Record Information
Version1.0
Creation date2015-10-09 22:28:35 UTC
Update date2017-01-19 02:36:13 UTC
FoodComEx IDPC000116
FoodDB RecordFDB004222
Chemical Information
NameGuanine
DescriptionGuanine, 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 Number73-40-5
Structure
Thumb
Synonyms
SynonymSource
2-Amino-1,7-dihydro-6H-Purin-6-onebiospider
2-Amino-1,9-dihydro-6H-purin-6-onebiospider
2-Amino-1,9-dihydro-purin-6-onebiospider
2-Amino-3,7-dihydro-6H-purin-6-onebiospider
2-Amino-6-hydroxy-1H-purinebiospider
2-Amino-6-hydroxypurinebiospider
2-amino-6-OxopurineChEBI
2-Amino-6-purinolbiospider
2-Amino-9H-purin-6-olbiospider
2-Amino-Hypoxanthinebiospider
2-Aminohypoxanthinebiospider
2(1H)-pyrimidinone, 4-amino-biospider
6-Hydroxy-2-aminopurinebiospider
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 1HMDB
CI natural white 1HMDB
Dew pearlHMDB
GuaChEBI
GuaninHMDB
Guanine enolHMDB
GUNHMDB
Hypoxanthine, 2-amino-biospider
MearlmaidHMDB
Mearlmaid aaHMDB
Natural pearl essenceHMDB
Natural white 1HMDB
NaturonHMDB
PathocidinHMDB
Pearl essenceHMDB
Stella polarisHMDB
Chemical FormulaC5H5N5O
IUPAC name2-amino-6,7-dihydro-3H-purin-6-one
InChI IdentifierInChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyUYTPUPDQBNUYGX-UHFFFAOYSA-N
Isomeric SMILESNC1=NC(=O)C2=C(N1)N=CN2
Average Molecular Weight151.1261
Monoisotopic Molecular Weight151.049409807
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-0.91HANSCH,C ET AL. (1995)
Experimental Water Solubility2.08 mg/mL at 37 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 300°CCD
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 3 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci A416
AKSci J20096
AKSci J92186
AKSci HMDB0000132
Glentham GE0617
MetaSci HMDB0000132
Toronto Research Chemicals G836000