LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

2,3-dinor-11b-PGF2alpha

Systematic Name

9S,11S,15S-trihydroxy-2,3-dinor-5Z,13E-prostadienoic acid

Synonyms

2,3-dinor-11b-Prostaglandin F2alpha

LM ID

LMFA03010011

Formula

C₁₈H₃₀O₅

Exact Mass

Calculate m/z

326.209325

Sum Composition

FA 18:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

2,3-dinor-11β-Prostaglandin F2α (2,3-dinor-11β-PGF2α) is a metabolite of PGD2 .^1,2 Urinary excretion of 2,3-dinor-11β-PGF2α is increased in patients with mast cell activation disease (MCAD) and has been used as a marker of increased PGD2 levels.³ 2,3-dinor-11 β-PGF2α levels are also increased in the urine of patients with asthma and are positively correlated with impaired lung function.⁴

This information has been provided by Cayman Chemical

References

1. Liston, T.E., and Roberts, L.J., II Metabolic fate of radiolabeled prostaglandin D2 in a normal human male volunteer. The Journal of Biological Chemisty 260(24), 13172-13180 (1985).

2. Song, W.L., Wang, M., Ricciotti, E., et al. Tetranor PGDM, an abundant urinary metabolite reflects biosynthesis of prostaglandin D2 in mice and humans. The Journal of Biological Chemisty 283(2), 1179-1188 (2008).

3. Castells, M., and Butterfield, J. Mast cell activation syndrome and mastocytosis: Initial treatment options and long-term management. J. Allergy Clin. Immunol. Pract. 7(4), 1097-1106 (2019).

4. Kolmert, J., Gómez, C., Balgoma, D., et al. Urinary leukotriene E4 and prostaglandin D2 metabolites increase in adult and childhood severe asthma characterized by type 2 inflammation. A clinical observational study. Am. J. Respir. Crit. Care Med. 203(1), 37-53 (2021).

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)

IDKLJIUIJUVJNR-KSJYGFEGSA-N

InChi (Click to copy)

InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h5-6,10-11,13-17,19-21H,2-4,7-9,12H2,1H3,(H,22,23)/b6-5-,11-10+/t13-,14+,15+,16-,17-/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CC(=O)O