Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:16 UTC
HMDB IDHMDB00300
Secondary Accession NumbersNone
Metabolite Identification
Common NameUracil
DescriptionUracil is a common naturally occurring pyrimidine found in RNA, it base pairs with adenine and is replaced by thymine in DNA. Methylation of uracil produces thymine. Uracil's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for many important biochemical reactions. UDP and UTP regulate CPSase II activity in animals. UDP-glucose regulates the conversion of glucose to galactose in the liver and other tissues in the process of carbohydrate metabolism. Uracil is also involved in the biosynthesis of polysaccharides and the transportation of sugars containing aldehydes.
Structure
Thumb
Synonyms
  1. 2,4-Dihydroxypyrimidine
  2. 2,4-Dioxopyrimidine
  3. 2,4-Pyrimidinediol
  4. 2,4-Pyrimidinedione
  5. Hybar X
  6. Pirod
  7. Pyrod
  8. Uracil
Chemical FormulaC4H4N2O2
Average Molecular Weight112.0868
Monoisotopic Molecular Weight112.027277382
IUPAC Name1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional IUPAC Nameuracil
CAS Registry Number66-22-8
SMILES
O=C1NC=CC(=O)N1
InChI Identifier
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChI KeyISAKRJDGNUQOIC-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassDiazines
Sub ClassPyrimidines and Pyrimidine Derivatives
Other Descriptors
  • Pyrimidines and Pyrimidine Derivatives
  • Pyrimidines(KEGG)
  • a pyrimidine base(Cyc)
  • a pyrimidine-related compound(Cyc)
  • pyrimidine nucleobase(ChEBI)
  • pyrimidone(ChEBI)
Substituents
  • Hydropyrimidine
Direct ParentPyrimidones
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Pantothenate and CoA biosynthesis
  • Component of Pyrimidine metabolism
  • Component of beta-Alanine metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point330 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.6 mg/mLNot Available
LogP-1.07HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility26.5 g/LALOGPS
logP-1.2ALOGPS
logP-0.86ChemAxon
logS-0.63ALOGPS
pKa (strongest acidic)9.77ChemAxon
pKa (strongest basic)-5.5ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area58.2ChemAxon
rotatable bond count0ChemAxon
refractivity25.97ChemAxon
polarizability9.37ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Amniotic Fluid
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Beta-Alanine MetabolismSMP00007map00410
Pyrimidine MetabolismSMP00046map00240
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Amniotic FluidDetected and Quantified0.87 +/- 0.69 uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified0.17 (0.097-0.26) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified2.10 +/- 1.02 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.2 uMAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal
UrineDetected and Quantified12.0 (2.0-22.0) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified2.5 (2.37-3.5) umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
UrineDetected and Quantified10.13 +/- 5.43 umol/mmol creatinineChildren (1-13 year old)BothNormal
UrineDetected and Quantified6.81 +/- 5.09 umol/mmol creatinineAdolescent (13-18 years old)BothNormal
UrineDetected and Quantified12.29 +/- 5.78 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified9.5 (2.6-22.8) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified4.99 umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified2.25 +/- 0.98 uMAdult (>18 years old)BothCanavan disease
UrineDetected and Quantified35.0 (20.0-50.0) umol/mmol creatinineChildren (1-13 year old)BothArgininemia
UrineDetected and Quantified265.0 (30.0-500.0) umol/mmol creatinineChildren (1-13 year old)BothCarbamoyl phosphate synthetase deficiency
UrineDetected and Quantified100.0 (50.0-150.0) umol/mmol creatinineChildren (1-13 year old)BothDihydropyrimidine dehydrogenase deficiency
UrineDetected and Quantified6.00 +/- 4.00 umol/mmol creatinineAdult (>18 years old)BothHypertension
UrineDetected and Quantified5.00 +/- 4.00 umol/mmol creatinineAdult (>18 years old)BothCerebral infarction
UrineDetected and Quantified8.00 +/- 13.00 umol/mmol creatinineAdult (>18 years old)BothMalignancy
UrineDetected and Quantified7.00 +/- 6.00 umol/mmol creatinineAdult (>18 years old)BothLiver dysfunction
UrineDetected and Quantified20.24 +/- 7.24 umol/mmol creatinineAdult (>18 years old)BothCanavan disease
UrineDetected and Quantified6.6 +/- 2.5 umol/mmol creatinineAdult (>18 years old)BothNephropathy
Associated Disorders and Diseases
Disease References
Argininemia
Canavan disease
  • Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. Pubmed: 16139832
Carbamoyl Phosphate Synthetase Deficiency
Dihydropyrimidine dehydrogenase deficiency
Hypertension
  • Hayashi K, Kidouchi K, Sumi S, Mizokami M, Orito E, Kumada K, Ueda R, Wada Y: Possible prediction of adverse reactions to pyrimidine chemotherapy from urinary pyrimidine levels and a case of asymptomatic adult dihydropyrimidinuria. Clin Cancer Res. 1996 Dec;2(12):1937-41. Pubmed: 9816152
Associated OMIM IDs
DrugBank IDDB03419
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB006426
KNApSAcK IDC00001513
Chemspider ID1141
KEGG Compound IDC00106
BioCyc IDURACIL
BiGG ID33879
Wikipedia LinkUracil
NuGOwiki LinkHMDB00300
Metagene LinkHMDB00300
METLIN ID258
PubChem Compound1174
PDB IDURA
ChEBI ID17568
References
Synthesis ReferenceBurckhalter, J. H.; Scarborough, Homer C. The synthesis of uracils as anticonvulsants. Journal of the American Pharmaceutical Association (1912-1977) (1955), 44 545-50.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
  2. 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
  3. Hofmann U, Schwab M, Seefried S, Marx C, Zanger UM, Eichelbaum M, Murdter TE: Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):371-80. Pubmed: 12798197
  4. van Lenthe H, van Kuilenburg AB, Ito T, Bootsma AH, van Cruchten A, Wada Y, van Gennip AH: Defects in pyrimidine degradation identified by HPLC-electrospray tandem mass spectrometry of urine specimens or urine-soaked filter paper strips. Clin Chem. 2000 Dec;46(12):1916-22. Pubmed: 11106323
  5. Jiang H, Jiang J, Hu P, Hu Y: Measurement of endogenous uracil and dihydrouracil in plasma and urine of normal subjects by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Mar 25;769(1):169-76. Pubmed: 11936689
  6. Allgayer H, Kolb M, Stuber V, Kruis W: Effects of bile acids on base hydroxylation in a model of human colonic mucosal DNA. Cancer Detect Prev. 2002;26(1):85-9. Pubmed: 12088208
  7. Jakobs C, Sweetman L, Nyhan WL, Gruenke L, Craig JC, Wadman SK: Stable isotope dilution analysis of orotic acid and uracil in amniotic fluid. Clin Chim Acta. 1984 Nov 15;143(2):123-33. Pubmed: 6391739
  8. van Kuilenburg AB, van Lenthe H, Loffler M, van Gennip AH: Analysis of pyrimidine synthesis "de novo" intermediates in urine and dried urine filter- paper strips with HPLC-electrospray tandem mass spectrometry. Clin Chem. 2004 Nov;50(11):2117-24. Epub 2004 Sep 16. Pubmed: 15375016
  9. Spector T, Harrington JA, Porter DJ: 5-Ethynyluracil (776C85): inactivation of dihydropyrimidine dehydrogenase in vivo. Biochem Pharmacol. 1993 Dec 14;46(12):2243-8. Pubmed: 8274158
  10. Mani S, Kugler JW, Sciortino DF, Garcia JC, Ansari RH, Humerickhouse R, Michelassi F, Posner MC, Shulman KL, Schilsky RL, List M, Vokes EE, Benner S: Phase II trial of uracil/tegafur (UFT) plus leucovorin in patients with advanced pancreatic carcinoma: a University of Chicago phase II consortium study. Ann Oncol. 1998 Sep;9(9):1035-7. Pubmed: 9818081
  11. Tomita T, Tajima T, Ishibashi M, Tagaya N, Aoki H, Itoh S, Kadowaki A, Kogure H, Tajima Y: [Study on the concentrations of 5-fluorouracil (5-FU), tegafur (ET) and uracil in bile: comparison of UFT or FT] Gan To Kagaku Ryoho. 1989 Dec;16(12):3755-62. Pubmed: 2512859
  12. Duthie SJ, McMillan P: Uracil misincorporation in human DNA detected using single cell gel electrophoresis. Carcinogenesis. 1997 Sep;18(9):1709-14. Pubmed: 9328165
  13. Bayer AS, Galpin JE, Theofilopoulos AN, Guze LB: Neurological disease associated with Mycoplasma pneumoniae pneumonitis: demonstration of viable Mycoplasma pneumoniae in cerebrospinal fluid and blood by radioisotopic and immunofluorescent tissue culture techniques. Ann Intern Med. 1981 Jan;94(1):15-20. Pubmed: 6778283
  14. Feliu J, Mel R, Borrega P, Lopez Gomez L, Escudero P, Dorta J, Castro J, Vazquez-Estevez SE, Bolanos M, Espinosa E, Gonzalez Baron M: Phase II study of a fixed dose-rate infusion of gemcitabine associated with uracil/tegafur in advanced carcinoma of the pancreas. Ann Oncol. 2002 Nov;13(11):1756-62. Pubmed: 12419748
  15. Mashiyama ST, Courtemanche C, Elson-Schwab I, Crott J, Lee BL, Ong CN, Fenech M, Ames BN: Uracil in DNA, determined by an improved assay, is increased when deoxynucleosides are added to folate-deficient cultured human lymphocytes. Anal Biochem. 2004 Jul 1;330(1):58-69. Pubmed: 15183762
  16. DeAngelis LM, Kreis W, Chan K, Dantis E, Akerman S: Pharmacokinetics of ara-C and ara-U in plasma and CSF after high-dose administration of cytosine arabinoside. Cancer Chemother Pharmacol. 1992;29(3):173-7. Pubmed: 1733548
  17. Stover PJ, Garza C: Bringing individuality to public health recommendations. J Nutr. 2002 Aug;132(8 Suppl):2476S-2480S. Pubmed: 12163715
  18. Duthie SJ, Hawdon A: DNA instability (strand breakage, uracil misincorporation, and defective repair) is increased by folic acid depletion in human lymphocytes in vitro. FASEB J. 1998 Nov;12(14):1491-7. Pubmed: 9806758
  19. Hanaue H, Kurosawa T, Kitano Y, Miyakawa S, Nemoto A, Yamamoto H, Asagoe T, Takada T, Yasuda H, Shikata J: Anticancer drug distribution in lymph and blood during adjuvant chemotherapy after surgery for gastric carcinoma. A study with a combined preparation of 1-(2-tetrahydrofuryl)-5-fluorouracil and uracil. Cancer. 1987 May 1;59(9):1571-6. Pubmed: 3103905

Enzymes

Gene Name:
DPYD
Uniprot ID:
Q12882
Reactions
Dihydrouracil + NADP unknown Uracil + NADPHdetails
Dihydrouracil + NADP unknown Uracil + NADPH + Hydrogen Iondetails
Gene Name:
PNP
Uniprot ID:
P00491
Reactions
Deoxyuridine + Phosphoric acid unknown Uracil + Deoxyribose 1-phosphatedetails
Gene Name:
TYMP
Uniprot ID:
P19971
Reactions
Deoxyuridine + Phosphoric acid unknown Uracil + Deoxyribose 1-phosphatedetails
Gene Name:
UPP1
Uniprot ID:
Q16831
Reactions
Uridine + Phosphoric acid unknown Uracil + Ribose 1-phosphatedetails
Gene Name:
UPP2
Uniprot ID:
O95045
Reactions
Uridine + Phosphoric acid unknown Uracil + Ribose 1-phosphatedetails
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Gene Name:
UPRT
Uniprot ID:
Q96BW1
Reactions
Uridine 5'-monophosphate + Pyrophosphate unknown Uracil + Phosphoribosyl pyrophosphatedetails