Showing Compound Diethylstilbesterol (FDB007498)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:38 UTC

Update date

2019-11-26 03:01:41 UTC

Primary ID

FDB007498

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Diethylstilbesterol

Description

Diethylstilbestrol, also known as DES, 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. Diethylstilbestrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Diethylstilbestrol is found, on average, in the highest concentration within gram beans. This could make diethylstilbestrol a potential biomarker for the consumption of these foods. Diethylstilbestrol is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.

CAS Number

56-53-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
DES	HMDB
Diethylstilbesterol	HMDB
Diethylstilbestrol BP	HMDB
Diethylstilboesterol	HMDB
Dietilestilbestrol	HMDB
Percutatrine oestrogenique iscovesco	HMDB
Rcra waste number u089	HMDB
trans-Diethylstilbesterol	HMDB
trans-Diethylstilbestrol	HMDB
trans-Diethylstilboesterol	HMDB
(E)-3,4-bis(4-hydroxyphenyl)-3-hexene	manual
(E)-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol	manual
4,4'-Dihydroxy-a,b-diethylstilbene	Generator
4,4'-dihydroxy-alpha,beta-diethylstilbene	manual
4,4'-Dihydroxy-α,β-diethylstilbene	Generator
a,Alpha'-diethyl-(e)-4,4'-stilbenediol	Generator
alpha,alpha'-diethyl-(E)-4,4'-stilbenediol	manual
Diethylstilbestrol	manual
Diethylstilbestrol bp	HMDB
Diethylstilbestrolum	ChEBI
Distilbene	ChEBI
trans-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol	manual
α,alpha'-diethyl-(e)-4,4'-stilbenediol	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	4.62	ALOGPS
logP	5.19	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.13	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	4	ChemAxon
Refractivity	83.24 m³·mol⁻¹	ChemAxon
Polarizability	30.69 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

Chemical Formula

C18H20O2

IUPAC name

4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

InChI Identifier

InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3

InChI Key

RGLYKWWBQGJZGM-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

268.3502

Monoisotopic Molecular Weight

268.146329884

Classification

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

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Cancer

Gastrointestinal disorders:

Observation:

Bleeding

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Environmental role:

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Indirect biological role:

Carcinogen

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	170.5 oC
Boiling Point	Not Available
Experimental Water Solubility	0.012 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	5.07	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Diethylstilbesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-0390000000-d064f732675ea9894f2c	Spectrum
Predicted GC-MS	Diethylstilbesterol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0awa-1019000000-1cc583dcfd41002dd339	Spectrum
Predicted GC-MS	Diethylstilbesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-f2a65d0f5428a0bf0096	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0690000000-6b39aa057a8cb6eb1def	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-2950000000-4f5e80bdea64d9365cc7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-9bda79387111e5798094	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-7c62326707d11881c098	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ll-2490000000-de50c09ba9f659d1b047	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-e89c3535f3d6cda6ed7d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ap0-0190000000-93dd0c6a4d49918f7fc7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0300-0790000000-15fa3a704fd6a8d70eab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0890000000-ce8b26781cf43b806840	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0930000000-ff4502b2ae61ffdf7a9a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052p-1950000000-6890970b5e5ae4ffaf87	2021-09-22	View Spectrum