Structure Database (LMSD)
Common Name
9-cis-retinal
Systematic Name
Synonyms
3D model of 9-cis-retinal
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
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
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
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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Created at
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Updated at
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