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Orotic Acid Monohydrate

CAT: 0572-TRC-O691500-100GSize: 100 gDry Ice: NoHazardous: No
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CAT#:0572-TRC-O691500-100GSize:100 g
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CAS Number
50887-69-9
Synonyms
4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-, monohydrate (9CI); Orotic acid monohydrate
Hazard Statement
Causes skin irritation.
Purity
>95% (HPLC)
Smiles
O.OC(=O)C1=CC(=O)NC(=O)N1
Molecular Formula
C5 H4 N2 O4 . H2 O
Molecular Weight
174.11
InChI
InChI=1S/C5H4N2O4.H2O/c8-3-1-2(4(9)10)6-5(11)7-3;/h1H,(H,9,10)(H2,6,7,8,11);1H2
Additionnal Information
IUPAC name: 2,4-dioxo-1H-pyrimidine-6-carboxylic acid;hydrate
Shipping Conditions
Room Temperature
Storage Conditions
+20°C

Chemical Information

4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-, hydrate (1:1)

Orotic acid is a minor dietary constituent. Indeed, until it was realized that it could be synthesized by humans, orotic acid was known as vitamin B-13. The richest dietary sources are cow's milk and other dairy products as well as root vegetables such as carrots and beets. Dietary intake probably contributes to a basal rate of orotic acid excretion in urine because fasting decreases excretion by ~50%. However, it is now apparent that most urinary orotic acid is synthesized in the body, where it arises as an intermediate in the pathway for the synthesis of pyrimidine nucleotides. Orotic acid is converted to UMP by UMP synthase, a multifunctional protein with both orotate phosphoribosyltransferase and orotidylate decarboxylase activity. The most frequently observed inborn error of pyrimidine nucleotide synthesis is a mutation of the multifunctional protein UMP synthase. This disorder prevents the conversion of orotic acid to UMP and thus to other pyrimidines. As a result, plasma orotic acid accumulates to high concentrations, and increased quantities appear in the urine. Indeed, urinary orotic acid is so markedly increased in individuals harboring a mutation in UMP synthase that orotic acid crystals can form in the urine. The urinary concentration of orotic acid in homozygotes can be of the order of millimoles per millimole creatinine. By comparison, the urinary level in unaffected individuals is ~ 1 umol/mmol creatinine. (A3380).

CAS Number50887-69-9
PubChem CID16218504
IUPAC Name2,4-dioxo-1H-pyrimidine-6-carboxylic acid;hydrate
Molecular FormulaC5H6N2O5
Molecular Weight174.11
Topological Polar Surface Area96.5
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Heavy Atom Count12
Formal Charge0
Complexity268
SMILES
C1=C(NC(=O)NC1=O)C(=O)O.O
InChI
InChI=1S/C5H4N2O4.H2O/c8-3-1-2(4(9)10)6-5(11)7-3;/h1H,(H,9,10)(H2,6,7,8,11);1H2
InChIKey
YXUZGLGRBBHYFZ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-, hydrate (1:1)
CAS: 50887-69-9
CID: 16218504
Formula: C5H6N2O5
MW: 174.11
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight174.11
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass174.02767130
Monoisotopic Mass174.02767130
Topological Polar Surface Area96.5 Ų
Heavy Atom Count12
Formal Charge0
Complexity268
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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