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

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

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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