prinaberel   Click here for help

GtoPdb Ligand ID: 6700

Synonyms: ERB 041 | ERB-041 | PF-00913086
PDB Ligand
Compound class: Synthetic organic
Comment: Prinaberel is an estrogen receptor beta (ERβ) agonist, with potential gynecological uses and antiinflammatory action [1-3].

The structure shown here matches that in the INN document for prinaberel, and as in the ChEMBL entry provided above. However, alternative tautomers are represented elsewhere including CID 5326893.
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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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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 1
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 66.49
Molecular weight 271.06
XLogP 3.23
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C=Cc1cc(O)cc2c1oc(n2)c1ccc(c(c1)F)O
Isomeric SMILES C=Cc1cc(O)cc2c1oc(n2)c1ccc(c(c1)F)O
InChI InChI=1S/C15H10FNO3/c1-2-8-5-10(18)7-12-14(8)20-15(17-12)9-3-4-13(19)11(16)6-9/h2-7,18-19H,1H2
InChI Key MQIMZDXIAHJKQP-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Catley MC, Birrell MA, Hardaker EL, de Alba J, Farrow S, Haj-Yahia S, Belvisi MG. (2008)
Estrogen receptor beta: expression profile and possible anti-inflammatory role in disease.
J Pharmacol Exp Ther, 326 (1): 83-8. [PMID:18375789]
2. Cvoro A, Tatomer D, Tee MK, Zogovic T, Harris HA, Leitman DC. (2008)
Selective estrogen receptor-beta agonists repress transcription of proinflammatory genes.
J Immunol, 180 (1): 630-6. [PMID:18097065]
3. Leventhal L, Brandt MR, Cummons TA, Piesla MJ, Rogers KE, Harris HA. (2006)
An estrogen receptor-beta agonist is active in models of inflammatory and chemical-induced pain.
Eur J Pharmacol, 553 (1-3): 146-8. [PMID:17056036]
4. Malamas MS, Manas ES, McDevitt RE, Gunawan I, Xu ZB, Collini MD, Miller CP, Dinh T, Henderson RA, Keith JC et al.. (2004)
Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-beta ligands.
J Med Chem, 47 (21): 5021-40. [PMID:15456246]
5. Roman-Blas JA, Castañeda S, Cutolo M, Herrero-Beaumont G. (2010)
Efficacy and safety of a selective estrogen receptor β agonist, ERB-041, in patients with rheumatoid arthritis: a 12-week, randomized, placebo-controlled, phase II study.
Arthritis Care Res (Hoboken), 62 (11): 1588-93. [PMID:20556817]