guanine

Also known as Gua, 2-amino-6-oxopurine, Stella Polaris, Mearlmaid AA, Pearl Essence, C.I. Natural White 1, CI Natural white 1, Naturon

Guanine () (symbol G or Gua) is one of the four main nucleotide bases 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.

OverviewAI-generated

Guanine is a compound with the chemical formula C₅H₅N₅O. Its IUPAC name is 2-amino-3,7-dihydropurin-6-one. The substance has a mass of 151.049 and a weight of 151.13. It decomposes at 360 and has a pKa of 9.92. The solubility of guanine is 0.068.

Chemical properties include a canonical SMILES string of C1=NC2=C(N1)C(=O)N=C(N2)N. The compound has a charge of 0, an xlogp of -1, and a tpsa of 96.2. It features 3 hydrogen bond donors and 2 hydrogen bond acceptors. Guanine is referenced by 956 other encyclopedia articles and has 81565 associated PubMed entries.

Synthesized by Vinony from 21 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

In the Vinony graph

Within Vinony's link graph, guanine is referenced by 956 other articles, and connects out to adenosine receptor, purine and nucleotide base.

It sits within the topics Chembox image size set, Chemical articles with multiple compound IDs and Cosmetics chemicals.

Its subject is documented across 71 Wikipedia language editions.

Chemical data

Formula: C5H5N5O
Molecular weight: 151.13 g/mol
IUPAC name: 2-amino-3,7-dihydropurin-6-one
SMILES: C1=NC2=C(N1)C(=O)N=C(N2)N
InChIKey: UYTPUPDQBNUYGX-UHFFFAOYSA-N
XLogP: -1
Polar surface area: 96.2 Å²
H-bond donors: 3
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: cutaneous melanoma, glioblastoma multiforme, lymphoma, neoplasm

via ChEMBL · EBI

Research

81,565 papers

Guanine Analogue-Based Assemblies: Construction and Luminescence Functions.ReviewLangmuir : the ACS journal of surfaces and colloids · 2022Qi P, Yi M, Song A et al.DOI: 10.1021/acs.langmuir.2c00705
Products of Oxidative Guanine Damage Form Base Pairs with Guanine.ReviewInternational journal of molecular sciences · 2020Kino K, Kawada T, Hirao-Suzuki M et al.DOI: 10.3390/ijms21207645
A new method for sequencing DNA.Proceedings of the National Academy of Sciences of the United States of America · 1977Maxam AM, Gilbert WDOI: 10.1073/pnas.74.2.560
Guanine-containing ssDNA and RNA induce dimeric and tetrameric structural forms of SAMHD1.Nucleic acids research · 2023Orris B, Sung MW, Bhat S et al.DOI: 10.1093/nar/gkad971
Developing guanine base editors for G-to-T editing in rice.Journal of integrative plant biology · 2024Liu L, Zhang Z, Wang C et al.DOI: 10.1111/jipb.13729
Studying the excited electronic states of guanine rich DNA quadruplexes by quantum mechanical methods: main achievements and perspectives.ReviewPhotochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2020Martínez-Fernández L, Esposito L, Improta RDOI: 10.1039/d0pp00065e
Nanostructure of Functional Larotaxel Liposomes Decorated with Guanine-Rich Quadruplex Nucleotide-Lipid Derivative for Treatment of Resistant Breast Cancer.ReviewSmall (Weinheim an der Bergstrasse, Germany) · 2021Li X, Li J, Xu J et al.DOI: 10.1002/smll.202007391
Halogen-Bonded Guanine Base Pairs, Quartets and Ribbons.International journal of molecular sciences · 2020Thornton NJ, van Mourik TDOI: 10.3390/ijms21186571

via PubMed

Wikidata facts

Has part: hydrogen
Named after: guano
Mass: 151.049

Show 10 more facts

Commons category: Guanine
chemical formula: C₅H₅N₅O
canonical SMILES: C1=NC2=C(N1)C(=O)N=C(N2)N
found in taxon: Streptomyces
crystal system: monoclinic crystal system
decomposition point: 360
pKa: 9.92
solubility: 0.068
described by source: Brockhaus and Efron Encyclopedic Dictionary
subject has role: primary metabolite

Sources (7)

via Wikidata · CC0

~6 min read

Encyclopedic overview

8 sections

Contents

Properties
History
Synthesis
Biosynthesis
Other occurrences and biological uses
See also
References
External links

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.

Excerpted from Wikipedia’s “guanine” article, available under the CC BY-SA 4.0 licence.