Structure Database (LMSD)
Common Name
13,14-dihydro-15-keto-PGE2
Systematic Name
9,15-dioxo-11R-hydroxy-5Z-prostenoic acid
Synonyms
- 13,14-dihydro-15-keto-Prostaglandin E2
LM ID
LMFA03010031
Formula
Exact Mass
Calculate m/z
352.224975
Sum Composition
Status
Curated
3D model of 13,14-dihydro-15-keto-PGE2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
13,14-dihydro-15-keto Prostaglandin E2 (13,14-dihydro-15-keto PGE2) is a metabolite of PGE2 and the primary PGE2 metabolite in plasma.1,2 It is formed from PGE2 via a 15-keto PGE2 intermediate by 15-oxo-PG Δ13 reductase.2 Unlike PGE2, 13,14-dihydro-15-keto PGE2 does not bind effectively to the PGE2 receptors EP2 and EP4 expressed in CHO cells (Kis = 12 and 57 µM, respectively) or induce adenylate cyclase activity in the same cells (EC50s = >18 and >38 µM, respectively). Levels of 13,14-dihydro-15-keto PGE2 are increased in the plasma of women in the third trimester of pregnancy and in women during and immediately after labor and delivery.3 Levels of 13,14-dihydro-15-keto PGE2 levels are decreased in tumor tissue compared to adjacent non-cancerous tissue isolated from patients with non-small cell lung cancer (NSCLC).4
This information has been provided by Cayman Chemical
References
1. Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E1 and E2 in man. The Journal of Biological Chemisty 246(22), 6713-6721 (1971).
2. Nishigaki, N., Negishi, M., and Ichikawa, A. Two Gs-coupled prostaglandin E receptor subtypes, EP2 and EP4, differ in desensitization and sensitivity to the metabolic inactivation of the agonist. Mol. Pharmacol. 50(4), 1031-1037 (1996).
4. Hughes, D., Otani, T., Yang, P., et al. NAD+-dependent 15-hydroxyprostaglandin dehydrogenase regulates levels of bioactive lipids in non-small cell lung cancer. Cancer Prev. Res. (Phila.) 1(4), 241-249 (2008).
Reactions
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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
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
String Representations
InChiKey (Click to copy)
CUJMXIQZWPZMNQ-XYYGWQPLSA-N
InChi (Click to copy)
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-17,19,23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,19-/m1/s1
SMILES (Click to copy)
[C@H]1(CCC(=O)CCCCC)[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O
Other Databases
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR1712
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
375.59
Topological Polar Surface Area
91.67
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
3.97
Molar Refractivity
96.75
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Updated at
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