FComEx: Guanine (PC000116)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:35 UTC

Update date

2017-01-19 02:36:13 UTC

FoodComEx ID

PC000116

FoodDB Record

FDB004222

Chemical Information

Name

Guanine

Description

Guanine, also known as G or mearlmaid aa, belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. Guanine is a moderately basic compound (based on its pKa). Guanine exists in all living species, ranging from bacteria to humans. Within humans, guanine participates in a number of enzymatic reactions. In particular, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme adenine phosphoribosyltransferase. In addition, guanine and ribose 1-phosphate can be biosynthesized from guanosine; which is catalyzed by the enzyme purine nucleoside phosphorylase. In humans, guanine is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Outside of the human body, Guanine is found, on average, in the highest concentration within beers and milk (cow). Guanine has also been detected, but not quantified in, several different foods, such as kombus, black radish, chinese cabbages, dills, and devilfish. This could make guanine a potential biomarker for the consumption of these foods. Guanine, with regard to humans, has been found to be associated with several diseases such as lewy body disease, frontotemporal dementia, colorectal cancer, and alzheimer's disease; guanine has also been linked to the inborn metabolic disorder lesch-nyhan syndrome. A 2-aminopurine carrying a 6-oxo substituent.

CAS Number

73-40-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Amino-1,7-dihydro-6H-Purin-6-one	biospider
2-Amino-1,9-dihydro-6H-purin-6-one	biospider
2-Amino-1,9-dihydro-purin-6-one	biospider
2-Amino-3,7-dihydro-6H-purin-6-one	biospider
2-Amino-6-hydroxy-1H-purine	biospider
2-Amino-6-hydroxypurine	biospider
2-amino-6-Oxopurine	ChEBI
2-Amino-6-purinol	biospider
2-Amino-9H-purin-6-ol	biospider
2-Amino-Hypoxanthine	biospider
2-Aminohypoxanthine	biospider
2(1H)-pyrimidinone, 4-amino-	biospider
6-Hydroxy-2-aminopurine	biospider
6H-Purin-6-one, 2-amino-1,7-dihydro- (9CI)	biospider
6H-Purin-6-one, 2-amino-1,9-dihydro-	biospider
6H-purin-6-one, 2-amino-3,7-dihydro-	biospider
C.I. natural white 1	HMDB
CI natural white 1	HMDB
Dew pearl	HMDB
Gua	ChEBI
Guanin	HMDB
Guanine enol	HMDB
GUN	HMDB
Hypoxanthine, 2-amino-	biospider
Mearlmaid	HMDB
Mearlmaid aa	HMDB
Natural pearl essence	HMDB
Natural white 1	HMDB
Naturon	HMDB
Pathocidin	HMDB
Pearl essence	HMDB
Stella polaris	HMDB

Chemical Formula

C5H5N5O

IUPAC name

2-amino-6,7-dihydro-3H-purin-6-one

InChI Identifier

InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

InChI Key

UYTPUPDQBNUYGX-UHFFFAOYSA-N

Isomeric SMILES

NC1=NC(=O)C2=C(N1)N=CN2

Average Molecular Weight

151.1261

Monoisotopic Molecular Weight

151.049409807

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purines and purine derivatives

Alternative Parents

Substituents

Purine
Hydroxypyrimidine
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:16235 )
2-aminopurines (CHEBI:16235 )
purine nucleobase (CHEBI:16235 )
purines (C00242 )
a purine base (GUANINE )
a purine (GUANINE )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-0.91	HANSCH,C ET AL. (1995)
Experimental Water Solubility	2.08 mg/mL at 37 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 300°	CCD

Foods of Origin