{[(2S,3R,4S,5S)-3,4-dihydroxy-5-(6-sulfanylidene-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 178545
• Molecular Formular: C10H13N4O7PS
• Molecular Mass: 364.271581
• Monoisotopic Mass: 364.02425641
• SMILES: n1c[nH]c2c(c1=S)ncn2[C@@H]1[C@H]([C@H]([C@@H](O1)COP(=O)(O)O)O)O
• Canonical SMILES: O[C@H]1[C@@H](O)[C@@H](O[C@@H]1n1cnc2c1[nH]cnc2=S)COP(=O)(O)O
• InChI: InChI=1S/C10H13N4O7PS/c15-6-4(1-20-22(17,18)19)21-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)23/h2-4,6-7,10,15-16H,1H2,(H,11,12,23)(H2,17,18,19)/t4-,6-,7-,10-/m0/s1
• InChIKey: ZKRFOXLVOKTUTA-DEGSGYPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4S,5S)-3,4-dihydroxy-5-(6-sulfanylidene-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4S,5S)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid
• Synonyms: 6-Thio-5'-inosinic Acid; 6-Mercaptopurine Ribonucleoside 5'-Phosphate; 6-Mercaptopurine Ribonucleotide; 6-Thio-IMP; 6-Thioinosine 5'-Phosphate; 6-Thioinosine 5'-Phosphoric Acid; 6-Thioinosinic Acid; NSC 520722; 6-Thioinosine Phosphate

Database IDs

• CAS Number: 53-83-8
• PubChem SID: 164234455
• PubChem CID: 71752525

CALCULATED PROPERTIES

• Acid pKa: 1.222486
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -4.2872467
• LogD (pH = 7.4): -5.4738035
• Log P: -3.5116045
• Molar Refractivity: 79.7622 cm^3
• Polarizability: 31.088028 Å^3
• Polar Surface Area: 158.66 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Solid
• Melting Point: 149-155°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - T344500

A metabolite of 6-Mercaptopurine.

REFERENCES

• Parker, W., et al.: Cancer Res., 51, 2386 (1991)
• Munagala, N., et al.: J. Biol. Chem., 275, 37072 (1991)
• Guddat, L., et al.: Protein Sci., 11, 1626 (1991)
• Pinkel, D., et al.: J. Clin. Oncol., 11, 1826 (1991)
• Tripathy, D., et al.: Oncologist, 12, 375