Structure Database (LMSD)
Common Name
8R-HETE
Systematic Name
8R-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid
Synonyms
- 8-HETE
3D model of 8R-HETE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
8(R)-HETE is biosynthesized by lipoxygenation of arachidonic acid in marine invertebrates such as gorgonian corals and starfish.1,2 Stereochemical assignment of the (R) enantiomer is based on comparison of chiral HPLC retention times to published results. 3
This information has been provided by Cayman Chemical
References
2. Brash, A.R., Baertschi, S.W., Ingram, C.D., et al. On non-cyclooxygenase prostaglandin synthesis in the sea whip coral, Plexaura Homomalla: An 8(R)-lipoxygenase pathway leads to formation of an α-ketol and a racemic prostanoid. J. Biol. Chem. 262(33), 15829-15839 (1987).
3. Meijer, L., Brash, A.R., Bryant, R.W., et al. Stereospecific induction of starfish oocyte maturation by (8R)-hydroxyeicosatetraenoic acid. J. Biol. Chem. 261(36), 17040-17047 (1986).
String Representations
InChiKey (Click to copy)
NLUNAYAEIJYXRB-GTYUHVKWSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m0/s1
SMILES (Click to copy)
C(/C=C/[C@H](O)C/C=C\CCCC(=O)O)=C/C/C=C\CCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
367.73
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
5.47
Molar Refractivity
97.94
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Created at
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Updated at
21st Nov 2021