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537306

Sigma-Aldrich

D-Hydroorotic acid

98%

Synonym(s):

R-2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid, Dihydro-D-orotic acid

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About This Item

Empirical Formula (Hill Notation):
C5H6N2O4
CAS Number:
5988-53-4
Molecular Weight:
158.11
MDL number:
MFCD01862150
UNSPSC Code:
12352005
PubChem Substance ID:
24878210
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D −33°, c = 1 in NaHCO3

mp

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-/m1/s1

InChI key

UFIVEPVSAGBUSI-UWTATZPHSA-N

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Rebecca L Fagan et al.
Biochemistry, 48(30), 7169-7178 (2009-06-18)
Dihydroorotate dehydrogenases (DHODs) catalyze the only redox step in de novo pyrimidine biosynthesis, the oxidation of dihydroorotate (DHO) to orotate (OA). During the reaction, the hydrogen at C6 of DHO is transferred to N5 of the isoalloxazine ring of an
Al-Walid A Mohsen et al.
Biochemistry, 43(21), 6498-6510 (2004-05-26)
Dihydroorotate dehydrogenase B (DHODB) is a complex iron-sulfur flavoprotein that catalyzes the conversion of dihydroorotate to orotate and the reduction of NAD(+). The enzyme is a dimer of heterodimers containing an FMN, an FAD, and a 2Fe-2S center. UV-visible, EPR
Jonathan P Combe et al.
The Journal of biological chemistry, 281(26), 17977-17988 (2006-04-21)
Dihydroorotate dehydrogenase B (DHODB) catalyzes the oxidation of dihydroorotate (DHO) to orotate and is found in the pyrimidine biosynthetic pathway. The Lactococcus lactis enzyme is a dimer of heterodimers containing FMN, FAD, and a 2Fe-2S center. Lys-D48 is found in
Pengfei Zhang et al.
Biochemistry, 48(4), 766-778 (2009-01-09)
In prokaryotes, the first three enzymes in pyrimidine biosynthesis, carbamoyl phosphate synthetase (CPS), aspartate transcarbamoylase (ATC), and dihydroorotase (DHO), are commonly expressed separately and either function independently (Escherichia coli) or associate into multifunctional complexes (Aquifex aeolicus). In mammals the enzymes
Danny T Huang et al.
Biochemistry, 45(27), 8275-8283 (2006-07-06)
Dihydroorotase (DHOase, EC 3.5.2.3) from the extreme thermophile Bacillus caldolyticus has been subcloned, sequenced, expressed, and purified as a monomer. The catalytic properties of this thermophilic DHOase have been compared with another type I enzyme, the DHOase domain from hamster
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