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
3D model of 11beta-PGF2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
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
Admin
Created at
-
Updated at
14th Jan 2025