LIPID MAPS

Structure Database (LMSD)

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Common Name

12S-HHTrE

Systematic Name

12S-hydroxy-5Z,8E,10E-heptadecatrienoic acid

Synonyms

12-HHTrE
12-HHT

LM ID

LMFA03050002

Formula

C₁₇H₂₈O₃

Exact Mass

Calculate m/z

280.203845

Sum Composition

FA 17:3;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

12(S)-HHTrE is a product of the cyclooxygenase (COX) pathway and one of the primary arachidonic acid metabolites of human platelets.¹ It is biosynthesized by thromboxane (TXA2) synthase from prostaglandin H2 (PGH2) concurrently with TXA2. 12(S)-HHTrE is a natural lipid agonist of the leukotriene B2 receptor BLT2 in vivo that induces chemotaxis of mast cells and accelerates wound closure.^2,3 12(S)-HHTrE is avidly oxidized to 12-oxoHTrE by porcine 15-hydroxy PGDH.⁴

This information has been provided by Cayman Chemical

References

1. Liu, M., Saeki, K., Matsunobu, T., et al. 12-hydroxyheptadecatrienoic acid promotes epidermal wound healing by accelerating keratinocyte migration via the BLT2 receptor. J. Exp. Med. 211(6), 1063-1078 (2014).

2. Okuno, T., Iizuka, Y., Okazaki, H., et al. 12(S)-hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2. J. Exp. Med. 205(4), 759-766 (2008).

3. Diczfalusy, U., Falardeau, P., and Hammarström, S. Conversion of prostaglandin endoperoxides to C17-hydroxy acids catalyzed by human platelet thromboxane synthase. FEBS Lett. 84, 271-274 (1977).

4. Liu, Y., Yoden, K., Shen, R.F., et al. 12-L-Hydroxy-5,8,10-heptadecatrienoic acid (HHT) is an excellent substrate for NAD+-dependent 15-hydroxyprostaglandin dehydrogenase. Biochem. Biophys. Res. Commun. 129, 268-274 (1985).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

KUKJHGXXZWHSBG-WBGSEQOASA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C(=C/C/C=C/C=C/[C@@H](O)CCCCC)/CCCC(=O)O