disodium {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl (hydrogen phosphonatooxy)phosphonate

• ChemBase ID: 133688
• Molecular Formular: C9H14N3Na2O14P3
• Molecular Mass: 527.119983
• Monoisotopic Mass: 526.9484006
• SMILES: c1cn(c(=O)nc1N)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)([O-])OP(=O)(O)[O-])O)O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)[O-])[O-])O)O[C@H]([C@@H]1O)n1ccc(nc1=O)N.[Na+].[Na+]
• InChI: InChI=1S/C9H16N3O14P3.2Na/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18;;/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18);;/q;2*+1/p-2/t4-,6-,7-,8-;;/m1../s1
• InChIKey: NFQMDTRPCFJJND-WFIJOQBCSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl (hydrogen phosphonatooxy)phosphonate
• IUPAC Traditional name: disodium [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl hydrogen phosphonatooxyphosphonate
• Synonyms: CTP; Cytidine 5′-triphosphate disodium salt; CTP-Na2; Cytidine 5′-triphosphate disodium solution

Database IDs

• CAS Number: 81012-87-5; 36051-68-0
• EC Number: 252-849-3
• MDL Number: MFCD00078193
• PubChem SID: 24892417; 24893072; 162227965; 24893144
• PubChem CID: 16219171

CALCULATED PROPERTIES

• Acid pKa: 0.9455692
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -10.441421
• LogD (pH = 7.4): -11.174953
• Log P: -4.10738
• Molar Refractivity: 84.9201 cm^3
• Polarizability: 35.437332 Å^3
• Polar Surface Area: 273.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 113 °C; 235.4 °F

Safety Information

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

Product Information

• Purity: ~95%; ≥95%
• Concentration: 100 mM in H2O (adjusted to pH 7 with Sodium Hydroxide)
• Foreign Activity: DNase and RNase, none detected
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C9H16N3O14P3Na2

DETAILS

Sigma Aldrich - C9274

Biochem/physiol Actions
P2X4 purinergic receptor agonist.
Preparation Note
Prepared by the enzymatic phosphorylation of 5′-CMP.

Sigma Aldrich - C1506

Biochem/physiol Actions
P2X4 purinergic receptor agonist.

Sigma Aldrich - C8552

Application
Cytidine 5′-triphosphate disodium salt is used as a nucleoside triphosphate for RNA synthesis reactions.
Biochem/physiol Actions
CTP is incorporated into RNA via phosphodiester bond formation catalyzed by various RNA polymerases.