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Human Metabolome Database Version 3.5

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Showing metabocard for Estradiol (HMDB00151)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:59 -0700
HMDB ID HMDB00151
Secondary Accession Numbers
  • HMDB04448
  • HMDB04481
Metabolite Identification
Common Name Estradiol
Description Estradiol is the most potent form of mammalian estrogenic steroids. Estradiol is produced in the ovaries. The ovary requires both luteinizing hormone (LH) and follicle-stimulating hormone (FSH) to produce sex steroids. LH stimulates the cells surrounding the follicle to produce progesterone and androgens. The androgens diffuse across the basement membrane to the granulosa cell layer, where, under the action of FSH, they are aromatized to estrogens, mainly estradiol. The ovary shows cyclical activity, unlike the testis that is maintained in a more or less constant state of activity. Hormone secretions vary according to the phase of the menstrual cycle. In the developing follicle LH receptors (LH-R) are only located on the thecal cells and FSH receptors (FSHR) on the granulosa cells. The dominant pre-ovulatory follicle develops LH-Rs on the granulosa cells prior to the LH surge. Thecal cells of the preovulatory follicle also develop the capacity to synthesize estradiol and this persists when the thecal cells become incorporated into the corpus luteum. After ovulation, the empty follicle is remodelled and plays an important role in the second half or luteal phase of the menstrual cycle. This phase is dominated by progesterone and, to a lesser extent, estradiol secretion by the corpus luteum. estradiol is also synthesized locally from cholesterol through testosterone in the hippocampus and acts rapidly to modulate neuronal synaptic plasticity. Localization of estrogen receptor alpha (ERalpha) in spines in addition to nuclei of principal neurons implies that synaptic ERalpha is responsible for rapid modulation of synaptic plasticity by endogenous estradiol. estradiol is a potent endogenous antioxidant which suppresses hepatic fibrosis in animal models, and attenuates induction of redox sensitive transcription factors, hepatocyte apoptosis and hepatic stellate cells activation by inhibiting a generation of reactive oxygen species in primary cultures. This suggests that the greater progression of hepatic fibrosis and hepatocellular carcinoma in men and postmenopausal women may be due, at least in part, to lower production of estradiol and a reduced response to the action of estradiol. estradiol has been reported to induce the production of interferon (INF)-gamma in lymphocytes, and augments an antigen-specific primary antibody response in human peripheral blood mononuclear cells. IFN-gamma is a potent cytokine with immunomodulatory and antiproliferative properties. Therefore, female subjects, particularly before menopause, may produce antibodies against hepatitis B virus e antigen and hepatitis B virus surface antigen at a higher frequency than males with chronic hepatitis B virus infection. The estradiol-Dihydrotestosterone model of prostate cancer (PC) proposes that the first step in the development of most PC and breast cancer (BC) occurs when aromatase converts testosterone to estradiol. (PMID: 17708600 Link_out, 17678531 Link_out, 17644764 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-3,17b-Estradiol
  2. (17b)-Estra-1,3,5(10)-triene-3,17-diol
  3. 13b-Methyl-1,3,5(10)-gonatriene-3,17b-ol
  4. 17b-Estradiol
  5. 17b-Oestradiol
  6. 3,17-Epidihydroxyestratriene
  7. 3,17b-Dihydroxyestra-1,3,5(10)-triene
  8. 3,17b-Estradiol
  9. Aerodiol
  10. Agofollin
  11. Altrad
  12. Amnestrogen
  13. Aquadiol
  14. b-Estradiol
  15. Bardiol
  16. beta-Estradiol
  17. Climaderm
  18. Climara
  19. Compudose
  20. Corpagen
  21. D-Estradiol
  22. D-Oestradiol
  23. delta-Estradiol
  24. delta-Oestradiol
  25. Dermestril
  26. Dihydro-Theelin
  27. Dihydrofollicular hormone
  28. Dihydrofolliculin
  29. Dihydromenformon
  30. Dihydrotheelin
  31. Dihydroxyestrin
  32. Dimenformon
  33. Diogyn
  34. Diogynets
  35. Divigel
  36. Encore
  37. Epiestriol 50
  38. Estra-1,3,5(10)-triene-3,17b-diol
  39. Estrace
  40. Estraderm TTS
  41. Estradiol
  42. Estradiol-17-beta
  43. Estradot
  44. Estraldine
  45. Estring Vaginal Ring
  46. Estroclim
  47. Estroclim 50
  48. Estrogel
  49. Estrogel HBF
  50. Estrovite
  51. Evorel
  52. Femestral
  53. Femogen
  54. Follicyclin
  55. Gelestra
  56. Ginosedol
  57. Gynergon
  58. Gynoestryl
  59. Lamdiol
  60. Macrodiol
  61. Menorest
  62. Nordicol
  63. Oesclim
  64. Oestergon
  65. Oestra-1,3,5(10)-triene-3,17b-diol
  66. Oestradiol
  67. Oestrogel
  68. Oestroglandol
  69. Ovahormon
  70. Ovasterol
  71. Ovastevol
  72. Ovocyclin
  73. Ovocylin
  74. Perlatanol
  75. Primofol
  76. Profoliol
  77. Profoliol B
  78. Progynon
  79. Progynon DH
  80. Sandrena 1
  81. Syndiol
  82. Systen
  83. Vivelle
  84. Zumenon
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-2,4,6-triene-5,14-diol
Traditional IUPAC Name estradiol
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
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Estrogens and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Hydroxysteroids
  • a steroid(Cyc)
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Phenanthrene
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
  • Sesquiterpene Backbone
  • Tetralin
Direct Parent Estrogens and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
  • Endogenous
  • Food
Biofunction
  • Anti-menopausal Agents
  • Anticholesteremic Agents
  • Cell signaling
  • Component of Androgen and estrogen metabolism
  • Estrogens
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
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
Water Solubility 0.021 g/L ALOGPS
LogP 3.57 ALOGPS
LogP 3.75 ChemAxon
LogS -4.11 ALOGPS
pKa (strongest acidic) 10.33 ChemAxon
pKa (strongest basic) -0.88 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 40.46 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 79.9 ChemAxon
Polarizability 32.13 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (JEOL JMS-01-SG-2)
MS/MS Spectrum EI-B (HITACHI RMU-6E)
MS/MS Spectrum EI-B (HITACHI M-52)
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Neuron
  • Placenta
  • Testes
  • Epidermis
  • Brain
  • Prostate
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Platelet
  • Gonads
  • Spleen
  • Stratum Corneum
  • Uterus
Pathways
Name SMPDB Link KEGG Link
Androgen and Estrogen Metabolism SMP00068 map00150 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.00015 +/- 0.000075 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.00009 (0.0-0.00018) uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
0.00009 (0.0-0.00018) uM Adult (>18 years old) Female Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0000011 +/- 0.0000003 uM Adult (>18 years old) Female Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0000007 - 0.000011 uM Adult (>18 years old) Female Normal Not Available
Saliva Detected and Quantified
Article_icon
<1.00 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.00059 +/- 0.00025 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
0.0011 +/- 0.00061 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.000095 +/- 0.000036 uM Adult (>18 years old) Male Positive coronary arteriograms Not Available
Blood Detected and Quantified
Article_icon
0.00011 +/- 0.00005 uM Adult (>18 years old) Male Minor electrocardiongraphic abnormalities and/or arrhythmia with negative coronary arteriograms Not Available
Blood Detected and Quantified
Article_icon
0.00039 (0.000037-0.00073) uM Adult (>18 years old) Female Menstrual cycle Follicular phase
Blood Detected and Quantified
Article_icon
0.00092 (0.00037-0.0015) uM Adult (>18 years old) Female Menstrual cycle Midcycle
Blood Detected and Quantified
Article_icon
0.00050 (0.000055-0.00095) uM Adult (>18 years old) Female Menstrual cycle Luteal phase
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.000006 (0.0000007-0.000011) uM Adult (>18 years old) Female Gynecological diseases (benign) Not Available
Urine Detected and Quantified
Article_icon
0.0016 +/- 0.0011 umol/mmol creatinine Adult (>18 years old) Female Stress urinary incontinence Not Available
Associated Disorders and Diseases
Disease References
Menstrual cycle
    • The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.
    Benign gynecological diseases
    • Murakami K, Nakagawa T, Shozu M, Uchide K, Koike K, Inoue M: Changes with aging of steroidal levels in the cerebrospinal fluid of women. Maturitas. 1999 Sep 24;33(1):71-80. Pubmed: 10585175 Link_out
      Associated OMIM IDs None
      DrugBank ID DB00783 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB000362
      KNApSAcK ID Not Available
      Chemspider ID 5554 Link_out
      KEGG Compound ID C00951 Link_out
      BioCyc ID CPD-352 Link_out
      BiGG ID 36456 Link_out
      Wikipedia Link Estradiol Link_out
      NuGOwiki Link HMDB00151 Link_out
      Metagene Link HMDB00151 Link_out
      METLIN ID 263 Link_out
      PubChem Compound 5757 Link_out
      PDB ID EST Link_out
      ChEBI ID 16469 Link_out
      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
      1. 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. Pubmed: 16060908 Link_out
      2. 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. Pubmed: 7955523 Link_out
      3. 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. Pubmed: 16155259 Link_out
      4. 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. Pubmed: 15887853 Link_out
      5. 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. Pubmed: 16148373 Link_out
      6. Hamden KE, Ford PW, Whitman AG, Dyson OF, Cheng SY, McCubrey JA, Akula SM: Raf-induced vascular endothelial growth factor augments Kaposi's sarcoma-associated herpesvirus infection. J Virol. 2004 Dec;78(23):13381-90. Pubmed: 15542692 Link_out
      7. 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. Pubmed: 14632858 Link_out
      8. 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. Pubmed: 16487434 Link_out
      9. 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. Pubmed: 15811930 Link_out
      10. 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. Pubmed: 11929836 Link_out
      11. Chabbert-Buffet N, Bouchard P: [Physiology and exploration of the gonadotropic axis] Rev Prat. 1999 Jun 15;49(12):1270-6. Pubmed: 10488657 Link_out
      12. 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. Pubmed: 14561431 Link_out
      13. Elliott KJ, Cable NT, Reilly T: Does oral contraceptive use affect maximum force production in women? Br J Sports Med. 2005 Jan;39(1):15-9. Pubmed: 15618333 Link_out
      14. 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. Pubmed: 8567793 Link_out
      15. 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. Pubmed: 1777462 Link_out
      16. 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. Pubmed: 15886248 Link_out
      17. Archer JS, Love-Geffen TE, Herbst-Damm KL, Swinney DA, Chang JR: Effect of estradiol versus estradiol and testosterone on brain-activation patterns in postmenopausal women. Menopause. 2006 May-Jun;13(3):528-37. Pubmed: 16735951 Link_out
      18. Anwar A, McTernan PG, Anderson LA, Askaa J, Moody CG, Barnett AH, Eggo MC, Kumar S: Site-specific regulation of oestrogen receptor-alpha and -beta by oestradiol in human adipose tissue. Diabetes Obes Metab. 2001 Oct;3(5):338-49. Pubmed: 11703424 Link_out
      19. Tanko LB, Christiansen C: Effects of 17beta-oestradiol plus different doses of drospirenone on adipose tissue, adiponectin and atherogenic metabolites in postmenopausal women. J Intern Med. 2005 Dec;258(6):544-53. Pubmed: 16313478 Link_out
      20. Sulcova J, Hampl R, Hill M, Starka L, Novacek A: Delayed effects of short-term transdermal application of 7-oxo-dehydroepiandrosterone on its metabolites, some hormonal steroids and relevant proteohormones in healthy male volunteers. Clin Chem Lab Med. 2005;43(2):221-7. Pubmed: 15843221 Link_out
      Enzymes
      Name: Estradiol 17-beta-dehydrogenase 2
      Reactions:
      • testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+ [RN:R01836]
      Gene Name: HSD17B2
      Uniprot ID: P37059 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2B28
      Reactions:
      • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
      Gene Name: UGT2B28
      Uniprot ID: Q9BY64 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Estrogen receptor beta
      Reactions:
        Gene Name: ESR2
        Uniprot ID: Q92731 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Estradiol 17-beta-dehydrogenase 8
        Reactions:
        • testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+ [RN:R01836]
        Gene Name: HSD17B8
        Uniprot ID: Q92506 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 2B4
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT2B4
        Uniprot ID: P06133 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 1-4
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT1A4
        Uniprot ID: P22310 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 2B7
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT2B7
        Uniprot ID: P16662 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 2B15
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT2B15
        Uniprot ID: P54855 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 2A1
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT2A1
        Uniprot ID: Q9Y4X1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 1-1
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT1A1
        Uniprot ID: P22309 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 1-9
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT1A9
        Uniprot ID: O60656 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 1-3
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT1A3
        Uniprot ID: P35503 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 2B17
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT2B17
        Uniprot ID: O75795 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 1-6
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT1A6
        Uniprot ID: P19224 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 1-5
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT1A5
        Uniprot ID: P35504 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP-glucuronosyltransferase 2B11
        Reactions:
        • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
        Gene Name: UGT2B11
        Uniprot ID: O75310 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Estradiol 17-beta-dehydrogenase 11
        Reactions:
        • estradiol-17beta + NAD(P)+ = estrone + NAD(P)H + H+ [RN:R02352 R02353]
        Gene Name: HSD17B11
        Uniprot ID: Q8NBQ5 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Estradiol 17-beta-dehydrogenase 1
        Reactions:
        • estradiol-17beta + NAD(P)+ = estrone + NAD(P)H + H+ [RN:R02352 R02353]
        Gene Name: HSD17B1
        Uniprot ID: P14061 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 3-keto-steroid reductase
        Reactions:
        • 4alpha-methyl-5alpha-cholest-7-en-3beta-ol + NADP+ = 4alpha-methyl-5alpha-cholest-7-en-3-one + NADPH + H+ [RN:R05691]
        Gene Name: HSD17B7
        Uniprot ID: P56937 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 3A4
        Reactions:
        • (1) taurochenodeoxycholate + NADPH + H+ + O2 = taurohyocholate + NADP+ + H2O [RN:R07205]
        • (2) lithocholate + NADPH + H+ + O2 = hyodeoxycholate + NADP+ + H2O [RN:R07206]
        Gene Name: CYP3A4
        Uniprot ID: P08684 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2C9
        Reactions:
        • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
        Gene Name: CYP2C9
        Uniprot ID: P11712 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2C19
        Reactions:
        • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
        Gene Name: CYP2C19
        Uniprot ID: P33261 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2E1
        Reactions:
        • --- []
        Gene Name: CYP2E1
        Uniprot ID: P05181 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 3A43
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP3A43
        Uniprot ID: Q9HB55 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 1B1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP1B1
        Uniprot ID: Q16678 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2C18
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2C18
        Uniprot ID: P33260 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2F1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2F1
        Uniprot ID: P24903 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 4X1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP4X1
        Uniprot ID: Q8N118 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2B6
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2B6
        Uniprot ID: P20813 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 3A5
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP3A5
        Uniprot ID: P20815 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 1A1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP1A1
        Uniprot ID: P04798 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2A13
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2A13
        Uniprot ID: Q16696 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 3A7
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP3A7
        Uniprot ID: P24462 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 4B1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP4B1
        Uniprot ID: P13584 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 4Z1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP4Z1
        Uniprot ID: Q86W10 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 1A2
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP1A2
        Uniprot ID: P05177 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 19A1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP19A1
        Uniprot ID: P11511 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2C8
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2C8
        Uniprot ID: P10632 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2S1
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2S1
        Uniprot ID: Q96SQ9 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2J2
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2J2
        Uniprot ID: P51589 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2A7
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2A7
        Uniprot ID: P20853 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450 2A6
        Reactions:
        • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
        Gene Name: CYP2A6
        Uniprot ID: P11509 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Sex hormone-binding globulin
        Reactions:
          Gene Name: SHBG
          Uniprot ID: P04278 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Nuclear receptor subfamily 1 group I member 2
          Reactions:
            Gene Name: NR1I2
            Uniprot ID: O75469 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Estrogen receptor
            Reactions:
              Gene Name: ESR1
              Uniprot ID: P03372 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: 17-beta-hydroxysteroid dehydrogenase type 6
              Reactions:
              • retinol + NAD+ = retinal + NADH + H+ [RN:R02124]
              Gene Name: HSD17B6
              Uniprot ID: O14756 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: UDP-glucuronosyltransferase 2A3
              Reactions:
              • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
              Gene Name: UGT2A3
              Uniprot ID: Q6UWM9 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytochrome P450, family 1, subfamily A, polypeptide 1
              Reactions:
                Gene Name: CYP1A1
                Uniprot ID: A0N0X8 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Estradiol 17-beta-dehydrogenase 12
                Reactions:
                • estradiol-17beta + NAD(P)+ = estrone + NAD(P)H + H+ [RN:R02352 R02353]
                Gene Name: HSD17B12
                Uniprot ID: Q53GQ0 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: HCG2039726, isoform CRA_f
                Reactions:
                  Gene Name: UGT1A10
                  Uniprot ID: Q5DT02 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: HCG2039726, isoform CRA_e
                  Reactions:
                    Gene Name: UGT1A8
                    Uniprot ID: Q5DSZ6 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: UDP glycosyltransferase 1 family polypeptide A7
                    Reactions:
                      Gene Name: UGT1A7
                      Uniprot ID: Q5DSZ7 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Cytochrome P450 2D6
                      Reactions:
                        Gene Name: CYP2D6
                        Uniprot ID: Q6NWU0 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Transporters
                        Name: Solute carrier organic anion transporter family member 1B1
                        Reactions:
                        • --- []
                        Gene Name: SLCO1B1
                        Uniprot ID: Q9Y6L6 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Solute carrier organic anion transporter family member 2B1
                        Reactions:
                        • --- []
                        Gene Name: SLCO2B1
                        Uniprot ID: O94956 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Multidrug resistance protein 1
                        Reactions:
                        • ATP + H2O + xenobioticin = ADP + phosphate + xenobioticout [RN:R00086]
                        Gene Name: ABCB1
                        Uniprot ID: P08183 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: ATP-binding cassette sub-family G member 2
                        Reactions:
                          Gene Name: ABCG2
                          Uniprot ID: Q9UNQ0 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Solute carrier family 22 member 11
                          Reactions:
                            Gene Name: SLC22A11
                            Uniprot ID: Q9NSA0 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Solute carrier family 22 member 1
                            Reactions:
                            • --- []
                            Gene Name: SLC22A1
                            Uniprot ID: O15245 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Solute carrier organic anion transporter family member 1A2
                            Reactions:
                            • --- []
                            Gene Name: SLCO1A2
                            Uniprot ID: P46721 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Solute carrier family 22 member 2
                            Reactions:
                              Gene Name: SLC22A2
                              Uniprot ID: O15244 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: Solute carrier family 22 member 3
                              Reactions:
                                Gene Name: SLC22A3
                                Uniprot ID: O75751 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA