nitrobenzylmercaptopurine ribonucleoside   Click here for help

GtoPdb Ligand ID: 4512

Abbreviated name: NBMPR
Synonyms: NBTI | nitrobenzylthioinosine
Compound class: Synthetic organic
Comment: NBMPR is a equilibrative nucleoside transporter 1 (ENT1) inhibitor. Alternative isomeric structures are reported including the (2R,3S,4R,5R) form that has PubChem CID 65407. NBMPR is chemically distinct from dilazep and crystallisation and mutagenesis studies show that these two inhibitors utilise different binding mechanisms at ENT1 [6]. The crystal structure of ENT1 in complex with NBMPR is deposited in the Protein Data Bank under accession code 6OB6 [6]..
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 202.19
Molecular weight 435.08
XLogP 1
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)O)(SCc1ccccc1[N+](=O)[O-])n1cnc2c1ncnc2O
Isomeric SMILES OC[C@H]1O[C@@]([C@@H]([C@@H]1O)O)(SCc1ccccc1[N+](=O)[O-])n1cnc2c1ncnc2O
InChI InChI=1S/C17H17N5O7S/c23-5-11-13(24)14(25)17(29-11,21-8-20-12-15(21)18-7-19-16(12)26)30-6-9-3-1-2-4-10(9)22(27)28/h1-4,7-8,11,13-14,23-25H,5-6H2,(H,18,19,26)/t11-,13-,14-,17+/m1/s1
InChI Key NVQXRTPYOZKYMZ-GDLHICMESA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2S,3R,4S,5R)-2-(6-hydroxy-9H-purin-9-yl)-5-(hydroxymethyl)-2-{[(2-nitrophenyl)methyl]sulfanyl}oxolane-3,4-diol
Synonyms Click here for help
NBTI | nitrobenzylthioinosine
Database Links Click here for help
GtoPdb PubChem SID 178101238
PubChem CID 23624146
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