Details of the Drug

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Irregularities	N.A.	Withdrawn from market	[1]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

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL31669
CAS Number: 5635-50-7
UNII: 10BI795R7D
DrugBank ID: DB07931
TTD ID: D0C4FT

Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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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]
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]
DNA endonuclease RBBP8 (RBBP8)	OTRHJ3GI	CTIP_HUMAN	Gene/Protein Processing	[4]
DNA-binding protein inhibitor ID-3 (ID3)	OTUULW5Z	ID3_HUMAN	Gene/Protein Processing	[4]

Molecular Interaction Atlas (MIA)

MIA Detail

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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.