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Human Metabolome Database Version 3.5

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Showing metabocard for Testosterone (HMDB00234)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:08 -0700
HMDB ID HMDB00234
Secondary Accession Numbers None
Metabolite Identification
Common Name Testosterone
Description Testosterone is the most important androgen in potency and quantity. Testosterone is synthesized and released by the Leydig cells that lie between the tubules and comprise less than 5% of the total testicular volume. testosterone diffuses into the seminiferous tubules where it is essential for maintaining spermatogenesis. Some binds to an androgen-binding protein (ABP) that is produced by the Sertoli cells and is homologous to the sex-hormone binding globulin that transports testosterone in the general circulation. The ABP carries testosterone in the testicular fluid where it maintains the activity of the accessory sex glands and may also help to retain testosterone within the tubule and bind excess free hormone. Some testosterone is converted to estradiol by Sertoli cell-derived aromatase enzyme. Leydig cell steroidogenesis is controlled primarily by luteinizing hormone with negative feedback of testosterone on the hypothalamic-pituitary axis. The requirement of spermatogenesis for high local concentrations of testosterone means that loss of androgen production is likely to be accompanied by loss of spermatogenesis. Indeed, if testicular androgen production is inhibited by the administration of exogenous androgens then spermatogenesis ceases. This is the basis of using exogenous testosterone as a male contraceptive. testosterone is converted to dihydrotestosterone by 5a-reductase type 2 (EC 1.3.1.22, SRD5A2), the androgen with the highest affinity for the androgen receptor. SRD5A2 deficiency illustrates the importance of dihydrotestosterone for external virilization, as individuals with this condition have normal male internal structures but their external genitalia are of female appearance. There is now clear evidence that the human fetal testis and also the fetal adrenal gland is capable of testosterone biosynthesis during the first trimester. Regardless of the source of androgen production, the target tissue responds by male sexual differentiation of the external genitalia by the end of the first trimester. It is clear that testicular damage may result in loss of testosterone production or the loss of spermatogenesis or both. Loss of androgen production results in hypogonadism, the symptoms of which reflect the functions of testosterone. Male hypogonadism is defined as failure of the testes to produce normal amounts of testosterone, combined with signs and symptoms of androgen deficiency. Systemic testosterone levels fall by about 1% each year in men. Therefore, with increasing longevity and the aging of the population, the number of older men with testosterone deficiency will increase substantially over the next several decades. Serum testosterone levels decrease progressively in aging men, but the rate and magnitude of decrease vary considerably. Approximately 1% of healthy young men have total serum testosterone levels below normal; in contrast, approximately 20% of healthy men over age 60 years have serum testosterone levels below normal. (PMID: 17904450 Link_out, 17875487 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-testosterone
  2. (+-)-8-iso-testosterone
  3. (+-)-retrotestosterone
  4. (+-)-testosterone
  5. (17b)-17-hydroxy-androst-4-en-3-one
  6. 13-Iso-testosterone
  7. 17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
  8. 17-Hydroxy-androst-4-en-3-one
  9. 17-Hydroxy-D4-androsten-3-one
  10. 17a-Hydroxy-(13a)-androst-4-en-3-one
  11. 17a-Hydroxy-13a-androst-4-en-3-one
  12. 17a-Hydroxy-14b-androst-4-en-3-one
  13. 17a-Hydroxy-androst-4-en-3-one
  14. 17b-Hydroxy-(10a)-androst-4-en-3-one
  15. 17b-Hydroxy-(13a)-androst-4-en-3-one
  16. 17b-Hydroxy-(8a)-androst-4-en-3-one
  17. 17b-Hydroxy-(8a,10a)-androst-4-en-3-one
  18. 17b-Hydroxy-(9b)-androst-4-en-3-one
  19. 17b-Hydroxy-(9b,10a)-androst-4-en-3-one
  20. 17b-Hydroxy-13a-androst-4-en-3-one
  21. 17b-Hydroxy-8a-androst-4-en-3-one
  22. 17b-Hydroxy-androst-4-en-3-on
  23. 17b-Hydroxy-androst-4-en-3-one
  24. 17b-Hydroxy-D4-androsten-3-one
  25. 17b-Hydroxyandrost-4-en-3-one
  26. 17b-Hydroxyandrost-4-ene-3-one
  27. 17b-Testosterone
  28. 4-Androsten-3-one-17b-ol
  29. 8-Iso-testosterone
  30. 9b,10a-Testosterone
  31. 9b-Testosterone
  32. Androderm
  33. AndroGel
  34. Androlin
  35. Andronaq
  36. Andropatch
  37. Androst-4-en-17b-ol-3-one
  38. Androst-4-ene-17b-ol-3-one
  39. Andrusol
  40. Cristerona T
  41. D4-Androsten-17b-ol-3-one
  42. Epitestosteron
  43. Geno-cristaux Gremy
  44. Homosteron
  45. Homosterone
  46. Lumitestosteron
  47. Mertestate
  48. Neotestis
  49. Oreton
  50. Orquisteron
  51. Perandren
  52. Percutacrine androgenique
  53. Primotest
  54. Primoteston
  55. Rac-17b-hydroxy-(13a)androst-4-en-3-one
  56. Rac-17b-hydroxy-(8a)-androst-4-en-3-one
  57. Rac-17b-hydroxy-(9b,10a)androst-4-en-3-one
  58. Rac-17b-hydroxy-androst-4-en-3-one
  59. Relibra
  60. Retrotestosterone
  61. Sustanon
  62. Sustanone
  63. Sustason 250
  64. Synandrol F
  65. Teslen
  66. Testandrone
  67. Testiculosterone
  68. Testim
  69. Testobase
  70. Testoderm
  71. Testogel
  72. Testolent
  73. Testolin
  74. Testopropon
  75. Testosteroid
  76. Testosteron
  77. Testoviron Schering
  78. Testoviron T
  79. Testro AQ
  80. Testrone
  81. Testryl
  82. Tostrelle
  83. Tostrex
  84. Viatrel
  85. Virormone
  86. Virosterone
Chemical Formula C19H28O2
Average Molecular Weight 288.4244
Monoisotopic Molecular Weight 288.20893014
IUPAC Name (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Name testosterone
CAS Registry Number 58-22-0
SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
InChI Key MUMGGOZAMZWBJJ-DYKIIFRCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Androgens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Hydroxysteroids
  • Ketosteroids
  • a hormone(Cyc)
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct Parent Androgens and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • 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 155 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0234 mg/mL Not Available
LogP 3.32 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.033 g/L ALOGPS
LogP 2.99 ALOGPS
LogP 3.37 ChemAxon
LogS -3.94 ALOGPS
pKa (strongest acidic) 19.09 ChemAxon
pKa (strongest basic) -0.88 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 84.43 ChemAxon
Polarizability 33.93 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-80)
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
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
  • Testes
  • Brain
  • Gonads
  • Sperm
  • Hypothalamus
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
0.00125 +/- 0.00042 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.013 (0.0083-0.0286) uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
0.0094 +/- 0.0014 uM Adult (>18 years old) Male Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.00101 (0.00002-0.002) uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.00065 +/- 0.00012 uM Adult (>18 years old) Male Normal Not Available
Saliva Detected and Quantified
Article_icon
0.00120 (0.00108-0.00133) uM Adult (>18 years old) Male Normal Not Available
Saliva Detected and Quantified
Article_icon
0.000677 (0.000590-0.000764) uM Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
0.000121 +/- 0.00002149 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
1.07 +/- 0.19 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
9.31 (3.31-19.95) uM Adult (>18 years old) Male Cadmium exposure Not Available
Blood Detected and Quantified
Article_icon
0.010 +/- 0.013 uM Adolescent (13-18 years old) Male Hypogonadism Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
3.400e-05 +/- 1.665e-05 uM Adult (>18 years old) Not Specified Leuprolide acetate-induce hypogonadism Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.000497 +/- 0.000222 uM Adult (>18 years old) Not Specified Leuprolide acetate-induced hypogonadism with testosterone replacment Not Available
Associated Disorders and Diseases
Disease References
Hypogonadism
    • http://en.wikipedia.org/wiki/Testosterone
    Cadmium exposure
    • Zeng X, Lin T, Zhou Y, Kong Q: Alterations of serum hormone levels in male workers occupationally exposed to cadmium. J Toxicol Environ Health A. 2002 Apr 12;65(7):513-21. Pubmed: 11939709 Link_out
      Associated OMIM IDs None
      DrugBank ID DB00624 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB011544
      KNApSAcK ID C00003675 Link_out
      Chemspider ID 5791 Link_out
      KEGG Compound ID C00535 Link_out
      BioCyc ID Not Available
      BiGG ID 35280 Link_out
      Wikipedia Link Testosterone Link_out
      NuGOwiki Link HMDB00234 Link_out
      Metagene Link HMDB00234 Link_out
      METLIN ID 390 Link_out
      PubChem Compound 6013 Link_out
      PDB ID TES Link_out
      ChEBI ID 17347 Link_out
      References
      Synthesis Reference Ercoli, Alberto; De Ruggieri, Pietro. An improved method of preparing testosterone, dihydrotestosterone, and some of their esters. Journal of the American Chemical Society (1953), 75 650-3.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Handelsman DJ: Clinical review: The rationale for banning human chorionic gonadotropin and estrogen blockers in sport. J Clin Endocrinol Metab. 2006 May;91(5):1646-53. Epub 2006 Feb 14. Pubmed: 16478815 Link_out
      2. Duschek EJ, Gooren LJ, Netelenbos C: Comparison of effects of the rise in serum testosterone by raloxifene and oral testosterone on serum insulin-like growth factor-1 and insulin-like growth factor binding protein-3. Maturitas. 2005 Jul 16;51(3):286-93. Pubmed: 15978972 Link_out
      3. 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
      4. Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95. Pubmed: 10625505 Link_out
      5. Huang I, Jones J, Khorram O: Human seminal plasma nitric oxide: correlation with sperm morphology and testosterone. Med Sci Monit. 2006 Mar;12(3):CR103-6. Epub 2006 Feb 23. Pubmed: 16501419 Link_out
      6. Hussein A, Ozgok Y, Ross L, Niederberger C: Clomiphene administration for cases of nonobstructive azoospermia: a multicenter study. J Androl. 2005 Nov-Dec;26(6):787-91; discussion 792-3. Pubmed: 16291975 Link_out
      7. Ahtiainen JP, Pakarinen A, Alen M, Kraemer WJ, Hakkinen K: Short vs. long rest period between the sets in hypertrophic resistance training: influence on muscle strength, size, and hormonal adaptations in trained men. J Strength Cond Res. 2005 Aug;19(3):572-82. Pubmed: 16095405 Link_out
      8. Landman AD, Sanford LM, Howland BE, Dawes C, Pritchard ET: Testosterone in human saliva. Experientia. 1976;32(7):940-1. Pubmed: 954994 Link_out
      9. Knickmeyer RC, Wheelwright S, Taylor K, Raggatt P, Hackett G, Baron-Cohen S: Gender-typed play and amniotic testosterone. Dev Psychol. 2005 May;41(3):517-28. Pubmed: 15910159 Link_out
      10. Fejes I, Koloszar S, Szollosi J, Zavaczki Z, Pal A: Is semen quality affected by male body fat distribution? Andrologia. 2005 Oct;37(5):155-9. Pubmed: 16266392 Link_out
      11. Jarow JP, Zirkin BR: The androgen microenvironment of the human testis and hormonal control of spermatogenesis. Ann N Y Acad Sci. 2005 Dec;1061:208-20. Pubmed: 16467270 Link_out
      12. Rovensky J, Radikova Z, Imrich R, Greguska O, Vigas M, Macho L: Gonadal and adrenal steroid hormones in plasma and synovial fluid of patients with rheumatoid arthritis. Endocr Regul. 2004 Dec;38(4):143-9. Pubmed: 15841793 Link_out
      13. Klimek M, Pabian W, Tomaszewska B, Kolodziejczyk J: Levels of plasma ACTH in men from infertile couples. Neuro Endocrinol Lett. 2005 Aug;26(4):347-50. Pubmed: 16136011 Link_out
      14. Cutolo M, Sulli A, Capellino S, Villaggio B, Montagna P, Pizzorni C, Paolino S, Seriolo B, Felli L, Straub RH: Anti-TNF and sex hormones. Ann N Y Acad Sci. 2006 Jun;1069:391-400. Pubmed: 16855166 Link_out
      15. Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. Pubmed: 1620285 Link_out
      16. Shores MM, Matsumoto AM, Sloan KL, Kivlahan DR: Low serum testosterone and mortality in male veterans. Arch Intern Med. 2006 Aug 14-28;166(15):1660-5. Pubmed: 16908801 Link_out
      17. Bhasin S, Cunningham GR, Hayes FJ, Matsumoto AM, Snyder PJ, Swerdloff RS, Montori VM: Testosterone therapy in adult men with androgen deficiency syndromes: an endocrine society clinical practice guideline. J Clin Endocrinol Metab. 2006 Jun;91(6):1995-2010. Epub 2006 May 23. Pubmed: 16720669 Link_out
      18. 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
      19. Jarow JP, Wright WW, Brown TR, Yan X, Zirkin BR: Bioactivity of androgens within the testes and serum of normal men. J Androl. 2005 May-Jun;26(3):343-8. Pubmed: 15867001 Link_out
      20. Bridger T, MacDonald S, Baltzer F, Rodd C: Randomized placebo-controlled trial of metformin for adolescents with polycystic ovary syndrome. Arch Pediatr Adolesc Med. 2006 Mar;160(3):241-6. Pubmed: 16520442 Link_out
      Enzymes
      Name: Amine oxidase [flavin-containing] A
      Reactions:
      • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
      Gene Name: MAOA
      Uniprot ID: P21397 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Estrogen sulfotransferase
      Reactions:
      • 3'-phosphoadenylyl sulfate + estrone = adenosine 3',5'-bisphosphate + estrone 3-sulfate [RN:R02350]
      Gene Name: SULT1E1
      Uniprot ID: P49888 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aldo-keto reductase family 1 member C3
      Reactions:
      • trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+ [RN:R00814]
      Gene Name: AKR1C3
      Uniprot ID: P42330 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      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: 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: 3-oxo-5-beta-steroid 4-dehydrogenase
      Reactions:
      • (1) 5beta-cholestan-3-one + NADP+ = cholest-4-en-3-one + NADPH + H+ [RN:R02609]
      • (2) 17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+ = cortisone + NADPH + H+ [RN:R02893]
      Gene Name: AKR1D1
      Uniprot ID: P51857 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 3-oxo-5-alpha-steroid 4-dehydrogenase 2
      Reactions:
      • a 3-oxo-5alpha-steroid + acceptor = a 3-oxo-Delta4-steroid + reduced acceptor [RN:R02643]
      Gene Name: SRD5A2
      Uniprot ID: P31213 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 3-oxo-5-alpha-steroid 4-dehydrogenase 1
      Reactions:
      • a 3-oxo-5alpha-steroid + acceptor = a 3-oxo-Delta4-steroid + reduced acceptor [RN:R02643]
      Gene Name: SRD5A1
      Uniprot ID: P18405 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cholesterol side-chain cleavage enzyme, mitochondrial
      Reactions:
      • cholesterol + reduced adrenal ferredoxin + O2 = pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin + H2O [RN:R02724]
      Gene Name: CYP11A1
      Uniprot ID: P05108 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glutathione S-transferase A3
      Reactions:
      • RX + glutathione = HX + R-S-glutathione [RN:R03522 R08511 R08512]
      Gene Name: GSTA3
      Uniprot ID: Q16772 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Testosterone 17-beta-dehydrogenase 3
      Reactions:
      • testosterone + NADP+ = androst-4-ene-3,17-dione + NADPH + H+ [RN:R01838]
      Gene Name: HSD17B3
      Uniprot ID: P37058 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: Androgen receptor
        Reactions:
          Gene Name: AR
          Uniprot ID: P10275 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Serum albumin
          Reactions:
            Gene Name: ALB
            Uniprot ID: P02768 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Natriuretic peptides B
            Reactions:
              Gene Name: NPPB
              Uniprot ID: P16860 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: 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
              Reactions:
              • a 3-oxo-Delta5-steroid = a 3-oxo-Delta4-steroid [RN:R02644]
              Gene Name: HSD3B2
              Uniprot ID: P26439 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: Probable polyprenol reductase
                Reactions:
                • a 3-oxo-5alpha-steroid + acceptor = a 3-oxo-Delta4-steroid + reduced acceptor [RN:R02643]
                Gene Name: SRD5A3
                Uniprot ID: Q9H8P0 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: 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 4
                          Reactions:
                          • --- []
                          Gene Name: SLC22A4
                          Uniprot ID: Q9H015 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Sodium/bile acid cotransporter
                          Reactions:
                          • --- []
                          Gene Name: SLC10A1
                          Uniprot ID: Q14973 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 3
                          Reactions:
                            Gene Name: SLC22A3
                            Uniprot ID: O75751 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Solute carrier family 22 member 7
                            Reactions:
                              Gene Name: SLC22A7
                              Uniprot ID: Q9Y694 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA