Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Androstenedione (HMDB00053)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:49 -0700
HMDB ID HMDB00053
Secondary Accession Numbers None
Metabolite Identification
Common Name Androstenedione
Description Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (4)-Androsten-3,17-dione
  2. 17-Ketotestosterone
  3. 3,17-Dioxoandrost-4-ene
  4. 4-Androsten-3,17-dione
  5. 4-Androstene-3,17-dione
  6. 4-Androstenedione
  7. Androst-4-ene-3,17-dione
  8. Androstendione
  9. Androstenedione
  10. D4-Androstene-3,17-dione
  11. Delta4-androstenedione
  12. Fecundin
  13. [4-14C]-androstenedione
  14. [4-14C]androst-4-ene-3,17-dione
Chemical Formula C19H26O2
Average Molecular Weight 286.4085
Monoisotopic Molecular Weight 286.193280076
IUPAC Name (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Traditional IUPAC Name 4-androstenedione
CAS Registry Number 63-05-8
SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChI Key AEMFNILZOJDQLW-QAGGRKNESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Androgens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Ketosteroids
  • a 3-oxo-&Delta;<SUP>4</SUP>-steroid(Cyc)
Substituents
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • 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
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 170 - 173 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0578 mg/mL Not Available
LogP 2.75 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.027 g/L ALOGPS
LogP 2.93 ALOGPS
LogP 3.93 ChemAxon
LogS -4.03 ALOGPS
pKa (strongest acidic) 19.03 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 34.14 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 83.61 ChemAxon
Polarizability 33.05 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 (HITACHI M-80)
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Placenta
  • Testes
  • Kidney
  • Liver
  • Prostate
  • Adrenal Gland
  • Skin
  • Adipose Tissue
  • Adrenal Cortex
  • Gonads
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
0.0059 (0.0023-0.0094) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.00315 (0.00000-0.00630) uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.00061 +/- 0.00022 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.0022 (0.0010-0.0034) uM Children (1-13 year old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.005 (0.0024-0.0070) uM Adolescent (13-18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.0040 (0.0013-0.0066) uM Children (1-13 year old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.001 (0.00034-0.00170) uM Children (1-13 year old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.0057 (0.00069-0.01) uM Adult (>18 years old) Female 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
Urine Detected and Quantified
Article_icon
0.090 +/- 0.058 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
0.0068 +/- 0.0013 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
0.0066 +/- 0.0038 uM Adult (>18 years old) Female Polycystic ovary syndrome (PCOS) Measured in plasma, after pioglitazone treatment
Blood Detected and Quantified
Article_icon
0.0090 +/- 0.0046 uM Adult (>18 years old) Female Polycystic ovary syndrome (PCOS) Measured in plasma before pioglitazone treatment
Blood Detected and Quantified
Article_icon
0.0090 +/- 0.0065 uM Adult (>18 years old) Both Cushing's syndrome Not Available
Blood Detected and Quantified
Article_icon
0.0031 +/- 0.0030 uM Adult (>18 years old) Both Cushing's syndrome Not Available
Urine Detected and Quantified
Article_icon
0.090 +/- 0.073 umol/mmol creatinine Adult (>18 years old) Female Thyroid cancer Not Available
Urine Detected and Quantified
Article_icon
0.0017 +/- 0.00034 umol/mmol creatinine Adult (>18 years old) Both Rheumatoid arthritis Rheumatoid arthritis with prednisolone treatment
Urine Detected and Quantified
Article_icon
0.0025 +/- 0.00071 umol/mmol creatinine Adult (>18 years old) Both Rheumatoid arthritis Rheumatoid arthritis without prednisolone...
Urine Detected and Quantified
Article_icon
0.0025 +/- 0.00042 umol/mmol creatinine Adult (>18 years old) Both Systemic lupus erythematosus (SLE) Systemic lupus erythematosus (SLE) with...
Urine Detected and Quantified
Article_icon
0.0047 +/- 0.0005 umol/mmol creatinine Adult (>18 years old) Both Systemic lupus erythematosus (SLE) Systemic lupus erythematosus (SLE) without...
Associated Disorders and Diseases
Disease References
Normal
    • The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.
    Polycystic ovary syndrome
    • Berria R, Gastaldelli A, Lucidi S, Belfort R, De Filippis E, Easton C, Brytzki R, Cusi K, Jovanovic L, DeFronzo R: Reduction in hematocrit level after pioglitazone treatment is correlated with decreased plasma free testosterone level, not hemodilution, in women with polycystic ovary syndrome. Clin Pharmacol Ther. 2006 Aug;80(2):105-14. Epub 2006 Jun 30. Pubmed: 16890572 Link_out
      Cushing's Syndrome
      • Mune T, Morita H, Yasuda K, Murayama M, Yamakita N, Miura K: Elevated plasma 19-hydroxyandrostenedione levels in Cushing's disease: stimulation with ACTH and inhibition with metyrapone. Clin Endocrinol (Oxf). 1993 Mar;38(3):265-72. Pubmed: 8384536 Link_out
        Rheumatoid arthritis
        • Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. Pubmed: 15249323 Link_out
          Thyroid cancer
          • Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. Pubmed: 14643447 Link_out
            Associated OMIM IDs
            DrugBank ID Not Available
            Phenol Explorer Compound ID Not Available
            Phenol Explorer Metabolite ID Not Available
            FoodDB ID FDB021807
            KNApSAcK ID Not Available
            Chemspider ID 5898 Link_out
            KEGG Compound ID C00280 Link_out
            BioCyc ID ANDROST4ENE Link_out
            BiGG ID 2210012 Link_out
            Wikipedia Link Androstenedione Link_out
            NuGOwiki Link HMDB00053 Link_out
            Metagene Link HMDB00053 Link_out
            METLIN ID 2795 Link_out
            PubChem Compound 6128 Link_out
            PDB ID ASD Link_out
            ChEBI ID 16422 Link_out
            References
            Synthesis Reference Egorova, Olga V.; Gulevskaya, Seraphima A.; Puntus, Irina F.; Filonov, Andrey E.; Donova, Marina V. Production of androstenedione using mutants of Mycobacterium sp. Journal of Chemical Technology and Biotechnology (2002), 77(2), 141-147.
            Material Safety Data Sheet (MSDS) Not Available
            General References
            1. Berkovitz GD, Guerami A, Brown TR, MacDonald PC, Migeon CJ: Familial gynecomastia with increased extraglandular aromatization of plasma carbon19-steroids. J Clin Invest. 1985 Jun;75(6):1763-9. Pubmed: 3924954 Link_out
            2. 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
            3. 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
            4. van Vloten WA, van Haselen CW, van Zuuren EJ, Gerlinger C, Heithecker R: The effect of 2 combined oral Contraceptives containing either drospirenone or cyproterone acetate on acne and seborrhea. Cutis. 2002 Apr;69(4 Suppl):2-15. Pubmed: 12096825 Link_out
            5. Jasuja R, Ramaraj P, Mac RP, Singh AB, Storer TW, Artaza J, Miller A, Singh R, Taylor WE, Lee ML, Davidson T, Sinha-Hikim I, Gonzalez-Cadavid N, Bhasin S: Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. J Clin Endocrinol Metab. 2005 Feb;90(2):855-63. Epub 2004 Nov 2. Pubmed: 15522925 Link_out
            6. Egloff M, Savoure N, Tardivel-Lacombe J, Massart C, Nicol M, Degrelle H: Influence of sex hormone binding globulin and serum albumin on the conversion of androstenedione to testosterone by human erythrocytes. Acta Endocrinol (Copenh). 1981 Jan;96(1):136-40. Pubmed: 7192922 Link_out
            7. Zarrilli S, Lombardi G, Paesano L, Di Somma C, Colao A, Mirone V, De Rosa M: Hormonal and seminal evaluation of Leydig cell tumour patients before and after orchiectomy. Andrologia. 2000 May;32(3):147-54. Pubmed: 10863969 Link_out
            8. Heikkila R, Aho K, Heliovaara M, Hakama M, Marniemi J, Reunanen A, Knekt P: Serum testosterone and sex hormone-binding globulin concentrations and the risk of prostate carcinoma: a longitudinal study. Cancer. 1999 Jul 15;86(2):312-5. Pubmed: 10421267 Link_out
            9. Schlaghecke R, Kley HK, Kruskemper HL: The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma. Steroids. 1984 Jul;44(1):23-33. Pubmed: 6100340 Link_out
            10. King DS, Sharp RL, Vukovich MD, Brown GA, Reifenrath TA, Uhl NL, Parsons KA: Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial. JAMA. 1999 Jun 2;281(21):2020-8. Pubmed: 10359391 Link_out
            11. Johansson A, Henriksson A, Olofsson BO, Olsson T: Adrenal steroid dysregulation in dystrophia myotonica. J Intern Med. 1999 Apr;245(4):345-51. Pubmed: 10356596 Link_out
            12. Atkinson G, Campbell DJ, Cawood ML, Oakey RE: Steroids in human intrauterine fluids of early pregnancy. Clin Endocrinol (Oxf). 1996 Apr;44(4):435-40. Pubmed: 8706310 Link_out
            13. Zarrilli S, Paesano L, Mirone V, Finelli L, De Rosa M: [Evaluation of seminal and hormonal parameters in idiopathic varicocele before and after surgical intervention] Chir Ital. 1998 Mar-Aug;50(2-4):21-8. Pubmed: 11762080 Link_out
            14. Berria R, Gastaldelli A, Lucidi S, Belfort R, De Filippis E, Easton C, Brytzki R, Cusi K, Jovanovic L, DeFronzo R: Reduction in hematocrit level after pioglitazone treatment is correlated with decreased plasma free testosterone level, not hemodilution, in women with polycystic ovary syndrome. Clin Pharmacol Ther. 2006 Aug;80(2):105-14. Epub 2006 Jun 30. Pubmed: 16890572 Link_out
            15. Thomson S, Wallace AM, Cook B: A 125I-radioimmunoassay for measuring androstenedione in serum and in blood-spot samples from neonates. Clin Chem. 1989 Aug;35(8):1706-12. Pubmed: 2758640 Link_out
            16. Riikonen RS: How do cryptogenic and symptomatic infantile spasms differ? Review of biochemical studies in Finnish patients. J Child Neurol. 1996 Sep;11(5):383-8. Pubmed: 8877606 Link_out
            17. Azurmendi A, Braza F, Sorozabal A, Garcia A, Braza P, Carreras MR, Munoz JM, Cardas J, Sanchez-Martin JR: Cognitive abilities, androgen levels, and body mass index in 5-year-old children. Horm Behav. 2005 Aug;48(2):187-95. Pubmed: 15878571 Link_out
            18. Schairer C, Hill D, Sturgeon SR, Fears T, Mies C, Ziegler RG, Hoover RN, Sherman ME: Serum concentrations of estrogens, sex hormone binding globulin, and androgens and risk of breast hyperplasia in postmenopausal women. Cancer Epidemiol Biomarkers Prev. 2005 Jul;14(7):1660-5. Pubmed: 16030098 Link_out
            19. Feldman PS, Kovacs K, Horvath E, Adelson GL: Malignant Leydig cell tumor: clinical, histologic and electron microscopic features. Cancer. 1982 Feb 15;49(4):714-21. Pubmed: 7055782 Link_out
            Enzymes
            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: Cytochrome P450 11B1, mitochondrial
            Reactions:
            • a steroid + reduced adrenal ferredoxin + O2 = an 11beta-hydroxysteroid + oxidized adrenal ferredoxin + H2O [RN:R02726]
            Gene Name: CYP11B1
            Uniprot ID: P15538 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: 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: 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: Steroid 17-alpha-hydroxylase/17,20 lyase
            Reactions:
            • a steroid + AH2 + O2 = a 17alpha-hydroxysteroid + A + H2O [RN:R02131]
            Gene Name: CYP17A1
            Uniprot ID: P05093 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 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: Androgen receptor
            Reactions:
              Gene Name: AR
              Uniprot ID: P10275 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Leptin
              Reactions:
                Gene Name: LEP
                Uniprot ID: P41159 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: Cytochrome P450, family 1, subfamily A, polypeptide 1
                Reactions:
                  Gene Name: CYP1A1
                  Uniprot ID: A0N0X8 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: HSD17B3 protein
                  Reactions:
                    Gene Name: HSD17B3
                    Uniprot ID: Q6FH62 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Mutated cytochrome P-450c11 protein
                    Reactions:
                      Gene Name: Not Available
                      Uniprot ID: Q8TDD0 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Cytochrome P450, family 17, subfamily A, polypeptide 1
                      Reactions:
                        Gene Name: CYP17A1
                        Uniprot ID: Q1HB44 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