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CHEBI:17568 - uracil

ChEBI IDCHEBI:17568
ChEBI Nameuracil
Stars
DefinitionA common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription.
Secondary ChEBI IDsCHEBI:9882, CHEBI:15288, CHEBI:27210, CHEBI:46375
Last Modified14 May 2020
DownloadsMolfile
FormulaC4H4N2O2
Net Charge0
Average Mass112.088
Monoisotopic Mass112.02728
SMILESO=c1ccnc(=O)n1
InChIInChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChIKeyISAKRJDGNUQOIC-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cordyceps sinensis (ncbitaxon:72228) mycelium (BTO:0001436) PubMed (21848266) Ethanolic extract of dried mycelia
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Daphnia magna (ncbitaxon:35525) - Article (Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268)
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
Daphnia magna metabolite  A Daphnia metabolite produced by the species Daphnia magna.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
allergen  A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
Saccharomyces cerevisiae metabolite  Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Application:
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
uracil (CHEBI:17568) has role Daphnia magna metabolite (CHEBI:83056)
uracil (CHEBI:17568) has role Escherichia coli metabolite (CHEBI:76971)
uracil (CHEBI:17568) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
uracil (CHEBI:17568) has role allergen (CHEBI:50904)
uracil (CHEBI:17568) has role human metabolite (CHEBI:77746)
uracil (CHEBI:17568) has role mouse metabolite (CHEBI:75771)
uracil (CHEBI:17568) has role prodrug (CHEBI:50266)
uracil (CHEBI:17568) is a pyrimidine nucleobase (CHEBI:26432)
uracil (CHEBI:17568) is a pyrimidone (CHEBI:38337)
uracil (CHEBI:17568) is tautomer of (4S)-4-hydroxy-3,4-dihydropyrimidin-2(1H)-one (CHEBI:43254)
Incoming Relation(s)
({[(1R,2R)-2-(uracil-1-yl)cyclopentyl]oxy}methyl)phosphonic acid (CHEBI:42248) has functional parent uracil (CHEBI:17568)
(Z)-2-methylureidoacrylic acid (CHEBI:143867) has functional parent uracil (CHEBI:17568)
(5R)-6-hydroxy-5-[4-(2-hydroxyethyl)piperidin-1-yl]-5-phenyluracil (CHEBI:40990) has functional parent uracil (CHEBI:17568)
1-(3-O-phosphono-β-D-arabinofuranosyl)uracil (CHEBI:46271) has functional parent uracil (CHEBI:17568)
1-(ethoxymethyl)-5-isopropyl-6-(phenylsulfanyl)uracil (CHEBI:40152) has functional parent uracil (CHEBI:17568)
1-[3-(4-carboxypiperidin-1-yl)-3-deoxy-β-D-arabinofuranosyl]pyrimidine-2,4(1H,3H)-dione (CHEBI:44260) has functional parent uracil (CHEBI:17568)
1-methyluracil (CHEBI:69445) has functional parent uracil (CHEBI:17568)
1,3-dimethyluracil (CHEBI:74763) has functional parent uracil (CHEBI:17568)
1,5-dimethyluracil (CHEBI:74765) has functional parent uracil (CHEBI:17568)
2'-deoxyuridine (CHEBI:16450) has functional parent uracil (CHEBI:17568)
3-(5-bromouracil-1-yl)-L-alanine (CHEBI:47280) has functional parent uracil (CHEBI:17568)
3-(5-fluorouracil-1-yl)-L-alanine (CHEBI:42549) has functional parent uracil (CHEBI:17568)
3-(5-iodouracil-1-yl)-L-alanine (CHEBI:43500) has functional parent uracil (CHEBI:17568)
3-(uracil-1-yl)-L-alanine (CHEBI:15851) has functional parent uracil (CHEBI:17568)
3-methyluracil (CHEBI:74732) has functional parent uracil (CHEBI:17568)
3,5-dimethyluracil (CHEBI:74766) has functional parent uracil (CHEBI:17568)
4-[(1E,7E)-8-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl]benzoic acid (CHEBI:39893) has functional parent uracil (CHEBI:17568)
4-thiouracil (CHEBI:232485) has functional parent uracil (CHEBI:17568)
5-(4,5-dihydroxypentyl)uracil (CHEBI:132195) has functional parent uracil (CHEBI:17568)
5-[3-(benzyloxy)benzyl]-6-hydroxy-1-[(2-hydroxyethoxy)methyl]pyrimidine-2,4(1H,3H)-dione (CHEBI:40929) has functional parent uracil (CHEBI:17568)
5-acetamido-6-formamido-3-methyluracil (CHEBI:32643) has functional parent uracil (CHEBI:17568)
5-benzyl-1-(2-hydroxyethoxymethyl)uracil (CHEBI:41037) has functional parent uracil (CHEBI:17568)
5-benzyloxybenzylacyclouridine (CHEBI:39579) has functional parent uracil (CHEBI:17568)
5-bromouracil (CHEBI:20552) has functional parent uracil (CHEBI:17568)
5-carboxy-2'-deoxyuridine (CHEBI:102485) has functional parent uracil (CHEBI:17568)
5-chloro-6-{[(2Z)-2-iminopyrrolidin-1-yl]methyl}uracil (CHEBI:47334) has functional parent uracil (CHEBI:17568)
5-chlorouracil (CHEBI:60762) has functional parent uracil (CHEBI:17568)
5-diazouracil (CHEBI:34454) has functional parent uracil (CHEBI:17568)
5-fluorouracil (CHEBI:46345) has functional parent uracil (CHEBI:17568)
5-hydroxymethyluracil (CHEBI:16964) has functional parent uracil (CHEBI:17568)
5-hydroxyuracil (CHEBI:29115) has functional parent uracil (CHEBI:17568)
5-iodouracil (CHEBI:43636) has functional parent uracil (CHEBI:17568)
5-nitrouracil (CHEBI:60763) has functional parent uracil (CHEBI:17568)
5,6-dihydrouracil (CHEBI:15901) has functional parent uracil (CHEBI:17568)
5,6-dihydroxyuracil (CHEBI:132197) has functional parent uracil (CHEBI:17568)
6-(3,5-dimethylbenzyl)-1-(ethoxymethyl)-5-isopropyluracil (CHEBI:42702) has functional parent uracil (CHEBI:17568)
6-[(1-deoxy-D-ribityl)methyl]-5-[(1E)-3-oxobut-1-en-1-yl]uracil (CHEBI:149716) has functional parent uracil (CHEBI:17568)
6-[(1,2-dideoxy-D-ribityl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149751) has functional parent uracil (CHEBI:17568)
6-[(1,3-dideoxy-D-ribityl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149756) has functional parent uracil (CHEBI:17568)
6-[(1,4-dideoxy-D-ribityl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149744) has functional parent uracil (CHEBI:17568)
6-[(1,5-dideoxy-D-ribityl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149720) has functional parent uracil (CHEBI:17568)
6-[(2-hydroxyethyl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149753) has functional parent uracil (CHEBI:17568)
6-[(3-hydroxypropyl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149757) has functional parent uracil (CHEBI:17568)
6-[(4-hydroxybutyl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149748) has functional parent uracil (CHEBI:17568)
6-[(5-hydroxypentyl)amino]-5-[(E)-(2-oxopropylidene)amino]uracil (CHEBI:149728) has functional parent uracil (CHEBI:17568)
6-benzyl-1-(benzyloxymethyl)-5-isopropyluracil (CHEBI:45910) has functional parent uracil (CHEBI:17568)
6-cyclohexylsulfanyl-1-ethoxymethyl-5-isopropyluracil (CHEBI:62748) has functional parent uracil (CHEBI:17568)
6-methyl-5-[(1E)-3-oxobut-1-en-1-yl]uracil (CHEBI:149702) has functional parent uracil (CHEBI:17568)
6-methyluracil (CHEBI:74733) has functional parent uracil (CHEBI:17568)
6-propyl-2-thiouracil (CHEBI:8502) has functional parent uracil (CHEBI:17568)
aminouracil (CHEBI:22532) has functional parent uracil (CHEBI:17568)
butafenacil (CHEBI:143863) has functional parent uracil (CHEBI:17568)
dasabuvir (CHEBI:85182) has functional parent uracil (CHEBI:17568)
emivirine (CHEBI:44143) has functional parent uracil (CHEBI:17568)
orotate (CHEBI:30839) has functional parent uracil (CHEBI:17568)
orotic acid (CHEBI:16742) has functional parent uracil (CHEBI:17568)
saflufenacil (CHEBI:142824) has functional parent uracil (CHEBI:17568)
thiouracil (CHEBI:348530) has functional parent uracil (CHEBI:17568)
tipiracil (CHEBI:90879) has functional parent uracil (CHEBI:17568)
uracil-5-carboxylic acid (CHEBI:17477) has functional parent uracil (CHEBI:17568)
uracil-6-ylacetic acid (CHEBI:46371) has functional parent uracil (CHEBI:17568)
uridine (CHEBI:16704) has functional parent uracil (CHEBI:17568)
uridines (CHEBI:27242) has functional parent uracil (CHEBI:17568)
uracil-1-yl group (CHEBI:30759) is substituent group from uracil (CHEBI:17568)
(4S)-4-hydroxy-3,4-dihydropyrimidin-2(1H)-one (CHEBI:43254) is tautomer of uracil (CHEBI:17568)
IUPAC Name 
pyrimidine-2,4(1H,3H)-dione
Synonyms  Source
UracilKEGG COMPOUND
UChEBI
2,4(1H,3H)-pyrimidinedioneNIST Chemistry WebBook
URACILPDBeChem
UrazilChEBI
UraIUBMB
UniProt Name  Source
uracilUniProt
Manual XrefsDatabases
C00106KEGG COMPOUND
URAPDBeChem
D00027KEGG DRUG
DB03419DrugBank
HMDB0000300HMDB
URACILMetaCyc
UracilWikipedia
C00001513KNApSAcK
Registry NumbersSources
Gmelin:2896Gmelin
Reaxys:606623Reaxys
CAS:66-22-8KEGG COMPOUND
CAS:66-22-8ChemIDplus
CAS:66-22-8NIST Chemistry WebBook
Citations