tretinoin   

GtoPdb Ligand ID: 2644

Synonyms: all-trans-retinoic acid (ATRA) | Altreno® (0.05% lotion) | Avita® (0.025% gel) | Renova® (0.02% cream)
tretinoin is an approved drug (FDA (1995))
Comment: Tretinoin is a naturally occurring derivative of vitamin A (retinoic acid) and as such is an agonist at the retinoic acid receptors. Tretinoin binds to α, β, and γ isoforms of the retinoic acid receptor. Retionoids are important regulators of cell reproduction, proliferation, and differentiation.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
Isomeric SMILES C/C(=C\C=C\C(=C\C(=O)O)\C)/C=C/C1=C(C)CCCC1(C)C
InChI 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+
InChI Key SHGAZHPCJJPHSC-YCNIQYBTSA-N
Bioactivity Comments
All-trans-retinoic acid appears to have highest affinity for retinioc acid receptor-β [2].
Natural/Endogenous Targets
Target
Peroxisome proliferator-activated receptor-β/δ
RAR-related orphan receptor-β
Retinoic acid receptor-α
Retinoic acid receptor-β
Retinoic acid receptor-γ
Testicular receptor 4
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoic acid receptor-γ Hs Agonist Agonist 9.6 pKd - 1,3-5,9
pKd 9.6 [1,3-5,9]
Retinoic acid receptor-α Hs Agonist Agonist 9.4 pKd - 1,3-5,9
pKd 9.4 [1,3-5,9]
Peroxisome proliferator-activated receptor-β/δ Hs Agonist Full agonist 7.8 pKd - 7
pKd 7.8 [7]
Retinoic acid receptor-β Hs Agonist Agonist 9.4 pKi - 3-5,9
pKi 9.4 [3-5,9]
RAR-related orphan receptor-β Hs Antagonist Antagonist 6.6 pKi - 8
pKi 6.6 [8]
Retinoic acid receptor-γ Hs Agonist Agonist 9.7 pEC50 - 2
pEC50 9.7 (EC50 2x10-10 M) [2]
Retinoic acid receptor-β Hs Agonist Agonist 7.9 pEC50 - 2
pEC50 7.9 (EC50 1.2x10-8 M) [2]
Retinoic acid receptor-α Hs Agonist Agonist 7.8 pEC50 - 2
pEC50 7.8 (EC50 1.7x10-8 M) [2]
Testicular receptor 4 Hs Agonist Full agonist 4.6 pEC50 - 10
pEC50 4.6 (EC50 2.38x10-5 M) [10]
RAR-related orphan receptor-β Hs Antagonist Antagonist 9.8 pIC50 - 8
pIC50 9.8 [8]
RAR-related orphan receptor-β Hs Agonist Agonist - - - 8
[8]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Ligand mentioned in the following text fields