Structure Database (LMSD)
Common Name
PGA2
Systematic Name
9-oxo-15S-hydroxy-5Z,10Z,13E-prostatrienoic acid
Synonyms
- Prostaglandin A2
LM ID
LMFA03010035
Formula
Exact Mass
Calculate m/z
334.21441
Sum Composition
Status
Curated
3D model of PGA2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Prostaglandin A2 (PGA2) is a naturally occurring prostaglandin in gorgonian corals where it may function in self defense. It is generally not present in mammals. PGA2 has low biological potency in most bioassays, but it does show some antiviral/antitumor activity.1 At a 25 µM concentration, PGA2 blocks the cell cycle progression of NIH 3T3 cells at the G1 and G2/M phase.2 It has also been shown to act as a vasodilator with natriuretic properties.3
This information has been provided by Cayman Chemical
References
1. Fukushima, M., Kato, T., Narumiya, S., et al. Prostaglandin A and J: Antitumor and antiviral prostaglandins. Adv. Prostaglandin Thromboxane Leukot. Res. 19, 415-418 (1989).
2. Frolich, J.C., Sweetman, B.J., Carr, K., et al. Assessment of the levels of PGA2 in human plasma by gas chromatography-mass spectrometry. Prostaglandins 10(1), 185-195 (1975).
3. Hitomi, M., Shu, J., Strom, D., et al. Prostaglandin A2 blocks the activation of G1 phase cyclin-dependent kinase without altering mitogen-activated protein kinase stimulation. The Journal of Biological Chemisty 271(16), 9376-9383 (1996).
Reactions
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String Representations
InChiKey (Click to copy)
MYHXHCUNDDAEOZ-FOSBLDSVSA-N
InChi (Click to copy)
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
1
Aromatic Rings
0
Rotatable Bonds
12
Van der Waals Molecular Volume
364.16
Topological Polar Surface Area
74.60
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
4.34
Molar Refractivity
96.17
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Updated at
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