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]..
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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

For advanced searching click here to open chemical structure editor

Similar Ligands Click here for help
2-chloroadenosine
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor; Equilibrative nucleoside transporter 1; Equilibrative nucleoside transporter 2
CCPA
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
[3H]CCPA
Click here for ligand page
Targets
A1 receptor
cyclopentyladenosine
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
(R)-PIA
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
(S)-PIA
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
APNEA
Click here for ligand page
Targets
A2A receptor
CGS 24012
Click here for ligand page
Targets
A2A receptor
CV-1674
Click here for ligand page
Targets
A2A receptor
CV-1808
Click here for ligand page
Targets
A2A receptor
N(6)-cyclohexyladenosine
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
metrifudil
Click here for ligand page
Targets
A2A receptor
AB-NECA
Click here for ligand page
Targets
A2B receptor
I-ABA
Click here for ligand page
Targets
A3 receptor
[125I]APNEA
Click here for ligand page
Targets
A3 receptor
adenosine
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor; Adenosine deaminase; Adenosine kinase; Equilibrative nucleoside transporter 1; Equilibrative nucleoside transporter 2; Equilibrative nucleoside transporter 3; Plasma membrane monoamine transporter; Sodium/nucleoside cotransporter 2; Solute carrier family 28 member 3; TRPM4; phosphatidylinositol 4-kinase type 2 alpha; phosphatidylinositol 4-kinase type 2 beta... click on ligand to see complete list
GR79236
Click here for ligand page
Targets
A1 receptor; A2A receptor
[3H]nitrobenzylmercaptopurine ribonucleoside
Click here for ligand page
Targets
Equilibrative nucleoside transporter 1
cordycepin
Click here for ligand page
Targets
Equilibrative nucleoside transporter 3
tubercidin
Click here for ligand page
Targets
Equilibrative nucleoside transporter 1; Equilibrative nucleoside transporter 2; Equilibrative nucleoside transporter 3
S-adenosyl methionine
Click here for ligand page
Targets
S-Adenosylmethionine carrier; S-Adenosylmethionine decarboxylase
cladribine
Click here for ligand page
Targets
Equilibrative nucleoside transporter 1; Equilibrative nucleoside transporter 2; Equilibrative nucleoside transporter 3; Sodium/nucleoside cotransporter 2; Solute carrier family 28 member 3
fludarabine
Click here for ligand page
Targets
Equilibrative nucleoside transporter 3; Sodium/nucleoside cotransporter 2; ribonucleotide reductase catalytic subunit M1; ribonucleotide reductase regulatory subunit M2
vidarabine
Click here for ligand page
Targets
Equilibrative nucleoside transporter 1; Equilibrative nucleoside transporter 2; Sodium/nucleoside cotransporter 2
2',5'-dideoxyadenosine
Click here for ligand page
2'-deoxyadenosine
Click here for ligand page
Targets
Adenosine deaminase
3-deazaadenosine
Click here for ligand page
Targets
S-Adenosylhomocysteine hydrolase
S-adenosyl-L-methioninamine
Click here for ligand page
AMA
Click here for ligand page
Targets
Histidine decarboxylase
DRB
Click here for ligand page
Targets
Casein kinase 2
S-adenosylhomocysteine
Click here for ligand page
Targets
S-Adenosylhomocysteine hydrolase
TCPA
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
2'-Me-CCPA
Click here for ligand page
Targets
A3 receptor
tecadenoson
Click here for ligand page
Targets
A1 receptor; A2A receptor
GS9667
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
binodenoson
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
regadenoson
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
HEMADO
Click here for ligand page
Targets
A1 receptor; A2A receptor; A2B receptor; A3 receptor
[3H]HEMADO
Click here for ligand page
Targets
A3 receptor
triciribine
Click here for ligand page
5-Cl-5-deoxy-(±)-ENBA
Click here for ligand page
Targets
A1 receptor
clofarabine
Click here for ligand page
Targets
ribonucleotide reductase catalytic subunit M1; ribonucleotide reductase regulatory subunit M2
bromo-deaza-SAH
Click here for ligand page
Targets
DNA methyltransferase 1; DOT1 like histone lysine methyltransferase
LLY-283
Click here for ligand page
Targets
protein arginine methyltransferase 5
compound 6c [PMID: 34435786]
Click here for ligand page
Targets
A3 receptor
TO507
Click here for ligand page
Targets
CoV Non-structural protein 14