12-hydroxyheptadecatrienoic acid   Click here for help

GtoPdb Ligand ID: 6159

Abbreviated name: 12-HHT
Synonyms: 12S-HHTrE
Compound class: Metabolite
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 57.53
Molecular weight 280.2
XLogP 5.03
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCCCCC(C=CC=CCC=CCCCC(=O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O)O
InChI InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1
InChI Key KUKJHGXXZWHSBG-WBGSEQOASA-N
References
1. Geng Y, Li W, Wong NK, Xue F, Li Q, Zhang Y, Xu J, Deng Z, Zhou Y. (2024)
Discovery of Artemisinins as Microsomal Prostaglandins Synthase-2 Inhibitors for the Treatment of Colorectal Cancer via Chemoproteomics.
J Med Chem, 67 (3): 2083-2094. [PMID:38287228]
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. Takusagawa F. (2013)
Microsomal prostaglandin E synthase type 2 (mPGES2) is a glutathione-dependent heme protein, and dithiothreitol dissociates the bound heme to produce active prostaglandin E2 synthase in vitro.
J Biol Chem, 288 (14): 10166-10175. [PMID:23426368]
4. Yamada T, Komoto J, Watanabe K, Ohmiya Y, Takusagawa F. (2005)
Crystal structure and possible catalytic mechanism of microsomal prostaglandin E synthase type 2 (mPGES-2).
J Mol Biol, 348 (5): 1163-76. [PMID:15854652]
5. Yamada T, Takusagawa F. (2007)
PGH2 degradation pathway catalyzed by GSH-heme complex bound microsomal prostaglandin E2 synthase type 2: the first example of a dual-function enzyme.
Biochemistry, 46 (28): 8414-24. [PMID:17585783]
6. 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]