3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

• ChemBase ID: 128746
• Molecular Formular: C10H12N2O8
• Molecular Mass: 288.21088
• Monoisotopic Mass: 288.05936535
• SMILES: O=C(O)c1n(c(=O)[nH]c(=O)c1)[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(=O)[nH]c(=O)cc1C(=O)O
• InChI: InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1
• InChIKey: FKCRAVPPBFWEJD-XVFCMESISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• IUPAC Traditional name: orotidine
• Synonyms: Uridine-6-carboxylic acid; Orotidine; 3-Ribofuranosylorotic acid; 6-Carboxyuridind; orotate riboside; Orotidine

Database IDs

• CAS Number: 314-50-1
• MDL Number: MFCD00057418
• PubChem SID: 162223052
• PubChem CID: 92751
• Chemspider ID: 83729
• Wikipedia Title: Orotidine

CALCULATED PROPERTIES

• Acid pKa: 2.856693
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -5.3788705
• LogD (pH = 7.4): -6.2791777
• Log P: -2.7876155
• Molar Refractivity: 59.8709 cm^3
• Polarizability: 23.452755 Å^3
• Polar Surface Area: 156.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 200°C
• Density: x.xxx g/cm^3

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - O9505

Application
Orotidine, a nucleoside found naturally in fungi, bacteria and plants, may be used as a reference for the determination of presence of orotidine in urine or plasma due to urea cycle-related (transamidation) metabolic deficiencies or diseases.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. O9505.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.