(2S,3R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide

• ChemBase ID: 171601
• Molecular Formular: C12H15IN6O4
• Molecular Mass: 434.18977
• Monoisotopic Mass: 434.01995099
• SMILES: n1c(nc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)C(=O)NCC)O)O)I
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(I)nc2N
• InChI: InChI=1S/C12H15IN6O4/c1-2-15-10(22)7-5(20)6(21)11(23-7)19-3-16-4-8(14)17-12(13)18-9(4)19/h3,5-7,11,20-21H,2H2,1H3,(H,15,22)(H2,14,17,18)/t5-,6?,7+,11-/m1/s1
• InChIKey: YEBHQRSEUJCFMN-MYLVMTIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• IUPAC Traditional name: (2S,3R,5R)-5-(6-amino-2-iodopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• Synonyms: 1-(6-Amino-2-iodo-9H-purin-9-yl)-1-deoxy-N-ethyl-β-D-ribofuranuronamide; 2-Iodo-NECA; 2-Iodo-5'-ethylcarboxamido Adenosine

Database IDs

• CAS Number: 141018-29-3
• PubChem SID: 164227511
• PubChem CID: 45039581

CALCULATED PROPERTIES

• Acid pKa: 12.377309
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.9512903
• LogD (pH = 7.4): -0.9512919
• Log P: -0.9512873
• Molar Refractivity: 87.2336 cm^3
• Polarizability: 34.345924 Å^3
• Polar Surface Area: 148.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMF
• Apperance: White to Off-White Solid
• Melting Point: >198°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I706000

A potent selective adenosine receptor agonist.

REFERENCES

• Reiger, J.M., et al.: J. Med. Chem., 44, 531 (2001)