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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:41:25 UTC
HMDB IDHMDB0000145
Secondary Accession Numbers
  • HMDB0004449
  • HMDB00145
  • HMDB04449
Metabolite Identification
Common NameEstrone
DescriptionEstrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961 , 17513923 , 17470679 , 17464097 ).
Structure
Data?1582752113
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
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point258 - 260 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.03 mg/mLNot Available
LogP3.13HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg170.62930932474
[M+H]+MetCCS_train_pos164.30530932474
[M-H]-Not Available170.629http://allccs.zhulab.cn/database/detail?ID=AllCCS00000181
[M+H]+Not Available164.583http://allccs.zhulab.cn/database/detail?ID=AllCCS00000181
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.27231661259
DarkChem[M-H]-162.18431661259
AllCCS[M+H]+166.57132859911
AllCCS[M-H]-173.79132859911
DeepCCS[M-2H]-211.54530932474
DeepCCS[M+Na]+186.12730932474
AllCCS[M+H]+166.632859911
AllCCS[M+H-H2O]+163.232859911
AllCCS[M+NH4]+169.732859911
AllCCS[M+Na]+170.632859911
AllCCS[M-H]-173.832859911
AllCCS[M+Na-2H]-173.532859911
AllCCS[M+HCOO]-173.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Estrone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C33277.3Standard polar33892256
Estrone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C32661.4Standard non polar33892256
Estrone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C32707.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Estrone,1TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O2664.0Semi standard non polar33892256
Estrone,1TMS,isomer #2C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C2640.1Semi standard non polar33892256
Estrone,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C2674.5Semi standard non polar33892256
Estrone,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C2497.6Standard non polar33892256
Estrone,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C2830.9Standard polar33892256
Estrone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]122950.6Semi standard non polar33892256
Estrone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C2913.0Semi standard non polar33892256
Estrone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C3214.9Semi standard non polar33892256
Estrone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C2910.8Standard non polar33892256
Estrone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C3083.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Estrone GC-MS (1 TMS)splash10-05ox-3951000000-8bc438f505b3cf49b21f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estrone GC-MS (1 MEOX; 1 TMS)splash10-003u-4942000000-a72ea34d85d9d524c2472014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estrone GC-MS (1 MEOX; 1 TMS)splash10-0019-8931000000-aad9803af812c7c40f532014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estrone EI-B (Non-derivatized)splash10-00di-2940000000-2d417e7ecb4a8b87b8172017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estrone EI-B (Non-derivatized)splash10-00di-0980000000-5b293db89a0f2efeb7842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estrone GC-MS (Non-derivatized)splash10-05ox-3951000000-8bc438f505b3cf49b21f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estrone GC-MS (Non-derivatized)splash10-003u-4942000000-a72ea34d85d9d524c2472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estrone GC-MS (Non-derivatized)splash10-0019-8931000000-aad9803af812c7c40f532017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-1970000000-871531490fb22b8fe12f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone GC-MS (1 TMS) - 70eV, Positivesplash10-009t-1093000000-a8d755d13e3b819514c82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estrone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-2930000000-c99df908474247066a2b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-0190000000-071e67516e11357ff64e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4j-4910000000-20e059a7c508ba492af32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-067i-9700000000-9ff5214f08822f238fa92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone EI-B (HITACHI M-80) , Positive-QTOFsplash10-00di-2940000000-3b9744c27d6a3d2eff6e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone LC-ESI-qTof , Positive-QTOFsplash10-0ukc-2690000000-7afb48e267c7b334213b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone Linear Ion Trap , negative-QTOFsplash10-014i-0690000000-a76244de959b06ec896e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOFsplash10-0a59-0910000000-4a1bc1cbc90c3e5281e62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOFsplash10-0a59-0900000000-0830d4ad43804976f5082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0390000000-41440e74b3f0b5f365d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0390000000-fdc0255246e3a9013d0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone , positive-QTOFsplash10-0a59-2910000000-fc5173d435c3c7fc603c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone LC-ESI-QFT , positive-QTOFsplash10-00di-0390000000-25cecb1c4785e7bffd562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone 35V, Positive-QTOFsplash10-0pb9-0930000000-d947dbed0baa600d21a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone 10V, Positive-QTOFsplash10-00di-0190000000-38b40bed2e5c895d292f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone 20V, Positive-QTOFsplash10-0pc0-0920000000-391eea72f6dda0eaa3c22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone 45V, Negative-QTOFsplash10-0159-0900000000-350b322964f2315bf5052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone 30V, Negative-QTOFsplash10-014i-0690000000-277d92852a8f35c82f112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone 40V, Negative-QTOFsplash10-0002-0910000000-db57c4d24dab84acfe272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estrone 60V, Negative-QTOFsplash10-014i-0900000000-61f2965f743c194d46282021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone 10V, Positive-QTOFsplash10-00di-0190000000-64cf013a5b0ad5e8bf562017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone 20V, Positive-QTOFsplash10-00fr-0590000000-40418c285df2157226dc2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone 40V, Positive-QTOFsplash10-0fb9-6980000000-724c68b368fbe3d38f5e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone 10V, Negative-QTOFsplash10-014i-0090000000-6778bd7122813b501c1e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone 20V, Negative-QTOFsplash10-014i-0090000000-0f2e0b96bc30b346c5812017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estrone 40V, Negative-QTOFsplash10-0f9i-1090000000-9ccbd9f351dd1f8e52cb2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00017 +/- 0.000071 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00020 (0.00011-0.00030) uMAdult (>18 years old)MaleNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.00012 (0.0-0.00024) uMAdult (>18 years old)FemaleNormal
    • The Merck Manual,...
details
UrineDetected and Quantified0.0013 +/- 0.00085 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00022 (0.00013-0.00038) uMAdult (>18 years old)Male
Severe coronary artery disease
details
BloodDetected and Quantified0.00021 (0.00011-0.00037) uMAdult (>18 years old)BothMinor electrocardiongraphic abnormalities and/or arrhythmia with negative coronary arteriograms details
BloodDetected and Quantified0.00035 (0.00014-0.00056) uMAdult (>18 years old)FemaleMenstrual cycle (follicular phase)
    • The Merck Manual,...
details
BloodDetected and Quantified0.00050 (0.00028-0.00074) uMAdult (>18 years old)FemaleMenstrual cycle (midcycle)
    • The Merck Manual,...
details
BloodDetected and Quantified0.00030 (0.00018-0.00042) uMAdult (>18 years old)FemaleMenstrual cycle (luteal phase)
    • The Merck Manual,...
details
BloodDetected and Quantified<0.00004 uMChildren (1-13 years old)Female
Aromatase deficiency
details
BloodDetected and Quantified0.000111-0.000318 uMAdult (>18 years old)MaleX-linked ichthyosis details
Associated Disorders and Diseases
Disease References
Menstrual cycle
  1. (). The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.. .
Aromatase deficiency
  1. Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
X-linked ichthyosis
  1. Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDESTRONE
MarkerDB IDMDB00000069
Good Scents IDNot Available
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)Download (PDF)
General References
  1. Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [PubMed:16598814 ]
  2. Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed:10997942 ]
  3. Kuhl H, Wiegratz I: Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications? Climacteric. 2007 Aug;10(4):344-53. [PubMed:17653961 ]
  4. Parker WH, Broder MS, Liu Z, Shoupe D, Farquhar C, Berek JS: Ovarian conservation at the time of hysterectomy for benign disease. Clin Obstet Gynecol. 2007 Jun;50(2):354-61. [PubMed:17513923 ]
  5. Stanway SJ, Delavault P, Purohit A, Woo LW, Thurieau C, Potter BV, Reed MJ: Steroid sulfatase: a new target for the endocrine therapy of breast cancer. Oncologist. 2007 Apr;12(4):370-4. [PubMed:17470679 ]
  6. Ito K: Hormone replacement therapy and cancers: the biological roles of estrogen and progestin in tumorigenesis are different between the endometrium and breast. Tohoku J Exp Med. 2007 May;212(1):1-12. [PubMed:17464097 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 62 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ARSD
Uniprot ID:
P51689
Molecular weight:
64859.3
General function:
Involved in catalytic activity
Specific function:
May be essential for the correct composition of cartilage and bone matrix during development. Has no activity toward steroid sulfates
Gene Name:
ARSE
Uniprot ID:
P51690
Molecular weight:
65668.4
General function:
Involved in 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. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
Gene Name:
SULT1E1
Uniprot ID:
P49888
Molecular weight:
35126.185
Reactions
Phosphoadenosine phosphosulfate + Estrone → Adenosine 3',5'-diphosphate + Estrone sulfatedetails
General function:
Involved in oxidoreductase activity
Specific function:
Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:
HSD17B2
Uniprot ID:
P37059
Molecular weight:
42784.75
Reactions
Estradiol + NAD(P)(+) → Estrone + NAD(P)Hdetails
Estradiol + NAD → Estrone + NADH + Hydrogen Iondetails
Estradiol + NADP → Estrone + NADPH + Hydrogen Iondetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:
HSD17B8
Uniprot ID:
Q92506
Molecular weight:
26973.56
Reactions
Estradiol + NAD(P)(+) → Estrone + NAD(P)Hdetails
Estradiol + NAD → Estrone + NADH + Hydrogen Iondetails
Estradiol + NADP → Estrone + NADPH + Hydrogen Iondetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0

Only showing the first 10 proteins. There are 62 proteins in total.