Structure Database (LMSD)

Common Name
11-cis-Retinol
Systematic Name
11Z-retinol
Synonyms
LM ID
LMPR01090005
Formula
C20H30O
Exact Mass
Calculate m/z
286.229665
Status
Curated
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Classification

Category
Main Class
Sub Class
Prenol Lipids [PR]
Isoprenoids [PR01]
Retinoids [PR0109]

Biological Context

11-cis Retinol is an isomer of vitamin A . It is formed from vitamin A, via a trans-retinyl ester intermediate, by the enzyme RPE65 in the retinal pigment epithelium and then converted to 11-cis retinal as part of the visual cycle.1,2 11-cis Retinol is an agonist of salamander and human red rod opsins expressed in COS cells and an inverse agonist of salamander red cone opsin, as well as human red and green cone opsins expressed in COS cells.3 It promotes pigment formation in cone, but not rod, photoreceptors.

This information has been provided by Cayman Chemical

References

1. Ala-Laurila, P., Cornwall, M.C., Crouch, R.K., et al. The action of 11-cis-retinol on cone opsins and intact cone photoreceptors. J. Biol. Chem. 284(24), 16492-16500 (2009).
2. Guignard, T.J.P., Jin, M., Pequignot, M.O., et al. FATP1 inhibits 11-cis retinol formation via interaction with the visual cycle retinoid isomerase RPE65 and lecithin: Retinol acyltransferase. J. Biol. Chem. 285(24), 18759-18768 (2010).
3. Rando, R.R. The biochemistry of the visual cycle. Chem. Rev. 101(7), 1881-1896 (2001).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
FPIPGXGPPPQFEQ-IOUUIBBYSA-N
InChi (Click to copy)
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
SMILES (Click to copy)
C1(/C=C/C(/C)=C/C=C\C(\C)=C\CO)=C(C)CCCC1(C)C

Other Databases

KEGG ID
C00899
HMDB ID
HMDB0006216
CHEBI ID
16302
PubChem CID
5280382
SwissLipids ID
SLM:000000983
Cayman ID
33207
GuidePharm ID
6670

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 337.79
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 5.80
Molar Refractivity 93.70

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Updated at
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