Structure Database (LMSD)
Common Name
Anandamide O-phosphate
Systematic Name
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine-O-phosphate
Synonyms
3D model of Anandamide O-phosphate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid (CB) to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as Δ9-THC .1,2 Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).2 The phosphate ester of AEA, AEA-P, has been tested as a water soluble prodrug version of AEA in the treatment of C6 glioma cells in vivo. Here it acts with essentially the same potency as AEA.3 However, when tested for inhibition of AEA binding to isolated rat brain CB1 receptors, AEA-P is about 5-fold less potent as an agonist with a Ki of about 200 nM.4 The phosphate esters of AEA and its analogs are also structural variants of lysophosphatidic acid (LPA). However, the effects of AEA-P on the various LPA receptors have not been tested.
This information has been provided by Cayman Chemical
References
1. Fowler, C.J., Jonsson, K.O., Andersson, A., et al. Inhibition of C6 glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: Variability in response and involement of arachidonic acid. Biochem. Pharmacol. 66(5), 757-767 (2003).
2. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J. Med. Chem. 40(5), 659-667 (1997).
3. Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA 90(16), 7656-7660 (1993).
4. Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258(5090), 1946-1949 (1992).
References
String Representations
InChiKey (Click to copy)
PZPHIQQEQWCEGG-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C22H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)23-20-21-28-29(25,26)27/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)(H2,25,26,27)/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)NCCOP(O)(O)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
0
Aromatic Rings
0
Rotatable Bonds
18
Van der Waals Molecular Volume
450.74
Topological Polar Surface Area
95.86
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
6
logP
6.27
Molar Refractivity
120.12
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Created at
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Updated at
5th Apr 2022