(1S,2R,3S,5R)-3-amino-5-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentane-1,2-diol hydrate dihydrochloride

• ChemBase ID: 155630
• Molecular Formular: C11H18Cl2IN5O3
• Molecular Mass: 466.10279
• Monoisotopic Mass: 464.98314282
• SMILES: c1c(c2c(ncnc2n1[C@@H]1C[C@@H]([C@H]([C@H]1O)O)N)N)I.O.Cl.Cl
• Canonical SMILES: N[C@H]1C[C@H]([C@@H]([C@@H]1O)O)n1cc(c2c1ncnc2N)I.O.Cl.Cl
• InChI: InChI=1S/C11H14IN5O2.2ClH.H2O/c12-4-2-17(6-1-5(13)8(18)9(6)19)11-7(4)10(14)15-3-16-11;;;/h2-3,5-6,8-9,18-19H,1,13H2,(H2,14,15,16);2*1H;1H2/t5-,6+,8+,9-;;;/m0.../s1
• InChIKey: INMLNTBMPNIKQK-HWZUHWJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3S,5R)-3-amino-5-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentane-1,2-diol hydrate dihydrochloride
• IUPAC Traditional name: (1S,2R,3S,5R)-3-amino-5-{4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl}cyclopentane-1,2-diol hydrate dihydrochloride
• Synonyms: N7-[(1′R,2′S,3′R,4′S)-2′,3′-dihydroxy-4′-aminocyclopentyl]-4-amino-5-iodopyrrolopyrimidine dihydrochloride hydrate; A-134974 dihydrochloride hydrate

Database IDs

• MDL Number: MFCD08692561
• PubChem SID: 162249768; 24890697
• PubChem CID: 16218887

CALCULATED PROPERTIES

• Acid pKa: 13.221139
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.752414
• LogD (pH = 7.4): -2.8266869
• Log P: -0.6155731
• Molar Refractivity: 79.1461 cm^3
• Polarizability: 30.67993 Å^3
• Polar Surface Area: 123.21 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: off-white to light tan solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H14IN5O2 · 2HCl · xH2O

DETAILS

Sigma Aldrich - A2846

Legal Information
Sold under license from Abbott Laboratories.
Biochem/physiol Actions
A-134974 is a novel and selective adenosine kinase (AK) inhibitor with IC50 = 60 pM. Systemic A-134974 (i.p.) dose dependently reduced hyperalgesia (ED50= 1 μmol/kg) and at higher doses, reduced locomotor activity (ED50 = 16 μmol/kg). Administration of A-134974 intrathecally (i.t.) was more potent (ED50= 6 nmol) at producing antihyperalgesia than delivering the compound by intracerebralventricular (ED50 = 100 nmol, i.c.v.) or intraplantar (ED50 >300 nmol) routes. In contrast, i.c.v. administration of A-134974 was more effective in reducing locomotor activity than i.t. administration (ED50 values were 1 and >100 nmol, respectively). Increasing the pretreatment time for i.t.-delivered A-134974 caused a greater reduction in locomotor activity (ED50= 10 nmol). This was due to diffusion of A-134974 (i.t.) to supraspinal sites. These data demonstrate that the novel AK inhibitor A-134974 potently reduces thermal hyperalgesia primarily through interactions with spinal sites, whereas its ability to depress locomotor activity is predominantly mediated by supraspinal sites.††