CHEBI:17568 - uracil

Main ChEBI Ontology Automatic Xrefs
ChEBI Name uracil
ChEBI ID CHEBI:17568
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46375, CHEBI:9882, CHEBI:15288, CHEBI:27210
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Formula C4H4N2O2
Net Charge 0
Average Mass 112.08684
InChI InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChIKey ISAKRJDGNUQOIC-UHFFFAOYSA-N
SMILES O=c1cc[nH]c(=O)[nH]1
Metabolite of Species Details
Daphnia magna (NCBI:35525) See: 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
Cordyceps sinensis (NCBI:72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing uracil (CHEBI:17568) has role Daphnia magna metabolite (CHEBI:83056)
uracil (CHEBI:17568) has role human metabolite (CHEBI:77746)
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 (5R)-6-hydroxy-5-[4-(2-hydroxyethyl)piperidin-1-yl]-5-phenyluracil (CHEBI:40990) has functional parent uracil (CHEBI:17568)
({[(1R,2R)-2-(uracil-1-yl)cyclopentyl]oxy}methyl)phosphonic acid (CHEBI:42248) 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)
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)
3,5-dimethyluracil (CHEBI:74766) 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)
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)
5,6-dihydrouracil (CHEBI:15901) 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-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)
6-(3,5-dimethylbenzyl)-1-(ethoxymethyl)-5-isopropyluracil (CHEBI:42702) 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-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)
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)
thiouracil (CHEBI:348530) 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 Sources
2,4(1H,3H)-pyrimidinedione NIST Chemistry WebBook
2,4-Dioxopyrimidine HMDB
2,4-Pyrimidinedione HMDB
U ChEBI
Ura CBN
Uracil KEGG COMPOUND
URACIL PDBeChem
uracil UniProt
Urazil ChEBI
Database Links Databases
C00001513 KNApSAcK
C00106 KEGG COMPOUND
D00027 KEGG DRUG
DB03419 DrugBank
HMDB00300 HMDB
URA PDBeChem
Uracil Wikipedia
URACIL MetaCyc
View more database links
Registry Numbers Types Sources
2896 Gmelin Registry Number Gmelin
606623 Beilstein Registry Number Beilstein
606623 Reaxys Registry Number Reaxys
66-22-8 CAS Registry Number KEGG COMPOUND
66-22-8 CAS Registry Number ChemIDplus
66-22-8 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
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Last Modified
10 March 2015