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Irregularities N.A. Withdrawn from market [1]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
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.