Milk Composition Database: Showing metabocard for Estrone (BMDB0000145)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:08 UTC

Update Date

2020-06-04 20:40:27 UTC

MCDB ID

BMDB0000145

Secondary Accession Numbers

BMDB00145

Metabolite Identification

Common Name

Estrone

Description

Estrone, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-1,3,5(10)-estratrien-17-one	ChEBI
Follicular hormone	ChEBI
Folliculin	ChEBI
Oestrone	ChEBI
(+)-Estrone	HMDB
1,3,5(10)-Estratrien-3-ol-17-one	HMDB
3-Hydroxy-17-keto-estra-1,3,5-triene	HMDB
3-Hydroxyestra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxyestra-1,3,5(10)-triene-17-one	HMDB
3-Hydroxyoestra-1,3,5(10)-trien-17-one	HMDB
D1,3,5(10)-Estratrien-3-ol-17-one	HMDB
Estrone, (+-)-isomer	HMDB
Hyrex brand OF estrone	HMDB
Estrone, (9 beta)-isomer	HMDB
Estrovarin	HMDB
Kestrone	HMDB
Wehgen	HMDB
Estrone, (8 alpha)-isomer	HMDB
Hauck brand OF estrone	HMDB
Unigen	HMDB
Vortech brand OF estrone	HMDB

Chemical Formula

C₁₈H₂₂O₂

Average Molecular Weight

270.3661

Monoisotopic Molecular Weight

270.161979948

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 Number

53-16-7

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 Key

DNXHEGUUPJUMQT-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane 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

17-oxo steroid (CHEBI:17263 )
3-hydroxy steroid (CHEBI:17263 )
estrane (C00468 )
C18 steroids (estrogens) and derivatives (C00468 )
Estrane and derivatives (C00468 )
Estrogens (C00468 )
C18 steroids (estrogens) and derivatives (LMST02010004 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	258 - 260 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.03 mg/mL	Not Available
LogP	3.13	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	4.03	ALOGPS
logP	4.31	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.08 m³·mol⁻¹	ChemAxon
Polarizability	31.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-05ox-3951000000-8bc438f505b3cf49b21f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-003u-4942000000-a72ea34d85d9d524c247	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0019-8931000000-aad9803af812c7c40f53	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-2940000000-2d417e7ecb4a8b87b817	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-0980000000-5b293db89a0f2efeb784	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-05ox-3951000000-8bc438f505b3cf49b21f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003u-4942000000-a72ea34d85d9d524c247	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0019-8931000000-aad9803af812c7c40f53	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adl-1970000000-871531490fb22b8fe12f	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-009t-1093000000-a8d755d13e3b819514c8	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0190000000-071e67516e11357ff64e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4j-4910000000-20e059a7c508ba492af3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-067i-9700000000-9ff5214f08822f238fa9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00di-2940000000-3b9744c27d6a3d2eff6e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0ukc-2690000000-7afb48e267c7b334213b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0690000000-a76244de959b06ec896e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a59-0910000000-4a1bc1cbc90c3e5281e6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a59-0900000000-0830d4ad43804976f508	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0390000000-41440e74b3f0b5f365d7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0390000000-fdc0255246e3a9013d0a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a59-2910000000-fc5173d435c3c7fc603c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0390000000-25cecb1c4785e7bffd56	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0pb9-0930000000-d947dbed0baa600d21a1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-38b40bed2e5c895d292f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pc0-0920000000-391eea72f6dda0eaa3c2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0159-0900000000-350b322964f2315bf505	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0690000000-277d92852a8f35c82f11	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0910000000-db57c4d24dab84acfe27	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-014i-0900000000-61f2965f743c194d4628	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-64cf013a5b0ad5e8bf56	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-0590000000-40418c285df2157226dc	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-6980000000-724c68b368fbe3d38f5e	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-6778bd7122813b501c1e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-0f2e0b96bc30b346c581	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f9i-1090000000-9ccbd9f351dd1f8e52cb	2017-07-26	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-2930000000-c99df908474247066a2b	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.00004 +/- 0.00001 uM	PMID: 512140	details
Detected and Quantified	0.00013 +/- 0.00001 uM	PMID: 512140	details
Detected and Quantified	0.00003 - 0.00007 uM	PMID: 512140	details
Detected and Quantified	0.00021 uM	PMID: 512140	details
Detected and Quantified	0.00003 +/- 0.00001 uM	PMID: 17177502	details
Detected and Quantified	0.002 +/- 0.00024 uM	PMID: 17177502	details
Detected and Quantified	0.01 +/- 0.00014 uM	PMID: 17177502	details
Detected and Quantified	0.001 +/- 0.00022 uM	PMID: 17852390	details
Detected and Quantified	0.00052 uM	PMID: 18412364	details
Detected and Quantified	0.001 uM	PMID: 18412364	details
Detected and Quantified	0.0007 uM	PMID: 18412364	details
Detected and Quantified	0.00186 - 0.00209 uM	PMID: 19679050	details
Detected and Quantified	0.00002 uM	PMID: 20494161	details
Detected and Quantified	0.00002 uM	PMID: 20494161	details
Detected and Quantified	0.0001 uM	PMID: 20494161	details
Detected and Quantified	0.00001 uM	PMID: 20494161	details
Detected and Quantified	0.00003 uM	PMID: 20494161	details
Detected and Quantified	0.0001 +/- 0.00001 uM	PMID: 20541211	details
Detected and Quantified	0.0001 +/- 0.00001 uM	PMID: 20541211	details
Detected and Quantified	0.00012 +/- 0.00001 uM	PMID: 20541211	details
Detected and Quantified	0.00014 uM	PMID: 20541211	details
Detected and Quantified	0.0002 uM	PMID: 20541211	details
Detected and Quantified	0.0003 +/- 0.00001 uM	PMID: 20541211	details

External Links

HMDB ID

HMDB0000145

DrugBank ID

DB00655

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17263

References

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)

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Estrone (BMDB0000145)

Structure for BMDB0000145 (Estrone)