Structure via PubChem · Public domain (PubChem)
hypoxanthine
Sign in to saveAlso known as Hyp, 6-oxopurine, 9H-purin-6(1H)-one, purin-6(1H)-one, 6(1H)-purinone, 6-Hydroxy-1H-purine, 1H,7H-Hypoxanthine, 6-Hydroxypurine
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.
Chemical data
- Formula
- C5H4N4O
- Molecular weight
- 136.11 g/mol
- IUPAC name
- 1,7-dihydropurin-6-one
- SMILES
- C1=NC2=C(N1)C(=O)NC=N2
- InChIKey
- FDGQSTZJBFJUBT-UHFFFAOYSA-N
- XLogP
- -0.5
- Polar surface area
- 70.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
48,706 papers- Hypoxanthine as an indicator of hypoxia: its role in health and disease through free radical production.Pediatric research · 1988
- Molecular genetics of hypoxanthine-guanine phosphoribosyltransferase deficiency in man.Archives of internal medicine · 1985
- Hypoxanthine: a marker for asphyxia.Obstetrics and gynecology · 1988
- Hypoxanthine and xanthine in stored SAGM-blood.Scandinavian journal of haematology · 1986
- Plasma hypoxanthine and exercise.The American review of respiratory disease · 1987
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 136.039
Show 6 more facts
- found in taxon
- Streptomyces
- chemical formula
- C₅H₄N₄O
- Commons category
- Hypoxanthine
- canonical SMILES
- C1=NC2=C(N1)C(=O)N=CN2
- has characteristic
- bitterness
- subject has role
- primary metabolite
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Reactions
- Additional images
- References
- External links
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 bases of the DNA and RNA components adenine and guanine, which were found in trace amounts in meteorites, may have been formed by reactions occurring extraterrestrially in outer space.
Excerpted from Wikipedia’s “hypoxanthine” article, available under the CC BY-SA 4.0 licence.