Structure Database (LMSD)

Common Name
Retinal
Systematic Name
Retinal
Synonyms
LM ID
LMPR01090002
Formula
C20H28O
Exact Mass
Calculate m/z
284.214015
Status
Curated
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Classification

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

Biological Context

all-trans Retinal is a natural retinoid that is derived from vitamin A. It is the oxidation product of all-trans retinol and associates with cellular retinol-binding protein-I (CRBP-I) and CRBP-II (Kds = 50 and 90 nM, respectively), which are involved in the intracellular transport of retinol.1 all-trans Retinal is also an intermediate of the phototransduction pathway of photoreceptors, including rhodopsin and bacterial opsins.2 As a chemically reactive aldehyde, all-trans retinal can form toxic conjugates with proteins and lipids, leading to degeneration of the retina.2

This information has been provided by Cayman Chemical

References

1. Kiser, P.D., Golczak, M., Maeda, A., et al. Key enzymes of the retinoid (visual) cycle in vertebrate retina. Biochim. Biophys. Acta 1821(1), 137-151 (2012).
2. Noy, N. Retinoid-binding proteins: Mediators of retinoid action. Biochem. J. 348(Pt. 3), 481-495 (2000).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
NCYCYZXNIZJOKI-OVSJKPMPSA-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

Wikipedia
Retinal
KEGG ID
C00376
HMDB ID
HMDB0001358
CHEBI ID
17898
PubChem CID
638015
SwissLipids ID
SLM:000000435
Cayman ID
18449
PDB ID
RET
GuidePharm ID
2350

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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