Basic information
- CAS
38048-32-7- Standard SMILES
O=[N+]([O-])c1ccc(CSc2ncnc3c2ncn3C2OC(CO)C(O)C2O)cc1- InChIKey
DYCJFJRCWPVDHY-UHFFFAOYSA-N- Molecular formula
- C17H17N5O6S
- Average molar mass
- 419.4 g/mol
- Monoisotopic mass
- 419.08995445
Names & identifiers
- Preferred name
- 2-(Hydroxymethyl)-5-[6-[(4-nitrophenyl)methylsulfanyl]purin-9-yl]oxolane-3,4-diol
- IUPAC
- 2-(hydroxymethyl)-5-[6-[(4-nitrophenyl)methylsulfanyl]purin-9-yl]oxolane-3,4-diol
- English name
- S-(4-Nitrobenzyl)-6-thioinosine
- Molecular formula
- C17H17N5O6S
- Molecular weight
- 419.41
Names & synonyms
2-(Hydroxymethyl)-5-(6-((4-nitrobenzyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol1294455-79-06-(p-Nitrobenzylthio)inosineC17H17N5O6SOprea1_6211772-(hydroxymethyl)-5-[6-[(4-nitrophenyl)methylsulfanyl]purin-9-yl]oxolane-3,4-diolSCHEMBL290702CHEMBL306550HMS3370O01NSC296962ZINC13818312AKOS021983903
Show more names
NBTINBMPRnitrobenzylthioinosineNSC 2969624-nitrobenzylthioinosineS6-(4-nitrylbenzyl)thioinosineNBMPR (Nitrobenzylthioinosine)4-Nitrobenzyl-6-mercaptoinosine
S-(p-NITROBENZYL)-6-THIOINOSINENCGC00015732-02NCGC00163303-01ST085314DB-049231NBMPR (S-(4-Nitrobenzyl)-6-thioinosine)AH-034/11366206SR-01000393938
Database identifiers
- CAS
38048-32-7
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 185 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 577
Physicochemical properties
- Melting point
- 187 · 187-190 °C(lit.)
- Boiling point
- 770.2 · 770.2±70.0 °C(Predicted)
- Density
- 1.3904 · 1.3904 (rough estimate)
- refractive index
- 1.646 · 1.6460 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 0.1 M · 0.1 M HCl: slightly soluble
- form
- solid
- pka
- 13.08 · 13.08±0.70(Predicted)
- color
- white
- InChIKey
- DYCJFJRCWPVDHY-LSCFUAHRSA-N
- SMILES
- OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(SCc4ccc(cc4)[N+]([O-])=O)ncnc23
- CAS DataBase Reference
- 38048 · 38048-32-7(CAS DataBase Reference)
- FDA UNII
- 1 L2DZM2Z · GV1L2DZM2Z
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- UO9025000
- hs_code
- 29349990
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesIt 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, cardio
UsesS-(4-Nitrobenzyl)-6-thioinosine is a nucleoside analog and an inhibitor of the human equilibrative nucleoside transporter (hENT1) (1,2,3). Nucleoside transporter inhibitors are useful compounds to investigate anticancer, antiviral, cardioprotective, and neuroprotective agents.
General DescriptionS-(4-Nitrobenzyl)-6-thioinosine (NBTI) belongs to the family of S6-substituted 6-thiopurine nucleosides, which regulate nucleoside transport mechanisms in animals. It acts as a ligand of adenosine transporter. Binding sites for NBTI is located on brain capillaries. It functions as a covalent photoaffinity probe for nucleoside transport.
Upstream & downstream products
Upstream raw materials
Suppliers57 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…