disodium hydrate [(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate

• ChemBase ID: 155810
• Molecular Formular: C9H14N2Na2O13P2
• Molecular Mass: 466.140122
• Monoisotopic Mass: 465.97665034
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(O)[O-])O)O.O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(O)[O-])[O-])O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O.O.[Na+].[Na+]
• InChI: InChI=1S/C9H14N2O12P2.2Na.H2O/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18;;;/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18);;;1H2/q;2*+1;/p-2/t4-,6-,7-,8-;;;/m1.../s1
• InChIKey: RHBXRWOXLRCWIZ-LLWADOMFSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium hydrate [(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate
• IUPAC Traditional name: disodium hydrate [(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphonatooxyphosphonate
• Synonyms: 5′-UDP-Na2; Uridine 5′-diphosphate disodium salt hydrate; 尿苷-5′-二磷酸 二钠盐 水合物

Database IDs

• CAS Number: 27821-45-0
• EC Number: 248-678-9
• MDL Number: MFCD00149253
• Beilstein Number: 8817400
• PubChem SID: 24889986; 162249948
• PubChem CID: 16218790

CALCULATED PROPERTIES

• Acid pKa: 1.7717429
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -7.3636847
• LogD (pH = 7.4): -7.99675
• Log P: -2.9606066
• Molar Refractivity: 72.068 cm^3
• Polarizability: 30.072569 Å^3
• Polar Surface Area: 218.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (HPLC)
• Impurities: ≤15% water
• Empirical Formula (Hill Notation): C9H12N2Na2O12P2 · xH2O

DETAILS

Sigma Aldrich - 94330

Application
Uridine 5′-diphosphate (UDP) and Uridine 5′-triphosphate (UTP) may be used in studies on nucleic acid (RNA) biosynthesis and cell signaling. UDP is a nucleotide that upon phosphorylation to UTP becomes a substrate for enzymes such as RNA polymerase(s) and GTPases. These enzymes are involved in a wide range of applications from the synthesis of RNA to the regulation of G-coupled Protein Receptors (GPCR) and cell signaling molecules such as Rho-signaling via Guanine Nucleotide Exchange Factors (GEF).