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
LM ID
LMPR01090019
Formula
Exact Mass
Calculate m/z
300.20893
Status
Curated






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

Filter by species:
Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

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

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
VVA0018
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

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

Admin

Created at
-
Updated at
-