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CHEBI:17568 - uracil

Default Structure
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
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)
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Roles Classification
Biological Roles:
Saccharomyces cerevisiae metabolite  Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
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.
Daphnia magna metabolite  A Daphnia metabolite produced by the species Daphnia magna.
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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
2,4(1H,3H)-pyrimidinedioneNIST Chemistry WebBook
2,4-DioxopyrimidineHMDB
2,4-PyrimidinedioneHMDB
UChEBI
UraIUBMB
UracilKEGG COMPOUND
UniProt Name  Source
uracilUniProt
Manual XrefsDatabases
C00001513KNApSAcK
C00106KEGG COMPOUND
D00027KEGG DRUG
DB03419DrugBank
HMDB0000300HMDB
URAPDBeChem
UracilWikipedia
URACILMetaCyc
Registry NumbersSources
Gmelin:2896Gmelin
Reaxys:606623Reaxys
CAS:66-22-8KEGG COMPOUND
CAS:66-22-8ChemIDplus
CAS:66-22-8NIST Chemistry WebBook
Citations