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38048-32-7 molecular structure
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(2S,3R,4S,5S)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolane-3,4-diol

ChemBase ID: 175202
Molecular Formular: C17H17N5O6S
Molecular Mass: 419.41178
Monoisotopic Mass: 419.08995429
SMILES and InChIs

SMILES:
n1cnc2c(c1SCc1ccc(cc1)[N+](=O)[O-])ncn2[C@@H]1[C@H]([C@H]([C@@H](O1)CO)O)O
Canonical SMILES:
OC[C@@H]1O[C@@H]([C@H]([C@H]1O)O)n1cnc2c1ncnc2SCc1ccc(cc1)[N+](=O)[O-]
InChI:
InChI=1S/C17H17N5O6S/c23-5-11-13(24)14(25)17(28-11)21-8-20-12-15(21)18-7-19-16(12)29-6-9-1-3-10(4-2-9)22(26)27/h1-4,7-8,11,13-14,17,23-25H,5-6H2/t11-,13-,14-,17-/m0/s1
InChIKey:
DYCJFJRCWPVDHY-MJFSBKNWSA-N

Cite this record

CBID:175202 http://www.chembase.cn/molecule-175202.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S,3R,4S,5S)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolane-3,4-diol
IUPAC Traditional name
(2S,3R,4S,5S)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}purin-9-yl)oxolane-3,4-diol
Synonyms
6-S-[(4-Nitrophenyl)methyl]-6-thioinosine
6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine
S-(p-Nitrobenzyl)-6-mercapto-9-β-D-ribofuranosylpurine
NBMPR
NSC 296962
S-(4-Nitrobenzyl)-6-thioinosine
CAS Number
38048-32-7
PubChem SID
164231112
PubChem CID
38988593

DATA SOURCES

DATA SOURCES

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Data Source Data ID
TRC N493695 external link Add to cart
PubChem 38988593 external link
Data Source Data ID Price
TRC
N493695 external link Add to cart Please log in.
Data Source Data ID
PubChem 38988593 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Donor LogD (pH = 5.5) 0.8909769 
LogD (pH = 7.4) 0.9263837  Log P 0.92685854 
Molar Refractivity 103.2406 cm3 Polarizability 39.756 Å3
Polar Surface Area 159.34 Å2 Rotatable Bonds
Lipinski's Rule of Five true  Acid pKa 12.454004 
H Acceptors

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Ethyl Acetate expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
177-180°C expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - N493695 external link
It is a prototype inhibitor of the human equilibrative nucleoside transporter (hENT1), and is a high affinity ligand with a Kd of 0.1-1.0 nM. Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardioprotect

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Krug, E., et al.: J. Biol. Chem., 264, 10601 (1989)
  • • Griffiths, M., et al.: Biochem. J., 328, 739 (1989)
  • • Zhu, Z., et al.: J. Med. Chem., 46, 831 (1989)
  • • Baldwin, S., et al.: J. Biol. Chem., 280, 15880 (1989)
  • • Barnes, K., et al.: Circ. Res., 99, 510 (2006
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PATENTS

PATENTS

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INTERNET

INTERNET

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