Record Information
Version1.0
Creation date2010-04-08 22:06:08 UTC
Update date2019-11-27 17:10:31 UTC
Primary IDFDB004222
Secondary Accession Numbers
  • FDB006726
Chemical Information
FooDB NameGuanine
DescriptionOccurs widely in animals and plants. Component of nucleic acids (CCD) Guanine (G) is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine (uracil in RNA). In DNA, guanine is paired with cytosine. With the formula C5H5N5O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine.
CAS Number73-40-5
Structure
Thumb
Synonyms
SynonymSource
2-Amino-6-hydroxypurineChEBI
2-Amino-6-oxopurineChEBI
GChEBI
GuaChEBI
2-Amino-1,7-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-purin-6-oneHMDB
2-Amino-3,7-dihydro-6H-purin-6-oneHMDB
2-Amino-6-hydroxy-1H-purineHMDB
2-Amino-6-purinolHMDB
2-Amino-hypoxanthineHMDB
2-AminohypoxanthineHMDB
6-Hydroxy-2-aminopurineHMDB
C.I. natural white 1HMDB
CI natural white 1HMDB
Dew pearlHMDB
GuaninHMDB
Guanine enolHMDB
GUNHMDB
MearlmaidHMDB
Mearlmaid aaHMDB
Natural pearl essenceHMDB
Natural white 1HMDB
NaturonHMDB
PathocidinHMDB
Pearl essenceHMDB
Stella polarisHMDB
2-Amino-1,7-dihydro-6H-Purin-6-onebiospider
2-amino-6-OxopurineChEBI
2-Amino-9H-purin-6-olbiospider
2-Amino-Hypoxanthinebiospider
2(1H)-pyrimidinone, 4-amino-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
Hypoxanthine, 2-amino-biospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-1938000000-e15e09f2007f35659bb9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-3739000000-66a080b08ba9b9f82e20View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-5900000000-0a63148e3a8dc8d026dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1938000000-e15e09f2007f35659bb9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3739000000-66a080b08ba9b9f82e20View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-2928000000-073bf70794fe99ce737fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-2790000000-77e6b5b71c9ff6ad2b23View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ff0-5900000000-f103c75addeafe7ac6f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-2864e73c83444d566e9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-4229d3d01623054b4cebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-d5ae84fefadd84f988b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-7d48b2e8db6967e98407View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0900000000-67a7784963ec75cecaa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-4569516f23d8a712b434View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d928cac1226f19b8edc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-34059351f2cbd94a8accView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udj-0903100000-deb9c022884d7c98782eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-45d9db80ce4657ef1773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-1900000000-86b7ee5755cbb8236f5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-ba534850b64f39d81fa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-422f992621ab9626d1b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f89-0900000000-64e388178db73f06cb20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-f0a95c55947ca990359cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-45d9db80ce4657ef1773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-ba534850b64f39d81fa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f89-0900000000-64e388178db73f06cb20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-c2e1c1e8841cc741dac1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e74c005384d71f4787e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-de4a4c4479ea93d742b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9800000000-da506476184e5c2313a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-03d17084c3cb072c0237View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-c372e3ba919cba4f561fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-8ac435f998deda6437e1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-8900000000-699c510cfaf838ab1922View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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).