disodium [(2R,3S,5R)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-{[(4-nitrophenoxy)phosphinato]oxy}oxolan-2-yl]methyl 4-nitrophenyl phosphate

• ChemBase ID: 178597
• Molecular Formular: C22H20N4Na2O15P2
• Molecular Mass: 688.339062
• Monoisotopic Mass: 688.01957778
• SMILES: [nH]1c(=O)c(cn(c1=O)[C@H]1C[C@@H]([C@H](O1)COP(=O)(Oc1ccc(cc1)[N+](=O)[O-])[O-])OP(=O)(Oc1ccc(cc1)[N+](=O)[O-])[O-])C.[Na+].[Na+]
• Canonical SMILES: [O-][N+](=O)c1ccc(cc1)OP(=O)(OC[C@H]1O[C@H](C[C@@H]1OP(=O)(Oc1ccc(cc1)[N+](=O)[O-])[O-])n1cc(C)c(=O)[nH]c1=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C22H22N4O15P2.2Na/c1-13-11-24(22(28)23-21(13)27)20-10-18(41-43(35,36)40-17-8-4-15(5-9-17)26(31)32)19(38-20)12-37-42(33,34)39-16-6-2-14(3-7-16)25(29)30;;/h2-9,11,18-20H,10,12H2,1H3,(H,33,34)(H,35,36)(H,23,27,28);;/q;2*+1/p-2/t18-,19+,20+;;/m0../s1
• InChIKey: JTJRNERVYXCVSM-LRIMUOJLSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,5R)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-{[(4-nitrophenoxy)phosphinato]oxy}oxolan-2-yl]methyl 4-nitrophenyl phosphate
• IUPAC Traditional name: disodium [(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)-3-[(4-nitrophenoxyphosphinato)oxy]oxolan-2-yl]methyl 4-nitrophenyl phosphate
• Synonyms: 3'-Thymidylic Acid Mono(4-nitrophenyl) Ester 5'-(4-Nitrophenyl Hydrogen Phosphate) Disodium Salt; Thymidine-3',5'-di(p-nitrophenyl Phosphate) Disodium Salt

Database IDs

• CAS Number: 24418-12-0
• PubChem SID: 164234507
• PubChem CID: 71752548

CALCULATED PROPERTIES

• Acid pKa: 1.0510904
• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): -2.1526546
• LogD (pH = 7.4): -2.168172
• Log P: 2.585621
• Molar Refractivity: 138.0836 cm^3
• Polarizability: 54.203125 Å^3
• Polar Surface Area: 267.46 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: N/ABrown Solid
• Melting Point: 207-209°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T409900

An artificial chromophoric substrate as a synthetic substrate for bovine pancreatic deoxyribonuclease.

REFERENCES

• Liao, T.-H., et al.: J. Biol. Chem., 250, 3721 (1975)
• Weber, D., et al.: Biochemistry, 30, 6103 (1975)
• Pingoud, A., et al.: Eur. J. Biochem., 246, 1 (1975)
• Ho, H., et al.: Biochem. J., 339, 261 (1975)