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D7128

Sigma-Aldrich

L-Dihydroorotsäure

≥99%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C5H6N2O4
CAS-Nummer:
5988-19-2
Molekulargewicht:
158.11
MDL-Nummer:
MFCD00085339
UNSPSC-Code:
12352204
PubChem Substanz-ID:
24894080
NACRES:
NA.83

Qualitätsniveau

200

Assay

≥99%

Form

powder

mp (Schmelzpunkt)

254-255 °C (dec.) (lit.)

SMILES String

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

InChIKey

UFIVEPVSAGBUSI-REOHCLBHSA-N

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Anwendung

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

Biochem./physiol. Wirkung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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
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
Mihwa Lee et al.
Journal of molecular biology, 348(3), 523-533 (2005-04-14)
Escherichia coli dihydroorotase has been crystallized in the presence of the product, L-dihydroorotate (L-DHO), and the structure refined at 1.9A resolution. The structure confirms that previously reported (PDB entry 1J79), crystallized in the presence of the substrate N-carbamyl-D,L-aspartate (D, L-CA-asp)
Laura Martorano et al.
Disease models & mechanisms, 12(3) (2019-03-06)
Mitochondrial DNA depletion syndromes (MDS) are a group of rare autosomal recessive disorders with early onset and no cure available. MDS are caused by mutations in nuclear genes involved in mitochondrial DNA (mtDNA) maintenance, and characterized by both a strong
Michelle L Zaharik et al.
Microbiology (Reading, England), 153(Pt 8), 2472-2482 (2007-07-31)
Mutants capable of utilizing the pyrimidine biosynthetic intermediates carbamoylaspartate and dihydroorotate for growth were derived from pyrimidine auxotrophs of Salmonella enterica serovar Typhimurium LT2. The gain-of-function phenotypes both resulted from mutations in a single gene, yhiT, the third gene of
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