Hypoxanthine

Hypoxanthine

Names
IUPAC name 1H-purin-6(9H)-one
Identifiers
CAS Number	68-94-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17368 Y
ChEMBL	ChEMBL1427 Y
ChemSpider	768 Y
ECHA InfoCard	100.000.634
IUPHAR/BPS	4555
KEGG	C00262 Y
MeSH	Hypoxanthine
PubChem	790
UNII	2TN51YD919 Y
InChI 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
Chemical formula	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  (what is YN ?)
Infobox references

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 cell, 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.

It is one of the products of the action of xanthine oxidase on xanthine. However, more frequently in purine degradation, xanthine is formed from reduction of hypoxanthine by xanthine oxidoreductase.

Hypoxanthine-guanine phosphoribosyltransferase converts hypoxanthine into IMP in nucleotide salvage.