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L-Dihydroorotic acid

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L-Dihydroorotic acid Basic information
Product Name:L-Dihydroorotic acid
Synonyms:(S)-2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid;2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid;L-4,5-Dihydroorotic acid~(S)-(+)-2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid;(S)-(+)-HYDROOROTIC ACID;(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid;(S)-4,5-dihydroorotate;(S)-4,5-dihydroorotic acid;(S)-4-pyrimidinecarboxylic acid
CAS:5988-19-2
MF:C5H6N2O4
MW:158.11
EINECS:624-952-7
Product Categories:Heterocycles;Miscellaneous Biochemicals;Amino Acid Derivatives;5988-19-2
Mol File:5988-19-2.mol
L-Dihydroorotic acid Structure
L-Dihydroorotic acid Chemical Properties
Melting point 254-255 °C (dec.)(lit.)
Boiling point 283.16°C (rough estimate)
density 1.523
refractive index 1.5090 (estimate)
storage temp. Sealed in dry,2-8°C
solubility DMSO (Slightly), Water (Slightly, Heated, Sonicated)
pka2.82±0.20(Predicted)
form Powder
color White to off-white
Water Solubility Soluble in water (partly), and dimethyl formamide.
InChIInChI=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
InChIKeyUFIVEPVSAGBUSI-REOHCLBHSA-N
SMILESC1(=O)NC(=O)C[C@@H](C(O)=O)N1
CAS DataBase Reference5988-19-2(CAS DataBase Reference)
NIST Chemistry ReferenceOrotic acid, dihydro-, l-(5988-19-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
L-Dihydroorotic acid Usage And Synthesis
Chemical PropertiesWhite to off-white crystalline powder
UsesL-Dihydroorotic acid a metabolite.
DefinitionChEBI: (S)-dihydroorotic acid is the (S)-enantiomer of dihydroorotic acid that is an intermediate in the metabolism of pyridine. It has a role as a Saccharomyces cerevisiae metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a conjugate acid of a (S)-dihydroorotate. It is an enantiomer of a (R)-dihydroorotic acid.
Biochem/physiol ActionsL-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.
IC 50Microbial Metabolite; Human Endogenous Metabolite
L-Dihydroorotic acid Preparation Products And Raw materials
Raw materialsOrotic acid
Preparation ProductsDisodium 5'-Inosinate-->Ribavirin-->CALCIUM5'-RIBONUCLEOTIDES-->Idoxuridine
Tag:L-Dihydroorotic acid(5988-19-2) Related Product Information
1-METHYL-L-4,5-DIHYDROOROTIC ACID UDP SODIUM SALT 2'-Deoxyuridine Cytidine-5'-diphosphate disodium salt Inosine CTP xsodium ATP disodium salt Uridine-5'-diphosphate disodium salt Orotic acid Trisodium phosphate L-Dihydroorotic acid Sodium phosphate tribasic dodecahydrate Cytidine 5′-(tetrahydrogen triphosphate), xsodium salt, hydrate Sulbactum Sodium DL-Hydroorotic acid Uridine 5'-diphosphoric acid sodium salt D-Hydroorotic acid (S)-Benzyl 1-methyl-2,6-dioxohexahydropyrimidine-4-carboxylate