norendoxifen   

GtoPdb Ligand ID: 10204

Synonyms: Z-norendoxifen
Compound class: Synthetic organic
Comment: Norendoxifen is an active metabolite of tamoxifen. In addition to acting as an estrogen receptor modulator, norendoxifen also inhibits aromatase enzyme activity (i.e. inhibits estrogen biosynthesis) [1-2]. We show the Z isomer here as it is more potent in terms of ER modulation and in vivo activity compared to the E isomer.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 55.48
Molecular weight 359.19
XLogP 6.1
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES NCCOc1ccc(cc1)C(=C(c1ccccc1)CC)c1ccc(cc1)O
Isomeric SMILES NCCOc1ccc(cc1)/C(=C(\c1ccccc1)/CC)/c1ccc(cc1)O
InChI InChI=1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3/b24-23-
InChI Key YCQBLTPGQSYLHD-VHXPQNKSSA-N
Classification
Compound class Synthetic organic
Prodrug tamoxifen
IUPAC Name
4-[(~{Z})-1-[4-(2-aminoethoxy)phenyl]-2-phenylbut-1-enyl]phenol
Synonyms
Z-norendoxifen
Comments
Norendoxifen is an active metabolite of tamoxifen. In addition to acting as an estrogen receptor modulator, norendoxifen also inhibits aromatase enzyme activity (i.e. inhibits estrogen biosynthesis) [1-2]. We show the Z isomer here as it is more potent in terms of ER modulation and in vivo activity compared to the E isomer.
Database Links
BindingDB Ligand 50435004
ChEMBL Ligand CHEMBL2386284
GtoPdb PubChem SID 381118914
PubChem CID 68037237
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