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Guanine (FDB004222)

Record Information
Version1.0
Creation date2010-04-08 22:06:08 UTC
Update date2020-09-17 15:38:21 UTC
Primary IDFDB004222
Secondary Accession Numbers
  • FDB006726
Chemical Information
FooDB 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.31 g/LALOGPS
logP-0.92ALOGPS
logP-0.59ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.95ChemAxon
pKa (Strongest Basic)2.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.16 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.9 m³·mol⁻¹ChemAxon
Polarizability13.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionCryst.CCD
Mass CompositionC 39.74%; H 3.33%; N 46.34%; O 10.59%CCD
Melting PointMp 300°CCD
Boiling PointNot Available
Experimental Water Solubility2.08 mg/mL at 37 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-0.91HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-8900000000-699c510cfaf838ab19222015-03-01View Spectrum
GC-MSGuanine, non-derivatized, GC-MS Spectrumsplash10-0udi-1938000000-e15e09f2007f35659bb9Spectrum
GC-MSGuanine, 3 TMS, GC-MS Spectrumsplash10-0udi-3739000000-66a080b08ba9b9f82e20Spectrum
GC-MSGuanine, non-derivatized, GC-MS Spectrumsplash10-0udi-5900000000-0a63148e3a8dc8d026dfSpectrum
GC-MSGuanine, non-derivatized, GC-MS Spectrumsplash10-0udi-1938000000-e15e09f2007f35659bb9Spectrum
GC-MSGuanine, non-derivatized, GC-MS Spectrumsplash10-0udi-3739000000-66a080b08ba9b9f82e20Spectrum
GC-MSGuanine, non-derivatized, GC-MS Spectrumsplash10-0udi-2928000000-073bf70794fe99ce737fSpectrum
GC-MSGuanine, non-derivatized, GC-MS Spectrumsplash10-000t-2790000000-77e6b5b71c9ff6ad2b23Spectrum
Predicted GC-MSGuanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ff0-5900000000-f103c75addeafe7ac6f0Spectrum
Predicted GC-MSGuanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-2864e73c83444d566e9a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-4229d3d01623054b4ceb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-d5ae84fefadd84f988b42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-7d48b2e8db6967e984072012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0900000000-67a7784963ec75cecaa02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-4569516f23d8a712b4342012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d928cac1226f19b8edc32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-34059351f2cbd94a8acc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udj-0903100000-deb9c022884d7c98782e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-45d9db80ce4657ef17732012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-1900000000-86b7ee5755cbb8236f5b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-ba534850b64f39d81fa02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-422f992621ab9626d1b22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f89-0900000000-64e388178db73f06cb202012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-f0a95c55947ca990359c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-45d9db80ce4657ef17732017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-ba534850b64f39d81fa02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f89-0900000000-64e388178db73f06cb202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-c2e1c1e8841cc741dac12017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e74c005384d71f4787e52015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-de4a4c4479ea93d742b52015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9800000000-da506476184e5c2313a42015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-03d17084c3cb072c02372015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-c372e3ba919cba4f561f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-8ac435f998deda6437e12015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
ChemSpider ID744
ChEMBL IDCHEMBL219568
KEGG Compound IDC00242
Pubchem Compound ID764
Pubchem Substance IDNot Available
ChEBI ID16235
Phenol-Explorer IDNot Available
DrugBank IDDB02377
HMDB IDHMDB00132
CRC / DFC (Dictionary of Food Compounds) IDHHS79-J:HHS79-J
EAFUS IDNot Available
Dr. Duke IDGUANINE
BIGG ID34363
KNApSAcK IDNot Available
HET IDGUN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGuanine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
essentialDUKE
Enzymes
NameGene NameUniProt ID
Purine nucleoside phosphorylasePNPP00491
Adenine phosphoribosyltransferaseAPRTP07741
Guanine nucleotide-binding protein G(s) subunit alpha isoforms shortGNASP63092
Guanine nucleotide-binding protein G(q) subunit alphaGNAQP50148
Queuine tRNA-ribosyltransferase subunit QTRTD1QTRTD1Q9H974
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).