2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one hydrate

• ChemBase ID: 70207
• Molecular Formular: C10H15N5O5
• Molecular Mass: 285.2566
• Monoisotopic Mass: 285.10731861
• SMILES: OC[C@@H]1[C@@H](O)C[C@@H](O1)n1cnc2c(=O)[nH]c(N)nc12.O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.O
• InChI: InChI=1S/C10H13N5O4.H2O/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6;/h3-6,16-17H,1-2H2,(H3,11,13,14,18);1H2/t4-,5+,6+;/m0./s1
• InChIKey: LZSCQUCOIRGCEJ-FPKZOZHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one hydrate
• IUPAC Traditional name: 2-deoxyguanosine hydrate; 2'-deoxyguanosine hydrate
• Synonyms: 2′-Deoxyguanosine hydrate; 9-(2-Deoxy-β-D-ribofuranosyl)guanine; Guanine-2′-deoxyriboside; 2′-Deoxyguanosine monohydrate; 2'-Deoxyguanosine monohydrate; 2′-脱氧鸟苷 水合物; 2′-Deoxyguanosine 一水合物

Database IDs

• CAS Number: 312693-72-4; 207121-55-9
• EC Number: 213-505-8
• MDL Number: MFCD00150760
• Beilstein Number: 39814
• PubChem SID: 24894083; 24888365; 162035930; 24893307
• PubChem CID: 16218597

CALCULATED PROPERTIES

• Acid pKa: 10.158529
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.8056743
• LogD (pH = 7.4): -1.8062477
• Log P: -1.8055801
• Molar Refractivity: 63.1104 cm^3
• Polarizability: 23.620188 Å^3
• Polar Surface Area: 134.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M NH4OH: soluble50 mg/mL; 1 M NH4OH: soluble50 mg/mL, clear to very faintly turbid, yellow to brown
• Apperance: powder
• Melting Point: >300 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -30°, c = 0.2 in H2O

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC); 95+%; 99%; 99-100%
• Suitability: suitable for cell culture
• Empirical Formula (Hill Notation): C10H13N5O4 · H2O; C10H13N5O4 · xH2O

DETAILS

Sigma Aldrich - D7145

Application
Deoxyguanosine (dG) is a purine nucleoside that upon sequential phosphoylation (kinases) forms dGTP which is used by DNA polymerases and reverse transcriptases to synthesis DNA(s). Deoxyguanosine is the most electron rich of the four canonical bases and includes many nucleophilic sites which are susceptible to oxidative damage. This makes deoxyguanosine and its oxidized derivatives useful reagents to study mechanisms of oxidative damage to nucleosides and nucleotides.

Sigma Aldrich - 854999

Packaging
1 g in glass bottle
100 mg in glass bottle