Milk Composition Database: Showing metabocard for Estradiol (BMDB0000151)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:13 UTC

Update Date

2020-06-04 20:37:45 UTC

MCDB ID

BMDB0000151

Secondary Accession Numbers

BMDB00151

Metabolite Identification

Common Name

Estradiol

Description

Beta-Beta-beta-estradiol, also known as beta-beta-estradiol or beta-beta-estradiol, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, Beta-beta-estradiol is considered to be a steroid lipid molecule. Beta-Beta-beta-estradiol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Beta-Beta-beta-estradiol exists in all living organisms, ranging from bacteria to humans. In cattle, Beta-beta-estradiol is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Beta-Beta-beta-estradiol is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(17beta)-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
17beta Oestradiol	ChEBI
17beta-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
17beta-Oestradiol	ChEBI
beta-Estradiol	ChEBI
cis-Estradiol	ChEBI
Estradiol-17beta	ChEBI
Climara	Kegg
Divigel	Kegg
Estrace	Kegg
Estraderm	Kegg
Estrasorb	Kegg
Estring	Kegg
Estrogel	Kegg
Innofem	Kegg
Vagifem	Kegg
Vivelle	Kegg
(17b)-Estra-1,3,5(10)-triene-3,17-diol	Generator
(17Β)-estra-1,3,5(10)-triene-3,17-diol	Generator
17b Oestradiol	Generator
17Β oestradiol	Generator
17b-Estra-1,3,5(10)-triene-3,17-diol	Generator
17Β-estra-1,3,5(10)-triene-3,17-diol	Generator
17b-Oestradiol	Generator
17Β-oestradiol	Generator
b-Estradiol	Generator
Β-estradiol	Generator
Estradiol-17b	Generator
Estradiol-17β	Generator
(+)-3,17b-Estradiol	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17b-ol	HMDB
17b-Estradiol	HMDB
3,17-Epidihydroxyestratriene	HMDB
3,17b-Dihydroxyestra-1,3,5(10)-triene	HMDB
3,17b-Estradiol	HMDB
Aerodiol	HMDB
Agofollin	HMDB
Altrad	HMDB
Amnestrogen	HMDB
Aquadiol	HMDB
Bardiol	HMDB
Climaderm	HMDB
Compudose	HMDB
Corpagen	HMDB
D-Estradiol	HMDB
D-Oestradiol	HMDB
delta-Estradiol	HMDB
delta-Oestradiol	HMDB
Dermestril	HMDB
Dihydro-theelin	HMDB
Dihydrofollicular hormone	HMDB
Dihydrofolliculin	HMDB
Dihydromenformon	HMDB
Dihydrotheelin	HMDB
Dihydroxyestrin	HMDB
Dimenformon	HMDB
Diogyn	HMDB
Diogynets	HMDB
Encore	HMDB
Epiestriol 50	HMDB
Estra-1,3,5(10)-triene-3,17b-diol	HMDB
Estraderm TTS	HMDB
Estradiol-17-beta	HMDB
Estradot	HMDB
Estraldine	HMDB
Estring vaginal ring	HMDB
Estroclim	HMDB
Estroclim 50	HMDB
Estrogel HBF	HMDB
Estrovite	HMDB
Evorel	HMDB
Femestral	HMDB
Femogen	HMDB
Follicyclin	HMDB
Gelestra	HMDB
Ginosedol	HMDB
Gynergon	HMDB
Gynoestryl	HMDB
Lamdiol	HMDB
Macrodiol	HMDB
Menorest	HMDB
Nordicol	HMDB
Oesclim	HMDB
Oestergon	HMDB
Oestra-1,3,5(10)-triene-3,17b-diol	HMDB
Oestradiol	HMDB
Oestrogel	HMDB
Oestroglandol	HMDB
Ovahormon	HMDB
Ovasterol	HMDB
Ovastevol	HMDB
Ovocyclin	HMDB
Ovocylin	HMDB
Perlatanol	HMDB
Primofol	HMDB
Profoliol	HMDB
Profoliol b	HMDB
Progynon	HMDB
Progynon DH	HMDB
Sandrena 1	HMDB
Syndiol	HMDB
Systen	HMDB
Zumenon	HMDB
Estradiol hemihydrate, (17 alpha)-isomer	HMDB
Estradiol, (-)-isomer	HMDB
Estradiol, monosodium salt	HMDB
Estradiol-17 beta	HMDB
17 beta Oestradiol	HMDB
17 beta-Estradiol	HMDB
Estradiol 17 beta	HMDB
Estradiol monohydrate	HMDB
Estradiol orion brand	HMDB
Estradiol, (17-alpha)-isomer	HMDB
Estradiol, sodium salt	HMDB
17 beta Estradiol	HMDB
Estradiol hemihydrate	HMDB
Estradiol, (+-)-isomer	HMDB
Estradiol, (16 alpha,17 alpha)-isomer	HMDB
Estradiol-17 alpha	HMDB
Orion brand OF estradiol	HMDB
17 beta-Oestradiol	HMDB
Estradiol 17 alpha	HMDB
Estradiol 17beta	HMDB
Estradiol anhydrous	HMDB
Estradiol, (16 alpha,17 beta)-isomer	HMDB
Estradiol, (8 alpha,17 beta)-(+-)-isomer	HMDB
Estradiol, (8 alpha,17 beta)-isomer	HMDB
Estradiol, (9 beta,17 alpha)-isomer	HMDB
Estradiol, (9 beta,17 beta)-isomer	HMDB
Novartis pharmaceuticals brand OF estradiol	HMDB
Progynova	HMDB
Estradiol valeriante	HMDB
Estradiol valerate	HMDB
Delestrogen	HMDB
Progynon depot	HMDB
Progynon-depot	HMDB
Estradiol	ChEBI

Chemical Formula

C₁₈H₂₄O₂

Average Molecular Weight

272.382

Monoisotopic Molecular Weight

272.177630012

IUPAC Name

(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

Traditional Name

(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

CAS Registry Number

50-28-2

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

InChI Identifier

InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

InChI Key

VOXZDWNPVJITMN-ZBRFXRBCSA-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
17-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:16469 )
estradiol (CHEBI:16469 )
C18 steroids (estrogens) and derivatives (C00951 )
Estrane and derivatives (C00951 )
Estrogens (C00951 )
C18 steroids (estrogens) and derivatives (LMST02010001 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	178.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0036 mg/mL	Not Available
LogP	4.01	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	3.57	ALOGPS
logP	3.75	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	32.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-017r-1791100000-7b16254894cdcb8ee86d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-1980000000-b2dec84718861de189ec	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-3940000000-f3692a81f624f15d3e0b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-0960000000-be4e96105398cb805cd9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-0790000000-5c858378c15135811824	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-017r-1791100000-7b16254894cdcb8ee86d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-1490000000-9f16d080d50dcea52de4	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0udr-2279400000-cea6d26f1ab9c44b5160	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_1) - 70eV, Positive	Not Available	2021-11-05	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-05fr-0590000000-1dd83cbcb3d21edfbdbd	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-2900000000-f3279d6cdab9cf3800fd	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-8900000000-0efe28378f612aab8c3d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-00di-1980000000-b2dec84718861de189ec	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-00di-3940000000-f3692a81f624f15d3e0b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-00di-0960000000-be4e96105398cb805cd9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00di-0790000000-5c83456da6e28375ad51	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0490000000-c3c4658cfae36bedff30	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-1900000000-51d28e077b0aefa6aa1c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-2900000000-a22a9233ffbb9eb05a1b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0960000000-d2ee002f4c0363c04e83	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0960000000-2ad7c6e17386448419df	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-f73a7a19d55a4f78be01	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-0a4i-2900000000-a22a9233ffbb9eb05a1b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-0a4i-1900000000-51d28e077b0aefa6aa1c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-002b-0930000000-c177eb564c729479f2be	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0190000000-b572b380a16bb1b20b27	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-0960000000-d2ee002f4c0363c04e83	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0090000000-f906ca4989738e61667a	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0190000000-2924fb687c668eb8918a	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-0590000000-53eccf4b813f6992d38d	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-6890000000-c399a267a752cfdba323	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-274ccc6305612709fd33	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-afc94cc62691bfb34161	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-0190000000-8d49a19142b1bd1a09a1	2017-07-26	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-075a-2920000000-10218bfa5b56f829853e	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	2012-12-04	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	0.00001 +/- 0.00001 uM	PMID: 512140	details
Detected and Quantified	0.00002 +/- 0.00001 uM	PMID: 512140	details
Detected and Quantified	0.00002 - 0.00003 uM	PMID: 512140	details
Detected and Quantified	0.00004 - 0.00005 uM	PMID: 512140	details
Detected and Quantified	0.00012 +/- 0.00003 uM	PMID: 17177502	details
Detected and Quantified	0.0001 +/- 0.00001 uM	PMID: 17177502	details
Detected and Quantified	0.0002 +/- 0.00001 uM	PMID: 17177502	details
Detected and Quantified	0.00031 +/- 0.00002 uM	PMID: 17177502	details
Detected and Quantified	0.0002 +/- 0.00001 uM	PMID: 17177502	details
Detected and Quantified	0.0012 +/- 0.00013 uM	PMID: 17177502	details
Detected and Quantified	0.00008 +/- 0.00005 uM	PMID: 17852390	details
Detected and Quantified	0.00005 uM	PMID: 18412364	details
Detected and Quantified	0.00006 uM	PMID: 18412364	details
Detected and Quantified	0.00005 uM	PMID: 18412364	details
Detected and Quantified	0.00022 - 0.00024 uM	PMID: 19679050	details
Detected and Quantified	0.00001 uM	PMID: 20494161	details
Detected and Quantified	0.00001 uM	PMID: 20494161	details
Detected and Quantified	0.00001 uM	PMID: 20494161	details
Detected and Quantified	0.00001 uM	PMID: 20494161	details
Detected and Quantified	0.00001 uM	PMID: 20494161	details

External Links

HMDB ID

HMDB0000151

DrugBank ID

DB00783

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000362

KNApSAcK ID

Not Available

Chemspider ID

5554

KEGG Compound ID

C00951

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16469

References

Synthesis Reference

Vasiljeva, L. L.; Demin, P. M.; Kochev, D. M.; Lapitskaya, M. A.; Pivnitskya, K. K. New synthesis of estradiol from androsta-1,4-diene-3,17-dione. Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (1999), 48(3), 593-595.

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 ]

Showing metabocard for Estradiol (BMDB0000151)

Structure for BMDB0000151 (Estradiol)