GUANOSINE

CAS Number: 118-00-3
EC Number: 204-227-8
Molecular Formula: C10H13N5O5
Molecular weight: 283,24 g/mol

Guanosine is a purine nucleoside, in which the guanine attached to the C1 carbon of a ribose (ribofuranose) ring via a β-N9-glycosidic bond. 
Guanosine phosphorylated derivatives include GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate), and GTP (guanosine triphosphate). 

These guanosine derivatives are very important in various biochemical processes, such as synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction.
Guanosine is thought to have neuroprotective properties. 

Guanosine can reduce neuroinflammation, oxidative stress, and excitotoxicity, as well as exerting trophic effects in neuronal and glial cells. 
Guanosine is shown to be protective in central nervous system diseases including ischemic stroke, Alzheimer’s disease, Parkinson’s disease, spinal cord injury, nociception, and depression. 
Guanosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism.

Guanosine is an aromatic organic molecule and a purine nucleoside. 
Guanosine is present in the cerebrospinal fluid, intestinal cells, blood-brain barrier and in brain microvessels.

Guanosine is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond.

A purine nucleoside, guanine linked by Guanosine N9 nitrogen to the C1 carbon of ribose. 
Guanosine is a component of ribonucleic acid and Guanosine nucleotides play important roles in metabolism.

Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond.
Guanosine possesses anti-HSV activity.

Guanosine (symbol G or Guo) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. 
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 (cGMP). 
When guanine is attached by Guanosine N9 nitrogen to the C1 carbon of a deoxyribose ring Guanosine is known as deoxyguanosine.

Physical and chemical properties
Guanosine is a white, crystalline powder with no odor and mild saline taste.
Guanosine is very soluble in acetic acid, slightly soluble in water, insoluble in ethanol, diethyl ether, benzene and chloroform.

Pharmacology and Biochemistry of Guanosine:

Human Metabolite Information:

Tissue Locations:
Placenta
Prostate

Cellular Locations:
Extracellular
Lysosome
Mitochondria

Metabolite Pathways:
Adenine phosphoribosyltransferase deficiency (APRT)
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Azathioprine Action Pathway
Gout or Kelley-Seegmiller Syndrome
Lesch-Nyhan Syndrome (LNS)
Mercaptopurine Action Pathway
Mitochondrial DNA depletion syndrome

Biochem/physiol Actions of Guanosine:
Guanosine nucleoside elicits cellular effect as the guanine-based purinergic system. 
Guanosine modulates glutamate uptake by glutamate transporters. 

Guanosine may have neuroprotective functionality in central nervous system disorders. 
Guanosine promotes neurite arborization, outgrowth, proliferation and differentiation. 
Administration of guanosine replenished GTP and elicits protective function in renal ischemic injury.

Purification Methods of Guanosine:
Guanosine crystallises from water as a dihydrate. 
Dry Guanosine at 110o.

Functions of Guanosine:
Guanosine is required for an RNA splicing reaction in mRNA, when a "self-splicing" intron removes itself from the mRNA message by cutting at both ends, re-ligating, and leaving just the exons on either side to be translated into protein.

Application of Guanosine:
For use in cell culture applications as a precursor of GMP, GDP, GTP and cGMP.

Guanosine has been used:
As a reference standard for the analysis of glucosinolates by high-performance liquid chromatography with diode-array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI/MS)
As a component of Mouse Embryonic Fibroblasts (MEFs) culture

As a standard for the detection of residual RNA contaminant in oil palm plant genome samples by HPLC
For use in cell culture applications as a precursor of GMP, GDP, GTP and cGMP.

Guanosine is a purine nucleoside that upon sequential phosphoylation (kinases) forms GTP which is used by RNA polymerases to synthesis RNA(s). 
GTP is also important in a wide range of GTPase-dependent cell signaling processes. 
Guanosine is used in selective matricies such a guanosine gels (G-gels) for use in capillary electrophoresis chiral selection and other applications.

Sources of Guanosine:
Guanosine can be found in pancreas, clover, coffee plant, and pollen of pines.

Uses of Guanosine:
The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are structurally similar to guanosine.
Guanosine was also used to make regadenoson.

A constituent of nucleic acids.

Opacifying    
Skin conditioning
Skin-conditioning agent - miscellaneous

Potential Uses of Guanosine:
Biological additives

Use Classification of Guanosine:
Cosmetics - Opacifying; Skin conditioning

Handling and storage of Guanosine:

Precautions for safe handling:
Provide appropriate exhaust ventilation at places where dust is formed.

Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Store in cool place.

Safety Information of Guanosine:

Storage Class Code:
6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK: WGK 3

Personal Protective Equipment:
Dust mask type N95 (US), Eyeshields, Gloves

First aid measures of Guanosine:

If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.

In case of skin contact:
Wash off with soap and plenty of water.

In case of eye contact:
Flush eyes with water as a precaution.

If swallowed:
Never give anything by mouth to an unconscious person. 
Rinse mouth with water.

Indication of any immediate medical attention and special treatment needed:
No data available

Firefighting measures of Guanosine:

Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Special hazards arising from the substance or mixture:
Carbon oxides, Nitrogen oxides (NOx)
Combustible.

Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
 
Further information:
No data available

Accidental release measures of Guanosine:

Personal precautions, protective equipment and emergency procedures:
Avoid dust formation. 
Avoid breathing vapours, mist or gas.

Environmental precautions:
No special environmental precautions required.

Methods and materials for containment and cleaning up:
Sweep up and shovel. 
Keep in suitable, closed containers for disposal.

Identifiers of Guanosine:
CAS Number: 118-00-3
ChEBI: CHEBI:16750
ChEMBL: ChEMBL375655
ChemSpider: 6544
DrugBank: DB02857
ECHA InfoCard: 100.003.844
IUPHAR/BPS: 4567
KEGG: C00387
MeSH: Guanosine
PubChem CID: 765
UNII: 12133JR80S
CompTox Dashboard (EPA): DTXSID00893055
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 check
Key: NYHBQMYGNKIUIF-UUOKFMHZSA-N check
InChI=1/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
Key: NYHBQMYGNKIUIF-UUOKFMHZBU
SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N

Properties of Guanosine:
Biological source: synthetic
Quality Level: 200
Product line: BioReagent
Assay: ≥98%
Form: powder
Technique(s): cell culture | mammalian: suitable
mp: 250 °C (dec.) (lit.)
Solubility: 0.05 M acetic acid: 1 mg/mL, clear, colorless
Shipped in: ambient
Storage temp.: room temp
SMILES string: [H]O[H].NC1=Nc2c(ncn2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1
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
InChI key: NYHBQMYGNKIUIF-UUOKFMHZSA-N

Melting Point: 240ºC
Boiling Point: 756.6±70.0 °C at 760 mmHg
Flash Point: 411.4±35.7 °C
Molecular Formula: C10H13N5O5
Molecular Weight: 283.241
Density: 2.3±0.1 g/cm3

Molecular Weight: 283.24
XLogP3: -1.9
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 7
Rotatable Bond Count: 2
Exact Mass: 283.09166853
Monoisotopic Mass: 283.09166853
Topological Polar Surface Area: 155 Ų
Heavy Atom Count: 20
Complexity: 446
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Chemical formula: C10H13N5O5
Molar mass: 283.241
Appearance: white, crystalline powder
Odor: odorless
Melting point: 239 (decomposes)
Magnetic susceptibility (χ): -149.1·10−6 cm3/mol

Specifications of Guanosine:
Appearance: White to Almost white powder to crystal
Purity(HPLC): min. 98.0 area%
Purity(Nonaqueous Titration): min. 98.0 %
Specific rotation [a]20/D: -72.0 to -80.0 deg(C=1, 1mol/L NaOH sol.)

Related Molecules of Guanosine:    
3-Methyladenine
Hydrocortisone
Acetylcysteine
Tretinoin
Melatonine
Dinoprostone
Nicotinamide
Adenosine triphosphate
4-Acetamidophenol
Prostaglandin E1
Dehydroepiandrosterone
Corticosterone
Progesterone
Docosahexaenoic Acid
NAD+

Names of Guanosine:

IUPAC name of Guanosine:
Guanosine

Preferred IUPAC name of Guanosine:
2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,9-dihydro-6H-purin-6-one

Other names of Guanosine:
Guanine riboside

Synonyms of Guanosine:
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
2-Amino-9-(β-D-ribofuranosyl)-3,9-dihydro-6H-purin-6-on
MFCD00010182
2-amino-Inosine
Guanosine
2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,9-dihydro-6H-purin-6-one
6H-Purin-6-one, 2-amino-1,9-dihydro-9-β-D-ribofuranosyl-
9-(β-D-Ribofuranosyl)guanine
guanine riboside
Inosine,2-amino
2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one
2-Amino-9-(β-D-ribofuranosyl)-9H-purin-6-ol
EINECS 204-227-8
9-β-D-ribofuranosyl-Guanine
2-Amino-9-(β-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-on
vernine
2H-purin-6-ol, 3,9-dihydro-2-imino-9-β-D-ribofuranosyl-
USAF CB-11
Guanine-9-β-D-ribofuranoside
Guanosin
Guanosine Hydrate
Guanine, 9-β-D-ribofuranosyl-
2-Amino-9-β-D-ribofuranosyl-9H-purine-6(1H)-one
9-β-D-ribofuranosylguanine
9H-purin-6-ol, 2-amino-9-β-D-ribofuranosyl-
2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
Guanozin
guanosine
118-00-3
guanine riboside
vernine
Guanozin
USAF CB-11
Guanosin
Inosine, 2-amino-
L-GUANOSINE
Vernine (VAN)
9-beta-D-Ribofuranosylguanine
Guanine-9-beta-D-ribofuranoside
beta-D-Ribofuranoside, guanine-9
Guanine, 9-beta-D-ribofuranosyl-
2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-one
Inosine, 2-amino- (VAN)
Ribofuranoside, guanine-9, beta-D-
2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one
GUANINE-9:BETA-D-RIBOFURANOSIDE
Guo
DL-Guanosine
AI3-52065
MFCD00010182
NSC 19994
9-beta-D-ribofuranosyl-guanine
2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
Guanine, 9-beta-D-ribofuranosyl- (VAN)
UNII-12133JR80S
CHEBI:16750
GR
6H-Purin-6-one, 2-amino-1,9-dihydro-9-beta-D-ribofuranosyl-
9-(beta-D-Ribofuranosyl)guanine
26578-09-6
Guanosine, Anhydrous
12133JR80S
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
2-AMINO-9-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-6,9-DIHYDRO-1H-PURIN-6-ONE
2-amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one
EINECS 204-227-8
9-.beta.-D-ribofuranosylguanine
Ribonucleoside
Guanine, 9.beta.-d-ribofuranosyl-
.beta.-D-Ribofuranoside, guanine-9
3h-guanosine
2-amino-Inosine
1odj
2fqx
9-B-D-RIBOFURANOSYLGUANINE
[3H]-guanosine
Inosine, 2-amino
guanosine-1-15N
guanosine-2-13C
guanosine-3-15N
guanosine-8-13C
guanosine-9-15N
guanosine-N-15N-
guanosine-1'-13C
Guanosine, >=98%
ST057098
guanosine-N,1-15N2
bmse000091
bmse001018
Epitope ID:141493
9-b-D-ribofuranosyl-Guanine
SCHEMBL21217
2(3H)-Imino-9-.beta.-D-ribofuranosyl-9H-purin-6(1H)-one
b-D-Ribofuranoside guanine-9
9-beta-D-ribofuranosyl guanine
CHEMBL375655
GTPL4567
SGCUT00093
9-bet.-D-Ribofuranosyl-guanine
Guanine-9-ss--D-ribofuranoside
SCHEMBL12212184
9-(ss--D-Ribofuranosyl)guanine
Guanine-9-bet.-D-ribofuranoside
DTXSID00893055
guanosine-2-13C-N,1-15N2
9-beta-delta-ribofuranosyl-Guanine
Guanine-9-.beta.-D-ribofuranoside
GUANOSINE ULTRA PURE 100G
197227-95-5
beta-delta-Ribofuranoside guanine-9
Guanosine, >=97.0% (HPLC)
HY-N0097
STR04471
to_000053
ZINC1550030
BBL033925
BDBM50366814
guanosine-2-13C-N,1,3-15N3
s2439
STK801927
AKOS005622500
AKOS007930368
AKOS015896931
AKOS032949764
AM83933
CCG-267277
CS-W020018
DB02857
MCULE-2959607047
Ribofuranoside, guanine-9, .beta.-D-
9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-aminohydropurin -6-one
NCGC00142496-01
NCGC00142496-02
I890
DB-029875
G0171
Guanosine, Vetec(TM) reagent grade, >=98%
C00387
Guanosine, suitable for cell culture, BioReagent
A818517
Q422462
Q-201301
2-Amino-9-bet.-D-ribofuranosyl-9H-purine-6-(1H)-one
2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one
2-Amino-9-.beta.-D-ribofuranosyl-9-H-purine-6(1H)-one
2-Amino-1,9-dihydro-9.beta.-d-ribofuranosyl-6H-purin-6-one
6H-Purin-6-one, 2-amino-1,9-dihydro-9-beta-D-ribofuranosyl
2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one
6H-Purin-6-one, 2-amino-1,9-dihydro-9-.beta.-D-ribofuranosyl-
2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one (Guanosine)
(2R,3R,4S,5R)-2-(2-amino-6-hydroxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purin-6-one
103654-69-9
103654-70-2
146849-94-7
197227-93-3
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one
202933-46-8
244769-87-7
247226-75-1
250586-91-5
250586-97-1
30747-23-0