Hexestrol (CED0009941)

Record Information

Version

1.0

Creation Date

2014-09-11 05:14:13 UTC

Update Date

2026-05-14 18:49:31 UTC

SynCED ID

CED0009941

Secondary Accession Numbers

CHEM003697
T3D4740

Identification

Common Name

Hexestrol

Class

Small Molecule

Description

Hexestrol is an exogenous organic compound with the formula C18H22O2 and an average molecular weight of 270.37 g/mol. It exists as a solid at room temperature. Hexestrol belongs to the stilbenes, a class of phenylpropanoids and polyketides within the organic compounds. This compound is associated with four recorded sources, including building and construction floors, food preservation within food, food processing and cookware, and electrical and electronic equipment specifically relating to electrodes and conductors or conductive bodies characterised by the conductive materials. Hexestrol interacts with 15 recorded protein targets. These include aromatase (CYP19A1), estrogen receptor (ESR1), nuclear receptor subfamily 1 group I member 2 (NR1I2), and retinoic acid receptor RXR-beta (RXRB), along with 11 other proteins.

Contaminant Type

Drug
Organic Compound
Phenolic Antioxidant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Exestrol	Kegg
Dihydrodiethylstilbestrol	MeSH
Hexestrol, (r,r)-(+-)-isomer	MeSH
Hexestrol, (r,s)-isomer	MeSH
Hexestrol, (R-(r,r))-isomer	MeSH
Hexestrol, (S-(r,r))-isomer	MeSH

Chemical Formula

C₁₈H₂₂O₂

Average Molecular Mass

270.366 g/mol

Monoisotopic Mass

270.162 g/mol

CAS Registry Number

84-16-2

IUPAC Name

4-[4-(4-hydroxyphenyl)hexan-3-yl]phenol

Traditional Name

dihydrodiethylstilbestrol

SMILES

CCC(C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

PBBGSZCBWVPOOL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenoid (CHEBI:31669 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	185°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.98	ALOGPS
logP	5.37	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.66 m³·mol⁻¹	ChemAxon
Polarizability	31.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-000i-1930000000-6a1adfdbcb3abda20a52	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0190000000-8f8d59584b0b0cea9ac0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0490000000-c4d6493ceeb60d503349	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kci-2980000000-ae03d5aca3238c8ebadd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-6b24ab83eea5558633e0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-d44b82720a04d68e4545	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0frl-2390000000-88a03be7f0f2c97056b7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0590000000-b8c3b65112f8b8996e29	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-007a-2920000000-7c7efd262e5ac7c42273	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-2920000000-d8ae3809572afd0f275e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-a3d9c28ab975a7b818e3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0090000000-f6ff5a3f99889207c20f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0hfy-1980000000-1822d34b81398fb0cd72	Not Available	View Spectrum
MS	MS Spectrum	splash10-000i-1900000000-fe382bb3152ab42cd695	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2414.0 Log mg/kg [1400:4300]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000491		Industrial manufacturing & chemical processing	Not Available
CEDs000497	Floors?Floors in built environments can be a significant source of synthetic chemical contamination due to the materials and finishes used in their construction.	Building & Construction	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000684	Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	Prediction Confidence Score 0.437 Applicability Domain 0.522 Statistical Significance 9.20e-04 Supporting Reference Compounds 174 E-value 7.16213
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	Prediction Confidence Score 0.43 Applicability Domain 0.522 Statistical Significance 0.0018 Supporting Reference Compounds 201 E-value 13.8572
Click to view 3D structure	TyR1	H9TVJ1	Chilo suppressalis	Predicted (SEA)	Prediction Confidence Score 0.429 Applicability Domain 0.429 Statistical Significance 2.00e-05 Supporting Reference Compounds 1 E-value 0.155698
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.381 Applicability Domain 0.48 Statistical Significance 0.0134 Supporting Reference Compounds 593 E-value 104.629
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 3	Q64518	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.367 Applicability Domain 0.367 Statistical Significance 5.70e-04 Supporting Reference Compounds 1 E-value 4.43741
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	Prediction Confidence Score 0.364 Applicability Domain 0.48 Statistical Significance 0.0095 Supporting Reference Compounds 451 E-value 74.1125
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	Prediction Confidence Score 0.363 Applicability Domain 0.48 Statistical Significance 0.0106 Supporting Reference Compounds 506 E-value 82.6759
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.361 Applicability Domain 0.421 Statistical Significance 0.0141 Supporting Reference Compounds 472 E-value 109.612
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.358 Applicability Domain 0.48 Statistical Significance 0.0117 Supporting Reference Compounds 487 E-value 91.2393
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	Prediction Confidence Score 0.354 Applicability Domain 0.421 Statistical Significance 0.0115 Supporting Reference Compounds 332 E-value 89.5266
Click to view 3D structure	Polyunsaturated fatty acid lipoxygenase ALOX15	P12530	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.352 Applicability Domain 0.48 Statistical Significance 3.20e-04 Supporting Reference Compounds 47 E-value 2.49118
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 2	P11507	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.346 Applicability Domain 0.346 Statistical Significance 1.10e-04 Supporting Reference Compounds 1 E-value 0.856341
Click to view 3D structure	Carbonic anhydrase 3	P07451	Humans	Predicted (SEA)	Prediction Confidence Score 0.341 Applicability Domain 0.421 Statistical Significance 0.0016 Supporting Reference Compounds 64 E-value 12.7673
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.339 Applicability Domain 0.48 Statistical Significance 0.0216 Supporting Reference Compounds 536 E-value 168.388
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.337 Applicability Domain 0.48 Statistical Significance 0.014 Supporting Reference Compounds 386 E-value 108.989
Click to view 3D structure	Estrogen-related receptor gamma	P62508	Humans	Predicted (SEA)	Prediction Confidence Score 0.336 Applicability Domain 0.48 Statistical Significance 5.00e-04 Supporting Reference Compounds 18 E-value 3.89246
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.48 Statistical Significance 0.0127 Supporting Reference Compounds 340 E-value 98.8685
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.48 Statistical Significance 0.0127 Supporting Reference Compounds 208 E-value 99.2578
Click to view 3D structure	Substance-K receptor	P21452	Humans	Predicted (SEA)	Prediction Confidence Score 0.33 Applicability Domain 0.48 Statistical Significance 0.0139 Supporting Reference Compounds 118 E-value 108.288
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	Prediction Confidence Score 0.328 Applicability Domain 0.48 Statistical Significance 0.0161 Supporting Reference Compounds 391 E-value 125.493
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.327 Applicability Domain 0.48 Statistical Significance 0.0488 Supporting Reference Compounds 955 E-value 379.904
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.327 Applicability Domain 0.48 Statistical Significance 0.0289 Supporting Reference Compounds 686 E-value 225.14
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	Prediction Confidence Score 0.326 Applicability Domain 0.48 Statistical Significance 0.0052 Supporting Reference Compounds 136 E-value 40.6373
Click to view 3D structure	Estrogen receptor	P49884	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.324 Applicability Domain 0.324 Statistical Significance 4.00e-05 Supporting Reference Compounds 1 E-value 0.311397
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 0.4 Statistical Significance 0.0231 Supporting Reference Compounds 372 E-value 179.91
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Not Available
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Known	Not Available
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 3	Q14994	Humans	Known	Not Available
Click to view 3D structure	Progesterone receptor	P06401	Humans	Known	Not Available
Click to view 3D structure	Androgen receptor	P10275	Humans	Known	Not Available
Click to view 3D structure	Translocator protein	P30536	Humans	Known	Not Available
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Known	Not Available
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Known	Not Available
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Known	Not Available
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Known	Not Available
Click to view 3D structure	Aromatase	P11511	Humans	Known	Not Available
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Known	Not Available
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Known	Not Available
Click to view 3D structure	Retinoic acid receptor RXR-beta	P28702	Humans	Known	Not Available
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0253645

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Hexestrol

Chemspider ID

3480

ChEBI ID

Not Available

PubChem Compound ID

3606

Kegg Compound ID

C13101

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

U.S. Patent 2,357,985; U.S. Patent 2,421,401.

MSDS

Not Available

General References

Liehr JG, Ballatore AM, Dague BB, Ulubelen AA: Carcinogenicity and metabolic activation of hexestrol. Chem Biol Interact. 1985 Oct;55(1-2):157-76. [PubMed: 2998630]

Hexestrol (CED0009941)

Structure for CHEM003697: Hexestrol

No pathways found

Structure