sodium (3aR,4R,6R,6aR)-4-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-1,3,5,2λ5-furo[3,4-d][1,3,2λ5]dioxaphosphol-2-olate

• ChemBase ID: 132979
• Molecular Formular: C9H11N3NaO7P
• Molecular Mass: 327.163071
• Monoisotopic Mass: 327.02323062
• SMILES: c1cn(c(=O)nc1N)[C@H]1[C@H]2[C@@H]([C@H](O1)CO)OP(=O)(O2)[O-].[Na+]
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]2[C@@H]1OP(=O)(O2)[O-])n1ccc(nc1=O)N.[Na+]
• InChI: InChI=1S/C9H12N3O7P.Na/c10-5-1-2-12(9(14)11-5)8-7-6(4(3-13)17-8)18-20(15,16)19-7;/h1-2,4,6-8,13H,3H2,(H,15,16)(H2,10,11,14);/q;+1/p-1/t4-,6-,7-,8-;/m1./s1
• InChIKey: SQOIXCJUYWSZDW-IAIGYFSYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3aR,4R,6R,6aR)-4-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-2-olate
• IUPAC Traditional name: sodium 2',3'-cyclic cmp
• Synonyms: Cytidine Cyclic 2',3'-(Hydrogen Phosphate) Sodium Salt; Cyclic(2',3')-CMP Sodium Salt; Cytidine 2',3'-Cyclic Phosphate Sodium Salt; NSC 238924; Sodium Cytidine-2',3'-cyclophosphate; Cytidine-2',3'-cyclic Monophosphate Sodium Salt; 2′,3′-Cyclic CMP monosodium salt; 2′,3′-cCMP; Cytidine 2′,3′-cyclophosphate sodium salt; Cytidine 2′:3′-cyclic mono-phos-phate monosodium salt; Cyclic cytidylic acid; 环胞苷酸

Database IDs

• CAS Number: 15718-51-1
• EC Number: 239-813-2
• MDL Number: MFCD00135656
• Beilstein Number: 4086446
• PubChem SID: 24893179; 162227256
• PubChem CID: 23679069

CALCULATED PROPERTIES

• Acid pKa: 1.7687207
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -4.382497
• LogD (pH = 7.4): -4.4007072
• Log P: -2.1239915
• Molar Refractivity: 60.517 cm^3
• Polarizability: 24.769234 Å^3
• Polar Surface Area: 146.74 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥96.0% (HPLC); 95-99%
• Impurities: ≤12% water
• Empirical Formula (Hill Notation): C9H11N3NaO7P

DETAILS

Sigma Aldrich - C9630

Application
Cytidine 2′,3′-cyclic monophosphate (2′,3′-CyclicCMP) (2′,3′-cCMP) is used as a model substrate for kinetic analysis of various ribonucleases, especially ribonuclease A.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C9630.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 30275

Application
suitable as substrate for RNase A
Other Notes
Substrate for the assay of pancreatic ribonuclease (EC 3.1.27.5)1

Toronto Research Chemicals - C998320

Cytidine 2’,3’-Cyclic Monophosphate is a key compound in the enzymic synthesis of short oligoribonucleotides.

REFERENCES

• Tomasz, J., et al.: Nucleic Acid Chem., 2, 875 (1978)