Hypoxanthine

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.

Hypoxanthine
Names
Preferred IUPAC name
1,9-Dihydro-6H-purin-6-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.634
KEGG
MeSH Hypoxanthine
PubChem CID
UNII
  • InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) Y
    Key: FDGQSTZJBFJUBT-UHFFFAOYSA-N Y
  • InChI=1/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
    Key: FDGQSTZJBFJUBT-UHFFFAOYAJ
SMILES
  • c1[nH]c2c(n1)[nH]cnc2=O
Properties
C5H4N4O
Molar mass 136.112
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

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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