raloxifene   Click here for help

GtoPdb Ligand ID: 2820

Synonyms: Evista® | LY-156758 | Optruma® | raloxifene hydrochloride
Approved drug PDB Ligand
raloxifene is an approved drug (FDA (1997), EMA (1998))
Compound class: Synthetic organic
Comment: Raloxifene is a selective estrogen receptor modulator (SERM).
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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: raloxifene

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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Click here for structure editor
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 2
Rotatable bonds 7
Topological polar surface area 98.24
Molecular weight 473.17
XLogP 5.65
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 Oc1ccc2c(c1)sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O
Isomeric SMILES Oc1ccc2c(c1)sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O
InChI InChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2
InChI Key GZUITABIAKMVPG-UHFFFAOYSA-N
References
1. Henke BR, Drewry DH, Jones SA, Stewart EL, Weaver SL, Wiethe RW. (2001)
2-Amino-4,6-diarylpyridines as novel ligands for the estrogen receptor.
Bioorg Med Chem Lett, 11 (14): 1939-42. [PMID:11459665]
2. Ishii Y, Takeuchi K. (2018)
Therapeutic agent for nonalcoholic fatty liver disease.
Patent number: WO2018198842A1. Assignee: National University Corporation Kyushu University. Priority date: 14/04/2018. Publication date: 01/11/2018.
3. Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. (1997)
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
Endocrinology, 138 (3): 863-70. [PMID:9048584]
4. Petrie WK, Dennis MK, Hu C, Dai D, Arterburn JB, Smith HO, Hathaway HJ, Prossnitz ER. (2013)
G protein-coupled estrogen receptor-selective ligands modulate endometrial tumor growth.
Obstet Gynecol Int, 2013: 472720. [PMID:24379833]
5. Stauffer SR, Coletta CJ, Tedesco R, Nishiguchi G, Carlson K, Sun J, Katzenellenbogen BS, Katzenellenbogen JA. (2000)
Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-alpha-selective agonists.
J Med Chem, 43 (26): 4934-47. [PMID:11150164]