butyric acid   Click here for help

GtoPdb Ligand ID: 1059

Synonyms: butanoic acid | butyrate | C4
PDB Ligand Immunopharmacology Ligand
Comment: Butyric acid (butyrate) inhibits class I and II HDACs [2,8].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 37.3
Molecular weight 88.05
XLogP 0.74
No. Lipinski's rules broken 0
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Canonical SMILES CCCC(=O)O
InChI InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
1. Brown AJ, Goldsworthy SM, Barnes AA, Eilert MM, Tcheang L, Daniels D, Muir AI, Wigglesworth MJ, Kinghorn I, Fraser NJ et al.. (2003)
The Orphan G protein-coupled receptors GPR41 and GPR43 are activated by propionate and other short chain carboxylic acids.
J Biol Chem, 278 (13): 11312-9. [PMID:12496283]
2. Fass DM, Shah R, Ghosh B, Hennig K, Norton S, Zhao WN, Reis SA, Klein PS, Mazitschek R, Maglathlin RL et al.. (2010)
Effect of Inhibiting Histone Deacetylase with Short-Chain Carboxylic Acids and Their Hydroxamic Acid Analogs on Vertebrate Development and Neuronal Chromatin.
ACS Med Chem Lett, 2 (1): 39-42. [PMID:21874153]
3. Le Poul E, Loison C, Struyf S, Springael JY, Lannoy V, Decobecq ME, Brezillon S, Dupriez V, Vassart G, Van Damme J et al.. (2003)
Functional characterization of human receptors for short chain fatty acids and their role in polymorphonuclear cell activation.
J Biol Chem, 278 (28): 25481-9. [PMID:12711604]
4. Nilsson NE, Kotarsky K, Owman C, Olde B. (2003)
Identification of a free fatty acid receptor, FFA2R, expressed on leukocytes and activated by short-chain fatty acids.
Biochem Biophys Res Commun, 303 (4): 1047-52. [PMID:12684041]
5. Schaffer JE, Lodish HF. (1994)
Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein.
Cell, 79 (3): 427-36. [PMID:7954810]
6. Schmidt J, Smith NJ, Christiansen E, Tikhonova IG, Grundmann M, Hudson BD, Ward RJ, Drewke C, Milligan G, Kostenis E et al.. (2011)
Selective orthosteric free fatty acid receptor 2 (FFA2) agonists: identification of the structural and chemical requirements for selective activation of FFA2 versus FFA3.
J Biol Chem, 286 (12): 10628-40. [PMID:21220428]
7. Stahl A, Hirsch DJ, Gimeno RE, Punreddy S, Ge P, Watson N, Patel S, Kotler M, Raimondi A, Tartaglia LA et al.. (1999)
Identification of the major intestinal fatty acid transport protein.
Mol Cell, 4 (3): 299-308. [PMID:10518211]
8. Verma MS, Fink MJ, Salmon GL, Fornelos N, Ohara TE, Ryu SH, Vlamakis H, Xavier RJ, Stappenbeck TS, Whitesides GM. (2018)
A Common Mechanism Links Activities of Butyrate in the Colon.
ACS Chem Biol, 13 (5): 1291-1298. [PMID:29584955]
9. Xiong Y, Miyamoto N, Shibata K, Valasek MA, Motoike T, Kedzierski RM, Yanagisawa M. (2004)
Short-chain fatty acids stimulate leptin production in adipocytes through the G protein-coupled receptor GPR41.
Proc Natl Acad Sci USA, 101 (4): 1045-50. [PMID:14722361]