CHEBI:16235 - guanine

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ChEBI Name guanine
ChEBI ID CHEBI:16235
Definition A 2-aminopurine carrying a 6-oxo substituent.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42948, CHEBI:14371, CHEBI:14372, CHEBI:24443, CHEBI:5563
Supplier Information No supplier information found for this compound.
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4-Hydroxynonenal, or 4-hydroxy-2E-nonenal or 4-hydroxy-2-nonenal or 4-HNE or HNE, (C9H16O2), is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion. Early identification and characterization of 4-hydroxynonenal was reported by Esterbauer, et al., who also obtained the same compound synthetically. The topic has since been often reviewed, and one source describes the compound as "the most studied LPO (lipid peroxidation) product with pleiotropic capabilities".
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Formulae C5H5N5O
C5H5N5O
Net Charge 0
Average Mass 151.126
Monoisotopic Mass 151.04941
InChI InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChIKey UYTPUPDQBNUYGX-UHFFFAOYSA-N
SMILES C12=C(N=C(NC1=O)N)NC=N2
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing guanine (CHEBI:16235) has parent hydride 9H-purine (CHEBI:35589)
guanine (CHEBI:16235) has role Escherichia coli metabolite (CHEBI:76971)
guanine (CHEBI:16235) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
guanine (CHEBI:16235) has role algal metabolite (CHEBI:84735)
guanine (CHEBI:16235) has role human metabolite (CHEBI:77746)
guanine (CHEBI:16235) has role mouse metabolite (CHEBI:75771)
guanine (CHEBI:16235) is a 2-aminopurines (CHEBI:20702)
guanine (CHEBI:16235) is a oxopurine (CHEBI:25810)
guanine (CHEBI:16235) is a purine nucleobase (CHEBI:26386)
Incoming 1,N2-ethenoguanine (CHEBI:134096) has functional parent guanine (CHEBI:16235)
1H,3H,5H-pyrimido[1,2-α]purin-2,6,10-trione (CHEBI:233252) has functional parent guanine (CHEBI:16235)
2-oxo-ethenoguanine (CHEBI:233226) has functional parent guanine (CHEBI:16235)
3H,5H-pyrimido[1,2-α]purin-6,10-dione (CHEBI:233251) has functional parent guanine (CHEBI:16235)
7,8-dihydro-8-oxoguanine (CHEBI:52617) has functional parent guanine (CHEBI:16235)
7-(2'-oxo-heptyl)-1,N2-ethenoguanine (CHEBI:233227) has functional parent guanine (CHEBI:16235)
7-(2'-oxo-heptyl)-2-oxo-ethenoguanine (CHEBI:233228) has functional parent guanine (CHEBI:16235)
8-hydroxy-7-methylguanine (CHEBI:74064) has functional parent guanine (CHEBI:16235)
8-oxoguanine (CHEBI:44605) has functional parent guanine (CHEBI:16235)
9-(2-deoxy-2-fluoro-5-O-phosphono-β-D-arabinofuranosyl)guanine (CHEBI:42701) has functional parent guanine (CHEBI:16235)
9-[2-(phosphonomethoxy)ethyl]guanine (CHEBI:7880) has functional parent guanine (CHEBI:16235)
N2,3-ethenoguanine (CHEBI:134095) has functional parent guanine (CHEBI:16235)
N2-carboxyethylguanine (CHEBI:62032) has functional parent guanine (CHEBI:16235)
O6-methyl-2'-deoxyguanosine (CHEBI:27549) has functional parent guanine (CHEBI:16235)
acyclovir (CHEBI:2453) has functional parent guanine (CHEBI:16235)
ganciclovir (CHEBI:465284) has functional parent guanine (CHEBI:16235)
guanosine (CHEBI:16750) has functional parent guanine (CHEBI:16235)
guanosines (CHEBI:24458) has functional parent guanine (CHEBI:16235)
guanyl deoxyribonucleotide residue (CHEBI:60801) has functional parent guanine (CHEBI:16235)
guanyl nucleotide (CHEBI:61292) has functional parent guanine (CHEBI:16235)
methylguanine (CHEBI:25305) has functional parent guanine (CHEBI:16235)
N2-(ADP-D-ribosyl)-guanine(2−) (CHEBI:142716) has functional parent guanine (CHEBI:16235)
nelarabine (CHEBI:63612) has functional parent guanine (CHEBI:16235)
penciclovir (CHEBI:7956) has functional parent guanine (CHEBI:16235)
pyrimido[1,2-α]purin-10(3H)-one (CHEBI:233250) has functional parent guanine (CHEBI:16235)
valacyclovir (CHEBI:35854) has functional parent guanine (CHEBI:16235)
valganciclovir (CHEBI:63635) has functional parent guanine (CHEBI:16235)
xanthine (CHEBI:15318) has functional parent guanine (CHEBI:16235)
guanin-9-yl group (CHEBI:30755) is substituent group from guanine (CHEBI:16235)
IUPAC Name
2-amino-1,9-dihydro-6H-purin-6-one
Synonyms Sources
2-Amino-6-hydroxypurine KEGG COMPOUND
2-amino-6-oxopurine ChEBI
G ChEBI
Gua CBN
Guanine KEGG COMPOUND
GUANINE PDBeChem
guanine UniProt
Manual Xrefs Databases
C00001501 KNApSAcK
C00242 KEGG COMPOUND
DB02377 DrugBank
Guanine Wikipedia
GUANINE MetaCyc
GUN PDBeChem
HMDB0000132 HMDB
View more database links
Registry Numbers Types Sources
147911 Reaxys Registry Number Reaxys
431879 Gmelin Registry Number Gmelin
73-40-5 CAS Registry Number KEGG COMPOUND
73-40-5 CAS Registry Number ChemIDplus
73-40-5 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
22770225 PubMed citation Europe PMC
8070089 PubMed citation Europe PMC
Last Modified
24 June 2019
General Comment
2010-12-22 Guanine is one of the four main nucleobases found in the nucleic acids DNA and RNA.