3-{4-[2-({6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}amino)ethyl]phenyl}propanoic acid hydrate hydrochloride

• ChemBase ID: 155197
• Molecular Formular: C23H32ClN7O7
• Molecular Mass: 553.99588
• Monoisotopic Mass: 553.20517408
• SMILES: CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1nc(nc2N)NCCc1ccc(cc1)CCC(=O)O)O)O.O.Cl
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(NCCc1ccc(cc1)CCC(=O)O)nc2N.O.Cl
• InChI: InChI=1S/C23H29N7O6.ClH.H2O/c1-2-25-21(35)18-16(33)17(34)22(36-18)30-11-27-15-19(24)28-23(29-20(15)30)26-10-9-13-5-3-12(4-6-13)7-8-14(31)32;;/h3-6,11,16-18,22,33-34H,2,7-10H2,1H3,(H,25,35)(H,31,32)(H3,24,26,28,29);1H;1H2/t16-,17+,18-,22+;;/m0../s1
• InChIKey: VIRPCGAECNOLOO-VBQNEDDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[2-({6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}amino)ethyl]phenyl}propanoic acid hydrate hydrochloride
• IUPAC Traditional name: 3-{4-[2-({6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl}amino)ethyl]phenyl}propanoic acid hydrate hydrochloride
• Synonyms: 2-p-(2-Carboxyethyl)phenethylamino-5′-N-ethylcarboxamidoadenosine hydrochloride hydrate; CGS-21680 hydrochloride hydrate

Database IDs

• CAS Number: 124182-57-6(anhydrous)
• MDL Number: MFCD11045878
• PubChem SID: 24277698; 162249335
• PubChem CID: 71312097

CALCULATED PROPERTIES

• Acid pKa: 4.850968
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -0.65979576
• LogD (pH = 7.4): -2.407914
• Log P: -0.32791242
• Molar Refractivity: 129.9465 cm^3
• Polarizability: 49.147076 Å^3
• Polar Surface Area: 197.74 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble20 mg/mL; DMSO: >10 mg/mL
• Apperance: white solid

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ADORA2A(135), ADORA2B(136)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H29N7O6 · HCl · xH2O

DETAILS

Sigma Aldrich - C141

Caution
Hygroscopic
Biochem/physiol Actions
Adenosine receptor agonist, which possesses selectivity for A2 verses A1 receptors.