Structure Database (LMSD)

Common Name
11beta-PGF2
Systematic Name
9S,11S,15S-trihydroxy-5Z,13E-prostadienoic acid
Synonyms
  • 11beta-Prostaglandin F2
  • 9alpha,11beta-PGF2
  • 11beta-PGF2alpha
LM ID
LMFA03010036
Formula
Exact Mass
Calculate m/z
354.240626
Sum Composition
Status
Curated


Classification

Biological Context

11β-Prostaglandin F2α (11β-PGF2α) is the primary metabolite of PGD2 .1 It is formed from PGD2 via the NADPH-dependent aldo-keto reductase PGF synthase (PGFS) in the liver or lung.2 11β-PGF2α induces contraction of isolated cat iris sphincter, which endogenously expresses high levels of PGF2α (FP) receptors, with an EC50 value of 0.045 µM.1 It also induces contraction of isolated human bronchial smooth muscle when used at concentrations ranging from 0.1 to 30 µM.3 11β-PGF2α (0.1 and 1 µM) induces phosphorylation of ERK and CREB, as well as increases the viability of MCF-7 breast cancer cells stably expressing the FP receptor when used at concentrations of 0.1 and 1 µM.4

This information has been provided by Cayman Chemical

References

3. Giles, H., Bolofo, M.L., Lydford, S.J., et al. A comparative study of the prostanoid receptor profile of 9α 11 β-prostaglandin F2 and prostaglandin D2. Br. J. Pharmacol. 104(2), 541-549 (1991).

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)
PXGPLTODNUVGFL-ZWAKLXPCSA-N
InChi (Click to copy)
InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19-/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\CCCC(=O)O

Other Databases

KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR1719
PubChem CID
SwissLipids ID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 378.23
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 3.90
Molar Refractivity 99.68

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Created at
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Updated at
14th Jan 2025