug? Yes (FDA (1996), EMA (1999))
IUPAC Name Click here for help
4-Phenylbutanoic acid
Synonyms Click here for help
4-phenylbutanoic acid | Ammonaps® | Buphenyl® | gamma-phenylbutyric acid | triButyrate
Database Links Click here for help
ChEMBL Ligand CHEMBL1469
DrugCentral Ligand 24
GtoPdb PubChem SID 252166688
PubChem CID 4775
RCSB PDB Ligand CLT
Search Google for chemical match using the InChIKey OBKXEAXTFZPCHS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OBKXEAXTFZPCHS
UniChem Compound Search for chemical match using the InChIKey OBKXEAXTFZPCHS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OBKXEAXTFZPCHS-UHFFFAOYSA-N
Wikipedia Sodium phenylbutyrate