Human Metabolome Database Version 3.5

Showing metabocard for Citric acid (HMDB00094)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:24:45 -0600
HMDB ID HMDB00094
Secondary Accession Numbers None
Metabolite Identification
Common Name Citric acid
Description Citric acid (citrate) is a weak acid that is formed in the tricarboxylic acid cycle or that may be introduced with diet. The evaluation of plasma citric acid is scarcely used in the diagnosis of human diseases. On the contrary urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in bone diseases. The importance of hypocitraturia should be considered with regard to bone mass, urine crystallization and urolithiasis. (PMID 12957820 Link_out) The secretory epithelial cells of the prostate gland of humans and other animals posses a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes. The regulatory regions of these genes contain the necessary response elements that confer the ability of both hormones to control gene transcription. Protein kinase c (PKC) is the signaling pathway for the prolactin regulation of the metabolic genes in prostate cells. testosterone and prolactin regulation of these metabolic genes (which are constitutively expressed in all mammalian cells) is specific for these citrate-producing cells. (PMID 12198595 Link_out) Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Little information is available as the condition appears to be rare, but like other types of food intolerance it is often described as a "pseudo-allergic" reaction.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Hydroxy-1,2,3-propanetricarboxylate
  2. 2-Hydroxy-1,2,3-propanetricarboxylic acid
  3. 3-Carboxy-3-hydroxypentane-1,5-dioate
  4. 3-Carboxy-3-hydroxypentane-1,5-dioic acid
  5. Aciletten
  6. Anhydrous citrate
  7. Anhydrous citric acid
  8. beta-Hydroxytricarballylate
  9. beta-Hydroxytricarballylic acid
  10. Chemfill
  11. Citraclean
  12. Citrate
  13. Citretten
  14. Citric acid
  15. Citro
  16. E 330
  17. Hydrocerol A
  18. Kyselina citronova
  19. Suby G
  20. Uro-trainer
Chemical Formula C6H8O7
Average Molecular Weight 192.1235
Monoisotopic Molecular Weight 192.02700261
IUPAC Name 2-hydroxypropane-1,2,3-tricarboxylic acid
Traditional IUPAC Name citric acid
CAS Registry Number 77-92-9
SMILES OC(=O)CC(O)(CC(O)=O)C(O)=O
InChI Identifier InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChI Key KRKNYBCHXYNGOX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Tricarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Branched Fatty Acids
  • Organic Compounds
  • tricarboxylic acid(ChEBI)
Substituents
  • Alpha Hydroxy Acid
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Short Chain Hydroxy Acid
  • Succinic Acid
  • Tertiary Alcohol
Direct Parent Tricarboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glyoxylate and dicarboxylate metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 153 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 592.0 mg/mL Not Available
LogP -1.64 AVDEEF,A (1997)
Predicted Properties
Property Value Source
Water Solubility 106 g/L ALOGPS
LogP -1.33 ALOGPS
LogP -1.3 ChemAxon
LogS -0.26 ALOGPS
pKa (strongest acidic) 3.05 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 132.13 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 35.62 ChemAxon
Polarizability 15.47 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Citric Acid Cycle SMP00057 map00020 Link_out
Transfer of Acetyl Groups into Mitochondria SMP00466 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
54.2 +/- 0.8 uM Children (1-13 year old) Both Normal
Blood Detected and Quantified
190.0 (30.0-400.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
88.0 +/- 33.0 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
122.0 +/- 30.0 uM Children (1-13 year old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
114.2 +/- 27 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
225 +/- 96 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
400.0 +/- 170.0 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
350.0 +/- 240.0 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
370.0 (110.0 - 630.0) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
176.0 +/- 50.0 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Saliva Detected and Quantified
1 to 4456 uM Adult (>18 years old) Male Comment normal
Urine Detected and Quantified
972.5 (89.5-1647.7) umol/mmol creatinine Newborn (0-30 days old) Both Normal
Urine Detected and Quantified
708.9 (25.2-3168.4) umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
208.6 (33.2-445.1) umol/mmol creatinine Children (1-13 year old) Both Normal
Urine Detected and Quantified
184.2 (58.7-651.7) umol/mmol creatinine Adolescent (13-18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Normal
Urine Detected and Quantified
300.0 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
371(102-611) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
46.87-484.31 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
203 (49-600) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
181.0 +/- 97.0 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
Urine Detected and Quantified
242.0 +/- 129.6 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
Urine Detected and Quantified
119.45 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Shaykhutdino...
Urine Detected and Quantified
172.8 +/- 87.4 umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
155 (70-226) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
280.6 +/- 115.2 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
271.8 +/- 90.0 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
440.6 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
242.34 (81.79 – 403.84) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Lorena Ivona...
Urine Detected and Quantified
226.32 +/- 98.12 umol/mmol creatinine Infant (0-1 year old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 80.2 +/- 44.9 uM Adult (>18 years old) Not Specified Heart Transplant
Blood Detected and Quantified 141.3 +/- 54.7 uM Adult (>18 years old) Both Comment Hyperoxalemia
Blood Detected and Quantified 117.6 +/- 37.2 uM Adult (>18 years old) Both Comment Hyperoxalemia
Cerebrospinal Fluid (CSF) Detected and Quantified 2400.0 uM Adult (>18 years old) Both Canavan Disease
Urine Detected and Quantified 268.0 (53.0-1111.0) umol/mmol creatinine Not Specified Both Lung cancer
Urine Detected and Quantified 154 umol/mmol creatinine Adult (>18 years old) Female Rhabdomyolysis
Urine Detected and Quantified 181.5 +/- 5.7 umol/mmol creatinine Adult (>18 years old) Both 3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
Urine Detected and Quantified 191.7 +/- 4.1 umol/mmol creatinine Adult (>18 years old) Both 3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
Urine Detected and Quantified 80.9 +/- 1.8 umol/mmol creatinine Adult (>18 years old) Both Arginosuccinic aciduria
Urine Detected and Quantified 689.6 +/- 47.3 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia
Urine Detected and Quantified 712.3 +/- 82.8 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia
Urine Detected and Quantified 457.6 +/- 17.5 umol/mmol creatinine Adult (>18 years old) Both Tyrosinemia I
Urine Detected and Quantified 81.8 +/- 10.4 umol/mmol creatinine Adult (>18 years old) Both Phenylketonuria
Urine Detected and Quantified 291.9 +/- 14.6 umol/mmol creatinine Adult (>18 years old) Both Phenylketonuria
Urine Detected and Quantified 576.1 +/- 15.2 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease
Urine Detected and Quantified 304.51 (105.96 – 586.60) umol/mmol creatinine Adult (>18 years old) Both Type 1 diabetes Mellitus
  • Lorena Ivona...
Urine Detected and Quantified 11.2 umol/mmol creatinine Adult (>18 years old) Both Paraquat poisoning
Associated Disorders and Diseases
Disease References
Paraquat poisoning
  • Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. Pubmed: 9625050 Link_out
      Canavan disease
      • Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054 Link_out
          Lung Cancer
          • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. Pubmed: 18953024 Link_out
              Hyperoxalemia
              • Ogawa Y, Machida N, Jahana M, Gakiya M, Chinen Y, Oda M, Morozumi M, Sugaya K: Major factors modulating the serum oxalic acid level in hemodialysis patients. Front Biosci. 2004 Sep 1;9:2901-8. Pubmed: 15353324 Link_out
                  Rhabdomyolysis
                  • Bairaktari E, Seferiadis K, Liamis G, Psihogios N, Tsolas O, Elisaf M: Rhabdomyolysis-related renal tubular damage studied by proton nuclear magnetic resonance spectroscopy of urine. Clin Chem. 2002 Jul;48(7):1106-9. Pubmed: 12089184 Link_out
                      Associated OMIM IDs
                      DrugBank ID DB04272 Link_out
                      DrugBank Metabolite ID Not Available
                      Phenol Explorer Compound ID Not Available
                      Phenol Explorer Metabolite ID Not Available
                      FoodDB ID FDB012586
                      KNApSAcK ID C00007619 Link_out
                      Chemspider ID 305 Link_out
                      KEGG Compound ID C00158 Link_out
                      BioCyc ID CIT Link_out
                      BiGG ID 34080 Link_out
                      Wikipedia Link Citric acid Link_out
                      NuGOwiki Link HMDB00094 Link_out
                      Metagene Link HMDB00094 Link_out
                      METLIN ID 124 Link_out
                      PubChem Compound 311 Link_out
                      PDB ID CIT Link_out
                      ChEBI ID 30769 Link_out
                      References
                      Synthesis Reference Evans, D. W. S. Hydrolysis of ethyl methylenecitrate [5,5-bis(ethoxycarbonylmethyl)-1,3-dioxolan-4-one] and an attempted synthesis of agaric acid. Journal of the Chemical Society (1959), 1313-14.
                      Material Safety Data Sheet (MSDS) Download (PDF)
                      General References
                      1. Moreno AJ, Brown JM, Salinas JA, Feaster BL 3rd, Brown TJ: Ga-67 positivity in sarcoidosis of the skin with coincident thyroid uptake of uncertain etiology. Clin Nucl Med. 1984 Mar;9(3):165-6. Pubmed: 6705419 Link_out
                      2. Wenk J, Foitzik A, Achterberg V, Sabiwalsky A, Dissemond J, Meewes C, Reitz A, Brenneisen P, Wlaschek M, Meyer-Ingold W, Scharffetter-Kochanek K: Selective pick-up of increased iron by deferoxamine-coupled cellulose abrogates the iron-driven induction of matrix-degrading metalloproteinase 1 and lipid peroxidation in human dermal fibroblasts in vitro: a new dressing concept. J Invest Dermatol. 2001 Jun;116(6):833-9. Pubmed: 11407968 Link_out
                      3. Wei R, Han JJ, Bai B, Ren DL, Chen B, Yang MF, Xia ZL: Analysis of factors influencing the blood levels and activities of tissue-type plasminogen activator (t-PA). Clin Hemorheol Microcirc. 2003;29(3-4):351-6. Pubmed: 14724361 Link_out
                      4. McBane RD 2nd, Karnicki K, Tahirkheli N, Miller RS, Owen WG: Platelet characteristics associated with coronary artery disease. J Thromb Haemost. 2003 Jun;1(6):1296-303. Pubmed: 12871333 Link_out
                      5. Jurasovic J, Cvitkovic P, Pizent A, Colak B, Telisman S: Semen quality and reproductive endocrine function with regard to blood cadmium in Croatian male subjects. Biometals. 2004 Dec;17(6):735-43. Pubmed: 15689116 Link_out
                      6. Mairiang E, Hanpanich P, Sriboonlue P: In vivo 31P-MRS assessment of muscle-pH, cytolsolic-[Mg2+] and phosphorylation potential after supplementing hypokaliuric renal stone patients with potassium and magnesium salts. Magn Reson Imaging. 2004 Jun;22(5):715-9. Pubmed: 15172066 Link_out
                      7. Tammen H, Schulte I, Hess R, Menzel C, Kellmann M, Mohring T, Schulz-Knappe P: Peptidomic analysis of human blood specimens: comparison between plasma specimens and serum by differential peptide display. Proteomics. 2005 Aug;5(13):3414-22. Pubmed: 16038021 Link_out
                      8. Chiueh CC, Andoh T, Lai AR, Lai E, Krishna G: Neuroprotective strategies in Parkinson's disease: protection against progressive nigral damage induced by free radicals. Neurotox Res. 2000 May;2(2-3):293-310. Pubmed: 16787846 Link_out
                      9. Batchelor WB, Tolleson TR, Huang Y, Larsen RL, Mantell RM, Dillard P, Davidian M, Zhang D, Cantor WJ, Sketch MH Jr, Ohman EM, Zidar JP, Gretler D, DiBattiste PM, Tcheng JE, Califf RM, Harrington RA: Randomized COMparison of platelet inhibition with abciximab, tiRofiban and eptifibatide during percutaneous coronary intervention in acute coronary syndromes: the COMPARE trial. Comparison Of Measurements of Platelet aggregation with Aggrastat, Reopro, and Eptifibatide. Circulation. 2002 Sep 17;106(12):1470-6. Pubmed: 12234950 Link_out
                      10. A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. Pubmed: 16351159 Link_out
                      11. Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. Pubmed: 9625050 Link_out
                      12. Wan KW, Malgesini B, Verpilio I, Ferruti P, Griffiths PC, Paul A, Hann AC, Duncan R: Poly(amidoamine) salt form: effect on pH-dependent membrane activity and polymer conformation in solution. Biomacromolecules. 2004 May-Jun;5(3):1102-9. Pubmed: 15132705 Link_out
                      13. Solheim BG, Flesland O, Brosstad F, Mollnes TE, Seghatchian J: Improved preservation of coagulation factors after pre-storage leukocyte depletion of whole blood. Transfus Apher Sci. 2003 Oct;29(2):133-9. Pubmed: 12941351 Link_out
                      14. Seiffert D, Thomas BE, Bradley JD, Munzer DA, Tchinnes MA, Kornhauser DM, Cain VA, Hua TA, Feuerstein GZ, Martin DE, Stern AM: Effects of the glycoprotein IIb/IIIa antagonist Roxifiban on P-selectin expression, fibrinogen binding, and microaggregate formation in a phase I dose-finding study: no evidence for platelet activation during treatment with a glycoprotein IIb/IIIa antagonist. Platelets. 2003 May;14(3):179-87. Pubmed: 12850842 Link_out
                      15. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012 Link_out
                      16. Odvina CV, Mason RP, Pak CY: Prevention of thiazide-induced hypokalemia without magnesium depletion by potassium-magnesium-citrate. Am J Ther. 2006 Mar-Apr;13(2):101-8. Pubmed: 16645424 Link_out
                      17. Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054 Link_out
                      18. Commodari F, Arnold DL, Sanctuary BC, Shoubridge EA: 1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient. NMR Biomed. 1991 Aug;4(4):192-200. Pubmed: 1931558 Link_out
                      19. McBane RD 2nd, Karnicki K, Miller RS, Owen WG: The impact of peripheral arterial disease on circulating platelets. Thromb Res. 2004;113(2):137-45. Pubmed: 15115669 Link_out
                      20. Abe T, Kobata H, Hanba Y, Kitabata Y, Narukawa N, Hasegawa H, Abe T, Fukagawa M: Study of plasma exchange for liver failure: beneficial and harmful effects. Ther Apher Dial. 2004 Jun;8(3):180-4. Pubmed: 15154867 Link_out
                      21. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
                      22. Caudarella R, Vescini F, Buffa A, Stefoni S: Citrate and mineral metabolism: kidney stones and bone disease. Front Biosci. 2003 Sep 1;8:s1084-106. Pubmed: 12957820 Link_out
                      23. Costello LC, Franklin RB: Testosterone and prolactin regulation of metabolic genes and citrate metabolism of prostate epithelial cells. Horm Metab Res. 2002 Aug;34(8):417-24. Pubmed: 12198595 Link_out

                      Enzymes
                      Name: ATP-citrate synthase
                      Reactions:
                      ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic acid unknown Adenosine triphosphate + Citric acid + Coenzyme A details
                      Adenosine triphosphate + Citric acid + Coenzyme A unknown ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic acid details
                      Gene Name: ACLY
                      Uniprot ID: P53396 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Citrate synthase, mitochondrial
                      Reactions:
                      Acetyl-CoA + Water + Oxalacetic acid unknown Citric acid + Coenzyme A details
                      Citric acid + Coenzyme A unknown Acetyl-CoA + Water + Oxalacetic acid details
                      Gene Name: CS
                      Uniprot ID: O75390 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Aldose reductase
                      Reactions: Not Available
                      Gene Name: AKR1B1
                      Uniprot ID: P15121 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Macrophage migration inhibitory factor
                      Reactions: Not Available
                      Gene Name: MIF
                      Uniprot ID: P14174 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Heparan sulfate glucosamine 3-O-sulfotransferase 3A1
                      Reactions: Not Available
                      Gene Name: HS3ST3A1
                      Uniprot ID: Q9Y663 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Glycine N-methyltransferase
                      Reactions: Not Available
                      Gene Name: GNMT
                      Uniprot ID: Q14749 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Inosine triphosphate pyrophosphatase
                      Reactions: Not Available
                      Gene Name: ITPA
                      Uniprot ID: Q9BY32 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenine phosphoribosyltransferase
                      Reactions: Not Available
                      Gene Name: APRT
                      Uniprot ID: P07741 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Ribonuclease pancreatic
                      Reactions: Not Available
                      Gene Name: RNASE1
                      Uniprot ID: P07998 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Beta-Ala-His dipeptidase
                      Reactions: Not Available
                      Gene Name: CNDP1
                      Uniprot ID: Q96KN2 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Betaine--homocysteine S-methyltransferase 1
                      Reactions: Not Available
                      Gene Name: BHMT
                      Uniprot ID: Q93088 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cGMP-specific 3',5'-cyclic phosphodiesterase
                      Reactions: Not Available
                      Gene Name: PDE5A
                      Uniprot ID: O76074 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Aconitate hydratase, mitochondrial
                      Reactions:
                      Citric acid unknown Isocitric acid details
                      Citric acid unknown cis-Aconitic acid + Water details
                      Gene Name: ACO2
                      Uniprot ID: Q99798 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Cytoplasmic aconitate hydratase
                      Reactions:
                      Citric acid unknown Isocitric acid details
                      Citric acid unknown cis-Aconitic acid + Water details
                      Gene Name: ACO1
                      Uniprot ID: P21399 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Malate dehydrogenase, mitochondrial
                      Reactions: Not Available
                      Gene Name: MDH2
                      Uniprot ID: P40926 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Proto-oncogene tyrosine-protein kinase Src
                      Reactions: Not Available
                      Gene Name: SRC
                      Uniprot ID: P12931 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Angiogenin
                      Reactions: Not Available
                      Gene Name: ANG
                      Uniprot ID: P03950 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Eosinophil cationic protein precursor
                      Reactions: Not Available
                      Gene Name: RNASE3
                      Uniprot ID: P12724 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Uridine-cytidine kinase 2
                      Reactions: Not Available
                      Gene Name: UCK2
                      Uniprot ID: Q9BZX2 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Citrate lyase subunit beta-like protein, mitochondrial
                      Reactions: Not Available
                      Gene Name: CLYBL
                      Uniprot ID: Q8N0X4 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: L-amino-acid oxidase
                      Reactions: Not Available
                      Gene Name: IL4I1
                      Uniprot ID: Q96RQ9 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Beta-citryl-glutamate synthase B
                      Reactions:
                      Adenosine triphosphate + Citric acid + L-Glutamic acid unknown ADP + Phosphoric acid + beta-citryl-L-glutamate details
                      Gene Name: RIMKLB
                      Uniprot ID: Q9ULI2 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1
                      Reactions: Not Available
                      Gene Name: CTDSP1
                      Uniprot ID: Q9GZU7 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Carboxypeptidase B
                      Reactions: Not Available
                      Gene Name: CPB1
                      Uniprot ID: P15086 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Transporters
                      Name: Solute carrier organic anion transporter family member 2B1
                      Reactions: Not Available
                      Gene Name: SLCO2B1
                      Uniprot ID: O94956 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA