Structure Database (LMSD)
Common Name
11-cis-retinal
Systematic Name
Synonyms
3D model of 11-cis-retinal
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
11-cis Retinal is a chromophore that binds to opsin in the mammalian visual system as an inverse agonist forming the inactive conformation of rhodopsin.1 When 11-cis retinal absorbs a photon of light, it isomerizes to form all-trans retinal beginning the phototransduction cycle, which is the basis for mammalian vision. A G121L mutation in opsin allows 11-cis retinal to bind as a partial agonist and activate rhodopsin in the absence of light.2 In a moth model of carotenoid deficiency-induced low visual sensitivity, 11-cis retinal application to compound eyes restored visual sensitivity almost completely.3
This information has been provided by Cayman Chemical
References
1. Tradtrantip, L., Sonawane, N.D., Namkung, W., et al. Nanomolar potency pyrimido-pyrrolo-quinoxalinedione CFTR inhibitor reduces cyst size in a polycystic kidney disease model. J. Med. Chem. 52(20), 6447-6455 (2009).
2. Bennett, R.R., and White, R.H. 11-cis retinal restores visual function in vitamin A-deficient Manduca. Vis. Neurosci. 6(5), 473-479 (1991).
3. Han, M., Lou, J., Nakanishi, K., et al. Partial agonist activity of 11-cis-retinal in rhodopsin mutants. The Journal of Biological Chemisty 272(37), 23081-23085 (1997).
String Representations
InChiKey (Click to copy)
NCYCYZXNIZJOKI-IOUUIBBYSA-N
InChi (Click to copy)
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
SMILES (Click to copy)
C1C(C)(C)C(/C=C/C(/C)=C/C=C\C(\C)=C\C=O)=C(C)CC1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
1
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
335.15
Topological Polar Surface Area
17.07
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
1
logP
5.72
Molar Refractivity
92.19
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Updated at
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