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2004-06-0 molecular structure
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(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 and InChIs

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

Cite this record

CBID:91860 http://www.chembase.cn/molecule-91860.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Log P -1.0322737  Molar Refractivity 64.0478 cm3
Polarizability 25.42824 Å3 Polar Surface Area 113.52 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Acid pKa 12.454003  H Acceptors
H Donor LogD (pH = 5.5) -1.032419 
LogD (pH = 7.4) -1.0322793 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
158-162 °C (dec.)(lit.) expand Show data source
158-162°C expand Show data source
158-162°C dec. expand Show data source
Optical Rotation
[α]20/D -43±1°, c = 0.8% in H2O expand Show data source
Storage Condition
0°C expand Show data source
Storage Warning
Irritant/Store at -20oC expand Show data source
RTECS
UO7520800 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
≥99.0% (HPLC) expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C10H11ClN4O4 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Apollo Scientific Apollo Scientific Sigma Aldrich Sigma Aldrich
Apollo Scientific Ltd - OR7990T external link
A substrate for the enzyme adenosine deaminase.
Sigma Aldrich - C8276 external link
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 external link
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

REFERENCES

REFERENCES

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PATENTS

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