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

• ChemBase ID: 156530
• Molecular Formular: C11H14N4O4
• Molecular Mass: 266.25326
• Monoisotopic Mass: 266.10150495
• SMILES: c1cn(c2c1c(ncn2)N)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc2c1ncnc2N
• InChI: InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
• InChIKey: HDZZVAMISRMYHH-KCGFPETGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: tubercidin
• Synonyms: 7-Deazaadenosine; Tubercidin

Database IDs

• CAS Number: 69-33-0
• EC Number: 200-703-4
• MDL Number: MFCD00056012
• Beilstein Number: 38498
• PubChem SID: 162250667
• PubChem CID: 6245

CALCULATED PROPERTIES

• Acid pKa: 12.455672
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.802182
• LogD (pH = 7.4): -1.4864898
• Log P: -1.27846
• Molar Refractivity: 65.3716 cm^3
• Polarizability: 25.36341 Å^3
• Polar Surface Area: 126.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UY8870000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2

Product Information

• Purity: ≥99.0% (HPLC)
• Biological Source: from Streptomyces tubercidicus
• Empirical Formula (Hill Notation): C11H14N4O4

DETAILS

Sigma Aldrich - 93747

Biochem/physiol Actions
Toxic adenosine analog with antiviral,1 antitrypanosomal,2 and antifungal functions. Mode of action: Inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal,3 inhibits mammalian SAH hydrolase (SAHH),4 and blocks purine biosynthesis in Candida famata.5