Guanosine (YMDB00509)

Identification

YMDB ID

YMDB00509

Name

Guanosine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Guanosine is a purine nucleoside. It is formed by a molecule of guanine attached to a ribose sugar molecule. Guanosine is the RNA nucleoside G. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP). These forms play important roles in various biochemical processes such as synthesis of nucleic acids and proteins, photosynthesis, muscle contraction and intracellular signal transduction.

Structure

MOL SDF PDB SMILES InChI

Synonyms

β-D-ribofuranosyl-6H-purin-6-one
β-D-ribofuranosyl-9H-purin-6(1H)-one
2-Amino-1,9-dihydro-9-&beta
2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one
2-Amino-1,9-dihydro-9beta-d-ribofuranosyl-6H-purin-6-one
2-amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one
2-amino-Inosine
2(3H)-Imino-9-&beta
2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-one
6H-Purin-6-one, 2-amino-1,9-dihydro-9-beta-d-ribofuranosyl-
9-β-D-ribofuranosylguanine
9-b-D-ribofuranosyl-Guanine
9-beta-d-Arabinofuranosylguanine
9-beta-D-ribofuranosylguanine
9-beta-delta-ribofuranosyl-Guanine
b-D-Ribofuranoside guanine-9
beta-d-Ribofuranoside, guanine-9
beta-delta-Ribofuranoside guanine-9
GMP
guanine riboside
Guanine-9:beta-D-ribofuranoside
Guanine, 9beta-d-ribofuranosyl-
Guanosin
Guanosine
Guanosine, anhydrous
Guanozin
Guo
ribonucleoside
Vernine
2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one
9-beta-D-Ribofuranosyl-guanine
G
Guanine-9-beta-D-ribofuranoside
2(3H)-Imino-9-b-D-ribofuranosyl-9H-purin-6(1H)-one
2(3H)-Imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-one
2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one
2-Amino-9-b-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one
2-Amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one
9-Β-D-ribofuranosyl-guanine
Guanine-9-b-D-ribofuranoside
Guanine-9-β-D-ribofuranoside
2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one

CAS number

118-00-3

Weight

Average: 283.2407
Monoisotopic: 283.091668551

InChI Key

NYHBQMYGNKIUIF-UUOKFMHZSA-N

InChI

InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1

IUPAC Name

2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

Traditional IUPAC Name

guanosine

Chemical Formula

C₁₀H₁₃N₅O₅

SMILES

NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Imidazopyrimidine
Purine
Hydroxypyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Heteroaromatic compound
Azole
Imidazole
Tetrahydrofuran
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Primary alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanosines (CHEBI:16750 )
Ribonucleosides (C00387 )

Physical Properties

State

Solid

Charge

Melting point

239 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.7 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-1.90 [SANGSTER (1993)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	15.3 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.7	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.16	ChemAxon
pKa (Strongest Basic)	0.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.62 m³·mol⁻¹	ChemAxon
Polarizability	26.03 Å³	ChemAxon
Number of Rings	3	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

Guanosine monophosphate + water → phosphate + Guanosine

water + Guanosine → D-Ribose + Guanine

Adenosine triphosphate + Guanosine → Guanosine monophosphate + hydron + ADP

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) (5 TMS)	splash10-0f7k-1952000000-c57c052c65f3fa9504af	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0feb-0963000000-c91b93f300b50fbc99c1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9440000000-361092fc2dc5206fe655	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00di-9421000000-b2b15c03b8206196f59f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f7k-1952000000-c57c052c65f3fa9504af	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0feb-0963000000-c91b93f300b50fbc99c1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9440000000-361092fc2dc5206fe655	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9421000000-b2b15c03b8206196f59f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zml-9670000000-793c36e66ed6430b932b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0159-4945800000-86e8114119c47d85cc53	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0900000000-ef0cae7d67f9e803f2b2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0900000000-68fb606342b8bb123bb7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f89-0900000000-48d32b9d62eda760619e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f7k-0920000000-f3db23cc762b5fb860e4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-5da62630f03e15d8707c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-1fa2eb473b57a37ecd45	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-d71a3d2995d32c692eb7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0390000000-ff54fe98a9c0e1bc104c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-c023445b0f47e6e7267b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-a094aa75c261cdce24de	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-e114cc69f7ab438abb39	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001j-0795222100-55ad26c7c4d9f64dd759	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-9450dc04b32ca468e146	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-0147dd895ffbecfa9668	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-5d00bb466dd23f062b86	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0f89-0690030010-86fae3a6cae3e2b3de2c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-97217b0084eeac14e7e1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0900000000-d0c65e36192b7ebdaae8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0090000000-bb8ef433eba795395fe3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0090000000-4ceff605ca97b7c0774a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0ue9-0960000000-1c286e55d437f33a29b3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-0900000000-7149427a8c09f429fdbe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0zgi-0900000000-5de849ca7144ca8afe05	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-053r-0900000000-f97dbc10f152af4df778	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0ue9-0970000000-045435f1be487a94195c	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0udl-9400000000-5a915ef7129c50e638a7	JSpectraViewer \| MoNA
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	13C 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
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
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

Synthesis Reference:

Tang, Shengrong; Huang, Weihong; Hou, Zuorong. Process of guanosine production by fermentation. Gongye Weishengwu (1998), 28(4), 11-16.

External Links:

Resource	Link
CHEBI ID	16750
HMDB ID	HMDB00133
Pubchem Compound ID	6802
Kegg ID	C00387
ChemSpider ID	6544
FOODB ID	FDB003632
Wikipedia	Guanosine
BioCyc ID	GUANOSINE

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. 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.

Structure for #<Compound:0xa744be64>

Enzymes

Reactions

Reactions