estrone (PAMDB120524)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120524
Identification
Name: estrone
Description:The main Estrogens estrogens in humans are estrone, 17β-estradiol and estriol, which differ in the number of hydroxyl groups (one for estrone, two for 17β-estradiol and three for estriol). 17β-estradiol is about 10 times as potent as estrone and about 80 times as potent as estriol in its estrogenic effect. 17β-estradiol is the predominant estrogen in non-pregenant women during their reproductive years in terms of serum levels. estrone Estrone is the predominant circulating estrogen in women during menopause and estriol is the predominant circulating estrogen during pregnancy.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • hydroxyestronesfolliculinestrovarin
  • 3-hydroxyl-1,3,5(10)-estratien-17-oneestrolfollicular hormoneprogynon
Chemical Formula: C18H22O2
Average Molecular Weight: 270.371
Monoisotopic Molecular Weight: 270.162
InChI Key: DNXHEGUUPJUMQT-CBZIJGRNSA-N
InChI:InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
CAS number: 53-16-7
IUPAC Name:(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0?,??0??,???heptadeca-2(7),3,5-trien-14-one
Traditional IUPAC Name: estrone
SMILES:CC12([CH](CCC(=O)1)[CH]4([CH](CC2)C3(C(=CC(O)=CC=3)CC4)))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Steroids and steroid derivatives
Sub ClassEstrane steroids
Direct Parent Estrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketone
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular Framework Aromatic homopolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 258 - 260 °C
Experimental Properties:
PropertyValueReference
Melting Point258 - 260 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.03 mg/mLNot Available
LogP3.13HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0039 mg/mLALOGPS
logP4.03ALOGPS
logP4.31ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.08 m3·mol-1ChemAxon
Polarizability31.27 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
estrone-sulfate + Water → estrone + Sulfate + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-05ox-3951000000-8bc438f505b3cf49b21fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-003u-4942000000-a72ea34d85d9d524c247View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0019-8931000000-aad9803af812c7c40f53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0190000000-071e67516e11357ff64eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-4910000000-20e059a7c508ba492af3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-067i-9700000000-9ff5214f08822f238fa9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-2940000000-3b9744c27d6a3d2eff6eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-2930000000-c99df908474247066a2bView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [16598814 ]
  • Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [10997942 ]
  • Kuhl H, Wiegratz I: Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications? Climacteric. 2007 Aug;10(4):344-53. [17653961 ]
  • Parker WH, Broder MS, Liu Z, Shoupe D, Farquhar C, Berek JS: Ovarian conservation at the time of hysterectomy for benign disease. Clin Obstet Gynecol. 2007 Jun;50(2):354-61. [17513923 ]
  • Stanway SJ, Delavault P, Purohit A, Woo LW, Thurieau C, Potter BV, Reed MJ: Steroid sulfatase: a new target for the endocrine therapy of breast cancer. Oncologist. 2007 Apr;12(4):370-4. [17470679 ]
  • Ito K: Hormone replacement therapy and cancers: the biological roles of estrogen and progestin in tumorigenesis are different between the endometrium and breast. Tohoku J Exp Med. 2007 May;212(1):1-12. [17464097 ]
Synthesis Reference: Kocovsky, Paved; Baines, Richard S. Synthesis of estrone via a thallium(III)-mediated fragmentation of a 19-hydroxyandrost-5-ene precursor. Tetrahedron Letters (1993), 34(38), 6139-40.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
METABOLIGHTSMTBLC17263
HMDBHMDB00145
CHEMSPIDER5660
CHEBI141798
PUBCHEM698
LIGAND-CPDC00468
CAS53-16-7