(2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 91860
• Molecular Formular: C10H11ClN4O4
• Molecular Mass: 286.67174
• Monoisotopic Mass: 286.04688253
• SMILES: n1(c2c(c(ncn2)Cl)nc1)[C@@H]1O[C@H](CO)[C@H]([C@H]1O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2Cl
• InChI: InChI=1S/C10H11ClN4O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2/t4-,6-,7-,10-/m1/s1
• InChIKey: XHRJGHCQQPETRH-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: (2R,3R,4S,5R)-2-(6-Chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; 6-Chloropurine-9-beta-D-ribofuranoside; 6-Chloropurine-9-β-D-ribofuranoside; 6-Chloropurine-9-?-D-ribofuranoside; 6-Chloropurine-9-riboside 99%; 6-Chloropurine-9-β-D-ribofuranoside; 6-CHLOROPURINE RIBOSIDE; 6-Chloropurine riboside; 6-氯嘌呤-9-β-D-呋喃核糖苷; 6-氯嘌呤核苷

Database IDs

• CAS Number: 5399-87-1; 623925-46-2; 2004-06-0
• EC Number: 217-904-8; 226-438-4
• MDL Number: MFCD00005738
• Beilstein Number: 40573
• PubChem SID: 24893040; 162078558; 24888323
• PubChem CID: 93003

CALCULATED PROPERTIES

• Log P: -1.0322737
• Molar Refractivity: 64.0478 cm^3
• Polarizability: 25.42824 Å^3
• Polar Surface Area: 113.52 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 12.454003
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.032419
• LogD (pH = 7.4): -1.0322793

PROPERTIES

Physical Property

• Melting Point: 158-162 °C (dec.)(lit.); 158-162°C; 158-162°C dec.
• Optical Rotation: [α]20/D -43±1°, c = 0.8% in H2O

Safety Information

• Storage Condition: 0°C
• Storage Warning: Irritant/Store at -20oC
• RTECS: UO7520800
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥99.0% (HPLC); 97%; 98%; 99%
• Empirical Formula (Hill Notation): C10H11ClN4O4

DETAILS

MP Biomedicals - 02101370

Crystalline

Apollo Scientific Ltd - OR7990T

A substrate for the enzyme adenosine deaminase.

Sigma Aldrich - C8276

Application
6-Chloropurine riboside is used to study the kinetics and substrate specificity of adenosine deaminase. 6-Chloropurine riboside is benzoylated to facilitate synthesis of nucleoside derivatives such as 9-(2,3-Di-deoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine. 6-Chloropurine riboside, especially after phosphorylation to NMP, NDP or NTP, is used as a purine substrate analogue in studies with enzymes such as Inosine monophosphate dehydrogenase (IMPDH); bacteriophage T4 RNA-ligase (EC 6.5.1.3) and pancreatic fibonuclease A.

Sigma Aldrich - 852481

Packaging
1, 5 g in glass bottle
Application
For a review of the geochemical and biological effects of this riboside, see Adv. Exp. Med. Biol. .1,2