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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:20:38 UTC
HMDB IDHMDB0015579
Secondary Accession Numbers
  • HMDB15579
Metabolite Identification
Common NameQuinestrol
DescriptionQuinestrol is only found in individuals that have used or taken this drug. It is a 3-cyclopentyl ether of ethinyl estradiol.Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
Structure
Thumb
Synonyms
ValueSource
17-alpha-Ethinylestradiol 3-cyclopentyl etherChEBI
17alpha-Ethynylestradiol 3-cyclopentyl etherChEBI
EstonChEBI
Estradiol-17-beta 3-cyclopentyl etherChEBI
EstrovisChEBI
Estrovis 4000ChEBI
EstrovisterChEBI
PlestrovisChEBI
QuileaChEBI
QuinestrolumChEBI
17-a-Ethinylestradiol 3-cyclopentyl etherGenerator
17-α-ethinylestradiol 3-cyclopentyl etherGenerator
17a-Ethynylestradiol 3-cyclopentyl etherGenerator
17α-ethynylestradiol 3-cyclopentyl etherGenerator
Estradiol-17-b 3-cyclopentyl etherGenerator
Estradiol-17-β 3-cyclopentyl etherGenerator
QuinestroloHMDB
Ethinyl estradiol 3 cyclopentyl etherMeSH
Parke davis brand OF quinestrolMeSH
Ethinyl estradiol 3-cyclopentyl etherMeSH
Chemical FormulaC25H32O2
Average Molecular Weight364.5204
Monoisotopic Molecular Weight364.240230268
IUPAC Name(1S,10R,11S,14R,15S)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol
Traditional Namequinestrol
CAS Registry Number152-43-2
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC1CCCC1)C=C3
InChI Identifier
InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1
InChI KeyPWZUUYSISTUNDW-VAFBSOEGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Alkyl aryl ether
  • Benzenoid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Ether
  • Acetylide
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0016 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP5.19ALOGPS
logP5.4ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity108.27 m³·mol⁻¹ChemAxon
Polarizability44.02 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001a-1398000000-24b78cbc71e43f9b5f86View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-2165900000-781ffc739b80bdecd9f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a59-2920000000-99119dee5db3aab05906View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3119000000-c081ebe349df6500cce1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5679000000-083b5505ec8847453fb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9010000000-61cd144aeff30afa3d84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1019000000-53e9c20e422b817daeeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2039000000-98c7bde745c0bb0f0c66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00n4-4090000000-126f2b3e60f8f02ea9a6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04575 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04575 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04575
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8694
KEGG Compound IDC07619
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuinestrol
METLIN IDNot Available
PubChem Compound9046
PDB IDNot Available
ChEBI ID8716
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Shyu C, Cavileer TD, Nagler JJ, Ytreberg FM: Computational estimation of rainbow trout estrogen receptor binding affinities for environmental estrogens. Toxicol Appl Pharmacol. 2011 Feb 1;250(3):322-6. doi: 10.1016/j.taap.2010.11.005. Epub 2010 Nov 12. [PubMed:21075131 ]