DNAmod: 5,6-dihydrouracil

Description

A pyrimidine obtained by formal addition of hydrogen across the 5,6-position of uracil.

Chemical properties

Chemical formula	Net charge	Average mass
C4H6N2O2	0	114.10272

5,6-dihydrouracil

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
dihydropyrimidine-2,4(1H,3H)-dione	O=C1CCNC(=O)N1	InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)	OIVLITBTBDPEFK-UHFFFAOYSA-N	dihydrouracile 2,4-dioxotetrahydropyrimidine hydrouracil dihydrouracil dihydro-2,4(1h,3h)-pyrimidinedione 5,6-dihydro-2,4-dihydroxypyrimidine 2,4(1h,3h)-pyrimidinedion ihydro- dihydropyrimidine-2,4(1h,3h)-dione

Database references:

CHEBI:15901

Citations

Aoun, R, et al. 2005. Concomitant monoreduction and hydrogenation of unsaturated cyclic imides to lactams catalyzed by ruthenium compounds. Angewandte Chemie (International Ed. in English). 44(13).
Ben Fredj, R, et al. 2008. The dihydrouracil/uracil ratio in plasma, clinical and genetic analysis for screening of dihydropyrimidine dehydrogenase deficiency in colorectal cancer patients treated with 5-fluorouracil. Pathologie-biologie. 57(6).
Kristensen, MH, et al. 2010. The value of dihydrouracil/uracil plasma ratios in predicting 5-fluorouracil-related toxicity in colorectal cancer patients. The Journal of International Medical Research. 38(4).
Roux, A, et al. 2012. Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Analytical Chemistry. 84(15).