4-hydroxytamoxifen   Click here for help

GtoPdb Ligand ID: 2817

Abbreviated name: 4HT
Synonyms: 4-OHT | afimoxifene
Compound class: Synthetic organic
Comment: A metabolite of the approved drug tamoxifen.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 32.7
Molecular weight 387.22
XLogP 6.73
No. Lipinski's rules broken 1
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Canonical SMILES CCC(=C(c1ccccc1)c1ccc(cc1)OCCN(C)C)c1ccc(cc1)O
Isomeric SMILES CC/C(=C(\c1ccccc1)/c1ccc(cc1)OCCN(C)C)/c1ccc(cc1)O
InChI InChI=1S/C26H29NO2/c1-4-25(20-10-14-23(28)15-11-20)26(21-8-6-5-7-9-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
1. Chao EY, Collins JL, Gaillard S, Miller AB, Wang L, Orband-Miller LA, Nolte RT, McDonnell DP, Willson TM, Zuercher WJ. (2006)
Structure-guided synthesis of tamoxifen analogs with improved selectivity for the orphan ERRgamma.
Bioorg Med Chem Lett, 16 (4): 821-4. [PMID:16307879]
2. Coward P, Lee D, Hull MV, Lehmann JM. (2001)
4-Hydroxytamoxifen binds to and deactivates the estrogen-related receptor gamma.
Proc Natl Acad Sci USA, 98 (15): 8880-4. [PMID:11447273]
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. Revankar CM, Cimino DF, Sklar LA, Arterburn JB, Prossnitz ER. (2005)
A transmembrane intracellular estrogen receptor mediates rapid cell signaling.
Science, 307 (5715): 1625-30. [PMID:15705806]