myristic acid   Click here for help

GtoPdb Ligand ID: 2806

Synonyms: C14:0 | myristate
PDB Ligand
Compound class: Metabolite
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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 12
Topological polar surface area 37.3
Molecular weight 228.21
XLogP 6.43
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCCCCCCCC(=O)O
Isomeric SMILES CCCCCCCCCCCCCC(=O)O
InChI InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
InChI Key TUNFSRHWOTWDNC-UHFFFAOYSA-N
References
1. Briscoe CP, Tadayyon M, Andrews JL, Benson WG, Chambers JK, Eilert MM, Ellis C, Elshourbagy NA, Goetz AS, Minnick DT et al.. (2003)
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
J Biol Chem, 278 (13): 11303-11. [PMID:12496284]
2. Itoh Y, Kawamata Y, Harada M, Kobayashi M, Fujii R, Fukusumi S, Ogi K, Hosoya M, Tanaka Y, Uejima H et al.. (2003)
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
Nature, 422 (6928): 173-6. [PMID:12629551]
3. Kotarsky K, Nilsson NE, Flodgren E, Owman C, Olde B. (2003)
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
Biochem Biophys Res Commun, 301 (2): 406-10. [PMID:12565875]
4. Nakano M, Kelly EJ, Rettie AE. (2009)
Expression and characterization of CYP4V2 as a fatty acid omega-hydroxylase.
Drug Metab Dispos, 37 (11): 2119-22. [PMID:19661213]
5. Song WK, Clouston P, MacLaren RE. (2019)
Presence of corneal crystals confirms an unusual presentation of Bietti's retinal dystrophy.
Ophthalmic Genet, 40 (5): 461-465. [PMID:31638456]
6. Watson SJ, Brown AJ, Holliday ND. (2012)
Differential signaling by splice variants of the human free fatty acid receptor GPR120.
Mol Pharmacol, 81 (5): 631-42. [PMID:22282525]