Estrogen metabolism (Homo sapiens)

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2-46656657688878776856626688888861666865DNA adductsDNA adductsDNA adductsDNA adductsOxygenUGT1A8UGT1A3OxygenNQO1COMTCYP1A1UGT1A9ARSEEstradiol-3,4-semiquinoneEstrone-17-glucuronide2-MethoxyestradiolCYP1B1EstroneCYP1A216a-Hydroxyestrone4-MethoxyestroneSuperoxideUGT1A1UGT1A8Estrone-3-glucuronide4-Methoxyestradiol-3-glucuronideUGT2B72-Methoxyestrone 3-glucuronideEstradiol-2,3-semiquinone2-hydroxy-estradiol-sulfateUGT1A9Estradiol sulfateSuperoxideUGT1A1CYP3A44-Methoxyestrone-3-glucuronideUGT1A1ARSCESTRADIOL2-Hydroxyestradiol2-HydroxyestroneUGT1A8Estradiol-2,3-quinoneUGT2B72-Methoxyestradiol-3-glucuronideEstrone-2,3-quinoneUGT1A8OxygenNQO1Estrone-3,4-quinone4-hydroxyestrone-3-glucuronideUGT1A82-hydroxyestradiol-3-glucuronideCYP1A1SULT1A1Estradiol-17-glucuronideSULT1E14-hydroxyestradiolUGT1A8Estradiol-3,4-quinoneEstradiol-3-glucuronide4-hydroxy-estradiol-4-glucuronideEstrone-3,4-semiquinoneCOMT4-hydroxy-estradiol-sulfateUGT1A8UGT1A1UGT1A1UGT1A82-MethoxyestroneSuperoxideGSTA12-hydroxy-estradiol-2-glucuronide4-MethoxyestradiolCYP1A2GSTM1UGT2B7Estrone sulfateCOMT2-Hydroxyestrone-3-glucuronideEstrone-2,3-semiquinoneOxygenSULT1A1CYP3A4COMTSuperoxideARSDSULT1A1UGT1A14-hydroxyestroneUGT1A8


Description

Estrogens are metabolized via hydroxylation by cytochrome P450 enzymes such as CYP1A1 and CYP3A4 and via conjugation by estrogen sulfotransferases (sulfation) and UDP-glucuronyltransferases (glucuronidation). In addition, estradiol is dehydrogenated by 17β-Hydroxysteroid dehydrogenase into the much less potent estrogen estrone. These reactions occur primarily in the liver, but also in other tissues.

Description source: Wikipedia.

This pathway is part the CPTAC Assay Portal.

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Quality Tags

Ontology Terms

 

Bibliography

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  1. Abel EL, Lyon RP, Bammler TK, Verlinde CL, Lau SS, Monks TJ, Eaton DL; ''Estradiol metabolites as isoform-specific inhibitors of human glutathione S-transferases.''; Chem Biol Interact, 2004 PubMed Europe PMC Scholia
  2. Cavalieri EL, Stack DE, Devanesan PD, Todorovic R, Dwivedy I, Higginbotham S, Johansson SL, Patil KD, Gross ML, Gooden JK, Ramanathan R, Cerny RL, Rogan EG; ''Molecular origin of cancer: catechol estrogen-3,4-quinones as endogenous tumor initiators.''; Proc Natl Acad Sci U S A, 1997 PubMed Europe PMC Scholia
  3. Lakhani NJ, Sarkar MA, Venitz J, Figg WD; ''2-Methoxyestradiol, a promising anticancer agent.''; Pharmacotherapy, 2003 PubMed Europe PMC Scholia
  4. Rogan EG, Badawi AF, Devanesan PD, Meza JL, Edney JA, West WW, Higginbotham SM, Cavalieri EL; ''Relative imbalances in estrogen metabolism and conjugation in breast tissue of women with carcinoma: potential biomarkers of susceptibility to cancer.''; Carcinogenesis, 2003 PubMed Europe PMC Scholia
  5. Raftogianis R, Creveling C, Weinshilboum R, Weisz J; ''Estrogen metabolism by conjugation.''; J Natl Cancer Inst Monogr, 2000 PubMed Europe PMC Scholia
  6. Shatalova EG, Walther SE, Favorova OO, Rebbeck TR, Blanchard RL; ''Genetic polymorphisms in human SULT1A1 and UGT1A1 genes associate with breast tumor characteristics: a case-series study.''; Breast Cancer Res, 2005 PubMed Europe PMC Scholia
  7. Guillemette C, Belanger A, Lepine J; ''Metabolic inactivation of estrogens in breast tissue by UDP-glucuronosyltransferase enzymes: an overview.''; Breast Cancer Res, 2004 PubMed Europe PMC Scholia
  8. Bianco NR, Perry G, Smith MA, Templeton DJ, Montano MM; ''Functional implications of antiestrogen induction of quinone reductase: inhibition of estrogen-induced deoxyribonucleic acid damage.''; Mol Endocrinol, 2003 PubMed Europe PMC Scholia

History

View all...
CompareRevisionActionTimeUserComment
134406view20:31, 21 July 2024EweitzEconomize layout
134405view20:28, 21 July 2024EweitzOntology Term : 'steroid hormone biosynthetic pathway' added !
106826view13:30, 17 September 2019MaintBotHMDB identifier normalization
106407view21:34, 28 August 2019KhanspersModified description
105587view04:44, 10 August 2019KhanspersModified description
96367view07:29, 10 March 2018EgonwReplaced a secondary ChEBI identifier with a primary identifier.
94909view23:56, 12 October 2017KhanspersModified description
94757view15:39, 5 October 2017EgonwGive many interactions mim annotation.
94227view21:33, 26 August 2017EgonwFor now, changed to the old format.
94189view14:11, 25 August 2017DeSlAnnotated all the metabolite nodes for which I could find IDs
86903view08:00, 14 July 2016MkutmonOntology Term : 'C18-steroid hormone biosynthetic pathway' added !
86902view08:00, 14 July 2016MkutmonOntology Term : 'PW:0000780' removed !
85083view22:34, 12 April 2016EgonwAdded a few metabolite identifiers.
80025view21:40, 30 April 2015Zaricorrected Ensembl ID for GSTA1
79793view16:05, 16 April 2015Mkutmonfixed unconnected line
63185view20:45, 8 May 2013MaintBotUpdating gpml version
59212view19:51, 22 February 2013MaintBotUpdated Ensembl and UniProt data source
48236view05:55, 17 May 2012MaintBotUpdating PubChem xrefs
45245view18:31, 7 October 2011AlexanderPicoOntology Term : 'estrogen biosynthetic pathway' added !
41215view23:45, 1 March 2011MaintBotRemoved redundant pathway information and comments
33412view14:50, 30 November 2009MaintBotRemoved group label
30275view20:34, 25 July 2009AlexanderPicofixed unsupported characters in Bibliography
30261view05:18, 25 July 2009AlexanderPicoModified categories
29863view11:06, 8 June 2009Pieter Giesbertzadded literature reference
29862view11:04, 8 June 2009Pieter Giesbertzmade some little additions
29861view10:37, 8 June 2009Pieter GiesbertzAdded literature reference
29655view09:56, 24 May 2009Pieter GiesbertzAdded literature reference
29456view09:11, 8 May 2009Pieter GiesbertzAdded literature references
29455view09:06, 8 May 2009Pieter GiesbertzAdded literature references
29454view08:56, 8 May 2009Pieter GiesbertzAdded literature references
29453view08:52, 8 May 2009Pieter GiesbertzAdded literature references
29452view08:23, 8 May 2009Pieter GiesbertzAdded literature references
29451view08:04, 8 May 2009Pieter GiesbertzAdded literature
29440view07:45, 7 May 2009Pieter GiesbertzAdded estradiol-glucuronides
29438view22:13, 6 May 2009Pieter GiesbertzAdded glucuronide metabolites
29339view15:04, 24 April 2009Pieter GiesbertzAdded compound identifiers
29325view09:52, 24 April 2009Pieter GiesbertzSpecify description
29320view13:27, 23 April 2009Pieter GiesbertzChanged CRYZ into NQO1
29319view13:13, 23 April 2009Pieter GiesbertzSpecify description
29318view12:45, 23 April 2009Pieter GiesbertzSpecify description
29317view11:57, 23 April 2009Pieter Giesbertzquinone part added
29316view11:28, 23 April 2009Pieter Giesbertzperiodical save
29279view07:36, 22 April 2009Pieter GiesbertzSpecify description
29278view23:28, 21 April 2009Pieter GiesbertzSpecify description
29229view09:15, 16 April 2009Pieter GiesbertzSpecify description
29228view14:42, 15 April 2009Pieter GiesbertzSpecify description
29227view14:37, 15 April 2009Pieter GiesbertzNew pathway

External references

DataNodes

View all...
NameTypeDatabase referenceComment
16a-HydroxyestroneMetaboliteHMDB00335 (HMDB)
2-HydroxyestradiolMetaboliteHMDB00338 (HMDB)
2-Hydroxyestrone-3-glucuronideMetabolite
2-HydroxyestroneMetaboliteHMDB00343 (HMDB)
2-Methoxyestradiol-3-glucuronideMetaboliteHMDB06765 (HMDB)
2-MethoxyestradiolMetaboliteHMDB00405 (HMDB)
2-Methoxyestrone 3-glucuronideMetaboliteHMDB04482 (HMDB)
2-MethoxyestroneMetaboliteHMDB00010 (HMDB)
2-hydroxy-estradiol-2-glucuronideMetabolite
2-hydroxy-estradiol-sulfateMetabolite
2-hydroxyestradiol-3-glucuronideMetabolite
4-Methoxyestradiol-3-glucuronideMetabolite
4-MethoxyestradiolMetaboliteHMDB00405 (HMDB)
4-Methoxyestrone-3-glucuronideMetaboliteCHEBI:137965 (ChEBI)
4-MethoxyestroneMetabolite194066 (PubChem-compound)
4-hydroxy-estradiol-4-glucuronideMetabolite90746-94-4 (CAS)
4-hydroxy-estradiol-sulfateMetabolite
4-hydroxyestradiolMetabolite5282360 (PubChem-compound)
4-hydroxyestrone-3-glucuronideMetaboliteCHEBI:136969 (ChEBI)
4-hydroxyestroneMetabolite9971251 (PubChem-compound)
ARSCGeneProduct412 (Entrez Gene)
ARSDGeneProductENSG00000006756 (Ensembl)
ARSEGeneProductENSG00000157399 (Ensembl)
COMTGeneProductENSG00000093010 (Ensembl)
CYP1A1GeneProductENSG00000140465 (Ensembl)
CYP1A2GeneProductENSG00000140505 (Ensembl)
CYP1B1GeneProductENSG00000138061 (Ensembl)
CYP3A4GeneProductENSG00000160868 (Ensembl)
ESTRADIOLMetaboliteCHEBI:23965 (ChEBI)
Estradiol sulfateMetabolite66416 (PubChem-compound)
Estradiol-17-glucuronideMetabolite5281887 (PubChem-compound)
Estradiol-2,3-quinoneMetaboliteHMDB60084 (HMDB)
Estradiol-2,3-semiquinoneMetabolite
Estradiol-3,4-quinoneMetaboliteHMDB60085 (HMDB)
Estradiol-3,4-semiquinoneMetabolite
Estradiol-3-glucuronideMetaboliteHMDB06224 (HMDB)
Estrone sulfateMetaboliteHMDB01425 (HMDB)
Estrone-17-glucuronideMetaboliteHMDB04483 (HMDB)
Estrone-2,3-quinoneMetabolite148381 (PubChem-compound)
Estrone-2,3-semiquinoneMetabolite
Estrone-3,4-quinoneMetabolite114862 (PubChem-compound)
Estrone-3,4-semiquinoneMetabolite
Estrone-3-glucuronideMetaboliteHMDB04483 (HMDB)
EstroneMetaboliteHMDB00145 (HMDB)
GSTA1GeneProductENSG00000243955 (Ensembl)
GSTM1GeneProductENSG00000134184 (Ensembl)
NQO1GeneProductENSG00000181019 (Ensembl)
OxygenMetaboliteHMDB01377 (HMDB)
SULT1A1GeneProductENSG00000196502 (Ensembl)
SULT1E1GeneProductENSG00000109193 (Ensembl)
SuperoxideMetaboliteHMDB02168 (HMDB)
UGT1A1GeneProduct54658 (Entrez Gene)
UGT1A3GeneProduct54659 (Entrez Gene)
UGT1A8GeneProductENSG00000167165 (Ensembl)
UGT1A9GeneProduct54600 (Entrez Gene)
UGT2B7GeneProductENSG00000171234 (Ensembl)

Annotated Interactions

No annotated interactions

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