1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 133603
• Molecular Formular: C10H14N2O6
• Molecular Mass: 258.22796
• Monoisotopic Mass: 258.08518618
• SMILES: c1c(c(=O)[nH]c(=O)n1C1CC(C(O1)CO)O)CO
• Canonical SMILES: OCC1OC(CC1O)n1cc(CO)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H14N2O6/c13-3-5-2-12(10(17)11-9(5)16)8-1-6(15)7(4-14)18-8/h2,6-8,13-15H,1,3-4H2,(H,11,16,17)
• InChIKey: IPAVKOYJGUMINP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)-3H-pyrimidine-2,4-dione
• Synonyms: 5-HMdU; HMdUdr; 5-Hydroxymethyl-2′-deoxyuridine

Database IDs

• CAS Number: 5116-24-5
• EC Number: 225-848-0
• MDL Number: MFCD00047489
• PubChem SID: 24895526; 162227880
• PubChem CID: 5201346

CALCULATED PROPERTIES

• Acid pKa: 9.590579
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.3998597
• LogD (pH = 7.4): -2.402584
• Log P: -2.3998249
• Molar Refractivity: 57.1867 cm^3
• Polarizability: 22.704432 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - H8631

Application
5-Hydroxymethyl-2′-deoxyuridine (HMdUdr) is a used as a marker for oxidative nucleic acid (DNA) damage. HMdUdr may be used as an antigen to create anti-HMdUdr antibodies.