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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
1. Daniels G, Ballif BA, Helias V, Saison C, Grimsley S, Mannessier L, Hustinx H, Lee E, Cartron JP, Peyrard T et al.. (2015)
Lack of the nucleoside transporter ENT1 results in the Augustine-null blood type and ectopic mineralization.
Blood, 125 (23): 3651-4. [PMID:25896650]
2. Grañe-Boladeras N, Williams D, Tarmakova Z, Stevanovic K, Villani LA, Mehrabi P, Siu KWM, Pastor-Anglada M, Coe IR. (2019)
Oligomerization of equilibrative nucleoside transporters: a novel regulatory and functional mechanism involving PKC and PP1.
FASEB J, 33 (3): 3841-3850. [PMID:30521377]
3. Hammond JR, Archer RG. (2004)
Interaction of the novel adenosine uptake inhibitor 3-[1-(6,7-diethoxy-2-morpholinoquinazolin-4-yl)piperidin-4-yl]-1,6-dimethyl-2,4(1H,3H)-quinazolinedione hydrochloride (KF24345) with the es and ei subtypes of equilibrative nucleoside transporters.
J Pharmacol Exp Ther, 308 (3): 1083-93. [PMID:14634039]
4. Sundaram M, Yao SY, Ng AM, Griffiths M, Cass CE, Baldwin SA, Young JD. (1998)
Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs.
J Biol Chem, 273 (34): 21519-25. [PMID:9705281]
5. Warraich S, Bone DB, Quinonez D, Ii H, Choi DS, Holdsworth DW, Drangova M, Dixon SJ, Séguin CA, Hammond JR. (2013)
Loss of equilibrative nucleoside transporter 1 in mice leads to progressive ectopic mineralization of spinal tissues resembling diffuse idiopathic skeletal hyperostosis in humans.
J Bone Miner Res, 28 (5): 1135-49. [PMID:23184610]
6. Wright NJ, Lee SY. (2019)
Structures of human ENT1 in complex with adenosine reuptake inhibitors.
Nat Struct Mol Biol, 26 (7): 599-606. [PMID:31235912]
7. Yao SY, Ng AM, Cass CE, Baldwin SA, Young JD. (2011)
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).
J Biol Chem, 286 (37): 32552-62. [PMID:21795683]