Showing Compound Card for Hexestrol (CDB000615)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 8 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:46:47 UTC
Updated at2020-11-18 16:35:20 UTC
CannabisDB IDCDB000615
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHexestrol
DescriptionHexestrol also known as hexanestrol, hexoestrol, and dihydrodiethylstilbestrol, 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. Along with diethylstilbestrol, hexestrol is one of the most potent known estrogens (PMID: 21013428 ). It is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol which was used to treat estrogen deficiency. Hexestrol has been available and used in ester forms, such as hexestrol diacetate, hexestrol dicaprylate, hexestrol diphosphate, and hexestrol dipropionate. When compared to estradiol, hexestrol has approximately 302% and 234% of the affinity the estrogen receptors ERα and ERβ, respectively (PMID: 9048584 ). Hexestrol has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HEXESTROL diphosphATE sodiumChEMBL
HEXESTROL diphosphoric acid sodiumGenerator
4,4'-(Diethylideneethylene)diphenolMeSH
Dienestrol, (e,e)-isomerMeSH
DienoestrolMeSH
ortho Brand OF dienestrolMeSH
ortho DienestrolMeSH
SynestrolMeSH
Dienestrol, (Z,e)-isomerMeSH
Dienestrol, (Z,Z)-isomerMeSH
OestrasidMeSH
DienestrolMeSH
DihydrodiethylstilbestrolMeSH
Hexestrol, (r*,r*)-(+-)-isomerMeSH
Hexestrol, (r*,s*)-isomerMeSH
Hexestrol, (R-(r*,r*))-isomerMeSH
Hexestrol, (S-(r*,r*))-isomerMeSH
Chemical FormulaC18H22O2
Average Molecular Weight270.37
Monoisotopic Molecular Weight270.162
IUPAC Name4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
Traditional Namehexestrol
CAS Registry Number84-16-2
SMILES
CC[C@@H]([C@@H](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/t17-,18+
InChI KeyPBBGSZCBWVPOOL-HDICACEKSA-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.98ALOGPS
logP5.37ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.66 m³·mol⁻¹ChemAxon
Polarizability31.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHexestrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1930000000-035978e5e68920c304e8Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-8f8d59584b0b0cea9ac02017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0490000000-c4d6493ceeb60d5033492017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kci-2980000000-ae03d5aca3238c8ebadd2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6b24ab83eea5558633e02017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-d44b82720a04d68e45452017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frl-2390000000-88a03be7f0f2c97056b72017-07-26View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Estrogen receptor betaESR214q23.2Q92731 details
Estrogen receptorESR16q25.1P03372 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Estrogen receptor betaESR214q23.2Q92731 details
Estrogen receptorESR16q25.1P03372 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Estrogen receptor betaESR214q23.2Q92731 details
Estrogen receptorESR16q25.1P03372 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Estrogen receptor betaESR214q23.2Q92731 details
Estrogen receptorESR16q25.1P03372 details
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB07931
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHexestrol
METLIN IDNot Available
PubChem Compound192197
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. SOLMSSEN UV: Synthetic estrogens and the relation between their structure and their activity. Chem Rev. 1945 Dec;37:481-598. doi: 10.1021/cr60118a004. [PubMed:21013428 ]
  2. Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. doi: 10.1210/endo.138.3.4979. [PubMed:9048584 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details
1. Estrogen receptor beta
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular weight:
59215.8
Enzyme Details
2. Estrogen receptor
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular weight:
66215.4