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Identification
YMDB IDYMDB00698
NameGuanine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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.
Structure
Thumb
Synonyms
  • 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
  • GUA
  • Guanin
  • Guanine
  • Guanine enol
  • GUN
  • Naturon
  • Pathocidin
  • 2-Amino-6-oxopurine
  • G
  • C.I. natural white 1
  • CI natural white 1
  • Dew pearl
  • Mearlmaid
  • Mearlmaid aa
  • Natural pearl essence
  • Natural white 1
  • Pearl essence
  • Stella polaris
CAS number73-40-5
WeightAverage: 151.1261
Monoisotopic: 151.049409807
InChI KeyUYTPUPDQBNUYGX-UHFFFAOYSA-N
InChIInChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
IUPAC Name2-amino-6,7-dihydro-3H-purin-6-one
Traditional IUPAC Name2-aminohypoxanthine
Chemical FormulaC5H5N5O
SMILESNC1=NC2=C(N=CN2)C(=O)N1
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
Charge0
Melting point360 °C
Experimental Properties
PropertyValueReference
Water Solubility2.08 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-0.91 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
water + GuanosineD-Ribose + Guanine
water + hydron + GuanineXanthine + Ammonium
Phosphoribosyl pyrophosphate + GuaninePyrophosphate + Guanosine monophosphate
2'-Deoxyguanosine + phosphate2-deoxy-D-ribofuranose 1-phosphate + Guanine
phosphate + GuanosineRibose 1-phosphate + Guanine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
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
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-de4a4c4479ea93d742b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9800000000-da506476184e5c2313a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-03d17084c3cb072c0237JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-c372e3ba919cba4f561fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-8ac435f998deda6437e1JSpectraViewer
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
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Cazzaniga, P., Pescini, D., Besozzi, D., Mauri, G., Colombo, S., Martegani, E. (2008). "Modeling and stochastic simulation of the Ras/cAMP/PKA pathway in the yeast Saccharomyces cerevisiae evidences a key regulatory function for intracellular guanine nucleotides pools." J Biotechnol 133:377-385.18023904
  • Iglesias-Gato, D., Martin-Marcos, P., Santos, M. A., Hinnebusch, A. G., Tamame, M. (2011). "Guanine nucleotide pool imbalance impairs multiple steps of protein synthesis and disrupts GCN4 translational control in Saccharomyces cerevisiae." Genetics 187:105-122.20980241
  • Saint-Marc, C., Daignan-Fornier, B. (2004). "GUD1 (YDL238c) encodes Saccharomyces cerevisiae guanine deaminase, an enzyme expressed during post-diauxic growth." Yeast 21:1359-1363.15565584
Synthesis Reference:Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
External Links:
ResourceLink
CHEBI ID16235
HMDB IDHMDB00132
Pubchem Compound ID764
Kegg IDC00242
ChemSpider ID744
FOODB IDFDB004222
WikipediaGuanine
BioCyc IDGUANINE

Enzymes

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:
PNP1
Uniprot ID:
Q05788
Molecular weight:
33754.60156
Reactions
Purine nucleoside + phosphate → purine + alpha-D-ribose 1-phosphate.
General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
Thiamine-regulated, high affinity import carrier of pyridoxine, pyridoxal and pyridoxamine
Gene Name:
TPN1
Uniprot ID:
P53099
Molecular weight:
64545.80078
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia
Gene Name:
GUD1
Uniprot ID:
Q07729
Molecular weight:
55203.19922
Reactions
Guanine + H(2)O → xanthine + NH(3).
General function:
Involved in nucleoside metabolic process
Specific function:
IMP + diphosphate = hypoxanthine + 5-phospho- alpha-D-ribose 1-diphosphate
Gene Name:
HPT1
Uniprot ID:
Q04178
Molecular weight:
25190.5
Reactions
IMP + diphosphate → hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate.
GMP + diphosphate → guanine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
Specific function:
Also acts on cytidine
Gene Name:
URH1
Uniprot ID:
Q04179
Molecular weight:
37960.0
Reactions
Uridine + H(2)O → D-ribose + uracil.

Transporters

General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
Probable purine-cytosine permease
Gene Name:
FCY21
Uniprot ID:
P40039
Molecular weight:
58049.60156
General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
This permease has a broad specificity towards purines, and also transport cytosine and 5-methylcytosine but neither uracil nor thymine
Gene Name:
FCY2
Uniprot ID:
P17064
Molecular weight:
58200.69922
General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
Probable purine-cytosine permease
Gene Name:
FCY22
Uniprot ID:
Q12119
Molecular weight:
57326.69922