tretinoin   Click here for help

GtoPdb Ligand ID: 2644

Synonyms: all-trans-retinoic acid (ATRA) | Altreno® (0.05% lotion) | Avita® (0.025% gel) | Renova® (0.02% cream)
Approved drug PDB Ligand
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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: tretinoin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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+
1. Allenby G, Bocquel MT, Saunders M, Kazmer S, Speck J, Rosenberger M, Lovey A, Kastner P, Grippo JF, Chambon P. (1993)
Retinoic acid receptors and retinoid X receptors: interactions with endogenous retinoic acids.
Proc Natl Acad Sci USA, 90 (1): 30-4. [PMID:8380496]
2. Charton J, Deprez-Poulain R, Hennuyer N, Tailleux A, Staels B, Deprez B. (2009)
Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives.
Bioorg Med Chem Lett, 19 (2): 489-92. [PMID:19058965]
3. Griffett K, Bedia-Diaz G, Hegazy L, de Vera IMS, Wanninayake US, Billon C, Koelblen T, Wilhelm ML, Burris TP. (2020)
The Orphan Nuclear Receptor TLX Is a Receptor for Synthetic and Natural Retinoids.
Cell Chem Biol, 27 (10): 1272-1284.e4. [PMID:32763139]
4. Keidel S, LeMotte P, Apfel C. (1994)
Different agonist- and antagonist-induced conformational changes in retinoic acid receptors analyzed by protease mapping.
Mol Cell Biol, 14 (1): 287-98. [PMID:8264595]
5. Klaholz BP, Mitschler A, Moras D. (2000)
Structural basis for isotype selectivity of the human retinoic acid nuclear receptor.
J Mol Biol, 302 (1): 155-70. [PMID:10964567]
6. Nagy L, Thomázy VA, Shipley GL, Fésüs L, Lamph W, Heyman RA, Chandraratna RA, Davies PJ. (1995)
Activation of retinoid X receptors induces apoptosis in HL-60 cell lines.
Mol Cell Biol, 15 (7): 3540-51. [PMID:7791761]
7. Richieri GV, Ogata RT, Zimmerman AW, Veerkamp JH, Kleinfeld AM. (2000)
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
Biochemistry, 39 (24): 7197-204. [PMID:10852718]
8. Shaw N, Elholm M, Noy N. (2003)
Retinoic acid is a high affinity selective ligand for the peroxisome proliferator-activated receptor beta/delta.
J Biol Chem, 278 (43): 41589-92. [PMID:12963727]
9. Stehlin-Gaon C, Willmann D, Zeyer D, Sanglier S, Van Dorsselaer A, Renaud JP, Moras D, Schüle R. (2003)
All-trans retinoic acid is a ligand for the orphan nuclear receptor ROR beta.
Nat Struct Biol, 10 (10): 820-5. [PMID:12958591]
10. Thacher SM, Vasudevan J, Chandraratna RA. (2000)
Therapeutic applications for ligands of retinoid receptors.
Curr Pharm Des, 6 (1): 25-58. [PMID:10637371]
11. 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]