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

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
Pubmed ID: 20671299

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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