Estradiol (CHEM003626)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (8)XML
Record Information
Version1.0
Creation Date2014-09-11 02:03:56 UTC
Update Date2026-04-17 17:20:20 UTC
Accession NumberCHEM003626
Identification
Common NameEstradiol
ClassSmall Molecule
DescriptionGenerally refers to the 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Various isomers can be synthesized.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Anti-Menopausal Agent
  • Contraceptive Agent
  • Drug
  • Estrogen
  • Food Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass272.382 g/mol
Monoisotopic Mass272.178 g/mol
CAS Registry Number50-28-2
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point151-152°C
Boiling PointNot Available
Solubility3.6 mg/L (at 27°C)
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-017r-1791100000-7b16254894cdcb8ee86dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1980000000-b2dec84718861de189ecSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-3940000000-f3692a81f624f15d3e0bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0960000000-be4e96105398cb805cd9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0790000000-5c858378c15135811824Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017r-1791100000-7b16254894cdcb8ee86dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1490000000-9f16d080d50dcea52de4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udr-2279400000-cea6d26f1ab9c44b5160Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-0590000000-1dd83cbcb3d21edfbdbdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-2900000000-f3279d6cdab9cf3800fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-0efe28378f612aab8c3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-00di-1980000000-b2dec84718861de189ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-00di-3940000000-f3692a81f624f15d3e0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-00di-0960000000-be4e96105398cb805cd9Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-0790000000-5c83456da6e28375ad51Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0490000000-c3c4658cfae36bedff30Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-1900000000-51d28e077b0aefa6aa1cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-2900000000-a22a9233ffbb9eb05a1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-d2ee002f4c0363c04e83Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-2ad7c6e17386448419dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-f73a7a19d55a4f78be01Spectrum
LC-MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-0a4i-2900000000-a22a9233ffbb9eb05a1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4i-1900000000-51d28e077b0aefa6aa1cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-002b-0930000000-c177eb564c729479f2beSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0190000000-b572b380a16bb1b20b27Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-0960000000-d2ee002f4c0363c04e83Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-0090000000-f906ca4989738e61667aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0190000000-2924fb687c668eb8918aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0590000000-53eccf4b813f6992d38dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6890000000-c399a267a752cfdba323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-274ccc6305612709fd33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-afc94cc62691bfb34161Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-0190000000-8d49a19142b1bd1a09a1Spectrum
MSMass Spectrum (Electron Ionization)splash10-075a-2920000000-10218bfa5b56f829853eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityEstradiol enters target cells freely (e.g., female organs, breasts, hypothalamus, pituitary) and interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.
MetabolismExogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450. Route of Elimination: Estradiol, estrone and estriol are excreted in the urine along with glucuronide and sulfate conjugates. Half Life: 36 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of urogenital symptoms associated with post-menopausal atrophy of the vagina (such as dryness, burning, pruritus and dyspareunia) and/or the lower urinary tract (urinary urgency and dysuria).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsCan cause nausea and vomiting, and withdrawal bleeding may occur in females.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00783
HMDB IDHMDB0000151
FooDB IDFDB000362
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID36456
BioCyc IDNot Available
METLIN ID263
PDB IDNot Available
Wikipedia LinkEstradiol
Chemspider ID5554
ChEBI ID16469
PubChem Compound ID5757
Kegg Compound IDC00951
YMDB IDNot Available
ECMDB IDECMDB24019
References
Synthesis Reference

Akira Nakagawa, Munehiko Hirano, Miyuki Shinmura, “Estradiol percutaneous administration preparations.” U.S. Patent US5248676, issued November, 1980.

MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. Schaap LA, Pluijm SM, Smit JH, van Schoor NM, Visser M, Gooren LJ, Lips P: The association of sex hormone levels with poor mobility, low muscle strength and incidence of falls among older men and women. Clin Endocrinol (Oxf). 2005 Aug;63(2):152-60.
10. Evagelatou M, Webster AD, Farrant J: Effects of 17 beta-oestradiol on function of lymphocytes from normal donors and patients with common variable immunodeficiency (CVID). Clin Exp Immunol. 1994 Nov;98(2):203-9.
11. Gibney MJ, Walsh M, Brennan L, Roche HM, German B, van Ommen B: Metabolomics in human nutrition: opportunities and challenges. Am J Clin Nutr. 2005 Sep;82(3):497-503.
12. Carnevale V, Scillitani A, Vecci E, D'Erasmo E, Romagnoli E, Paglia F, Pepe J, Baldini V, Santori C, De Geronimo S, Minisola S: Dehydroepiandrosterone sulfate and bone resorption rates as reflected by serum levels of C-terminal telopeptide of type I collagen: a study in healthy men. J Endocrinol Invest. 2005 Feb;28(2):102-5.
13. Jojua T, Sumbadze TS, Papava M: Secretion of sex hormones in patients with open angle glaucoma. Georgian Med News. 2005 Jul-Aug;(124-125):33-7.
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15. Lahdes-Vasama TT, Koskimaki JE, Streng TK, Fisch RD, Nilson EA, Santti RS, Tammela TL: Urodynamic findings in men operated on for an undescended testicle. BJU Int. 2003 Dec;92(9):972-6.
16. Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4.
17. Iranmanesh A, Veldhuis JD: Combined inhibition of types I and II 5 alpha-reductase selectively augments the basal (nonpulsatile) mode of testosterone secretion in young men. J Clin Endocrinol Metab. 2005 Jul;90(7):4232-7. Epub 2005 Apr 5.
18. Stabile LP, Davis AL, Gubish CT, Hopkins TM, Luketich JD, Christie N, Finkelstein S, Siegfried JM: Human non-small cell lung tumors and cells derived from normal lung express both estrogen receptor alpha and beta and show biological responses to estrogen. Cancer Res. 2002 Apr 1;62(7):2141-50.
19. Chabbert-Buffet N, Bouchard P: [Physiology and exploration of the gonadotropic axis]. Rev Prat. 1999 Jun 15;49(12):1270-6.
20. Schonknecht P, Henze M, Hunt A, Klinga K, Haberkorn U, Schroder J: Hippocampal glucose metabolism is associated with cerebrospinal fluid estrogen levels in postmenopausal women with Alzheimer's disease. Psychiatry Res. 2003 Oct 30;124(2):125-7.
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22. Blomquist CH, D'Ascoli PT: Gestational development of human placental 17 beta-hydroxysteroid oxidoreductase types 1 and 2. Hum Reprod. 1995 Oct;10(10):2685-9.
23. Fraser D, Padwick ML, Whitehead M, Coffer A, King RJ: Presence of an oestradiol receptor-related protein in the skin: changes during the normal menstrual cycle. Br J Obstet Gynaecol. 1991 Dec;98(12):1277-82.
24. Greb RR, Grieshaber K, Gromoll J, Sonntag B, Nieschlag E, Kiesel L, Simoni M: A common single nucleotide polymorphism in exon 10 of the human follicle stimulating hormone receptor is a major determinant of length and hormonal dynamics of the menstrual cycle. J Clin Endocrinol Metab. 2005 Aug;90(8):4866-72. Epub 2005 May 10.
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