Guanine (YMDB00698)

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Identification

YMDB ID

YMDB00698

Name

Guanine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Guanine, 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

MOL SDF PDB SMILES InChI

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 number

73-40-5

Weight

Average: 151.1261
Monoisotopic: 151.049409807

InChI Key

UYTPUPDQBNUYGX-UHFFFAOYSA-N

InChI

InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

IUPAC Name

2-amino-6,7-dihydro-3H-purin-6-one

Traditional IUPAC Name

2-aminohypoxanthine

Chemical Formula

C₅H₅N₅O

SMILES

NC1=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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purines 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:16235 )
2-aminopurines (CHEBI:16235 )
purine nucleobase (CHEBI:16235 )
purines (C00242 )
a purine base (GUANINE )
a purine (GUANINE )

Physical Properties

State

Solid

Charge

Melting point

360 °C

Experimental Properties

Property	Value	Reference
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

Property	Value	Source
Water Solubility	2.31 g/L	ALOGPS
logP	-0.92	ALOGPS
logP	-0.59	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	2.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.9 m³·mol⁻¹	ChemAxon
Polarizability	13.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
mitochondrion
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Purine metabolism

ec00230

SMPDB Reactions

Not Available

KEGG Reactions

water + Guanosine → D-Ribose + Guanine

water + hydron + Guanine → Xanthine + Ammonium

Phosphoribosyl pyrophosphate + Guanine → Pyrophosphate + Guanosine monophosphate

2'-Deoxyguanosine + phosphate ↔ 2-deoxy-D-ribofuranose 1-phosphate + Guanine

phosphate + Guanosine ↔ Ribose 1-phosphate + Guanine

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-1938000000-e15e09f2007f35659bb9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-3739000000-66a080b08ba9b9f82e20	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-5900000000-0a63148e3a8dc8d026df	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1938000000-e15e09f2007f35659bb9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-3739000000-66a080b08ba9b9f82e20	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-2928000000-073bf70794fe99ce737f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-2790000000-77e6b5b71c9ff6ad2b23	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ff0-5900000000-f103c75addeafe7ac6f0	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0901000000-2864e73c83444d566e9a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-2900000000-4229d3d01623054b4ceb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-d5ae84fefadd84f988b4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-7d48b2e8db6967e98407	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0uxr-0900000000-67a7784963ec75cecaa0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-4569516f23d8a712b434	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-d928cac1226f19b8edc3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-34059351f2cbd94a8acc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udj-0903100000-deb9c022884d7c98782e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-45d9db80ce4657ef1773	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-1900000000-86b7ee5755cbb8236f5b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-ba534850b64f39d81fa0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-422f992621ab9626d1b2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f89-0900000000-64e388178db73f06cb20	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-f0a95c55947ca990359c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-45d9db80ce4657ef1773	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-ba534850b64f39d81fa0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f89-0900000000-64e388178db73f06cb20	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-c2e1c1e8841cc741dac1	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-e74c005384d71f4787e5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-de4a4c4479ea93d742b5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-9800000000-da506476184e5c2313a4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-03d17084c3cb072c0237	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-c372e3ba919cba4f561f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-8ac435f998deda6437e1	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-8900000000-699c510cfaf838ab1922	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	16235
HMDB ID	HMDB00132
Pubchem Compound ID	764
Kegg ID	C00242
ChemSpider ID	744
FOODB ID	FDB004222
Wikipedia	Guanine
BioCyc ID	GUANINE

Enzymes

Protein Details

1. Purine nucleoside phosphorylase

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.

Protein Details

2. Vitamin B6 transporter TPN1

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

Protein Details

3. Probable guanine deaminase

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).

Protein Details

4. Hypoxanthine-guanine phosphoribosyltransferase

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.

Protein Details

5. Uridine nucleosidase

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

Protein Details

1. Purine-cytosine permease FCY21

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Probable purine-cytosine permease
Gene Name:: FCY21
Uniprot ID:: P40039
Molecular weight:: 58049.60156

Protein Details

2. Purine-cytosine permease FCY2

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

Protein Details

3. Purine-cytosine permease FCY22

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Probable purine-cytosine permease
Gene Name:: FCY22
Uniprot ID:: Q12119
Molecular weight:: 57326.69922

Structure for #<Compound:0xad0d2b24>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters