(2S,3S,4R,5R)-5-(2-chloro-6-{[(3-iodophenyl)methyl]amino}-9H-purin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide

• ChemBase ID: 155447
• Molecular Formular: C18H18ClIN6O4
• Molecular Mass: 544.73079
• Monoisotopic Mass: 544.01227877
• SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1nc(nc2NCc1cccc(c1)I)Cl)O)O
• Canonical SMILES: CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2NCc1cccc(c1)I
• InChI: InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1
• InChIKey: IPSYPUKKXMNCNQ-PFHKOEEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-5-(2-chloro-6-{[(3-iodophenyl)methyl]amino}-9H-purin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• IUPAC Traditional name: (2S,3S,4R,5R)-5-(2-chloro-6-{[(3-iodophenyl)methyl]amino}purin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• Synonyms: 2-Chloro-N6-(3-iodobenzyl)-adenosine-5′-N-methyluronamide; Cl-IB-MECA; Chloro-IB-MECA

Database IDs

• CAS Number: 163042-96-4
• MDL Number: MFCD01861178
• PubChem SID: 162249585; 24278354
• PubChem CID: 3035850

CALCULATED PROPERTIES

• Acid pKa: 12.380618
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.5097101
• LogD (pH = 7.4): 1.5097115
• Log P: 1.5097162
• Molar Refractivity: 118.749 cm^3
• Polarizability: 45.628353 Å^3
• Polar Surface Area: 134.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H18ClIN6O4

DETAILS

Sigma Aldrich - C277

Biochem/physiol Actions
A3 adenosine receptor agonist.