2-amino-5-{[(4,5-dihydroxycyclopent-2-en-1-yl)amino]methyl}-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one

• ChemBase ID: 129213
• Molecular Formular: C12H15N5O3
• Molecular Mass: 277.2792
• Monoisotopic Mass: 277.11748937
• SMILES: C1=CC(C(C1NCc1c[nH]c2c1c(=O)nc([nH]2)N)O)O
• Canonical SMILES: OC1C=CC(C1O)NCc1c[nH]c2c1c(=O)nc([nH]2)N
• InChI: InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)
• InChIKey: WYROLENTHWJFLR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-{[(4,5-dihydroxycyclopent-2-en-1-yl)amino]methyl}-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• IUPAC Traditional name: queuine
• Synonyms: 7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine; Queuine

Database IDs

• CAS Number: 72496-59-4
• PubChem SID: 162223510
• PubChem CID: 4630421; 114881
• MeSH Name: Queuine
• Wikipedia Title: Queuine

CALCULATED PROPERTIES

• Acid pKa: 9.123897
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.8636887
• LogD (pH = 7.4): -1.3523805
• Log P: -1.2098026
• Molar Refractivity: 72.9602 cm^3
• Polarizability: 26.96853 Å^3
• Polar Surface Area: 135.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false