myristic acid   Click here for help

GtoPdb Ligand ID: 2806

Synonyms: C14:0 | myristate
PDB Ligand
Compound class: Metabolite
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 CDK toolkit. 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 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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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.

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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]