(2R,3R,4S,5R)-2-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 4168
• Molecular Formular: C11H13IN4O4
• Molecular Mass: 392.14979
• Monoisotopic Mass: 391.99815292
• SMILES: OC[C@H]1O[C@@H](n2cc(c3c(ncnc23)N)I)[C@H](O)[C@@H]1O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(c2c1ncnc2N)I
• InChI: InChI=1S/C11H13IN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1
• InChIKey: WHSIXKUPQCKWBY-IOSLPCCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: 5-iodotubercidin
• Synonyms: 5-iodotubercidin; 4-Amino-5-iodo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine; 5-Iodotubericidin; 7-Iodo-7-deazaadenosine; 5-Iodotubericidin

Database IDs

• CAS Number: 24386-93-4
• MDL Number: MFCD00055131
• PubChem SID: 46506259; 160967600
• PubChem CID: 97297

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.455637
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.3952887
• LogD (pH = 7.4): -0.40726894
• Log P: -0.3495156
• Molar Refractivity: 78.7341 cm^3
• Polarizability: 30.722075 Å^3
• Polar Surface Area: 126.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.38
• LOG S: -2.04
• Solubility (Water): 3.61e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble0.7 mg/mL; 0.1 M NaOH: soluble0.8 mg/mL; DMSO: soluble36 mg/mL
• Apperance: tan solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90%

DETAILS

DrugBank - DB04604

Drug information: experimental

Sigma Aldrich - I100

Biochem/physiol Actions
5-Iodotubercidin increases fatty acid oxidation activity and glycogen synthesis in hepatocytes. 5-Iodotubercidin is also a potent inhibitor of adenosine uptake into brain.
Potent inhibitor of adenosine uptake into brain, and of adenosine kinase and subsequent metabolism of adenine nucleotides. In cultured rat hepatocytes, 5-iodotubercidin inhibits both acetyl-CoA carboxylase and de novo synthesis of fatty acids and cholesterol.1
Caution
Solutions may be stored frozen. Use promptly when thawed and protect from exposure to light.