You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 22:20:08 UTC
Update Date2020-06-04 20:40:27 UTC
MCDB ID BMDB0000145
Secondary Accession Numbers
  • BMDB00145
Metabolite Identification
Common NameEstrone
DescriptionEstrone, also known as folliculin or estrovarin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estrone is considered to be a steroid lipid molecule. Estrone is a drug which is used for management of perimenopausal and postmenopausal symptoms. Estrone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estrone exists in all living organisms, ranging from bacteria to humans. Estrone participates in a number of enzymatic reactions, within cattle. In particular, Estrone and phosphoadenosine phosphosulfate can be converted into estrone sulfate and adenosine 3',5'-diphosphate through the action of the enzyme estrogen sulfotransferase. In addition, Estrone can be converted into 2-hydroxyestrone; which is mediated by the enzyme cytochrome P450 1A1. In cattle, estrone is involved in the metabolic pathway called the estrone metabolism pathway. Estrone is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
3-Hydroxy-1,3,5(10)-estratrien-17-oneChEBI
Follicular hormoneChEBI
FolliculinChEBI
OestroneChEBI
(+)-EstroneHMDB
1,3,5(10)-Estratrien-3-ol-17-oneHMDB
3-Hydroxy-17-keto-estra-1,3,5-trieneHMDB
3-Hydroxyestra-1,3,5(10)-trien-17-oneHMDB
3-Hydroxyestra-1,3,5(10)-triene-17-oneHMDB
3-Hydroxyoestra-1,3,5(10)-trien-17-oneHMDB
D1,3,5(10)-Estratrien-3-ol-17-oneHMDB
Estrone, (+-)-isomerHMDB
Hyrex brand OF estroneHMDB
Estrone, (9 beta)-isomerHMDB
EstrovarinHMDB
KestroneHMDB
WehgenHMDB
Estrone, (8 alpha)-isomerHMDB
Hauck brand OF estroneHMDB
UnigenHMDB
Vortech brand OF estroneHMDB
Chemical FormulaC18H22O2
Average Molecular Weight270.3661
Monoisotopic Molecular Weight270.161979948
IUPAC Name(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
Traditional Name(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
CAS Registry Number53-16-7
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
InChI Identifier
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
InChI KeyDNXHEGUUPJUMQT-CBZIJGRNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens 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 FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
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
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.08 m³·mol⁻¹ChemAxon
Polarizability31.24 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-05ox-3951000000-8bc438f505b3cf49b21fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-003u-4942000000-a72ea34d85d9d524c247JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0019-8931000000-aad9803af812c7c40f53JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-2940000000-2d417e7ecb4a8b87b817JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0980000000-5b293db89a0f2efeb784JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05ox-3951000000-8bc438f505b3cf49b21fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003u-4942000000-a72ea34d85d9d524c247JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0019-8931000000-aad9803af812c7c40f53JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-1970000000-871531490fb22b8fe12fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009t-1093000000-a8d755d13e3b819514c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0190000000-071e67516e11357ff64eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-4910000000-20e059a7c508ba492af3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-067i-9700000000-9ff5214f08822f238fa9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-2940000000-3b9744c27d6a3d2eff6eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ukc-2690000000-7afb48e267c7b334213bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0690000000-a76244de959b06ec896eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0910000000-4a1bc1cbc90c3e5281e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0900000000-0830d4ad43804976f508JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0390000000-41440e74b3f0b5f365d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0390000000-fdc0255246e3a9013d0aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a59-2910000000-fc5173d435c3c7fc603cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0390000000-25cecb1c4785e7bffd56JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-64cf013a5b0ad5e8bf56JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0590000000-40418c285df2157226dcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-6980000000-724c68b368fbe3d38f5eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6778bd7122813b501c1eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-0f2e0b96bc30b346c581JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f9i-1090000000-9ccbd9f351dd1f8e52cbJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-2930000000-c99df908474247066a2bJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00004 +/- 0.00001 uM details
Detected and Quantified0.00013 +/- 0.00001 uM details
Detected and Quantified0.00003 - 0.00007 uM details
Detected and Quantified0.00021 uM details
Detected and Quantified0.00003 +/- 0.00001 uM details
Detected and Quantified0.002 +/- 0.00024 uM details
Detected and Quantified0.01 +/- 0.00014 uM details
Detected and Quantified0.001 +/- 0.00022 uM details
Detected and Quantified0.00052 uM details
Detected and Quantified0.001 uM details
Detected and Quantified0.0007 uM details
Detected and Quantified0.00186 - 0.00209 uM details
Detected and Quantified0.00002 uM details
Detected and Quantified0.00002 uM details
Detected and Quantified0.0001 uM details
Detected and Quantified0.00001 uM details
Detected and Quantified0.00003 uM details
Detected and Quantified0.0001 +/- 0.00001 uM details
Detected and Quantified0.0001 +/- 0.00001 uM details
Detected and Quantified0.00012 +/- 0.00001 uM details
Detected and Quantified0.00014 uM details
Detected and Quantified0.0002 uM details
Detected and Quantified0.0003 +/- 0.00001 uM details
HMDB IDHMDB0000145
DrugBank IDDB00655
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012798
KNApSAcK IDC00003663
Chemspider ID5660
KEGG Compound IDC00468
BioCyc IDNot Available
BiGG ID35059
Wikipedia LinkEstrone
METLIN ID264
PubChem Compound5870
PDB IDNot Available
ChEBI ID17263
References
Synthesis ReferenceKocovsky, 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)
General References
  1. Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. [PubMed:512140 ]
  2. Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e. [PubMed:17177502 ]
  3. Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
  4. Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]
  5. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]
  6. Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947. [PubMed:20494161 ]
  7. Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024. Epub 2010 May 25. [PubMed:20541211 ]