CHEBI:17368 - hypoxanthine

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ChEBI Name hypoxanthine
ChEBI ID CHEBI:17368
Definition A purine nucleobase that consists of purine bearing an oxo substituent at position 6.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:24762, CHEBI:43237, CHEBI:5841, CHEBI:14431
Supplier Information ChemicalBook:CB5378579, eMolecules:522216, eMolecules:5851666, eMolecules:538926, eMolecules:975947, eMolecules:711446, Selleckchem:hypoxanthine, ZINC000018153302
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Hypoxanthine is a naturally occurring purine derivative. It is occasionally found as a constituent of nucleic acids, where it is present in the anticodon of tRNA in the form of its nucleoside inosine. It has a tautomer known as 6-hydroxypurine. Hypoxanthine is a necessary additive in certain cells, bacteria, and parasite cultures as a substrate and nitrogen source. For example, it is commonly a required reagent in malaria parasite cultures, since Plasmodium falciparum requires a source of hypoxanthine for nucleic acid synthesis and energy metabolism. In August 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting hypoxanthine and related organic molecules, including the DNA and RNA components adenine and guanine, may have been formed extraterrestrially in outer space. The Pheretima aspergillum worm, used in Chinese medicine preparations, contains hypoxanthine.
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Formula C5H4N4O
Net Charge 0
Average Mass 136.11162
Monoisotopic Mass 136.03851
InChI InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChIKey FDGQSTZJBFJUBT-UHFFFAOYSA-N
SMILES O=c1[nH]cnc2nc[nH]c12
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525) 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): fundamental metabolite
Any metabolite produced by all living cells.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing hypoxanthine (CHEBI:17368) has functional parent adenine (CHEBI:16708)
hypoxanthine (CHEBI:17368) has role fundamental metabolite (CHEBI:78675)
hypoxanthine (CHEBI:17368) is a nucleobase analogue (CHEBI:67142)
hypoxanthine (CHEBI:17368) is a oxopurine (CHEBI:25810)
hypoxanthine (CHEBI:17368) is a purine nucleobase (CHEBI:26386)
Incoming 9-riburonosylhypoxanthine (CHEBI:17643) has functional parent hypoxanthine (CHEBI:17368)
inosine (CHEBI:17596) has functional parent hypoxanthine (CHEBI:17368)
methylhypoxanthine (CHEBI:73958) has functional parent hypoxanthine (CHEBI:17368)
IUPAC Name
1,7-dihydro-6H-purin-6-one
Synonyms Sources
6(1H)-purinone NIST Chemistry WebBook
6-oxopurine NIST Chemistry WebBook
9H-purin-6(1H)-one NIST Chemistry WebBook
Hyp CBN
Hypoxanthine KEGG COMPOUND
HYPOXANTHINE PDBeChem
hypoxanthine UniProt
purin-6(1H)-one NIST Chemistry WebBook
Purine-6-ol KEGG COMPOUND
Manual Xrefs Databases
C00001502 KNApSAcK
C00262 KEGG COMPOUND
DB04076 DrugBank
ECMDB00157 ECMDB
HMDB0000157 HMDB
HPA PDBeChem
Hypoxanthine Wikipedia
HYPOXANTHINE MetaCyc
YMDB00555 YMDB
View more database links
Registry Numbers Types Sources
464558 Gmelin Registry Number Gmelin
5811 Reaxys Registry Number Reaxys
68-94-0 CAS Registry Number KEGG COMPOUND
68-94-0 CAS Registry Number ChemIDplus
68-94-0 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
08 May 2019