9-(Tetrahydrofuran-2-yl)-9h-purin-6-amine
Basic information
- CAS
17318-31-9- Standard SMILES
Nc1ncnc2c1ncn2C1CCCO1- InChIKey
UKHMZCMKHPHFOT-UHFFFAOYSA-N- Molecular formula
- C9H11N5O
- Average molar mass
- 205.22 g/mol
- Monoisotopic mass
- 205.09635999
Overview
9-(tetrahydrofuryl)adenine is a nucleoside analogue that is adenine in which the nitrogen at position 9 has been substituted by a tetrahydrofuran-2-yl group. It is an adenylate cyclase inhibitor. It has a role as an EC 4.6.1.1 (adenylate cyclase) inhibitor. It is a member of oxolanes and a nucleoside analogue. It is functionally related to an adenine.
Names & identifiers
- Preferred name
- 9-(Tetrahydrofuran-2-yl)-9h-purin-6-amine
- IUPAC
- 9-(oxolan-2-yl)purin-6-amine
- English name
- SQ 22,536
- Molecular formula
- C9H11N5O
- Molecular weight
- 205.22
Names & synonyms
17318-31-99-(tetrahydrofuran-2-yl)-9h-purin-6-amineSQ22536SQ 225369H-Purin-6-amine, 9-(tetrahydro-2-furanyl)-9-(Tetrahydrofuryl)adenine9-(Tetrahydro-2-furanyl)-9H-purin-6-amine9-(oxolan-2-yl)purin-6-amineMFCD00210216BSPBio_001142KBioGR_000482CHEMBL64239
Show more names
Ax 100CS-2551Nsc 533399-THF-AdeSQ 22,536SQ-22536SQ22,536/InhibitorSQ22536 (NSC-53339)SQ22536, 10 mM in DMSO9-(Tetrahydrofuran-2-yl)
MLS002667588CHEBI:90232KBio2_005618HMS2235P22HMS3266A19HMS3676B05NSC53339NSC-53339
Database identifiers
- CAS
17318-31-9- PubChem CID
- 5270
- ChEMBL
CHEMBL64239- ChEBI
CHEBI:90232
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 78.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 239
Physicochemical properties
- Melting point
- 160 · 160-161℃
- Boiling point
- 474.8 · 474.8±55.0 °C(Predicted)
- Density
- 1.7 · 1.70±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: 21 mg/mL
- form
- solid
- pka
- 3.82 · 3.82±0.10(Predicted)
- color
- white to off-white
- InChI
- InChI=1S/C9H11N5O/c10-8-7-9(12-4-11-8)14(5-13-7)6-2-1-3-15-6/h4-6H,1-3H2,(H2,10,11,12)
- InChIKey
- UKHMZCMKHPHFOT-UHFFFAOYSA-N
- SMILES
- N1C2C(=NC=NC=2N)N(C2CCCO2)C=1
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
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
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 2934.99.9001
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
DescriptionSQ 22,536 is an inhibitor of adenylyl cyclase with an IC50 value of 13 μM for inhibition of prostaglandin E1-stimulated increase in cAMP in intact platelets. It has been used to evaluate adenylyl cyclase activity during iloprost-induced vasorelaxation of isolated pulmonary veins or aorta in several research paradigms, inhibiting cAMP elevation at concentrations of 100-300 μM without effecting relaxation.
UsesSQ 22,536 was used to study the role of adenylate cyclase in differentiation of PC12 cells and in gap junctional intercellular communication in breast cancer cells.
Additional notes
DefinitionChEBI: A nucleoside analogue that is adenine in which the nitrogen at position 9 has been substituted by a tetrahydrofuran-2-yl group. It is an adenylate cyclase inhibitor.
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