(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(4-oxo-6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-1-yl)oxane-2-carboxylic acid

• ChemBase ID: 177063
• Molecular Formular: C13H18N2O7S
• Molecular Mass: 346.35622
• Monoisotopic Mass: 346.08347193
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)n1c(=S)[nH]c(=O)cc1CCC)O)O)O
• Canonical SMILES: CCCc1cc(=O)[nH]c(=S)n1[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H18N2O7S/c1-2-3-5-4-6(16)14-13(23)15(5)11-9(19)7(17)8(18)10(22-11)12(20)21/h4,7-11,17-19H,2-3H2,1H3,(H,20,21)(H,14,16,23)/t7-,8-,9+,10-,11+/m0/s1
• InChIKey: FRRSJAKAIDIIKX-QUARPLMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(4-oxo-6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-1-yl)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(4-oxo-6-propyl-2-sulfanylidene-3H-pyrimidin-1-yl)oxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-(3,4-dihydro-4-oxo-6-propyl-2-thioxo-1(2H)-pyrimidinyl) β-D-Glucopyranuronic Acid; Propylthiouracil N-β-D-Glucuronide

Database IDs

• CAS Number: 33987-24-5
• PubChem SID: 164232973
• PubChem CID: 29986688

CALCULATED PROPERTIES

• Acid pKa: 3.6890817
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.4769797
• LogD (pH = 7.4): -4.073522
• Log P: -0.6662692
• Molar Refractivity: 81.3305 cm^3
• Polarizability: 32.04452 Å^3
• Polar Surface Area: 139.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 177-179°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P838315

A metabolite of Propylthiouracil.A representative lot was 90% pure by NMR.

REFERENCES

• Lindsay, R. H., et al.: J. Pharm. Sci., 63 1383 (1974)Taurog, A., et al.: Endocrinology, 122, 592 (1988)