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D7128

Sigma-Aldrich

L-Dihydroorotic acid

≥99%

Synonyme(s) :

2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid, L-Hydroorotic acid, Dihydro-L-orotic acid

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About This Item

Formule empirique (notation de Hill):
C5H6N2O4
Numéro CAS:
5988-19-2
Poids moléculaire :
158.11
Numéro MDL:
MFCD00085339
Code UNSPSC :
12352204
ID de substance PubChem :
24894080
Nomenclature NACRES :
NA.83

Pureté

≥99%

Forme

powder

Pf

254-255 °C (dec.) (lit.)

Chaîne SMILES 

OC(=O)[C@@H]1CC(=O)NC(=O)N1

InChI

1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)/t2-/m0/s1

Clé InChI

UFIVEPVSAGBUSI-REOHCLBHSA-N

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Application

L-Dihydroorotic acid has been used as a substrate in dihydroorotate dehydrogenase (DHODH) assay.

Actions biochimiques/physiologiques

L-Dihydroorotic acid (DHO) serves as a substrate for dihydroorotate dehydrogenase (DHODH), an enzyme in the de novo synthesis of pyrimidine. Inhibition of DHOH by its inhibitors causes a large accumulation of upstream metabolite DHO and a reduction in the uridine levels. Therefore, DHO and uridine can be used as biomarkers for pyrimidine synthesis for the clinical development of DHOH inhibitors.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Feng Yin et al.
Journal of pharmaceutical and biomedical analysis, 192, 113669-113669 (2020-10-30)
Uridine and L-dihydroorotate (DHO) are important intermediates of de novo as well as salvage pathways for the biosynthesis of pyrimidines, which are the building blocks of nucleic acids - DNA and RNA. These metabolites are known to be significant biomarkers
Daniel Ken Inaoka et al.
Biochemistry, 47(41), 10881-10891 (2008-09-24)
Dihydroorotate dehydrogenase (DHOD) from Trypanosoma cruzi (TcDHOD) is a member of family 1A DHOD that catalyzes the oxidation of dihydroorotate to orotate (first half-reaction) and then the reduction of fumarate to succinate (second half-reaction) in the de novo pyrimidine biosynthesis
Tamiko N Porter et al.
Biochemistry, 43(51), 16285-16292 (2004-12-22)
Dihydroorotase (DHO) is a zinc metalloenzyme that functions in the pathway for the biosynthesis of pyrimidine nucleotides by catalyzing the reversible interconversion of carbamoyl aspartate and dihydroorotate. A chemical mechanism was proposed on the basis of an analysis of the
Juliana Cheleski et al.
Analytical biochemistry, 399(1), 13-22 (2009-11-26)
Trypanosoma cruzi dihydroorotate dehydrogenase (TcDHODH) catalyzes the oxidation of l-dihydroorotate to orotate with concomitant reduction of fumarate to succinate in the de novo pyrimidine biosynthetic pathway. Based on the important need to characterize catalytic mechanism of TcDHODH, we have tailored
Idalia Sariego et al.
Parasitology international, 55(1), 11-16 (2005-09-21)
Dihydroorotate dehydrogenase (DHOD) is the fourth enzyme in the de novo pyrimidine biosynthetic pathway and is essential in Trypanosoma cruzi, the parasitic protist causing Chagas' disease. T. cruzi and human DHOD have different biochemical properties, including the electron acceptor capacities
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