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Merck

D7128

L-Dihydroorotic acid

≥99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H6N2O4
CAS Number:
5988-19-2
Molecular Weight:
158.11
NACRES:
NA.83
PubChem Substance ID:
24894080
UNSPSC Code:
12352204
MDL number:
MFCD00085339
Assay:
≥99%
Form:
powder

Key Documents

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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

SMILES string

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

InChI key

UFIVEPVSAGBUSI-REOHCLBHSA-N

assay

≥99%

form

powder

mp

254-255 °C (dec.) (lit.)

Quality Level

200

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Application

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

Biochem/physiol Actions

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000518540
0000518539
0000518539
0000518540
0000491070

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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
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
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
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
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
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