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Record Information
Version1.0
Creation Date2016-09-30 22:19:59 UTC
Update Date2020-06-04 20:46:51 UTC
MCDB ID BMDB0000132
Secondary Accession Numbers
  • BMDB00132
Metabolite Identification
Common 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 exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Guanine exists in all living species, ranging from bacteria to humans. Guanine has been found to be associated with several diseases known as colorectal cancer, alzheimer's disease, lewy body disease, and frontotemporal dementia; also guanine has been linked to the inborn metabolic disorders including lesch-nyhan syndrome.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC5H5N5O
Average Molecular Weight151.1261
Monoisotopic Molecular Weight151.049409807
IUPAC Name2-amino-6,7-dihydro-3H-purin-6-one
Traditional Name2-aminohypoxanthine
CAS Registry Number73-40-5
SMILES
NC1=NC(=O)C2=C(N1)N=CN2
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 KeyUYTPUPDQBNUYGX-UHFFFAOYSA-N
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.08 mg/mL at 37 °CNot Available
LogP-0.91HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-1938000000-e15e09f2007f35659bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-3739000000-66a080b08ba9b9f82e20JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-5900000000-0a63148e3a8dc8d026dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1938000000-e15e09f2007f35659bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3739000000-66a080b08ba9b9f82e20JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-2928000000-073bf70794fe99ce737fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-2790000000-77e6b5b71c9ff6ad2b23JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ff0-5900000000-f103c75addeafe7ac6f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-2864e73c83444d566e9aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-4229d3d01623054b4cebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-d5ae84fefadd84f988b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-7d48b2e8db6967e98407JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0900000000-67a7784963ec75cecaa0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-4569516f23d8a712b434JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d928cac1226f19b8edc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-34059351f2cbd94a8accJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udj-0903100000-deb9c022884d7c98782eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-45d9db80ce4657ef1773JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-1900000000-86b7ee5755cbb8236f5bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-ba534850b64f39d81fa0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-422f992621ab9626d1b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f89-0900000000-64e388178db73f06cb20JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-f0a95c55947ca990359cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-45d9db80ce4657ef1773JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-ba534850b64f39d81fa0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f89-0900000000-64e388178db73f06cb20JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-c2e1c1e8841cc741dac1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e74c005384d71f4787e5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-de4a4c4479ea93d742b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9800000000-da506476184e5c2313a4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-03d17084c3cb072c0237JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-c372e3ba919cba4f561fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-8ac435f998deda6437e1JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-8900000000-699c510cfaf838ab1922JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified6.5 uM details
HMDB IDHMDB0000132
DrugBank IDDB02377
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004222
KNApSAcK IDC00001501
Chemspider ID744
KEGG Compound IDC00242
BioCyc IDGUANINE
BiGG ID34363
Wikipedia LinkGuanine
METLIN ID315
PubChem Compound764
PDB IDNot Available
ChEBI ID16235
References
Synthesis ReferenceXiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]