Structure Database (LMSD)

Common Name
9-cis-retinal
Systematic Name
Synonyms
LM ID
LMPR01090017
Formula
C20H28O
Exact Mass
Calculate m/z
284.214015
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

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

Biological Context

9-cis Retinal is a natural retinoid that is produced by oxidation of 9-cis retinol by cis-retinol dehydrogenase (cRDH).1 It binds to cellular retinol-binding protein-I (CRBP-I) and CRBP-II (Kds = 8 and 5 nM, respectively) and to cellular retinaldehyde-binding protein (CRALBP; Kd = 53.3 nM).2,3 In vitro, 9-cis retinal inhibits differentiation of RCJ C5.18 chondrogenic cells into cartilage (IC50 = 8 nM).4 In vivo, it rescues cone electroretinogram (ERG) responses in Irbp-/- mice, which lack interphotoreceptor retinoid-binding protein and have diminished cone responses, when administered at a dose of 0.375 mg.5

This information has been provided by Cayman Chemical

References

1. Parker, R.O., Fan, J., Nickerson, J.M., et al. Normal cone function requires the interphotoreceptor retinoid binding protein. J. Neurosci. 29(14), 4616-4621 (2009).
2. Von Schroeder, H.P., Hashimoto, Y., and Heerschie, J.N.M. The effects of natural and synthetic retinoids on the differentiation of RCJ C5.18 chondrogenic cells. Teratology 50(1), 54-62 (1994).
3. Golovleva, I., Bhattacharya, S., Wu, Z., et al. Disease-causing mutations in the cellular retinaldehyde binding protein tighten and abolish ligand interactions. J. Biol. Chem. 278(14), 12397-12402 (2003).
4. Kane, M.A., Bright, F.V., and Napoli, J.L. Binding affinities of CRBPI and CRBPII for 9-cis-retinoids. Biochim. Biophys. Acta 1810(5), 514-518 (2011).
5. Mertz, J.R., Shang, E., Piantedosi, R., et al. Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation. A possible role in 9-cis-retinoic acid formation. J. Biol. Chem. 272(18), 11744-11749 (1997).

String Representations

InChiKey (Click to copy)
NCYCYZXNIZJOKI-MKOSUFFBSA-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=O)/C)=C(C)CC1

Other Databases

KEGG ID
C16681
HMDB ID
HMDB0006218
CHEBI ID
78273
LIPIDBANK ID
VVA0014
PubChem CID
6436082
Cayman ID
21692
GuidePharm ID
6673

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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