Guanine

Guanine (/ˈɡwɑːnɪn/ ⓘ) (symbol G or Gua) is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine (uracil in RNA). In DNA, guanine is paired with cytosine. The guanine nucleoside is called guanosine.

Not to be confused with Guanosine, Guanidine, Guanfacine, Guanamine, or Guanín.
Guanine
Names
Preferred IUPAC name
2-Amino-1,9-dihydro-6H-purin-6-one
Other names
2-amino-6-hydroxypurine,
2-aminohypoxanthine,
Guanine
Identifiers
3D model (JSmol)
147911
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.727
EC Number
  • 200-799-8
431879
KEGG
PubChem CID
RTECS number
  • MF8260000
UNII
  • InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) Y
    Key: UYTPUPDQBNUYGX-UHFFFAOYSA-N Y
  • InChI=1/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
    Key: UYTPUPDQBNUYGX-UHFFFAOYAE
SMILES
  • keto form: O=C1c2ncnc2nc(N)N1
  • enol form: Oc1c2ncnc2nc(N)n1
Properties
C5H5N5O
Molar mass 151.13 g/mol
Appearance White amorphous solid.
Density 2.200 g/cm3 (calculated)
Melting point 360 °C (680 °F; 633 K) decomposes
Boiling point Sublimes
Insoluble.
Acidity (pKa) 3.3 (amide), 9.2 (secondary), 12.3 (primary)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
NFPA 704 (fire diamond)
1
1
Flash point Non-flammable
Related compounds
Related compounds
 Cytosine; Adenine; Thymine; Uracil
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

With the formula C5H5N5O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. This unsaturated arrangement means the bicyclic molecule is planar.

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