alitretinoin   Click here for help

GtoPdb Ligand ID: 2645

Synonyms: 9-cis-retinoic acid | Panretin® | Toctino®
Approved drug PDB Ligand
alitretinoin is an approved drug (FDA (1999), EMA (2000))
Compound class: Metabolite or derivative
Comment: Alitretinoin is an important regulator of gene expression during normal growth and development, as well as in neoplasms. Alitretinoin is a retinoid receptor agonist.
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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: alitretinoin

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-ZVCIMWCZSA-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. Heyman RA, Mangelsdorf DJ, Dyck JA, Stein RB, Eichele G, Evans RM, Thaller C. (1992)
9-cis retinoic acid is a high affinity ligand for the retinoid X receptor.
Cell, 68 (2): 397-406. [PMID:1310260]
3. Kagechika H, Kawachi E, Hashimoto Y, Himi T, Shudo K. (1988)
Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.
J Med Chem, 31 (11): 2182-92. [PMID:3184125]
4. Keller C, Matzdorff AC, Kemkes-Matthes B. (1999)
Pharmacology of warfarin and clinical implications.
Semin Thromb Hemost, 25 (1): 13-6. [PMID:10327215]
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. Lala DS, Mukherjee R, Schulman IG, Koch SS, Dardashti LJ, Nadzan AM, Croston GE, Evans RM, Heyman RA. (1996)
Activation of specific RXR heterodimers by an antagonist of RXR homodimers.
Nature, 383 (6599): 450-3. [PMID:8837780]
7. Levin AA, Sturzenbecker LJ, Kazmer S, Bosakowski T, Huselton C, Allenby G, Speck J, Kratzeisen C, Rosenberger M, Lovey A. (1992)
9-cis retinoic acid stereoisomer binds and activates the nuclear receptor RXR alpha.
Nature, 355 (6358): 359-61. [PMID:1309942]
8. Mangelsdorf DJ, Borgmeyer U, Heyman RA, Zhou JY, Ong ES, Oro AE, Kakizuka A, Evans RM. (1992)
Characterization of three RXR genes that mediate the action of 9-cis retinoic acid.
Genes Dev, 6 (3): 329-44. [PMID:1312497]
9. 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]
10. 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]
11. Wallin R, Wajih N, Hutson SM. (2008)
VKORC1: a warfarin-sensitive enzyme in vitamin K metabolism and biosynthesis of vitamin K-dependent blood coagulation factors.
Vitam Horm, 78: 227-46. [PMID:18374197]