LIPID MAPS

Structure Database (LMSD)

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Common Name

13S-HOTrE(gamma)

Systematic Name

13S-hydroxy-6Z,9Z,11E-octadecatrienoic acid

Synonyms

6(Z),9(Z),11(E)-13S-HOTrE

LM ID

LMFA02000173

Formula

C₁₈H₃₀O₃

Exact Mass

Calculate m/z

294.219496

Sum Composition

FA 18:3;O

Status

Curated

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View Mass spectra (Pace-Asciak collection) (2)

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Classification

Biological Context

13(S)-HOTrE(γ) is an oxylipin, inhibitor of 5-lipoxygenase (5-LO; IC50 = 29 µM for the rat enzyme), and an active metabolite of the ω-6 fatty acid γ-linolenic acid.^1,2,3 It is formed from GLA by 12-LO and 15-LO-2. Vitreous levels of 13(S)-HOTrE(γ) are decreased in patients with proliferative diabetic retinopathy.⁴ Levels of 13(S)-HOTrE(γ) are also decreased in the amniotic fluid of patients with clinical chorioamnionitis at term following spontaneous labor and in the plasma of patients with pulmonary hypertension.^5,6

This information has been provided by Cayman Chemical

References

1. Haviv, F., Ratajczyk, J.D., DeNet, R.W., et al. Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues. J. Med. Chem. 30(2), 254-263 (1987).

2. Hamberg, M. ω6-Oxygenation of 6,9,12-octadecatrienoic acid in human platelets. Biochem. Biophys. Res. Commun. 117, 593-600 (1983).

3. Joshi, N., Hoobler, E.K., Perry, S., et al. Kinetic and structural investigations into the allosteric and pH effect on the substrate specificity of human epithelial 15-lipoxygenase-2. Biochemistry 52(45), 8026-8035 (2013).

4. Zhao, T., Wang, Y., Guo, X., et al. Altered oxylipin levels in human vitreous indicate imbalance in pro-/anti-inflammatory homeostasis in proliferative diabetic retinopathy. Exp. Eye Res. 214, 108799 (2022).

5. Maddipati, K.R., Romero, R., Chaiworapongsa, T., et al. Lipidomic analysis of patients with microbial invasion of the amniotic cavity reveals up-regulation of leukotriene B4. The FASEB Journal (2016).

6. McNeill, J.N., Roshandelpoor, A., Alotaibi, M., et al. The association of eicosanoids and eicosanoid-related metabolites with pulmonary hypertension. Eur. Respir .J. 62(4), 2300561 (2023).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipid Mediator Quantification in Isolated Human and Guinea Pig Airways: An Expanded Approach for Respiratory Research.,
Anal Chem, 2018

Pubmed ID: 30056696

DOI: 10.1021/acs.analchem.8b01651

String Representations

InChiKey (Click to copy)

HNBLUNXZQNJFRB-KYLWABQHSA-N

InChi (Click to copy)

InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h4,6-7,9,12,15,17,19H,2-3,5,8,10-11,13-14,16H2,1H3,(H,20,21)/b6-4-,9-7-,15-12+/t17-/m0/s1

SMILES (Click to copy)

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