General Information of Drug (ID: DM9AGWQ)

Drug Name
HEXESTROL
Synonyms
hexestrol; Dihydrodiethylstilbestrol; Vitestrol; Hexoestrolum; Exestrol; 5635-50-7; Stilbestrol, dihydro-; 4,4'-(1,2-Diethylethylene)diphenol; 4,4'-(hexane-3,4-diyl)diphenol; Synoestrolum; Hexanestrol; Cycloestrol; Esestrolo [DCIT]; Phenol, 4,4'-(1,2-diethyl-1,2-ethanediyl)bis-; Hexestrolum [INN-Latin]; Hexane, 3,4-bis(4-hydroxyphenyl)-; EINECS 227-082-2; 3,4-Bis(p-hydroxyphenyl)hexane; Hormoestrol; Syntrogene; Synthovo; Phenol, 4,4'-(1,2-diethylethylene)di-; CHEBI:31669; PBBGSZCBWVPOOL-UHFFFAOYSA-N; Hexestrol [INN]
Indication
Disease Entry ICD 11 Status REF
Irregularities N.A. Withdrawn from market [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 270.4
Logarithm of the Partition Coefficient (xlogp) 5.2
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C18H22O2
IUPAC Name
4-[4-(4-hydroxyphenyl)hexan-3-yl]phenol
Canonical SMILES
CCC(C1=CC=C(C=C1)O)C(CC)C2=CC=C(C=C2)O
InChI
InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3
InChIKey
PBBGSZCBWVPOOL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3606
ChEBI ID
CHEBI:31669
CAS Number
5635-50-7
UNII
10BI795R7D
DrugBank ID
DB07931
TTD ID
D0C4FT

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Inhibitor [2]
Estrogen receptor beta (ESR2) TTOM3J0 ESR2_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [3]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [3]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [3]
Aldo-keto reductase family 1 member C4 (AKR1C4) OTW2MMOF AK1C4_HUMAN Gene/Protein Processing [3]
Amphiregulin (AREG) OTJFOR67 AREG_HUMAN Gene/Protein Processing [4]
Calmin (CLMN) OT7U5J3T CLMN_HUMAN Gene/Protein Processing [4]
Carbonic anhydrase 12 (CA12) OT6WNFU8 CAH12_HUMAN Gene/Protein Processing [4]
CD44 antigen (CD44) OT9TTJ41 CD44_HUMAN Gene/Protein Processing [4]
Cyclin-G2 (CCNG2) OTII38K2 CCNG2_HUMAN Gene/Protein Processing [4]
Delta-aminolevulinic acid dehydratase (ALAD) OTHM9GSH HEM2_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2823).
2 Bone targeted drugs 2. synthesis of estrogens with hydroxyapatite affinity, Bioorg. Med. Chem. Lett. 6(9):1047-1050 (1996).
3 Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. Chem Biol Interact. 2003 Feb 1;143-144:503-13.
4 Moving toward integrating gene expression profiling into high-throughput testing: a gene expression biomarker accurately predicts estrogen receptor alpha modulation in a microarray compendium. Toxicol Sci. 2016 May;151(1):88-103.