2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

• ChemBase ID: 2011
• Molecular Formular: C5H4N2O4
• Molecular Mass: 156.09626
• Monoisotopic Mass: 156.01710662
• SMILES: OC(=O)c1cc(=O)[nH]c(=O)[nH]1
• Canonical SMILES: O=c1[nH]c(=O)[nH]c(c1)C(=O)O
• InChI: InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
• InChIKey: PXQPEWDEAKTCGB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• IUPAC Traditional name: orotic acid
• Synonyms: 6-Carboxyuracil; Orodin; Oropur; Orotonin; Orotonsan; 1,2,3,6-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid; Uracil-4-carboxylic acid; Orotic acid, anhydrous; Orotic acid; 6-Carboxy-2,4-dihydroxypyrimidine; 2,6-Dihydroxypyrimidine-4-carboxylic acid; Uracil-6-carboxylic acid; Orotic Acid; Orotic acid; 2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid; 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid; 无水乳清酸; 乳清酸

Database IDs

• CAS Number: 65-86-1
• EC Number: 200-619-8
• MDL Number: MFCD00006027
• Beilstein Number: 383901
• PubChem SID: 46508903; 24897967; 160965466
• PubChem CID: 967
• Chemspider ID: 942
• DrugBank ID: DB02262
• KEGG ID: C00295
• Unique Ingredient Identifier: 61H4T033E5
• Wikipedia Title: Orotic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.8272662
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.8449886
• LogD (pH = 7.4): -4.736972
• Log P: -1.2276645
• Molar Refractivity: 33.2746 cm^3
• Polarizability: 12.221098 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.89
• LOG S: -1.54
• Solubility (Water): 4.51e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.82 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Melting Point: ≥300 °C; 300-347°C; 344-347°C; 345-346°C
• Hydrophobicity(logP): -0.83 [SANGSTER (1994)]

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant
• RTECS: RM3180000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 22-36/38
• Safety Statements: 26; 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319; H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (titration); ≥98.0% (T); 97%
• Grade: anhydrous
• Salt Data: Free Base
• Suitability: plant cell culture tested
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C5H4N2O4

DETAILS

MP Biomedicals - 05215251

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02151790

Anhydrous
Crystalline
Free Acid

DrugBank - DB02262

Drug information: experimental

Selleck Chemicals - S2336

Research Area: Metabolic Disease
Biological Activity:
Orotic acid(6-Carboxyuracil) is a heterocyclic compound and an acid. It was once believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin but is instead manufactured in the body by intestinal flora. Its salts, known as orotates, are sometimes used as mineral carriers in some dietary supplements, to increase their bioavailability.Lithium orotate is the most frequently used in this manner. [1]

Sigma Aldrich - O2750

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.

REFERENCES

• http://en.wikipedia.org/wiki/Orotic_acid