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lauric acid   Click here for help

GtoPdb Ligand ID: 5534

Synonyms: dodecoic acid | dodecylic acid | duodecyclic acid | n-dodecanoic acid | vulvic acid
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

lauric acid is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 10
Topological polar surface area 37.3
Molecular weight 200.18
XLogP 5.29
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCCCCCCCC(=O)O
Isomeric SMILES CCCCCCCCCCCC(=O)O
InChI InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
InChI Key POULHZVOKOAJMA-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Durairaj P, Fan L, Machalz D, Wolber G, Bureik M. (2019)
Functional characterization and mechanistic modeling of the human cytochrome P450 enzyme CYP4A22.
FEBS Lett, 593 (16): 2214-2225. [PMID:31199497]
2. 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]
3. Powell PK, Wolf I, Lasker JM. (1996)
Identification of CYP4A11 as the major lauric acid omega-hydroxylase in human liver microsomes.
Arch Biochem Biophys, 335 (1): 219-26. [PMID:8914854]
4. Su P, Kaushal KM, Kroetz DL. (1998)
Inhibition of renal arachidonic acid omega-hydroxylase activity with ABT reduces blood pressure in the SHR.
Am J Physiol, 275 (2): R426-38. [PMID:9688677]
5. Wang J, Wu X, Simonavicius N, Tian H, Ling L. (2006)
Medium-chain fatty acids as ligands for orphan G protein-coupled receptor GPR84.
J Biol Chem, 281 (45): 34457-64. [PMID:16966319]
6. Yamaori S, Araki N, Shionoiri M, Ikehata K, Kamijo S, Ohmori S, Watanabe K. (2018)
A Specific Probe Substrate for Evaluation of CYP4A11 Activity in Human Tissue Microsomes and a Highly Selective CYP4A11 Inhibitor: Luciferin-4A and Epalrestat.
J Pharmacol Exp Ther, 366 (3): 446-457. [PMID:29976573]
7. Zöllner A, Dragan CA, Pistorius D, Müller R, Bode HB, Peters FT, Maurer HH, Bureik M. (2009)
Human CYP4Z1 catalyzes the in-chain hydroxylation of lauric acid and myristic acid.
Biol Chem, 390 (4): 313-7. [PMID:19090726]