12S-HPETE   Click here for help

GtoPdb Ligand ID: 2481

Synonyms: 12-(S)-HPETE | 12-(S)-hydroperoxyeicosatetraenoic acid
Compound class: Metabolite
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 15
Topological polar surface area 66.76
Molecular weight 336.23
XLogP 6.27
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCC=CCC(C=CC=CCC=CCCCC(=O)O)OO
Isomeric SMILES CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)OO
InChI InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1
InChI Key ZIOZYRSDNLNNNJ-LQWMCKPYSA-N
References
1. Hwang SW, Cho H, Kwak J, Lee SY, Kang CJ, Jung J, Cho S, Min KH, Suh YG, Kim D et al.. (2000)
Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances.
Proc Natl Acad Sci USA, 97 (11): 6155-60. [PMID:10823958]
2. Okuno T, Iizuka Y, Okazaki H, Yokomizo T, Taguchi R, Shimizu T. (2008)
12(S)-Hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2.
J Exp Med, 205 (4): 759-66. [PMID:18378794]
3. Yokomizo T, Kato K, Hagiya H, Izumi T, Shimizu T. (2001)
Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2.
J Biol Chem, 276 (15): 12454-9. [PMID:11278893]