potassium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

• ChemBase ID: 53528
• Molecular Formular: C5H3KN2O4
• Molecular Mass: 194.18662
• Monoisotopic Mass: 193.97298827
• SMILES: c1(cc(=O)[nH]c(=O)[nH]1)C(=O)[O-].[K+]
• Canonical SMILES: O=c1[nH]c(=O)[nH]c(c1)C(=O)[O-].[K+]
• InChI: InChI=1S/C5H4N2O4.K/c8-3-1-2(4(9)10)6-5(11)7-3;/h1H,(H,9,10)(H2,6,7,8,11);/q;+1/p-1
• InChIKey: DHBUISJCVRMTAZ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
• IUPAC Traditional name: potassium orotate; potassium ion orotate
• Synonyms: 6-Carboxy-2,4-dihydroxypyrimidine; Orotic acid potassium salt; Potassium 2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylate; 6-Carboxy-2,4-dihydroxy-pyrimidine; Uracil-6-carboxylic acid; OROTIC ACID MONOPOTASSIUM SALT; 乳清酸 钾盐

Database IDs

• CAS Number: 24598-73-0
• EC Number: 246-341-0
• MDL Number: MFCD00039118
• PubChem SID: 162058291; 24897970
• PubChem CID: 23665705

CALCULATED PROPERTIES

• Acid pKa: 2.827267
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.8447902
• LogD (pH = 7.4): -4.7215567
• Log P: -1.2276645
• Molar Refractivity: 44.1117 cm^3
• Polarizability: 12.101853 Å^3
• Polar Surface Area: 98.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: RM3201500
• German water hazard class: 2
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%

DETAILS

MP Biomedicals - 02156000

Monopotassium Salt
Crystalline

Sigma Aldrich - O2875

Application
Orotic acid (OA) is an intermediate in de novo pyrimidine biosynthesis that may be used to study the specificity and kinetics of orotate phosphoribosyltransferase (OPRT) which catalyzes the reversible phosphoribosyl transfer from 5′-phospho-α-d-ribose 1′-diphosphate (PRPP) to orotic acid (OA), forming pyrophosphate and orotidine 5′-monophosphate (OMP). Orotic acid is used as a starting material for the potential commercial bioproduction of uridine 5′-monophosphate (UMP) by microbes such as Corynebacterium ammoniagenes (ATCC 6872) or Saccharomyces cerevisiae. OA may be used to study the AMPK/SREBP-1 dependent cell signaling pathway and transcription regulation mechanisms that induce hepatic lipogenesis.