tamoxifen   Click here for help

GtoPdb Ligand ID: 1016

Synonyms: ICI-46474 | Nolvadex® | Soltamox®
Approved drug PDB Ligand
tamoxifen is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Tamoxifen can be classed as a mixed agonist/antagonist of the estrogen -α and -β receptors, as its activity depends on the tissue in which the receptor is expressed. ChEMBL classify this compound as an ERα modulator, while it is described as a selective estrogen receptor modulator by Burris et al. in their 2013 review [1]. Tamoxifen can be considered as a prodrug as its three main metabolites exhibit higher affinity and specificity than tamoxifen at the ERα and ERβ receptors.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 12.47
Molecular weight 371.22
XLogP 7.14
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCC(=C(c1ccccc1)c1ccc(cc1)OCCN(C)C)c1ccccc1
Isomeric SMILES CC/C(=C(\c1ccccc1)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
InChI InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
InChI Key NKANXQFJJICGDU-QPLCGJKRSA-N
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
CYP3A4 2
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPER Hs Agonist Full agonist 6.0 pKi - 4
pKi 6.0 [4]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Maxi Cl- Hs Activator (extracellular tamoxifen) - - - -
VRAC Hs Channel blocker - - - -
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-α Primary target of this compound Hs Agonist Agonist 7.8 pKi - 3
pKi 7.8 [3]
Estrogen receptor-α Primary target of this compound Hs Antagonist Antagonist 7.8 pKi - 3
pKi 7.8 [3]
Estrogen receptor-β Hs Antagonist Antagonist 7.2 pKi - 3
pKi 7.2 [3]
Estrogen receptor-β Hs Agonist Agonist 7.2 pKi - 3
pKi 7.2 [3]
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields