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Record Information
Version1.0
Creation Date2016-09-30 22:20:13 UTC
Update Date2020-06-04 20:37:45 UTC
MCDB ID BMDB0000151
Secondary Accession Numbers
  • BMDB00151
Metabolite Identification
Common NameEstradiol
DescriptionBeta-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
Thumb
Synonyms
ValueSource
(17beta)-Estra-1,3,5(10)-triene-3,17-diolChEBI
17beta OestradiolChEBI
17beta-Estra-1,3,5(10)-triene-3,17-diolChEBI
17beta-OestradiolChEBI
beta-EstradiolChEBI
cis-EstradiolChEBI
Estradiol-17betaChEBI
ClimaraKegg
DivigelKegg
EstraceKegg
EstradermKegg
EstrasorbKegg
EstringKegg
EstrogelKegg
InnofemKegg
VagifemKegg
VivelleKegg
(17b)-Estra-1,3,5(10)-triene-3,17-diolGenerator
(17Β)-estra-1,3,5(10)-triene-3,17-diolGenerator
17b OestradiolGenerator
17Β oestradiolGenerator
17b-Estra-1,3,5(10)-triene-3,17-diolGenerator
17Β-estra-1,3,5(10)-triene-3,17-diolGenerator
17b-OestradiolGenerator
17Β-oestradiolGenerator
b-EstradiolGenerator
Β-estradiolGenerator
Estradiol-17bGenerator
Estradiol-17βGenerator
(+)-3,17b-EstradiolHMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17b-olHMDB
17b-EstradiolHMDB
3,17-EpidihydroxyestratrieneHMDB
3,17b-Dihydroxyestra-1,3,5(10)-trieneHMDB
3,17b-EstradiolHMDB
AerodiolHMDB
AgofollinHMDB
AltradHMDB
AmnestrogenHMDB
AquadiolHMDB
BardiolHMDB
ClimadermHMDB
CompudoseHMDB
CorpagenHMDB
D-EstradiolHMDB
D-OestradiolHMDB
delta-EstradiolHMDB
delta-OestradiolHMDB
DermestrilHMDB
Dihydro-theelinHMDB
Dihydrofollicular hormoneHMDB
DihydrofolliculinHMDB
DihydromenformonHMDB
DihydrotheelinHMDB
DihydroxyestrinHMDB
DimenformonHMDB
DiogynHMDB
DiogynetsHMDB
EncoreHMDB
Epiestriol 50HMDB
Estra-1,3,5(10)-triene-3,17b-diolHMDB
Estraderm TTSHMDB
Estradiol-17-betaHMDB
EstradotHMDB
EstraldineHMDB
Estring vaginal ringHMDB
EstroclimHMDB
Estroclim 50HMDB
Estrogel HBFHMDB
EstroviteHMDB
EvorelHMDB
FemestralHMDB
FemogenHMDB
FollicyclinHMDB
GelestraHMDB
GinosedolHMDB
GynergonHMDB
GynoestrylHMDB
LamdiolHMDB
MacrodiolHMDB
MenorestHMDB
NordicolHMDB
OesclimHMDB
OestergonHMDB
Oestra-1,3,5(10)-triene-3,17b-diolHMDB
OestradiolHMDB
OestrogelHMDB
OestroglandolHMDB
OvahormonHMDB
OvasterolHMDB
OvastevolHMDB
OvocyclinHMDB
OvocylinHMDB
PerlatanolHMDB
PrimofolHMDB
ProfoliolHMDB
Profoliol bHMDB
ProgynonHMDB
Progynon DHHMDB
Sandrena 1HMDB
SyndiolHMDB
SystenHMDB
ZumenonHMDB
Estradiol hemihydrate, (17 alpha)-isomerHMDB
Estradiol, (-)-isomerHMDB
Estradiol, monosodium saltHMDB
Estradiol-17 betaHMDB
17 beta OestradiolHMDB
17 beta-EstradiolHMDB
Estradiol 17 betaHMDB
Estradiol monohydrateHMDB
Estradiol orion brandHMDB
Estradiol, (17-alpha)-isomerHMDB
Estradiol, sodium saltHMDB
17 beta EstradiolHMDB
Estradiol hemihydrateHMDB
Estradiol, (+-)-isomerHMDB
Estradiol, (16 alpha,17 alpha)-isomerHMDB
Estradiol-17 alphaHMDB
Orion brand OF estradiolHMDB
17 beta-OestradiolHMDB
Estradiol 17 alphaHMDB
Estradiol 17betaHMDB
Estradiol anhydrousHMDB
Estradiol, (16 alpha,17 beta)-isomerHMDB
Estradiol, (8 alpha,17 beta)-(+-)-isomerHMDB
Estradiol, (8 alpha,17 beta)-isomerHMDB
Estradiol, (9 beta,17 alpha)-isomerHMDB
Estradiol, (9 beta,17 beta)-isomerHMDB
Novartis pharmaceuticals brand OF estradiolHMDB
ProgynovaHMDB
Estradiol valerianteHMDB
Estradiol valerateHMDB
DelestrogenHMDB
Progynon depotHMDB
Progynon-depotHMDB
EstradiolChEBI
Chemical FormulaC18H24O2
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
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 Number50-28-2
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 KeyVOXZDWNPVJITMN-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens 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 FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0036 mg/mLNot Available
LogP4.01HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP3.57ALOGPS
logP3.75ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.9 m³·mol⁻¹ChemAxon
Polarizability32.12 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 (2 TMS)splash10-017r-1791100000-7b16254894cdcb8ee86dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1980000000-b2dec84718861de189ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-3940000000-f3692a81f624f15d3e0bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0960000000-be4e96105398cb805cd9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0790000000-5c858378c15135811824JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017r-1791100000-7b16254894cdcb8ee86dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1490000000-9f16d080d50dcea52de4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udr-2279400000-cea6d26f1ab9c44b5160JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-0590000000-1dd83cbcb3d21edfbdbdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-2900000000-f3279d6cdab9cf3800fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-0efe28378f612aab8c3dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-00di-1980000000-b2dec84718861de189ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-00di-3940000000-f3692a81f624f15d3e0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-00di-0960000000-be4e96105398cb805cd9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-0790000000-5c83456da6e28375ad51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0490000000-c3c4658cfae36bedff30JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-1900000000-51d28e077b0aefa6aa1cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-2900000000-a22a9233ffbb9eb05a1bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-d2ee002f4c0363c04e83JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-2ad7c6e17386448419dfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0190000000-2924fb687c668eb8918aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0590000000-53eccf4b813f6992d38dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6890000000-c399a267a752cfdba323JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-274ccc6305612709fd33JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-afc94cc62691bfb34161JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-0190000000-8d49a19142b1bd1a09a1JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-075a-2920000000-10218bfa5b56f829853eJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00001 +/- 0.00001 uM details
Detected and Quantified0.00002 +/- 0.00001 uM details
Detected and Quantified0.00002 - 0.00003 uM details
Detected and Quantified0.00004 - 0.00005 uM details
Detected and Quantified0.00012 +/- 0.00003 uM details
Detected and Quantified0.0001 +/- 0.00001 uM details
Detected and Quantified0.0002 +/- 0.00001 uM details
Detected and Quantified0.00031 +/- 0.00002 uM details
Detected and Quantified0.0002 +/- 0.00001 uM details
Detected and Quantified0.0012 +/- 0.00013 uM details
Detected and Quantified0.00008 +/- 0.00005 uM details
Detected and Quantified0.00005 uM details
Detected and Quantified0.00006 uM details
Detected and Quantified0.00005 uM details
Detected and Quantified0.00022 - 0.00024 uM details
Detected and Quantified0.00001 uM details
Detected and Quantified0.00001 uM details
Detected and Quantified0.00001 uM details
Detected and Quantified0.00001 uM details
Detected and Quantified0.00001 uM details
HMDB IDHMDB0000151
DrugBank IDDB00783
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000362
KNApSAcK IDNot Available
Chemspider ID5554
KEGG Compound IDC00951
BioCyc IDNot Available
BiGG ID36456
Wikipedia LinkEstradiol
METLIN ID263
PubChem Compound5757
PDB IDNot Available
ChEBI ID16469
References
Synthesis ReferenceVasiljeva, 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
  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 ]