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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:45 UTC
HMDB IDHMDB00094
Secondary Accession NumbersNone
Metabolite Identification
Common NameCitric acid
DescriptionCitric 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 ) 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 ) 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
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 FormulaC6H8O7
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
IUPAC Name2-hydroxypropane-1,2,3-tricarboxylic acid
Traditional IUPAC Namecitric acid
CAS Registry Number77-92-9
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 KeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassTricarboxylic 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 ParentTricarboxylic Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glyoxylate and dicarboxylate metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility592.0 mg/mLNot Available
LogP-1.64AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
Water Solubility106 g/LALOGPS
logP-1.3ALOGPS
logP-1.3ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.62ChemAxon
Polarizability15.47ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057map00020
Transfer of Acetyl Groups into MitochondriaSMP00466Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified54.2 +/- 0.8 uMChildren (1-13 years old)BothNormal details
BloodDetected and Quantified190.0 (30.0-400.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified88.0 +/- 33.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified122.0 +/- 30.0 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified114.2 +/- 27 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified225 +/- 96 uMNot SpecifiedBothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified400.0 +/- 170.0 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified350.0 +/- 240.0 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified370.0 (110.0 - 630.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified176.0 +/- 50.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
SalivaDetected and Quantified1 to 4456 uMAdult (>18 years old)Male
normal
details
UrineDetected and Quantified972.5 (89.5-1647.7) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified708.9 (25.2-3168.4) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified208.6 (33.2-445.1) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified184.2 (58.7-651.7) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified300.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified371(102-611) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified46.87-484.31 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified203 (49-600) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified181.0 +/- 97.0 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified242.0 +/- 129.6 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified119.45 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified172.8 +/- 87.4 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified155 (70-226) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified280.6 +/- 115.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified271.8 +/- 90.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified440.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified242.34 (81.79 – 403.84) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Lorena Ivona ŞTEF...
details
UrineDetected and Quantified226.32 +/- 98.12 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified80.2 +/- 44.9 uMAdult (>18 years old)Not SpecifiedHeart Transplant details
BloodDetected and Quantified141.3 +/- 54.7 uMAdult (>18 years old)Both
Hyperoxalemia
details
BloodDetected and Quantified117.6 +/- 37.2 uMAdult (>18 years old)Both
Hyperoxalemia
details
Cerebrospinal Fluid (CSF)Detected and Quantified2400.0 uMAdult (>18 years old)BothCanavan Disease details
UrineDetected and Quantified268.0 (53.0-1111.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected and Quantified154 umol/mmol creatinineAdult (>18 years old)FemaleRhabdomyolysis details
UrineDetected and Quantified181.5 +/- 5.7 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency details
UrineDetected and Quantified191.7 +/- 4.1 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency details
UrineDetected and Quantified80.9 +/- 1.8 umol/mmol creatinineAdult (>18 years old)BothArgininosuccinic aciduria (ASL) details
UrineDetected and Quantified689.6 +/- 47.3 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
UrineDetected and Quantified712.3 +/- 82.8 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
UrineDetected and Quantified457.6 +/- 17.5 umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I details
UrineDetected and Quantified81.8 +/- 10.4 umol/mmol creatinineAdult (>18 years old)BothPhenylketonuria details
UrineDetected and Quantified291.9 +/- 14.6 umol/mmol creatinineAdult (>18 years old)BothPhenylketonuria details
UrineDetected and Quantified576.1 +/- 15.2 umol/mmol creatinineAdult (>18 years old)BothMaple syrup urine disease details
UrineDetected and Quantified304.51 (105.96 – 586.60) umol/mmol creatinineAdult (>18 years old)BothType 1 diabetes Mellitus
    • Lorena Ivona ŞTEF...
details
UrineDetected and Quantified11.2 umol/mmol creatinineAdult (>18 years old)BothParaquat poisoning details
Associated Disorders and Diseases
Disease References
Canavan disease
  1. 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
Hyperoxalemia
  1. 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
Lung Cancer
  1. 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
Paraquat poisoning
  1. 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
Rhabdomyolysis
  1. 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
Associated OMIM IDs
DrugBank IDDB04272
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012586
KNApSAcK IDC00007619
Chemspider ID305
KEGG Compound IDC00158
BioCyc IDCIT
BiGG ID34080
Wikipedia LinkCitric acid
NuGOwiki LinkHMDB00094
Metagene LinkHMDB00094
METLIN ID124
PubChem Compound311
PDB IDCIT
ChEBI ID30769
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. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  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
  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

Enzymes

General function:
Involved in ATP citrate synthase activity
Specific function:
ATP citrate-lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Has a central role in de novo lipid synthesis. In nervous tissue it may be involved in the biosynthesis of acetylcholine.
Gene Name:
ACLY
Uniprot ID:
P53396
Molecular weight:
120838.27
Reactions
ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic acid → Adenosine triphosphate + Citric acid + Coenzyme Adetails
Adenosine triphosphate + Citric acid + Coenzyme A → ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic aciddetails
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Not Available
Gene Name:
CS
Uniprot ID:
O75390
Molecular weight:
51712.025
Reactions
Acetyl-CoA + Water + Oxalacetic acid → Citric acid + Coenzyme Adetails
Citric acid + Coenzyme A → Acetyl-CoA + Water + Oxalacetic aciddetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in cell surface binding
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:
MIF
Uniprot ID:
P14174
Molecular weight:
12476.19
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in IdoUA2S-GlcNS and also in IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
Gene Name:
HS3ST3A1
Uniprot ID:
Q9Y663
Molecular weight:
44899.155
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in folic acid binding
Specific function:
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
Gene Name:
GNMT
Uniprot ID:
Q14749
Molecular weight:
32742.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in nucleic acid binding
Specific function:
Endonuclease that catalyzes the cleavage of RNA on the 3' side of pyrimidine nucleotides. Acts on single stranded and double stranded RNA
Gene Name:
RNASE1
Uniprot ID:
P07998
Molecular weight:
17644.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in metallopeptidase activity
Specific function:
Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
Gene Name:
CNDP1
Uniprot ID:
Q96KN2
Molecular weight:
56691.6
General function:
Involved in zinc ion binding
Specific function:
Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline.
Gene Name:
BHMT
Uniprot ID:
Q93088
Molecular weight:
44998.205
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in catalytic activity
Specific function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP.
Gene Name:
PDE5A
Uniprot ID:
O76074
Molecular weight:
99984.14
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in metabolic process
Specific function:
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO2
Uniprot ID:
Q99798
Molecular weight:
85424.745
Reactions
Citric acid → Isocitric aciddetails
Citric acid → cis-Aconitic acid + Waterdetails
General function:
Involved in metabolic process
Specific function:
Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding. Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO1
Uniprot ID:
P21399
Molecular weight:
98398.14
Reactions
Citric acid → Isocitric aciddetails
Citric acid → cis-Aconitic acid + Waterdetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
P40926
Molecular weight:
35502.935
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in protein kinase activity
Specific function:
ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate
Gene Name:
SRC
Uniprot ID:
P12931
Molecular weight:
59834.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in nucleic acid binding
Specific function:
May function as a tRNA-specific ribonuclease that binds to actin on the surface of endothelial cells; once bound, angiogenin is endocytosed and translocated to the nucleus, thereby promoting the endothelial invasiveness necessary for blood vessel formation. Angiogenin induces vascularization of normal and malignant tissues. Abolishes protein synthesis by specifically hydrolyzing cellular tRNAs
Gene Name:
ANG
Uniprot ID:
P03950
Molecular weight:
16549.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Not Available
Specific function:
Cytotoxin and helminthotoxin with low-efficiency ribonuclease activity. Possesses a wide variety of biological activities. Exhibits antibacterial activity
Gene Name:
RNASE3
Uniprot ID:
P12724
Molecular weight:
18386.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Molecular weight:
29298.92
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in citrate (pro-3S)-lyase activity
Specific function:
Not Available
Gene Name:
CLYBL
Uniprot ID:
Q8N0X4
Molecular weight:
37359.0
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:
IL4I1
Uniprot ID:
Q96RQ9
Molecular weight:
65327.26
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in catalytic activity
Specific function:
Catalyzes the synthesis of beta-citryl-glutamate and N-acetyl-aspartyl-glutamate. Beta-citryl-glutamate is synthesized more efficiently than N-acetyl-aspartyl-glutamate (By similarity).
Gene Name:
RIMKLB
Uniprot ID:
Q9ULI2
Molecular weight:
42463.575
Reactions
Adenosine triphosphate + Citric acid + L-Glutamic acid → ADP + Phosphoric acid + beta-citryl-L-glutamatedetails
General function:
Involved in phosphatase activity
Specific function:
Preferentially catalyzes the dephosphorylation of 'Ser-5' within the tandem 7 residues repeats in the C-terminal domain (CTD) of the largest RNA polymerase II subunit POLR2A. Negatively regulates RNA polymerase II transcription, possibly by controlling the transition from initiation/capping to processive transcript elongation. Recruited by REST to neuronal genes that contain RE-1 elements, leading to neuronal gene silencing in non-neuronal cells.
Gene Name:
CTDSP1
Uniprot ID:
Q9GZU7
Molecular weight:
29127.765
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in metallocarboxypeptidase activity
Specific function:
Preferential release of a C-terminal lysine or arginine amino acid
Gene Name:
CPB1
Uniprot ID:
P15086
Molecular weight:
47367.1

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular weight:
76697.9
References
  1. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. Pubmed: 12724351