Structure Database (LMSD)
Common Name
Retinoic Acid
Systematic Name
3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acid
Synonyms
- Tretinoin/All-Trans Retinoic Acid
3D model of Retinoic Acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
all-trans Retinoic acid is a metabolite of vitamin A and a ligand for retinoic acid receptors (RARs) with IC50 values of 9, 3, and 10 nM for RARα, RARβ, and RARγ, respectively, in radioligand binding assays.1 It induces expression of a luciferase reporter in COS-7 cells expressing RARα, RARβ, or RARγ (EC50s = 169, 9, and 2 nM, respectively). all-trans Retinoic acid (17 nmol) reduces papilloma formation induced by phorbol 12-myristate 13-acetate (TPA) in mice.2 It reduces bile duct proliferation, hydroxyproline levels, and liver inflammation in a rat model of α-naphthylisothiocyanate-induced chronic cholestasis and reduces plasma levels of alkaline phosphatase and bile salts in the Mdr2-/- mouse model of cholestasis.3 all-trans Retinoic acid also reduces hepatic fat accumulation, triglycerides, body weight, and serum glucose levels in mice with Western diet-induced obesity.4
This information has been provided by Cayman Chemical
References
Reactions
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String Representations
InChiKey (Click to copy)
SHGAZHPCJJPHSC-YCNIQYBTSA-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(=O)O)/C)/C)=C(C)CC1
Other Databases
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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