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Dienestrol

July 24, 2017
Common Name

Dienestrol Description

Dienestrol is a synthetic, non-steroidal estrogen. It is an estrogen receptor agonist. Estrogens work partly by increasing a normal clear discharge from the vagina and making the vliva and urethra healthy. Using or applying an estrogen relieves or lessens: dryness and soreness in the vagina, itching, redness, or soreness of the vliva. Conditions that are treated with vaginal estrogens include a genital skin condition (vlivar atrophy), inflammation of the vagina (atrophic vaginitis), and inflammation of the urethra (atrophic urethritis). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 4,4'-Hydroxy-gamma,delta-diphenyl-beta,delta-hexadieneChEBI DehydrostilbestrolChEBI Di(P-oxyphenyl)-2,4-hexadieneChEBI P,P'-(diethylideneethylene)diphenolChEBI 4,4'-Hydroxy-g,delta-diphenyl-b,delta-hexadieneGenerator 4,4'-Hydroxy-γ,δ-diphenyl-β,δ-hexadieneGenerator 4,4'-Hydroxy-g,δ-diphenyl-b,δ-hexadieneGenerator DehydrostilboestrolHMDB DienesterolHMDB DienoestrolHMDB

Chemical Formlia

C18H18O2 Average Molecliar Weight

266.3343 Monoisotopic Molecliar Weight

266.13067982 IUPAC Name

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

di(p-oxyphenyl)-2,4-hexadiene CAS Registry Number

84-17-3 SMILES

CC=C(C(=CC)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

InChI Key

NFDFQCUYFHCNBW-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Phenylpropanoids and polyketides Sub Class

Stilbenes Direct Parent

Stilbenes Alternative Parents

  • Styrenes
  • 1-hydroxy-2-unsubstituted benzenoids
  • Organooxygen compounds
  • Hydrocarbon derivatives

    • Substituents

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

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • phenols (CHEBI:4518 )
  • olefinic compound (CHEBI:4518 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Estrogens, Non-Steroidal

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point227.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.23e-02 g/LNot Available LogP5.9Not Available

    Predicted Properties

    Property Value Source Water Solubility0.012 mg/mLALOGPS logP5.18ALOGPS logP4.83ChemAxon logS-4.3ALOGPS pKa (Strongest Acidic)9.1ChemAxon pKa (Strongest Basic)-6ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area40.46 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity84.36 m3·mol-1ChemAxon Polarizability30.3 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00890

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00890

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00890 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    580857 KEGG Compound ID

    C08090 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Dienestrol NuGOwiki Link

    HMDB15027 Metagene Link

    HMDB15027 METLIN ID

    Not Available PubChem Compound

    667476 PDB ID

    Not Available ChEBI ID

    217108

    Product: 4SC-203 (free base)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References Not Available

    Enzymes

    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
    References
    1. Juriansz RL, Huseby RA, Wilcox RB: Interactions of putative estrogens with the intracellular receptor complex in mouse Leydig cells: relationship to preneoplastic hyperplasia. Cancer Res. 1988 Jan 1;48(1):14-8. [PubMed:3334987 ]
    2. Grove RI, Korach KS: Estrogen stimulation of phosphatidylinositol metabolism in mouse uterine tissue. Endocrinology. 1987 Sep;121(3):1083-8. [PubMed:3622377 ]
    3. 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. [PubMed:9048584 ]
    4. Chae K, Lindzey J, McLachlan JA, Korach KS: Estrogen-dependent gene regulation by an oxidative metabolite of diethylstilbestrol, diethylstilbestrol-4,4″-quinone. Steroids. 1998 Mar;63(3):149-57. [PubMed:9558716 ]
    5. Bovee TF, Helsdingen RJ, Rietjens IM, Keijer J, Hoogenboom RL: Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. J Steroid Biochem Mol Biol. 2004 Jul;91(3):99-109. [PubMed:15276617 ]
    6. Maru BS, Tobias JH, Rivers C, Caunt CJ, Norman MR, McArdle CA: Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. Bone. 2009 Jan;44(1):102-12. doi: 10.1016/j.bone.2008.09.016. Epub 2008 Oct 11. [PubMed:18976723 ]
    7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 23242995

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