{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 70591
• Molecular Formular: C9H14N3O8P
• Molecular Mass: 323.196521
• Monoisotopic Mass: 323.05185105
• SMILES: P(=O)(O)(O)OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(=O)nc(cc1)N
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1ccc(nc1=O)N)COP(=O)(O)O
• InChI: InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
• InChIKey: IERHLVCPSMICTF-XVFCMESISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: cytidine monophosphate
• Synonyms: Cytidine 5'-Phosphate; Cytidine 5'-Phosphoric Acid; Cytidine Monophosphate; Cytidine Mono(dihydrogen phosphate)(Ester); Cytidylic Acid; Cytosine 5'-Monophosphate; Cytidine 5'-Monophosphate; 5'-Cytidylic acid; ((2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate; 5'-Cytidylic acid; Cytidine monophosphate; 5′-CMP; 5′-Cytidylic acid; C-5′-P; Cytidine 5′-monophosphate

Database IDs

• CAS Number: 63-37-6
• EC Number: 200-556-6
• MDL Number: MFCD00006544
• Beilstein Number: 46982
• PubChem SID: 24892358; 162036306
• PubChem CID: 6131
• CHEBI ID: 17361
• CHEMBL: 307679
• Chemspider ID: 5901
• Wikipedia Title: Cytidine_monophosphate

CALCULATED PROPERTIES

• Acid pKa: 1.247557
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -5.362577
• LogD (pH = 7.4): -6.4509172
• Log P: -3.1532001
• Molar Refractivity: 65.4177 cm^3
• Polarizability: 26.073345 Å^3
• Polar Surface Area: 175.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: crystalline; White Solid
• Melting Point: ~222 °C (dec.); 205-208°C
• Optical Rotation: [α]20/D +9±0.5°, c = 1% in 0.5 M Na2HPO4
• pKa: 0.8, 4.5, 6.3

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); ≥99% (HPLC); 95+%
• Grade: Sigma Grade
• Impurities: ~3% water
• Biological Source: from yeast
• Empirical Formula (Hill Notation): C9H14N3O8P

DETAILS

Sigma Aldrich - C1131

Application
Cytidine 5′-monophosphate (CMP) is used as a substrate of uridine monophosphate (UMP)/cytidine monophosphate (CMP) kinase (EC 2.7.4.4) to form CDP which upon phosphorylation to CTP supports DNA and RNA biosynthesis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1131.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C998305

A constituent of nucleic acids. It was isolated from yeast nucleic acid.

REFERENCES

• Parrou, J., et al.: Anal. Biochem., 248, 186 (1997)
• Phipps, A., et al.: Xenobiotica, 28, 527 (1997)
• Mohler, R., et al.: Anal. Chem., 78, 2700 (1997)