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

• ChemBase ID: 154438
• Molecular Formular: C12H17N5O4
• Molecular Mass: 295.29448
• Monoisotopic Mass: 295.12805405
• SMILES: CCNc1[nH]c(=O)c2c(n1)n(cn2)[C@H]1C[C@@H]([C@H](O1)CO)O
• Canonical SMILES: CCNc1[nH]c(=O)c2c(n1)n(cn2)[C@H]1C[C@@H]([C@H](O1)CO)O
• InChI: InChI=1S/C12H17N5O4/c1-2-13-12-15-10-9(11(20)16-12)14-5-17(10)8-3-6(19)7(4-18)21-8/h5-8,18-19H,2-4H2,1H3,(H2,13,15,16,20)/t6-,7+,8+/m0/s1
• InChIKey: VOKQFDULHQUWAV-XLPZGREQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(ethylamino)-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-(ethylamino)-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: N2-Et-dG; N2-Ethyl-2′-deoxyguanosine

Database IDs

• CAS Number: 101803-03-6
• MDL Number: MFCD01631004
• PubChem SID: 162248577
• PubChem CID: 15403643

CALCULATED PROPERTIES

• Acid pKa: 10.040932
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.1713176
• LogD (pH = 7.4): -1.1720346
• Log P: -1.1711627
• Molar Refractivity: 72.6336 cm^3
• Polarizability: 27.24439 Å^3
• Polar Surface Area: 121.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: white to off-white solid

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-33-40
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H351-H373
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H17N5O4

DETAILS

Sigma Aldrich - N3289

General description
N2-Et-dG, an adduct between DNA and the first metabolite of ethanol (acetaldehyde), strongly blocks transcription by RNA polymerases (RNAPs), including mammalian RNAPII and yeast RNAPII, E. coli RNAP, as well as T7 RNAP. All three of the multisubunit RNAPs incorporate a single rNTP residue opposite the N2-Et-dG lesion. The mammalian RNAPII exclusively incorporates cytidine monophosphate (CMP) opposite the N2-Et-dG lesion. The accessory transcription factor TFIIS does not usually act as a lesion bypass factor; instead, it stimulates the polymerase to remove the CMP incorporated opposite the lesion by mammalian RNAPII. N2-Et-dG reduces CTP incorporation by ~1500 fold.