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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Physico-chemical Properties
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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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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/)

References
1. Gardian G, Browne SE, Choi DK, Klivenyi P, Gregorio J, Kubilus JK, Ryu H, Langley B, Ratan RR, Ferrante RJ et al.. (2005)
Neuroprotective effects of phenylbutyrate in the N171-82Q transgenic mouse model of Huntington's disease.
J Biol Chem, 280 (1): 556-63. [PMID:15494404]
2. Iannitti T, Palmieri B. (2011)
Clinical and experimental applications of sodium phenylbutyrate.
Drugs R D, 11 (3): 227-49. [PMID:21902286]
3. Ryu H, Smith K, Camelo SI, Carreras I, Lee J, Iglesias AH, Dangond F, Cormier KA, Cudkowicz ME, Brown Jr RH et al.. (2005)
Sodium phenylbutyrate prolongs survival and regulates expression of anti-apoptotic genes in transgenic amyotrophic lateral sclerosis mice.
J Neurochem, 93 (5): 1087-98. [PMID:15934930]