trisodium ({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate

• ChemBase ID: 155401
• Molecular Formular: C9H12N2Na3O15P3
• Molecular Mass: 550.086573
• Monoisotopic Mass: 549.91436043
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])OP(=O)(O)[O-])O)O.[Na+].[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(=O)[nH]c1=O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C9H15N2O15P3.3Na/c12-5-1-2-11(9(15)10-5)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)(H,10,12,15)(H2,16,17,18);;;/q;3*+1/p-3/t4-,6-,7-,8-;;;/m1.../s1
• InChIKey: MMJGIWFJVDOPJF-LLWADOMFSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium ({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate
• IUPAC Traditional name: trisodium utp trianion
• Synonyms: Uridine 5'-(Tetrahydrogen Triphosphate) Trisodium Salt Hydrate; NSC 20260 Hydrate; Trisodium UTP Hydrate; UTP Trisodium Salt Hydrate; Utipina Hydrate; Uridine 5'-Triphosphate Trisodium Salt Hydrate; UTP; Uridine 5′-triphosphate trisodium salt solution; UTP Na3; Uridine 5′-triphosphate trisodium salt hydrate; 尿苷-5′-三磷酸酯 三钠盐 溶液; 尿苷-5′-三磷酸酯 三钠盐 水合物

Database IDs

• CAS Number: 19817-92-6(anhydrous)
• EC Number: 243-347-5
• MDL Number: MFCD00044310
• Beilstein Number: 3585234
• PubChem SID: 24900622; 162249539; 24900658; 24900436
• PubChem CID: 88265

CALCULATED PROPERTIES

• Acid pKa: 0.8952817
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -10.059212
• LogD (pH = 7.4): -10.794819
• Log P: -3.382405
• Molar Refractivity: 81.8192 cm^3
• Polarizability: 34.772614 Å^3
• Polar Surface Area: 267.41 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-68/20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H371
• GHS Precautionary statements: P260
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... P2RY2(5029)rat ... P2ry2(29597)

Product Information

• Purity: ≥96%; 90-95%
• Concentration: 100 mM in H2O (adjusted to pH 7 with Trizma®base)
• Foreign Activity: DNase and RNase, none detected
• Biological Source: from yeast
• Type: Type III; Type IV
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C9H12N2Na3O15P3 · xH2O

DETAILS

Sigma Aldrich - U6625

Biochem/physiol Actions
P2Y receptor agonist.

Sigma Aldrich - U1006

Application
For use in DNA-dependent RNA polymerase transcription
Biochem/physiol Actions
P2Y receptor agonist
Legal Information
Trizma is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - U6750

Biochem/physiol Actions
P2Y receptor agonist.

Toronto Research Chemicals - U830025

A polyphosphate analogue of the nucleoside uridine used in the preparation of potent and selective agonists at the G-protein-coupled P2Y receptors.

REFERENCES

• Pendergast, W. et al.: Bioorg. Med. Chem., 11, 157 (2001)