NP-MRD: Showing NP-Card for Guanosine (NP0001335)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2022-01-19 17:52:53 UTC

NP-MRD ID

NP0001335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Guanosine

Description

Guanosine (G), also known as 2-amino-inosine, 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 sugar moiety. Guanosine consists of a guanine base attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine is a white, crystalline powder with no odor and mild saline taste. It is very soluble in acetic acid, and slightly soluble in water, but insoluble in ethanol, diethyl ether, benzene, and chloroform. Guanosine exists in all living species, ranging from bacteria to plants to humans. High levels of guanosine can be found in clovers, coffee plants, and the pollen of pines. It has been detected, but not quantified in, several different foods, such as leeks, garlic, chicory roots, green bell peppers, and black-eyed peas. Guanosine plays an important role in various biochemical processes including the synthesis of nucleic acids such as RNA and intracellular signal transduction (cGMP). The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are both structurally similar to guanosine. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP). In humans, guanosine is involved in intracellular signalling through the adenosine receptors A1R and A2AR (PMID: 31847113 ). Evidence from rodent and cell models has shown a number of important neurotrophic and neuroprotective effects of guanosine. In particular, it is effective in preventing deleterious consequences of seizures, spinal cord injury, pain, mood disorders and aging-related diseases, such as ischemia, Parkinson’s and Alzheimer’s diseases (PMID: 27699087 ). Studies with rodent models of Parkinson’s disease have shown that guanosine decreases neuronal apoptotic cell death and increases dopaminergic neurons at substantia nigra pars compacta, accompanied by an improvement of motor symptoms in Parkinson’s disease (i.E. A reduction of bradykinesia). Guanosine promotes neurite arborization, outgrowth, proliferation and differentiation. Systemic administration of guanosine for eight weeks (8 mg/kg) has been shown to stimulate neuroprogenitors proliferation in the subventricular zone (SVZ) in a mouse model of Parkinsonism (PMID: 27699087 ). The effect of guanosine treatment is accompanied by an increased number of fibroblast growth factor (FGF-2)-positive cells which is an important regulator of neuroprogenitor/stem cell proliferation, survival and differentiation (PMID: 27699087 ). Guanosine prevents reactive oxygen species (ROS) generation and cell death in hippocampal slices subjected to the oxygen/glucose deprivation (PMID: 31847113 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000133
     RDKit          3D
Guanosine
 33 35  0  0  0  0  0  0  0  0999 V2000
    4.5878   -0.7612   -1.7302 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8079   -0.0580   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660   -0.0780   -0.7910 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    0.6033    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571    1.3357    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3757    1.8743    1.8674 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1847    1.5004    1.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074    0.7160    0.2985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6087    0.1007   -0.5325 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7947    0.8037   -0.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -0.1339   -0.7659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1628    0.4077   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820    1.5112   -1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985   -1.2396    0.1931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0349   -2.4361   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.3058   -0.0827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7405   -2.1505   -1.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335    1.3466    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920    2.0183    2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    0.6656    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -1.7994   -1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612   -0.2079   -2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    1.7974    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    0.1233   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -0.5225   -1.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3112    0.5371    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878   -0.4047   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672    2.3467   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -0.9502    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565   -3.0289    0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -1.6151    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -1.6757   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354    0.6793    0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
  8  4  1  0
 16  9  1  0
  1 21  1  0
  1 22  1  0
  7 23  1  0
  9 24  1  6
 11 25  1  6
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  1
 15 30  1  0
 16 31  1  1
 17 32  1  0
 20 33  1  0
M  END


  Mrv1652309032023532D          

 20 22  0  0  1  0            999 V2000
    0.9372   -1.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227   -1.4642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9371   -2.7017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516   -2.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516   -1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362   -1.2093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211   -1.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362   -2.5442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6911   -3.3290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2062   -3.9963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6911   -4.6639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4361   -5.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882   -6.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4757   -4.4089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1432   -4.8939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758   -3.5839    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1432   -3.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226   -2.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918   -2.7017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9372   -0.2267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 20  1  2  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2 18  1  0  0  0  0
 18  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001335

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C10H13N5O5

> <MOLECULAR_WEIGHT>
283.2407

> <EXACT_MASS>
283.091668551

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.0315249439995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.06

> <JCHEM_LOGP>
-2.706218196

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.456833616816144

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.15572249859448

> <JCHEM_PKA_STRONGEST_BASIC>
0.4462064218132451

> <JCHEM_POLAR_SURFACE_AREA>
155.22000000000003

> <JCHEM_REFRACTIVITY>
64.62109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guanosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000133
     RDKit          3D
Guanosine
 33 35  0  0  0  0  0  0  0  0999 V2000
    4.5878   -0.7612   -1.7302 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8079   -0.0580   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660   -0.0780   -0.7910 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    0.6033    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571    1.3357    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3757    1.8743    1.8674 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1847    1.5004    1.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074    0.7160    0.2985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6087    0.1007   -0.5325 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7947    0.8037   -0.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -0.1339   -0.7659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1628    0.4077   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820    1.5112   -1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985   -1.2396    0.1931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0349   -2.4361   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.3058   -0.0827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7405   -2.1505   -1.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335    1.3466    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920    2.0183    2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    0.6656    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -1.7994   -1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612   -0.2079   -2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    1.7974    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    0.1233   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -0.5225   -1.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3112    0.5371    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878   -0.4047   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672    2.3467   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -0.9502    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565   -3.0289    0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -1.6151    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -1.6757   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354    0.6793    0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
  8  4  1  0
 16  9  1  0
  1 21  1  0
  1 22  1  0
  7 23  1  0
  9 24  1  6
 11 25  1  6
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  1
 15 30  1  0
 16 31  1  1
 17 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       1.749  -1.963   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.416  -2.733   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       1.749  -5.043   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.083  -4.273   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.083  -2.733   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.548  -2.257   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.453  -3.503   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.548  -4.749   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.023  -6.214   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.118  -7.460   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.023  -8.706   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.547 -10.171   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.578 -11.315   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.488  -8.230   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.734  -9.135   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.488  -6.690   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.734  -5.785   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.416  -4.273   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -0.918  -5.043   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       1.749  -0.423   0.000  0.00  0.00           O+0
CONECT    1   20    2    5                                                  
CONECT    2    1   18                                                       
CONECT    3   18    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16    9   14   17                                                  
CONECT   17   16                                                            
CONECT   18    2    3   19                                                  
CONECT   19   18                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0000133
HETATM    1  N1  UNL     1       4.588  -0.761  -1.730  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.808  -0.058  -0.771  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.466  -0.078  -0.791  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.743   0.603   0.138  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.357   1.336   1.130  1.00  0.00           C  
HETATM    6  N3  UNL     1       1.376   1.874   1.867  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.185   1.500   1.365  1.00  0.00           C  
HETATM    8  N4  UNL     1       0.407   0.716   0.298  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.609   0.101  -0.532  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.795   0.804  -0.521  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.789  -0.134  -0.766  1.00  0.00           C  
HETATM   12  C7  UNL     1      -4.163   0.408  -0.471  1.00  0.00           C  
HETATM   13  O2  UNL     1      -4.482   1.511  -1.227  1.00  0.00           O  
HETATM   14  C8  UNL     1      -2.399  -1.240   0.193  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.035  -2.436  -0.109  1.00  0.00           O  
HETATM   16  C9  UNL     1      -0.906  -1.306  -0.083  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.740  -2.151  -1.180  1.00  0.00           O  
HETATM   18  C10 UNL     1       3.734   1.347   1.138  1.00  0.00           C  
HETATM   19  O5  UNL     1       4.292   2.018   2.048  1.00  0.00           O  
HETATM   20  N5  UNL     1       4.405   0.666   0.209  1.00  0.00           N  
HETATM   21  H1  UNL     1       4.630  -1.799  -1.814  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.161  -0.208  -2.402  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.793   1.797   1.774  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.233   0.123  -1.591  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.684  -0.522  -1.783  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.311   0.537   0.618  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.888  -0.405  -0.771  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.067   2.347  -0.850  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.508  -0.950   1.251  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.957  -3.029   0.656  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.321  -1.615   0.789  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.908  -1.676  -2.029  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.435   0.679   0.223  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3    3   20
CONECT    3    4
CONECT    4    5    5    8
CONECT    5    6   18
CONECT    6    7    7
CONECT    7    8   23
CONECT    8    9
CONECT    9   10   16   24
CONECT   10   11
CONECT   11   12   14   25
CONECT   12   13   26   27
CONECT   13   28
CONECT   14   15   16   29
CONECT   15   30
CONECT   16   17   31
CONECT   17   32
CONECT   18   19   19   20
CONECT   20   33
END

HMDB0000133
     RDKit          3D
Guanosine
 33 35  0  0  0  0  0  0  0  0999 V2000
    4.5878   -0.7612   -1.7302 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8079   -0.0580   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660   -0.0780   -0.7910 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    0.6033    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571    1.3357    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3757    1.8743    1.8674 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1847    1.5004    1.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074    0.7160    0.2985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6087    0.1007   -0.5325 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7947    0.8037   -0.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -0.1339   -0.7659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1628    0.4077   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820    1.5112   -1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985   -1.2396    0.1931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0349   -2.4361   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.3058   -0.0827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7405   -2.1505   -1.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335    1.3466    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920    2.0183    2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    0.6656    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -1.7994   -1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612   -0.2079   -2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    1.7974    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    0.1233   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -0.5225   -1.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3112    0.5371    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878   -0.4047   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672    2.3467   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -0.9502    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565   -3.0289    0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -1.6151    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -1.6757   -2.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354    0.6793    0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
  8  4  1  0
 16  9  1  0
  1 21  1  0
  1 22  1  0
  7 23  1  0
  9 24  1  6
 11 25  1  6
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  1
 15 30  1  0
 16 31  1  1
 17 32  1  0
 20 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-one	ChEBI
2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one	ChEBI
2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one	ChEBI
9-beta-D-Ribofuranosyl-guanine	ChEBI
G	ChEBI
Guanine riboside	ChEBI
Guanine-9-beta-D-ribofuranoside	ChEBI
Guanosin	ChEBI
Guo	ChEBI
2(3H)-Imino-9-b-D-ribofuranosyl-9H-purin-6(1H)-one	Generator
2(3H)-Imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-one	Generator
2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one	Generator
2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one	Generator
2-Amino-9-b-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one	Generator
2-Amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one	Generator
9-b-D-Ribofuranosyl-guanine	Generator
9-Β-D-ribofuranosyl-guanine	Generator
Guanine-9-b-D-ribofuranoside	Generator
Guanine-9-β-D-ribofuranoside	Generator
2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one	HMDB
2-Amino-inosine	HMDB
9-beta-delta-Ribofuranosyl-guanine	HMDB
b-D-Ribofuranoside guanine-9	HMDB
beta-delta-Ribofuranoside guanine-9	HMDB
Ribonucleoside	HMDB
Vernine	HMDB

Chemical Formula

C₁₀H₁₃N₅O₅

Average Mass

283.2407 Da

Monoisotopic Mass

283.09167 Da

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 Name

guanosine

CAS Registry Number

118-00-3

SMILES

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

InChI Identifier

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-01-19	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	v.dorna83@yahoo.com	Not Available	Not Available	2021-08-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-08-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Actinidia chinensis	FooDB	FooDB
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	FooDB	FooDB
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	FooDB
Apium graveolens	FooDB	FooDB
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Arabidopsis thaliana	LOTUS Database	35616633
Arachis hypogaea	FooDB	FooDB
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	FooDB
Artemisia dracunculus	FooDB	FooDB
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	FooDB
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	FooDB
Bison bison	FooDB	FooDB
Borago officinalis	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Ceratonia siliqua	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chlamydomonas reinhardtii	LOTUS Database	35616633
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea canephora	FooDB	FooDB
Colocasia esculenta	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	FooDB
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eurycoma longifolia	LOTUS Database	35616633
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Fritillaria cirrhosa	KNApSAcK Database	22123792
Gallus gallus	FooDB	FooDB
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glycine max	FooDB	FooDB
Gossypium	FooDB	FooDB
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Hordeum vulgare	FooDB	FooDB
Hyssopus officinalis L.	FooDB	FooDB
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Linum usitatissimum	FooDB	FooDB
Litchi chinensis	FooDB	FooDB
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	FooDB
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	FooDB
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Mycoplasmopsis bovis	LOTUS Database	35616633
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nephelium lappaceum	FooDB	FooDB
Neptunea antiqua	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Ophiocordyceps sinensis	LOTUS Database	35616633
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Ovis aries	FooDB	FooDB
Pachliopta aristolochiae	LOTUS Database	35616633
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	FooDB
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	FooDB
Peucedanum japonicum	LOTUS Database	35616633
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	FooDB
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	FooDB
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Pleurotus ostreatus	FooDB	FooDB
Polygonum alpinum	FooDB	FooDB
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	FooDB
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Rheum rhabarbarum	FooDB	FooDB
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Sauropus androgynus	KNApSAcK Database	22123792
Scorzonera hispanica	FooDB	FooDB
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sinocrassula indica	KNApSAcK Database	22123792
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	FooDB
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	FooDB
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Subergorgia suberosa	-	KNApSAcK
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Triticum	FooDB	FooDB
Triticum aestivum	KNApSAcK Database	22123792
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633
Typha angustifolia	FooDB	FooDB
Ulva pertusa	LOTUS Database	35616633
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays	LOTUS Database	35616633
Zea mays L.	KNApSAcK Database	22123792
Zingiber officinale	FooDB	FooDB
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

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

Experimental Properties

Property	Value	Reference
Melting Point	239 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.7 mg/mL at 18 °C	Not Available
LogP	-1.90	Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000133

DrugBank ID

DB02857

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

6802

PDB ID

Not Available

ChEBI ID

16750

Good Scents ID

rw1248901

References

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. [PubMed:15116424 ]
Traut TW: Physiological concentrations of purines and pyrimidines. Mol Cell Biochem. 1994 Nov 9;140(1):1-22. [PubMed:7877593 ]
Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]
Hartwick RA, Krstulovic AM, Brown PR: Identification and quantitation of nucleosides, bases and other UV-absorbing compounds in serum, using reversed-phase high-performance liquid chromatography. II. Evaluation of human sera. J Chromatogr. 1979 Dec 30;186:659-76. [PubMed:546939 ]
Saute JA, da Silveira LE, Soares FA, Martini LH, Souza DO, Ganzella M: Amnesic effect of GMP depends on its conversion to guanosine. Neurobiol Learn Mem. 2006 May;85(3):206-12. Epub 2005 Dec 1. [PubMed:16325434 ]
Lanznaster D, Massari CM, Markova V, Simkova T, Duroux R, Jacobson KA, Fernandez-Duenas V, Tasca CI, Ciruela F: Adenosine A1-A2A Receptor-Receptor Interaction: Contribution to Guanosine-Mediated Effects. Cells. 2019 Dec 13;8(12). pii: cells8121630. doi: 10.3390/cells8121630. [PubMed:31847113 ]
Lanznaster D, Dal-Cim T, Piermartiri TC, Tasca CI: Guanosine: a Neuromodulator with Therapeutic Potential in Brain Disorders. Aging Dis. 2016 Oct 1;7(5):657-679. doi: 10.14336/AD.2016.0208. eCollection 2016 Oct. [PubMed:27699087 ]
Lin HT, Chen CC, Chiao DJ, Chang TY, Chen XA, Young JJ, Kuo SC: Nanoparticular CpG-adjuvanted SARS-CoV-2 S1 protein elicits broadly neutralizing and Th1-biased immunoreactivity in mice. Int J Biol Macromol. 2021 Dec 15;193(Pt B):1885-1897. doi: 10.1016/j.ijbiomac.2021.11.020. Epub 2021 Nov 11. [PubMed:34774590 ]

Showing NP-Card for Guanosine (NP0001335)

MOL for NP0001335 (Guanosine)

3D MOL for NP0001335 (Guanosine)

3D SDF for NP0001335 (Guanosine)

3D-SDF for NP0001335 (Guanosine)

PDB for NP0001335 (Guanosine)

3D PDB for NP0001335 (Guanosine)

SMILES for NP0001335 (Guanosine)

INCHI for NP0001335 (Guanosine)

Structure for NP0001335 (Guanosine)

3D Structure for NP0001335 (Guanosine)