(2R,3R,4S)-2-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-5-methylideneoxolane-3,4-diol

• ChemBase ID: 154572
• Molecular Formular: C11H13N5O4
• Molecular Mass: 279.25202
• Monoisotopic Mass: 279.09675392
• SMILES: C=C1[C@H]([C@H]([C@](O1)(CO)n1cnc2c1ncnc2N)O)O
• Canonical SMILES: OC[C@]1(OC(=C)[C@H]([C@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C11H13N5O4/c1-5-7(18)8(19)11(2-17,20-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-4,7-8,17-19H,1-2H2,(H2,12,13,14)/t7-,8-,11-/m1/s1
• InChIKey: UZSSGAOAYPICBZ-SOCHQFKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-2-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-5-methylideneoxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S)-2-(6-aminopurin-9-yl)-2-(hydroxymethyl)-5-methylideneoxolane-3,4-diol
• Synonyms: 9-(6-Deoxy-D-β-erythro-hex-5-en-2-ulofuranosyl)adenine; Decoyinine

Database IDs

• CAS Number: 2004-04-8
• PubChem SID: 162248710
• PubChem CID: 121578

CALCULATED PROPERTIES

• Acid pKa: 12.180498
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.8056785
• LogD (pH = 7.4): -1.6977944
• Log P: -1.6962181
• Molar Refractivity: 68.3957 cm^3
• Polarizability: 26.112381 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

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

Product Information

• Empirical Formula (Hill Notation): C11H13N5O4

DETAILS

Sigma Aldrich - D1071

Application
Decoyinine is used to study the inhibition of cell wall synthesis , to lower intracellular GTP levels in Streptococcus mutans1, and to initiate sporulation in Bacillus2.
Biochem/physiol Actions
Decoyinine is a Xanthosine monophosphate (XMP) aminase inhibitor and GMP synthetase inhibitor. It inhibits RNA synthesis and reduces intracellular GTP levels. Decoyinine inhibits cell wall synthesis.