9-hydroxystearic acid   Click here for help

GtoPdb Ligand ID: 13240

Synonyms: 9-hydroxy-octadecanoic acid | 9-Hydroxyoctadecanoic acid
PDB Ligand
Compound class: Metabolite
Comment: 9-hydroxystearic acid (9-HSA) is an endogenous saturated fatty acid ligand of the free fatty acid receptor 4 (FFAR4, formerly GPR120) [1]. At the short FFAR4 isoform, 9-HSA shows no bias in signalling via Gi or Gq pathways.
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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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 3
Hydrogen bond donors 2
Rotatable bonds 16
Topological polar surface area 57.53
Molecular weight 300.48
XLogP 6.62
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 CCCCCCCCCC(CCCCCCCC(=O)O)O
Isomeric SMILES CCCCCCCCCC(CCCCCCCC(=O)O)O
InChI InChI=1S/C18H36O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)
InChI Key RKHXDCVAPIMDMG-UHFFFAOYSA-N
Classification Click here for help
Compound class Metabolite
IUPAC Name Click here for help
9-hydroxyoctadecanoic acid
Synonyms Click here for help
9-hydroxy-octadecanoic acid | 9-Hydroxyoctadecanoic acid
Database Links Click here for help
ChEBI CHEBI:136638
ChEMBL Ligand CHEMBL1093742
GtoPdb PubChem SID 491300022
LIPID MAPS LMFA02000127
PubChem CID 9570127
RCSB PDB Ligand 7NR
Search Google for chemical match using the InChIKey RKHXDCVAPIMDMG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RKHXDCVAPIMDMG
UniChem Compound Search for chemical match using the InChIKey RKHXDCVAPIMDMG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RKHXDCVAPIMDMG-UHFFFAOYSA-N