9-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-2-(dimethylamino)-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 153430
• Molecular Formular: C12H18N6O4
• Molecular Mass: 310.30912
• Monoisotopic Mass: 310.13895309
• SMILES: CN(C)c1[nH]c(=O)c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](N1)CO)O)O
• Canonical SMILES: OC[C@H]1N[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc([nH]c2=O)N(C)C
• InChI: InChI=1S/C12H18N6O4/c1-17(2)12-15-9-6(11(22)16-12)13-4-18(9)10-8(21)7(20)5(3-19)14-10/h4-5,7-8,10,14,19-21H,3H2,1-2H3,(H,15,16,22)/t5-,7-,8-,10+/m1/s1
• InChIKey: DTOKDSIGFSMANY-UZRKRJFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-2-(dimethylamino)-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 9-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-2-(dimethylamino)-1H-purin-6-one
• Synonyms: N2,N2-Dimethylguanosine

Database IDs

• CAS Number: 2140-67-2
• MDL Number: MFCD00057049
• PubChem SID: 162247569
• PubChem CID: 71311661

CALCULATED PROPERTIES

• Acid pKa: 9.970014
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.7829638
• LogD (pH = 7.4): -3.0656343
• Log P: -2.4840605
• Molar Refractivity: 76.3713 cm^3
• Polarizability: 28.704618 Å^3
• Polar Surface Area: 135.24 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: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C12H17N5O5

DETAILS

Sigma Aldrich - D1056

Application
Proposed as an indicator for tRNA half-life in normal vs. cancerous tissues.
Other Notes
Modified nucleoside found in tRNA and snRNA of archaebacteria and eukaryotes.