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))
Compound class: Metabolite or derivative
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: tretinoin

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
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]