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Record Information
Version1.0
Creation Date2016-09-30 22:20:08 UTC
Update Date2020-05-21 16:27:12 UTC
BMDB IDBMDB0000145
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-2940000000-2d417e7ecb4a8b87b817View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0980000000-5b293db89a0f2efeb784View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05ox-3951000000-8bc438f505b3cf49b21fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003u-4942000000-a72ea34d85d9d524c247View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0019-8931000000-aad9803af812c7c40f53View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-1970000000-871531490fb22b8fe12fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009t-1093000000-a8d755d13e3b819514c8View 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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ukc-2690000000-7afb48e267c7b334213bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0690000000-a76244de959b06ec896eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0910000000-4a1bc1cbc90c3e5281e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0900000000-0830d4ad43804976f508View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0390000000-41440e74b3f0b5f365d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0390000000-fdc0255246e3a9013d0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a59-2910000000-fc5173d435c3c7fc603cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0390000000-25cecb1c4785e7bffd56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-64cf013a5b0ad5e8bf56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0590000000-40418c285df2157226dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-6980000000-724c68b368fbe3d38f5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6778bd7122813b501c1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-0f2e0b96bc30b346c581View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f9i-1090000000-9ccbd9f351dd1f8e52cbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-2930000000-c99df908474247066a2bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Kidney
  • Liver
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000269 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified0.0018 uMNot SpecifiedNot Specified
Normal
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified0.00003699 +/- 0.000003699 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000125 +/- 0.000009986 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00003366 - 0.00007471 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000206 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000155 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000211 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000755 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000100 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000292 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00008507 +/- 0.00001110 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00008877 +/- 0.000007397 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000118 +/- 0.000003699 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000137 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000163 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000248 +/- 0.000007397 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00002922 +/- 0.000002589 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00167 +/- 0.000244 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00468 +/- 0.000141 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000565 +/- 0.000222 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000522 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000766 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000692 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00186 - 0.00209 uMNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00259 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone
details
BloodDetected and Quantified0.00707 uMNot SpecifiedNot Specified
Treated with estradiol benzoate
details
HMDB IDHMDB0000145
DrugBank IDDB00655
Phenol Explorer Compound IDNot Available
FooDB 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)Not Available
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 ]

Enzymes

General function:
Involved in estrone sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone (PubMed:1900200) (By similarity). Is a key enzyme in estrogen homeostasis, the sulfation of estrogens leads to their inactivation. Also sulfates dehydroepiandrosterone (DHEA), pregnenolone, (24S)-hydroxycholesterol and xenobiotic compounds like ethinylestradiol, equalenin, diethyl stilbesterol and 1-naphthol at significantly lower efficiency. Does not sulfonate cortisol, testosterone and dopamine (By similarity).
Gene Name:
SULT1E1
Uniprot ID:
P19217
Molecular weight:
34640.0
Reactions
Estrone + Phosphoadenosine phosphosulfate → Estrone sulfate + Adenosine 3',5'-diphosphatedetails
General function:
Lipid transport and metabolism
Specific function:
NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids (By similarity).
Gene Name:
HSD17B6
Uniprot ID:
Q3T001
Molecular weight:
36198.0
General function:
Lipid transport and metabolism
Specific function:
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinal to all-trans-retinol. May play a role in the regeneration of visual pigment at high light intensity.
Gene Name:
RDH8
Uniprot ID:
Q9N126
Molecular weight:
33956.0
Reactions
Estradiol + NADP → Estrone + NADPHdetails
General function:
Involved in binding
Specific function:
Catalyzes the second of the four reactions of the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process, allows the addition of two carbons to the chain of long- and very long-chain fatty acids/VLCFAs per cycle. This enzyme has a 3-ketoacyl-CoA reductase activity, reducing 3-ketoacyl-CoA to 3-hydroxyacyl-CoA, within each cycle of fatty acid elongation. Thereby, it may participate in the production of VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators. May also catalyze the transformation of estrone (E1) into estradiol (E2) and play a role in estrogen formation.
Gene Name:
HSD17B12
Uniprot ID:
Q5E9H7
Molecular weight:
34495.0