FComEx: Hypoxanthine (PC000140)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:47 UTC

Update date

2017-01-19 02:36:14 UTC

FoodComEx ID

PC000140

FoodDB Record

FDB003949

Chemical Information

Name

Hypoxanthine

Description

Hypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. A purine nucleobase that consists of purine bearing an oxo substituent at position 6. Hypoxanthine is a moderately basic compound (based on its pKa). Hypoxanthine exists in all living species, ranging from bacteria to humans. Within humans, hypoxanthine participates in a number of enzymatic reactions. In particular, hypoxanthine and ribose 1-phosphate can be biosynthesized from inosine; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, hypoxanthine and phosphoribosyl pyrophosphate can be biosynthesized from inosinic acid; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, hypoxanthine is involved in purine metabolism. Outside of the human body, Hypoxanthine is found, on average, in the highest concentration within beers and milk (cow). Hypoxanthine has also been detected, but not quantified in, several different foods, such as pigeon pea, green vegetables, lovages, gram beans, and arrowhead. This could make hypoxanthine a potential biomarker for the consumption of these foods. Hypoxanthine is a potentially toxic compound.

CAS Number

68-94-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,7-dihydro-6H-Purin-6-one	HMDB
1,7-Dihydro-6H-purine-6-one	biospider
1,9-Dihydro-purin-6-one	biospider
1H,7H-Hypoxanthine	biospider
3H-Purin-6-ol	biospider
4-Hydroxy-1H-purine	biospider
6-Hydroxy-1H-purine	biospider
6-Hydroxypurine	biospider
6-Oxopurine	biospider
6(1H)-Purinone	biospider
6H-Purin-6-one, 1,7-dihydro-	biospider
6H-Purin-6-one, 1,9-dihydro-	biospider
7H-Purin-6-ol	biospider
9H-Purin-6-ol	biospider
9H-Purin-6(1H)-one	biospider
Hyp	ChEBI
Hypoxanthine	biospider
Hypoxanthine enol	HMDB
Imidazo[5,4-d]pyrimidine, 6-hydroxy-	biospider
Purin-6-ol	biospider
Purin-6(1H)-one	biospider
Purin-6(3H)-one	biospider
Purine-6-ol	ChEBI
Sarcine	manual
Sarkin	HMDB
Sarkine	manual

Chemical Formula

C5H4N4O

IUPAC name

7H-purin-6-ol

InChI Identifier

InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

InChI Key

FDGQSTZJBFJUBT-UHFFFAOYSA-N

Isomeric SMILES

OC1=NC=NC2=C1NC=N2

Average Molecular Weight

136.1115

Monoisotopic Molecular Weight

136.03851077

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Hypoxanthines

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Pyrimidone
Pyrimidine
Azole
Imidazole
Vinylogous amide
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:17368 )
nucleobase analogue (CHEBI:17368 )
purine nucleobase (CHEBI:17368 )
Purine alkaloids (C00262 )
a purine-related compound (HYPOXANTHINE )
a purine base (HYPOXANTHINE )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-1.11	HANSCH,C ET AL. (1995)
Experimental Water Solubility	0.7 mg/mL at 23 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 360°	CCD

Foods of Origin