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D7128

Sigma-Aldrich

L-Dihydroorotic acid

≥99%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C5H6N2O4
Numero CAS:
5988-19-2
Peso molecolare:
158.11
Numero MDL:
MFCD00085339
Codice UNSPSC:
12352204
ID PubChem:
24894080
NACRES:
NA.83

Saggio

≥99%

Forma fisica

powder

Punto di fusione

254-255 °C (dec.) (lit.)

Stringa SMILE

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
UFIVEPVSAGBUSI-REOHCLBHSA-N

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Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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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
Mark A Anderson et al.
Biochemistry, 45(23), 7132-7139 (2006-06-07)
In the pyrimidine biosynthetic pathway, N-carbamyl-L-aspartate (CA-asp) is converted to L-dihydroorotate (DHO) by dihydroorotase (DHOase). The mechanism of this important reaction was probed using primary and secondary 15N and 13C isotope effects on the ring opening of DHO using isotope
E Takashima et al.
Parasitology international, 50(4), 273-278 (2001-11-24)
Using N2 cavitation, we established a protocol to prepare the active mitochondria from Plasmodium falciparum showing a higher succinate dehydrogenase activity than previously reported and a dihydroorotate-dependent respiration. The fact that fumarate partially inhibited the dihydroorotate dependent respiration suggests that
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
Yihan Wu et al.
Cell chemical biology, 24(12), 1437-1444 (2017-10-17)
Microbial natural products are genetically encoded by dedicated biosynthetic gene clusters (BGCs). A given BGC usually produces a family of related compounds that share a core but contain variable substituents. Though common, the reasons underlying this divergent biosynthesis are in
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