Structure Database (LMSD)

Common Name
Retinol
Systematic Name
Retinol
Synonyms
  • Vitamin A
LM ID
LMPR01090001
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

Vitamin A, also known as all-trans retinol, is an intermediate in retinol metabolism in animals. It is metabolized to retinoic acid , a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). RAR and RXR heterodimerize and act as ligand-dependent transcriptional regulators, with roles in development, reproduction, immunity, organogenesis, and cancer.1,2,3

This information has been provided by Cayman Chemical

References

1. Duong, V., and Rochette-Egly, C. The molecular physiology of nuclear retinoic acid receptors. From health to disease. Biochim. Biophys. Acta 1812(8), 1023-1031 (2011).
2. Rochette-Egly, C., and Germain, P. Dynamic and combinatorial control of gene expression by nuclear retinoic acid receptors (RARs). Nucl. Recept. Signal 7, e005 (2009).
3. Dollé, P. Developmental expression of retinoic acid receptors (RARs). Nucl. Recept. Signal 7, 1-13 (2009).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
FPIPGXGPPPQFEQ-OVSJKPMPSA-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=C/C(/C)=C/CO)=C(C)CC1

Other Databases

Wikipedia
Retinol
KEGG ID
C00473
HMDB ID
HMDB0000305
CHEBI ID
17336
PubChem CID
445354
SwissLipids ID
SLM:000000511
Cayman ID
20241
PDB ID
RTL
GuidePharm ID
4053

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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