Structure Database (LMSD)

Common Name
9-cis-retinoic acid
Systematic Name
Synonyms
  • Alitretinoin
LM ID
LMPR01090022
Formula
C20H28O2
Exact Mass
Calculate m/z
300.20893
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

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

Biological Context

9-cis Retinoic acid is a natural metabolite of vitamin A, derived from the intermediate all-trans retinoic acid .1 It potently activates all isoforms of retinoic acid receptor (RAR) (Ki = 0.5-27 nM) as well as retinoid X receptor (RXR) isoforms (Ki = 3.8-12 nM).2,3 RAR heterodimerizes with RXR, while RXR can homodimerize as well as heterodimerize with numerous partners in addition to RAR, thus allowing 9-cis retinoic acid to evoke a wide range of effects.4,1

This information has been provided by Cayman Chemical

References

1. Dawson, M.I., and Xia, Z. The retinoid X receptors and their ligands. Biochim. Biophys. Acta 1821(1), 21-56 (2012).
2. Kane, M.A. Analysis, occurrence, and function of 9-cis-retinoic acid. Biochim. Biophys. Acta 1821(1), 10-20 (2012).
3. Umemiya, H., Fukasawa, H., Ebisawa, M., et al. Regulation of retinoidal actions by diazepinylbenzoic acids. Retinoid synergists which activate the RXR-RAR heterodimers. J. Med. Chem. 40(26), 4222-4234 (1997).
4. Wong, M.F., Repa, J.J., Clagett-Dame, M., et al. Synthesis and receptor binding affinity of conformationally restricted retinoic acid analogues. Bioorg. Med. Chem. Lett. 7(17), 2313-2318 (1997).

String Representations

InChiKey (Click to copy)
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
InChi (Click to copy)
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
SMILES (Click to copy)
C1C(C)(C)C(/C=C/C(=C\C=C\C(\C)=C\C(O)=O)/C)=C(C)CC1

Other Databases

Wikipedia
Alitretinoin
KEGG ID
C15493
HMDB ID
HMDB0002369
CHEBI ID
50648
LIPIDBANK ID
VVA0021
PubChem CID
449171
Cayman ID
14587
PDB ID
9CR
GuidePharm ID
2645

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 1
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 343.94
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.60
Molar Refractivity 93.76

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Updated at
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