MiMeDB: Showing metabocard for Guanosine (MMDBc0000038)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:28:06 UTC

Update Date

2022-08-30 23:13:36 UTC

Metabolite ID

MMDBc0000038

Metabolite 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 moiety. Guanosine consists of a guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine is a moderately basic compound (based on its pKa). Guanosine exists in all living species, ranging from bacteria to humans. In humans, guanosine is involved in intracellular signalling through adenosine receptor A2B and adenosine. Outside of the human body, guanosine has been detected, but not quantified in, several different foods, such as leeks, garlic, chicory roots, green bell peppers, and black-eyed peas. This could make guanosine a potential biomarker for the consumption of these foods. Guanosine plays an important role in various biochemical processes such as the synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction (cGMP). Guanosine is a potentially toxic compound. It is very soluble in acetic acid, slightly soluble in water, and insoluble in ethanol, diethyl ether, benzene, and chloroform. The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are both structurally similar to guanosine. Guanosine was also used to make regadenoson. Guanosine is a white, crystalline powder with no odour and a mild saline taste. Guanosine is required for an RNA splicing reaction in mRNA when a "self-splicing" intron removes itself from the mRNA by cutting at both ends, re-ligating, and leaving just the exons on either side to be translated into protein. When guanine is attached by its N9 nitrogen to the C1 carbon of a deoxyribose ring it is known as deoxyguanosine. Guanosine can be found in clovers, coffee plants, and the pollen of pines. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP).

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>
MMDBc0000038

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₀H₁₃N₅O₅

Average Mass

283.2407

Monoisotopic Mass

283.091668551

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Extracellular
Lysosome
Mitochondria

Biospecimen Locations

Blood
Breast Milk
Cellular Cytoplasm
Feces
Placenta
Prostate
Saliva
Urine

Tissue Locations

Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo_sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo_sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo_sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo_sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo_sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo_sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo_sapiens
MMDBp0193933	Purine nucleoside phosphorylase	Enzyme	P00491	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Purine nucleoside phosphorylase deficiency	Increased	Association	Human Urine	HMDB	10102915
Eosinophilic esophagitis	Slight Increase	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	2	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	396	Human feces; Human pleural fluid plaque; Pig ; Human ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	381	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; River trout ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	133	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	218	Human feces; Human appendix biopsy; Human	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	5	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	2	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	7	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Candidatus Melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	6	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	2	Human feces	Metabolic reconstruction
Bacteria	Chlorobi	1
Bacteria/NULL	Proteobacteria	1	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; River trout ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	2	Human feces; Cattle ; Human	Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human	Detected and Quantified			35	588	Adult (>18 years old)	Both	Purine nucleoside phosphorylase (PNP) deficiency	HMDB	10102915
Human	Detected and Quantified			35.0	2588.0	Adult (>18 years old)	Both	Purine nucleoside phosphorylase (PNP) deficiency	HMDB	10102915
Human	Detected and Quantified	<0.1				Infant (0-1 year old)	Both	Normal	HMDB	30817767
Human	Detected and Quantified	0.05	0.02			Adult (>18 years old)	Both	Normal	HMDB	9129323
Human	Detected and Quantified	0.06	0.02			Adult (>18 years old)	Female	Normal	HMDB	9129323
Human	Detected and Quantified	0.06	0.02			Adult (>18 years old)	Both	Normal	HMDB	9129323
Human	Detected and Quantified	0.13		0.022	0.23	Adult (>18 years old)	Both	Normal	HMDB	15116424
Human	Detected and Quantified	0.8	0.5			Adult (>18 years old)	Both	Normal	HMDB	546939
Human	Detected and Quantified	1.01	1.59			Adult (>18 years old)	Female	Normal	HMDB	7702711
Human	Detected and Quantified	4.5	2.9			Adult (>18 years old)	Both	Normal	HMDB	7877593
Human	Detected and Quantified	13.601	7.764			Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified	7.8	8.736			Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified			0	11	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human	Detected and Quantified	0.101	0.0647			Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human	Detected and Quantified	0.227	0.617			Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human	Detected and Quantified	0.262	0.285			Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified					Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified					Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000133

DrugBank ID

DB02857

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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. doi: 10.1002/rcm.1400. [PubMed:15116424 ]
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. doi: 10.1016/s0021-9673(00)95286-5. [PubMed:546939 ]
Traut TW: Physiological concentrations of purines and pyrimidines. Mol Cell Biochem. 1994 Nov 9;140(1):1-22. doi: 10.1007/BF00928361. [PubMed:7877593 ]
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 ]
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. doi: 10.1016/j.nlm.2005.10.006. Epub 2005 Dec 1. [PubMed:16325434 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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 ]

Showing metabocard for Guanosine (MMDBc0000038)

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3D-SDF for #<Metabolite:0x00007f121c02acd0>

PDB for #<Metabolite:0x00007f121c02acd0>

3D PDB for #<Metabolite:0x00007f121c02acd0>

SMILES for #<Metabolite:0x00007f121c02acd0>

INCHI for #<Metabolite:0x00007f121c02acd0>

Structure for #<Metabolite:0x00007f121c02acd0>

3D Structure for #<Metabolite:0x00007f121c02acd0>