Record Information
Creation Date2012-05-31 10:21:39 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00132
Description:Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. 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. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin. (PMID: 16352449, 2435586)
  • 2-Amino-1,7-dihydro-6H-Purin-6-one
  • 2-Amino-1,9-dihydro-6H-purin-6-one
  • 2-Amino-1,9-dihydro-purin-6-one
  • 2-Amino-3,7-dihydro-6H-purin-6-one
  • 2-Amino-6-hydroxy-1H-purine
  • 2-Amino-6-hydroxypurine
  • 2-Amino-6-purinol
  • 2-Amino-Hypoxanthine
  • 2-Aminohypoxanthine
  • 6-Hydroxy-2-aminopurine
  • C.I. Natural White 1
  • CI Natural white 1
  • Dew Pearl
  • GUA
  • Guanin
  • Guanine
  • Guanine enol
  • GUN
  • Mearlmaid
  • Mearlmaid AA
  • Natural pearl essence
  • Natural White 1
  • Naturon
  • Pathocidin
  • Pearl Essence
  • Stella Polaris
Chemical Formula:C5H5N5O
Weight:Average: 151.1261
Monoisotopic: 151.049409807
CAS number:73-40-5
IUPAC Name:2-amino-6,7-dihydro-3H-purin-6-one
Traditional IUPAC Name:2-aminohypoxanthine
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentPurines and purine derivatives
Alternative Parents
  • 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
Melting point:360 °C
Experimental Properties:
Water Solubility:2.08 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-0.91 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
Water Solubility2.31 mg/mLALOGPS
pKa (Strongest Acidic)8.95ChemAxon
pKa (Strongest Basic)2.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.16 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.9 m3·mol-1ChemAxon
Polarizability13.34 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
SMPDB Pathways:
guanine and guanosine salvagePW002074 Pw002074Pw002074 greyscalePw002074 simple
preQ0 metabolismPW001893 Pw001893Pw001893 greyscalePw001893 simple
purine deoxyribonucleosides degradationPW002077 Pw002077Pw002077 greyscalePw002077 simple
purine ribonucleosides degradationPW002076 Pw002076Pw002076 greyscalePw002076 simple
KEGG Pathways:
EcoCyc Pathways:
  • guanine and guanosine salvage I PWY-6620
  • guanosine nucleotides degradation III PWY-6608
  • purine deoxyribonucleosides degradation PWY0-1297
  • purine ribonucleosides degradation to ribose-1-phosphate PWY0-1296
  • queuosine biosynthesis PWY-6700
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
188± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
3± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
3± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
65± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-1938000000-e15e09f2007f35659bb9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-3739000000-66a080b08ba9b9f82e20View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0ff0-5900000000-f103c75addeafe7ac6f0View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-5900000000-0a63148e3a8dc8d026dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-1938000000-e15e09f2007f35659bb9View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0udi-3739000000-66a080b08ba9b9f82e20View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-2928000000-073bf70794fe99ce737fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000t-2790000000-77e6b5b71c9ff6ad2b23View 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 Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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  • Liu Z, Li T, Wang E: Simultaneous determination of guanine, uric acid, hypoxanthine and xanthine in human plasma by reversed-phase high-performance liquid chromatography with amperometric detection. Analyst. 1995 Aug;120(8):2181-4. Pubmed: 7677251
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  • Weimann A, Belling D, Poulsen HE: Quantification of 8-oxo-guanine and guanine as the nucleobase, nucleoside and deoxynucleoside forms in human urine by high-performance liquid chromatography-electrospray tandem mass spectrometry. Nucleic Acids Res. 2002 Jan 15;30(2):E7. Pubmed: 11788733
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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Synthesis Reference:Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
Pubchem Compound ID764
Kegg IDC00242
ChemSpider ID744
Ligand ExpoGUN


General function:
Involved in queuine tRNA-ribosyltransferase activity
Specific function:
Exchanges the guanine residue with 7-aminomethyl-7- deazaguanine in tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr). After this exchange, a cyclopentendiol moiety is attached to the 7-aminomethyl group of 7-deazaguanine, resulting in the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis- dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine)
Gene Name:
Uniprot ID:
Molecular weight:
[tRNA]-guanine + queuine = [tRNA]-queuine + guanine.
[tRNA]-guanine + 7-aminomethyl-7-carbaguanine = [tRNA]-7-aminomethyl-7-carbaguanine + guanine.
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
This enzyme acts exclusively on hypoxanthine; it does not act on guanine
Gene Name:
Uniprot ID:
Molecular weight:
IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in nucleoside metabolic process
Specific function:
Acts on guanine, xanthine and to a lesser extent hypoxanthine
Gene Name:
Uniprot ID:
Molecular weight:
XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine.
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
Uniprot ID:
Molecular weight:
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate.
General function:
Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
Specific function:
Hydrolyzes cytidine or uridine to ribose and cytosine or uracil, respectively. Has a clear preference for cytidine over uridine. Strictly specific for ribonucleosides. Has a low but significant activity for the purine nucleoside xanthosine
Gene Name:
Uniprot ID:
Molecular weight:
A pyrimidine nucleoside + H(2)O = D-ribose + a pyrimidine base.
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis
Gene Name:
Uniprot ID:
Molecular weight:
AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia
Gene Name:
Uniprot ID:
Molecular weight:
Guanine + H(2)O = xanthine + NH(3).
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the nucleoside molecule, with the formation of the corresponding free bases and pentose-1-phosphate. This protein can degrade all purine nucleosides except adenosine and deoxyadenosine
Gene Name:
Uniprot ID:
Molecular weight:


General function:
Involved in transporter activity
Specific function:
Specific, proton motive force-dependent high-affinity transporter for xanthine
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Constitutes the receptor for colicin K and phage T6, and functions as substrate-specific channel for nucleosides and deoxynucleosides
Gene Name:
Uniprot ID:
Molecular weight: