Structure Database (LMSD)

Common Name
Tetranor-PGEM
Systematic Name
11R-hydroxy-9,15-dioxo-2,3,4,5-tetranor-prostan-1,20-dioic acid
Synonyms
  • Tetranor-Prostaglandin EM
LM ID
LMFA03010032
Formula
C16H24O7
Exact Mass
Calculate m/z
328.152205
Sum Composition
FA 16:4;O5
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

Biological Context

tetranor-Prostaglandin E metabolite (tetranor-PGEM) is the major urinary metabolite of PGE2 .1 Urine levels of tetranor-PGEM are increased in patients with diabetic nephropathy.2 Increased urine levels are also associated with a higher risk of breast cancer in postmenopausal women with a body mass index (BMI) of less than 25 kg/m2.3

This information has been provided by Cayman Chemical

References

1. Morita, Y., Kurano, M., Sakai, E., et al. Simultaneous analyses of urinary eicosanoids and related mediators identified tetranor-prostaglandin E metabolite as a novel biomarker of diabetic nephropathy. J. Lipid Res. 62, 100120 (2021).
2. Cui, Y., Shu, X.O., Gao, Y.T., et al. Urinary prostaglandin E2 metabolite and breast cancer risk. Cancer Epidemiol. Biomarkers Prev. 23(12), 2866-2873 (2014).
3. Neale, J.R., and Dean, B.J. Liquid chromatography-tandem mass spectrometric quantification of the dehydration product of tetranor PGE-M, the major urinary metabolite of prostaglandin E2 in human urine. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 871(1), 72-77 (2008).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Liquid chromatography-tandem mass spectrometric quantification of the dehydration product of tetranor PGE-M, the major urinary metabolite of prostaglandin E(2) in human urine.,
J Chromatogr B Analyt Technol Biomed Life Sci, 2008
Pubmed ID: 18632314

String Representations

InChiKey (Click to copy)
ZJAZCYLYLVCSNH-JHJVBQTASA-N
InChi (Click to copy)
InChI=1S/C16H24O7/c17-10(3-1-2-4-15(20)21)5-6-11-12(7-8-16(22)23)14(19)9-13(11)18/h11-13,18H,1-9H2,(H,20,21)(H,22,23)/t11-,12-,13-/m1/s1
SMILES (Click to copy)
[C@H]1(CCC(=O)CCCCC(=O)O)[C@H](O)CC(=O)[C@@H]1CCC(=O)O

Other Databases

CHEBI ID
73965
PubChem CID
161468
Cayman ID
14840

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 323.97
Topological Polar Surface Area 128.97
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 1.70
Molar Refractivity 80.34

Admin

Created at
-
Updated at
-