18-HETE   Click here for help

GtoPdb Ligand ID: 6924

Compound class: Metabolite or derivative
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 14
Topological polar surface area 57.53
Molecular weight 320.24
XLogP 6.26
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 CCC(CCC=CCC=CCC=CCC=CCCCC(=O)O)O
Isomeric SMILES CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
InChI InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-
InChI Key PPCHNRUZQWLEMF-XBOCNYGYSA-N
References
1. Esperón-Moldes U, Ginarte-Val M, Rodríguez-Pazos L, Fachal L, Martín-Santiago A, Vicente A, Jiménez-Gallo D, Guillén-Navarro E, Sampol LM, González-Enseñat MA et al.. (2020)
Novel CYP4F22 mutations associated with autosomal recessive congenital ichthyosis (ARCI). Study of the CYP4F22 c.1303C>T founder mutation.
PLoS One, 15 (2): e0229025. [PMID:32069299]
2. Feng C, Wang H, Lee M, Zhao J, Lin Z, Yang Y. (2017)
Two missense mutations in CYP4F22 in autosomal recessive congenital ichthyosis.
Clin Exp Dermatol, 42 (1): 98-100. [PMID:27735052]
3. Nilsson T, Ivanov IV, Oliw EH. (2010)
LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22.
Arch Biochem Biophys, 494 (1): 64-71. [PMID:19919823]
4. Nohara T, Ohno Y, Kihara A. (2021)
Impaired production of the skin barrier lipid acylceramide by CYP4F22 ichthyosis mutations.
J Dermatol Sci, 101 (1): 69-71. [PMID:33067036]
5. Ohno Y, Nakamichi S, Ohkuni A, Kamiyama N, Naoe A, Tsujimura H, Yokose U, Sugiura K, Ishikawa J, Akiyama M et al.. (2015)
Essential role of the cytochrome P450 CYP4F22 in the production of acylceramide, the key lipid for skin permeability barrier formation.
Proc Natl Acad Sci U S A, 112 (25): 7707-12. [PMID:26056268]