1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 144897
• Molecular Formular: C9H11IN2O6
• Molecular Mass: 370.09791
• Monoisotopic Mass: 369.96618408
• SMILES: c1c(c(=O)[nH]c(=O)n1[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)I
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(I)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11IN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
• InChIKey: RKSLVDIXBGWPIS-UAKXSSHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-3H-pyrimidine-2,4-dione
• Synonyms: 2,4-Dihydroxy-5-iodo-1-β-D-ribofuranosylpyrimidine; 5-Iodouridine; 5-Iodouridine; 2,4-二羟基-5-碘-1-β-D-呋喃核糖基嘧啶; 5-碘尿苷

Database IDs

• CAS Number: 1024-99-3
• EC Number: 213-833-1
• MDL Number: MFCD00006532
• Beilstein Number: 33665
• PubChem SID: 24888326; 162239109; 24881038
• PubChem CID: 1268108

CALCULATED PROPERTIES

• Acid pKa: 8.051656
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.4307604
• LogD (pH = 7.4): -1.5158877
• Log P: -1.4295567
• Molar Refractivity: 65.9146 cm^3
• Polarizability: 26.283192 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 205-207 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -23.5±1°, c = 1% in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); 95%; 96%
• Empirical Formula (Hill Notation): C9H11IN2O6

DETAILS

Sigma Aldrich - 852597

Packaging
1 g in glass bottle