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
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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Created at
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Updated at
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