sodium [(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2R,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl phosphate

• ChemBase ID: 132589
• Molecular Formular: C20H30N4NaO16P
• Molecular Mass: 636.432931
• Monoisotopic Mass: 636.12921181
• SMILES: CC(=O)N[C@@H]1[C@H](C[C@](OC1[C@@H]([C@@H](CO)O)O)(C(=O)O)OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1ccc(nc1=O)N)O)O)O.[Na+]
• Canonical SMILES: OC[C@H]([C@H](C1O[C@](C[C@@H]([C@H]1NC(=O)C)O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(nc1=O)N)[O-])C(=O)O)O)O.[Na+]
• InChI: InChI=1S/C20H31N4O16P.Na/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34;/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34);/q;+1/p-1/t8-,9+,10+,12+,13+,14+,15+,16?,17+,20+;/m0./s1
• InChIKey: VFRHSOGUONIUOR-CTFMUGKASA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium [(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2R,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl phosphate
• IUPAC Traditional name: sodium [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2R,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl phosphate
• Synonyms: CMP-NAN; CMP-NANA; CMP-NeuAc; CMP-Sialic acid; Cytidine-5′-monophospho-N-acetylneuraminic acid sodium salt; CMP-Neu5Ac

Database IDs

• CAS Number: 3063-71-6
• MDL Number: MFCD00151579
• Beilstein Number: 4224251
• PubChem SID: 162226866; 24893038
• PubChem CID: 23679065

CALCULATED PROPERTIES

• Acid pKa: 1.4845895
• H Acceptors: 16
• H Donor: 9
• LogD (pH = 5.5): -10.4701
• LogD (pH = 7.4): -11.445854
• Log P: -5.740562
• Molar Refractivity: 124.2984 cm^3
• Polarizability: 51.02455 Å^3
• Polar Surface Area: 323.52 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

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

Product Information

• Purity: ≥85% (HPCE); ≥85% (HPLC)
• Shipped in: wet ice
• Linear Formula: C20H31N4O16P

DETAILS

Sigma Aldrich - C8271

Application
Substrate for sialyltransferases. Used for the enzymatic sialylation of glycans.
Cytidine-5′-monophospho-N-acetylneuraminic acid (CMP-Sialic acid) is a substrate for sialyltransferases. It is used for the enzymatic sialylation of glycans.
Preparation Note
Enzymatically prepared by the method of Schauer, R., et al., Hoppe Seyler′s Z. Physiol. Chem., 353, 883 (1972).CMP-NAN is very acid-labile.

Sigma Aldrich - 27562

Application
Substrate for sialyltransferases. Used for the enzymatic sialylation of glycans.