Structure Database (LMSD)

Common Name
11-cis-retinal
Systematic Name
Synonyms
LM ID
LMPR01090003
Formula
Exact Mass
Calculate m/z
284.214015
Status
Curated


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

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

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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