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

• ChemBase ID: 177261
• Molecular Formular: C12H15N5O3
• Molecular Mass: 277.2792
• Monoisotopic Mass: 277.11748937
• SMILES: c1(nc(=O)c2c([nH]1)[nH]cc2CNC1C=C[C@@H]([C@@H]1O)O)N
• Canonical SMILES: O[C@H]1C=CC([C@H]1O)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)/t6?,7-,9+/m0/s1
• InChIKey: WYROLENTHWJFLR-RSPBLZPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-({[(4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• IUPAC Traditional name: 2-amino-5-({[(4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• Synonyms: 2-Amino-5-[[[(1S,4S,5R)-4,5-dihydroxy-2-cyclopenten-1-yl]amino]methyl]-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one Dihydrochloride; [1S-(1α,4β,5β)]-2-Amino-5-[[(4,5-dihydroxy-2-cyclopenten-1-yl)amino]methyl]-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one Dihydrochloride; Queuine Dihydrochloride

Database IDs

• CAS Number: 86496-18-6
• PubChem SID: 164233171
• PubChem CID: 44294294

CALCULATED PROPERTIES

• Acid pKa: 9.123912
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.863701
• LogD (pH = 7.4): -1.352395
• Log P: -1.2098165
• 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

DETAILS

Toronto Research Chemicals - Q525000

It is one of the modified base which is found at first anticodon position of specific tRNAs. Queuine promotes cell death and participates in regulation of cell proliferation.

REFERENCES

• Katze, J., et al.: Biochemistry, 23, 1171 (1984)
• Reisser, T., et al.: Eur. J. Biochem., 221, 979 (1984)
• Jin, Z., et al.: J. Biol. Chem., 281, 14446 (1984)