retinol   Click here for help

GtoPdb Ligand ID: 4053

Synonyms: all-trans-retinol
PDB Ligand
Comment: Retinol (vitamin A1) plays an essential role in (night) vision, normal bone and tooth development, reproduction, and is required for maintaining the integrity of skin and mucous membranes. It has antioxidant activity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 20.23
Molecular weight 286.23
XLogP 6.16
No. Lipinski's rules broken 1
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Isomeric SMILES OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
InChI 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+
1. Crabb JW, Carlson A, Chen Y, Goldflam S, Intres R, West KA, Hulmes JD, Kapron JT, Luck LA, Horwitz J et al.. (1998)
Structural and functional characterization of recombinant human cellular retinaldehyde-binding protein.
Protein Sci, 7 (3): 746-57. [PMID:9541407]
2. Kramlinger VM, Nagy LD, Fujiwara R, Johnson KM, Phan TT, Xiao Y, Enright JM, Toomey MB, Corbo JC, Guengerich FP. (2016)
Human cytochrome P450 27C1 catalyzes 3,4-desaturation of retinoids.
FEBS Lett, 590 (9): 1304-12. [PMID:27059013]
3. Zhou XE, Suino-Powell KM, Xu Y, Chan CW, Tanabe O, Kruse SW, Reynolds R, Engel JD, Xu HE. (2011)
The orphan nuclear receptor TR4 is a vitamin A-activated nuclear receptor.
J Biol Chem, 286 (4): 2877-85. [PMID:21068381]