ContaminantDB: Dienestrol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:36:06 UTC

Update Date

2016-11-09 01:15:25 UTC

Accession Number

CHEM016529

Identification

Common Name

Dienestrol

Class

Small Molecule

Description

Dienestrol (INN, USAN) (brand names Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol, numerous others), also known as dienoestrol (BAN), is a synthetic nonsteroidal estrogen of the stilbestrol group which is or was used to treat menopausal symptoms in the United States and Europe. It has been studied for use by rectal administration in the treatment of prostate cancer in men as well. The medication was introduced in the U.S. in 1947 by Schering as Synestrol and in France in 1948 as Cycladiene. Dienestrol is a close analogue of diethylstilbestrol. It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively.Dienestrol diacetate (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Dehydrostilbestrol	Kegg
DV	Kegg
Dienestrol, (Z,Z)-isomer	MeSH
Dienestrol, (e,e)-isomer	MeSH
4,4'-(Diethylideneethylene)diphenol	MeSH
Dienestrol, (Z,e)-isomer	MeSH
Oestrasid	MeSH
Dienoestrol	MeSH
Ortho dienestrol	MeSH
Synestrol	MeSH
ortho Brand OF dienestrol	MeSH
Dienestrol	MeSH

Chemical Formula

C₁₈H₁₈O₂

Average Molecular Mass

266.340 g/mol

Monoisotopic Mass

266.131 g/mol

CAS Registry Number

84-17-3

IUPAC Name

4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol

Traditional Name

dienestrol

SMILES

[H]\C(C)=C(/C(=C(\[H])C)/C1=CC=C(O)C=C1)\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+

InChI Key

NFDFQCUYFHCNBW-SCGPFSFSSA-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
Styrene
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

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.83	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-6	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	3	ChemAxon
Refractivity	84.36 m³·mol⁻¹	ChemAxon
Polarizability	30.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0190000000-4e899b7d114c0d12ce05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0390000000-e566be6b7c32827ae335	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff0-1960000000-df6e60b979760bb8716b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-9f83049c943023145fc4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-a561e18a5d83704153a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014v-2390000000-e667485e2f52b73a8c60	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

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

Dienestrol

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

667476

Kegg Compound ID

C08090

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dienestrol (CHEM016529)

Structure for CHEM016529: Dienestrol