propanoic acid   Click here for help

GtoPdb Ligand ID: 1062

Synonyms: propionate
PDB Ligand
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 37.3
Molecular weight 74.04
XLogP 0.17
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CCC(=O)O
Isomeric SMILES CCC(=O)O
InChI InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
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. 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]
3. 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]
4. 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]
5. 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]