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

• ChemBase ID: 132541
• Molecular Formular: C18H20IN7O4
• Molecular Mass: 525.30037
• Monoisotopic Mass: 525.06215016
• SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2NCc1ccc(c(c1)I)N)O)O
• Canonical SMILES: CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1ccc(c(c1)I)N
• InChI: InChI=1S/C18H20IN7O4/c1-21-17(29)14-12(27)13(28)18(30-14)26-7-25-11-15(23-6-24-16(11)26)22-5-8-2-3-10(20)9(19)4-8/h2-4,6-7,12-14,18,27-28H,5,20H2,1H3,(H,21,29)(H,22,23,24)/t12-,13+,14-,18+/m0/s1
• InChIKey: LOGOEBMHHXYBID-MOROJQBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-5-(6-{[(4-amino-3-iodophenyl)methyl]amino}-9H-purin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• IUPAC Traditional name: (2S,3S,4R,5R)-5-(6-{[(4-amino-3-iodophenyl)methyl]amino}purin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• Synonyms: 1-[6-[[(4-Amino-3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide; 3-Iodo-4-aminobenzyl-5′-N-methylcarboxamidoadenosine; N6-(4-Amino-3-iodobenzyl)-5′-N-methylcarbamoyladenosine; I-AB-MECA

Database IDs

• CAS Number: 152918-27-9
• MDL Number: MFCD00671784
• PubChem SID: 24895933; 162226818
• PubChem CID: 9958472

CALCULATED PROPERTIES

• Acid pKa: 12.393443
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.31462651
• LogD (pH = 7.4): -0.22897163
• Log P: -0.22776017
• Molar Refractivity: 117.9508 cm^3
• Polarizability: 44.719917 Å^3
• Polar Surface Area: 160.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble7 mg/mL; 0.1 M NaOH: soluble2 mg/mL; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.2 mg/mL; DMSO: soluble10 mg/mL; H2O: insoluble
• Apperance: off-white solid

Safety Information

• 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 ... ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

DETAILS

Sigma Aldrich - I145

Legal Information
Sold under license from the National Institutes of Health.
Biochem/physiol Actions
Reference standard for radioiodinated I-AB-MECA, a widely used, high affinity radioligand for the A3 adenosine receptor.