MiMeDB: Showing metabocard for Cyclic GMP (MMDBc0029763)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:40:37 UTC

Update Date

2024-10-13 14:38:33 UTC

Metabolite ID

MMDBc0029763

Metabolite Identification

Common Name

Cyclic GMP

Description

Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger.

Structure

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

HMDB0001314
     RDKit          3D
Cyclic GMP
 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.7949    2.6944   -0.2952 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017    1.2948   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671    0.7883    0.1330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1126   -0.5087    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589   -1.3780    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -2.5869    0.7150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -2.4781    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672   -1.2123    0.5762 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240   -0.5686    0.5428 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4551   -0.0072   -0.7504 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521    0.4327   -0.7188 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3398    0.7935   -2.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061    1.0505   -1.8392 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335    1.1080   -0.2265 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.6557    0.9755   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7059    2.5644    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -0.2241    0.6478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362   -0.7725   -0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4694   -1.5189    0.5759 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8632   -1.8999    1.8388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4517   -0.8683    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4245   -1.6531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6308    0.4398    0.0530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489    3.4127    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1760    3.0557   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -3.2800    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    0.1862    1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070    1.2890   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271    1.6263   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -0.1123   -2.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648    2.5337    1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001   -1.3539   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997   -2.4168   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -2.1957    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.7896   -0.0701 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
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  5 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
  8  4  1  0
 19  9  1  0
 18 11  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  9 27  1  1
 11 28  1  1
 12 29  1  0
 12 30  1  0
 16 31  1  0
 18 32  1  6
 19 33  1  6
 20 34  1  0
 23 35  1  0
M  END


  Mrv0541 02231219032D          

 23 26  0  0  1  0            999 V2000
    1.2019    0.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697    0.6774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349    0.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2818   -0.6044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1980    0.4308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8510    1.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125    1.5041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817    0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0703   -0.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4516   -0.3126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8719    0.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7755   -0.4342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382    0.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1641   -1.8306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2714   -0.3126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0626   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5284    0.4655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8619   -0.8997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204    0.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7650   -0.6461    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9387    0.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720   -1.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5431   -0.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  5  2  1  1  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  8 12  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  6  0  0  0
 11 17  1  0  0  0  0
 15 18  1  6  0  0  0
 17 19  1  1  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
  6  7  2  0  0  0  0
  9 12  1  0  0  0  0
 15 17  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029763

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1

> <INCHI_KEY>
ZOOGRGPOEVQQDX-UUOKFMHZSA-N

> <FORMULA>
C10H12N5O7P

> <MOLECULAR_WEIGHT>
345.2053

> <EXACT_MASS>
345.047434275

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.18621554882084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-1.98

> <JCHEM_LOGP>
-2.0959093467809238

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.156306471801443

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0500583837133326

> <JCHEM_PKA_STRONGEST_BASIC>
1.413587936272232

> <JCHEM_POLAR_SURFACE_AREA>
170.51999999999998

> <JCHEM_REFRACTIVITY>
71.715

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclic-GMP

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001314
     RDKit          3D
Cyclic GMP
 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.7949    2.6944   -0.2952 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017    1.2948   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671    0.7883    0.1330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1126   -0.5087    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589   -1.3780    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -2.5869    0.7150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -2.4781    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672   -1.2123    0.5762 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240   -0.5686    0.5428 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4551   -0.0072   -0.7504 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521    0.4327   -0.7188 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3398    0.7935   -2.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061    1.0505   -1.8392 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335    1.1080   -0.2265 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.6557    0.9755   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7059    2.5644    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -0.2241    0.6478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362   -0.7725   -0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4694   -1.5189    0.5759 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8632   -1.8999    1.8388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4517   -0.8683    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4245   -1.6531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6308    0.4398    0.0530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489    3.4127    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1760    3.0557   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -3.2800    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    0.1862    1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070    1.2890   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271    1.6263   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -0.1123   -2.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648    2.5337    1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001   -1.3539   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997   -2.4168   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -2.1957    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.7896   -0.0701 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
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  5 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
  8  4  1  0
 19  9  1  0
 18 11  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  9 27  1  1
 11 28  1  1
 12 29  1  0
 12 30  1  0
 16 31  1  0
 18 32  1  6
 19 33  1  6
 20 34  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       2.244   0.447   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.063   1.264   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.612   1.452   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.393  -1.128   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.370   0.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.589   2.814   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.197   2.808   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.006   0.836   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.865  -1.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.843  -0.584   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.628   1.744   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       5.181  -0.811   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.231   1.751   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       4.040  -3.417   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.373  -0.584   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.117  -1.848   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.853   0.869   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.476  -1.679   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.331   1.349   0.000  0.00  0.00           C+0
HETATM   20  P   UNK     0      -5.161  -1.206   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      -5.486   0.311   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.174  -2.756   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.614  -0.661   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2    7                                                       
CONECT    7    3    6                                                       
CONECT    8    3   12   13                                                  
CONECT    9    4   14   12                                                  
CONECT   10    5   15   16                                                  
CONECT   11    5   17                                                       
CONECT   12    8    9                                                       
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15   10   18   17                                                  
CONECT   16   10                                                            
CONECT   17   11   19   15                                                  
CONECT   18   15   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22   23   21                                             
CONECT   21   19   20                                                       
CONECT   22   20                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0001314
HETATM    1  N1  UNL     1      -3.795   2.694  -0.295  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.602   1.295  -0.034  1.00  0.00           C  
HETATM    3  N2  UNL     1      -2.367   0.788   0.133  1.00  0.00           N  
HETATM    4  C2  UNL     1      -2.113  -0.509   0.379  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.159  -1.378   0.468  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.649  -2.587   0.715  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.306  -2.478   0.780  1.00  0.00           C  
HETATM    8  N4  UNL     1      -0.967  -1.212   0.576  1.00  0.00           N  
HETATM    9  C5  UNL     1       0.324  -0.569   0.543  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.455  -0.007  -0.750  1.00  0.00           O  
HETATM   11  C6  UNL     1       1.752   0.433  -0.719  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.340   0.793  -2.032  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.706   1.051  -1.839  1.00  0.00           O  
HETATM   14  P1  UNL     1       4.134   1.108  -0.227  1.00  0.00           P  
HETATM   15  O3  UNL     1       5.656   0.975  -0.148  1.00  0.00           O  
HETATM   16  O4  UNL     1       3.706   2.564   0.462  1.00  0.00           O  
HETATM   17  O5  UNL     1       3.508  -0.224   0.648  1.00  0.00           O  
HETATM   18  C8  UNL     1       2.536  -0.772  -0.181  1.00  0.00           C  
HETATM   19  C9  UNL     1       1.469  -1.519   0.576  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.863  -1.900   1.839  1.00  0.00           O  
HETATM   21  C10 UNL     1      -4.452  -0.868   0.297  1.00  0.00           C  
HETATM   22  O7  UNL     1      -5.425  -1.653   0.375  1.00  0.00           O  
HETATM   23  N5  UNL     1      -4.631   0.440   0.053  1.00  0.00           N  
HETATM   24  H1  UNL     1      -3.549   3.413   0.431  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.176   3.056  -1.188  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.597  -3.280   0.967  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.432   0.186   1.329  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.807   1.289  -0.019  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.827   1.626  -2.541  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.285  -0.112  -2.699  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.565   2.534   1.437  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.000  -1.354  -0.982  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.200  -2.417  -0.053  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.825  -2.196   1.770  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.604   0.790  -0.070  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3    3   23
CONECT    3    4
CONECT    4    5    5    8
CONECT    5    6   21
CONECT    6    7    7
CONECT    7    8   26
CONECT    8    9
CONECT    9   10   19   27
CONECT   10   11
CONECT   11   12   18   28
CONECT   12   13   29   30
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   16   31
CONECT   17   18
CONECT   18   19   32
CONECT   19   20   33
CONECT   20   34
CONECT   21   22   22   23
CONECT   23   35
END

HMDB0001314
     RDKit          3D
Cyclic GMP
 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.7949    2.6944   -0.2952 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017    1.2948   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671    0.7883    0.1330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1126   -0.5087    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589   -1.3780    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -2.5869    0.7150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -2.4781    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672   -1.2123    0.5762 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240   -0.5686    0.5428 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4551   -0.0072   -0.7504 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521    0.4327   -0.7188 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3398    0.7935   -2.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061    1.0505   -1.8392 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335    1.1080   -0.2265 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.6557    0.9755   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7059    2.5644    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -0.2241    0.6478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362   -0.7725   -0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4694   -1.5189    0.5759 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8632   -1.8999    1.8388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4517   -0.8683    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4245   -1.6531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6308    0.4398    0.0530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489    3.4127    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1760    3.0557   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -3.2800    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    0.1862    1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070    1.2890   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271    1.6263   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -0.1123   -2.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648    2.5337    1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001   -1.3539   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997   -2.4168   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -2.1957    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    0.7896   -0.0701 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
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  5 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
  8  4  1  0
 19  9  1  0
 18 11  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  9 27  1  1
 11 28  1  1
 12 29  1  0
 12 30  1  0
 16 31  1  0
 18 32  1  6
 19 33  1  6
 20 34  1  0
 23 35  1  0
M  END

Synonyms

Value	Source
CGMP	ChEBI
Guanosine 3',5'-cyclic monophosphate	ChEBI
Guanosine 3',5'-cyclic phosphate	ChEBI
Guanosine cyclic monophosphate	ChEBI
Guanosine 3',5'-cyclic monophosphoric acid	Generator
Guanosine 3',5'-cyclic phosphoric acid	Generator
Guanosine cyclic monophosphoric acid	Generator
3',5'-Cyclic GMP	HMDB
3',5'-Guanosine	HMDB
3',5'-Guanosine monophosphate	HMDB
Cyclic 3',5'-guanosine monophosphate	HMDB
Cyclic guanosine 3',5'-monophosphate	HMDB
Cyclic-GMP	HMDB
Guanosine 3',5'-cyclic-monophosphate	HMDB
Guanosine 3',5'-monophosphate	HMDB
Guanosine cyclic-monophosphate	HMDB
Guanosine-cyclic-phosphoric-acid	HMDB
Cyclic 3',5'-monophosphate, guanosine	HMDB
GMP, Cyclic	HMDB
Guanosine cyclic-3',5'-monophosphate	HMDB
monoPhosphate, guanosine cyclic	HMDB
3',5'-monoPhosphate, guanosine cyclic	HMDB
Cyclic-3',5'-monophosphate, guanosine	HMDB
Guanosine cyclic 3',5'-monophosphate	HMDB
Guanosine cyclic 3,5 monophosphate	HMDB
Cyclic monophosphate, guanosine	HMDB
Guanosine cyclic 3',5' monophosphate	HMDB

Molecular Formula

C₁₀H₁₂N₅O₇P

Average Mass

345.2053

Monoisotopic Mass

345.047434275

IUPAC Name

9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one

Traditional Name

cyclic-GMP

CAS Registry Number

7665-99-8

SMILES

NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1

InChI Identifier

InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1

InChI Key

ZOOGRGPOEVQQDX-UUOKFMHZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Cyclic purine nucleotides

Direct Parent

3',5'-cyclic purine nucleotides

Alternative Parents

Substituents

3',5'-cyclic purine ribonucleotide
Pentose phosphate
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Purinone
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Vinylogous amide
Azole
Tetrahydrofuran
Heteroaromatic compound
Imidazole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Primary amine
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3',5'-cyclic purine nucleotide (CHEBI:16356 )
guanyl ribonucleotide (CHEBI:16356 )
3',5'-Cyclic nuclcleotides (C00942 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.79 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.05	ChemAxon
pKa (Strongest Basic)	1.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.72 m³·mol⁻¹	ChemAxon
Polarizability	29.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Golgi apparatus
Nucleus

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Kidney
Platelet
Smooth Muscle

Tissue Locations

Kidney
Platelet
Smooth Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192207	Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma	Enzyme	Q13956	Homo sapiens
MMDBp0192215	Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A	Unknown	P54750	Homo sapiens
MMDBp0192219	High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A	Unknown	O60658	Homo sapiens
MMDBp0192220	Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B	Enzyme	Q01064	Homo sapiens
MMDBp0192222	cGMP-inhibited 3',5'-cyclic phosphodiesterase B	Enzyme	Q13370	Homo sapiens
MMDBp0192226	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Enzyme	P51160	Homo sapiens
MMDBp0192233	High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A	Unknown	Q13946	Homo sapiens
MMDBp0192242	cGMP-inhibited 3',5'-cyclic phosphodiesterase A	Unknown	Q14432	Homo sapiens
MMDBp0192246	cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Unknown	Q9Y233	Homo sapiens
MMDBp0192247	Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C	Unknown	Q14123	Homo sapiens
MMDBp0192251	cAMP-specific 3',5'-cyclic phosphodiesterase 4B	Unknown	Q07343	Homo sapiens
MMDBp0192254	cAMP-specific 3',5'-cyclic phosphodiesterase 7B	Unknown	Q9NP56	Homo sapiens
MMDBp0192258	High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	Unknown	O76083	Homo sapiens
MMDBp0192259	cGMP-dependent 3',5'-cyclic phosphodiesterase	Unknown	O00408	Homo sapiens
MMDBp0192266	Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha	Enzyme	P16499	Homo sapiens
MMDBp0192272	High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B	Unknown	O95263	Homo sapiens
MMDBp0192273	cAMP-specific 3',5'-cyclic phosphodiesterase 4C	Unknown	Q08493	Homo sapiens
MMDBp0192276	Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit beta	Enzyme	P35913	Homo sapiens
MMDBp0192278	cAMP-specific 3',5'-cyclic phosphodiesterase 4D	Unknown	Q08499	Homo sapiens
MMDBp0192279	Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma	Enzyme	P18545	Homo sapiens
MMDBp0192282	Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit delta	Enzyme	O43924	Homo sapiens
MMDBp0192291	cAMP-specific 3',5'-cyclic phosphodiesterase 4A	Unknown	P27815	Homo sapiens
MMDBp0192296	cGMP-specific 3',5'-cyclic phosphodiesterase	Unknown	O76074	Homo sapiens
MMDBp0192343	Adenylate cyclase type 7	Unknown	P51828	Homo sapiens
MMDBp0192344	Adenylate cyclase type 4	Unknown	Q8NFM4	Homo sapiens
MMDBp0192345	Adenylate cyclase type 6	Unknown	O43306	Homo sapiens
MMDBp0192346	Adenylate cyclase type 5	Unknown	O95622	Homo sapiens
MMDBp0192347	Adenylate cyclase type 8	Unknown	P40145	Homo sapiens
MMDBp0192348	Adenylate cyclase type 9	Unknown	O60503	Homo sapiens
MMDBp0192349	Adenylate cyclase type 3	Unknown	O60266	Homo sapiens
MMDBp0192350	Adenylate cyclase type 1	Unknown	Q08828	Homo sapiens
MMDBp0192539	Adenylate cyclase type 2	Unknown	Q08462	Homo sapiens
MMDBp0192672	Atrial natriuretic peptide receptor 2	Unknown	P20594	Homo sapiens
MMDBp0192673	Guanylate cyclase soluble subunit beta-1	Unknown	Q02153	Homo sapiens
MMDBp0192674	Retinal guanylyl cyclase 1	Unknown	Q02846	Homo sapiens
MMDBp0192675	Guanylate cyclase soluble subunit alpha-3	Unknown	Q02108	Homo sapiens
MMDBp0192676	Atrial natriuretic peptide receptor 1	Unknown	P16066	Homo sapiens
MMDBp0192677	Heat-stable enterotoxin receptor	Unknown	P25092	Homo sapiens
MMDBp0192679	Guanylate cyclase soluble subunit alpha-2	Unknown	P33402	Homo sapiens
MMDBp0192682	Retinal guanylyl cyclase 2	Unknown	P51841	Homo sapiens
MMDBp0192683	Guanylate cyclase soluble subunit beta-2	Unknown	O75343	Homo sapiens
MMDBp0192724	Cyclic nucleotide-gated cation channel alpha-3	Unknown	Q16281	Homo sapiens
MMDBp0192726	Cyclic nucleotide-gated cation channel beta-3	Unknown	Q9NQW8	Homo sapiens
MMDBp0192728	cGMP-gated cation channel alpha-1	Enzyme	P29973	Homo sapiens
MMDBp0193961	Adenylate cyclase type 10	Unknown	Q96PN6	Homo sapiens
MMDBp0193969	Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A	Unknown	Q9HCR9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Ion Channels and Their Functional Role in Vascular Endothelium

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0026039	Cyclic GMP	Guanosine monophosphate	3',5'-cyclic-nucleotide phosphodiesterase	Formation of 2'-nucleotide products from 2',3'-cyclic substrates	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Headache		Association	Human Blood	HMDB	15196297

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	92	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	14	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	2	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	13	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	4	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	4	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Actinobacteria	1	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Cyanobacteria	1
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.0035	0.0003	uM	Adult (>18 years old)	Both	Sildenafil-induced headache	HMDB	15196297
Human Blood	Detected and Quantified	0.0055	0.0003	uM	Adult (>18 years old)	Male	Normal	HMDB	15196297
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0024	0.0005	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Smooth muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001314

DrugBank ID

DB02315

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

1485267

Wikipedia Link

Cyclic guanosine monophosphate

METLIN ID

6152

PubChem Compound

24316

PDB ID

Not Available

ChEBI ID

16356

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97. doi: 10.1210/jcem-42-6-1088. [PubMed:180045 ]
Peracchi M, Lombardi L, Maiolo AT, Bamonti-Catena F, Toschi V, Chiorboli O, Mozzana R, Polli EE: Plasma and urine cyclic nucleotide levels in patients with acute and chronic leukemia. Blood. 1983 Mar;61(3):429-34. [PubMed:6297636 ]
St Pierre MV, Schlenker T, Dufour JF, Jefferson DM, Fitz JG, Arias IM: Stimulation of cyclic guanosine monophosphate production by natriuretic peptide in human biliary cells. Gastroenterology. 1998 Apr;114(4):782-90. doi: 10.1016/s0016-5085(98)70592-x. [PubMed:9516399 ]
Hunter KA, Singh GJ, Simpkins CO: Cyclic gmp is a measure of physiologic stress. J Natl Med Assoc. 2001 Jul-Aug;93(7-8):256-62. [PubMed:11491275 ]
Martina V, Origlia C, Bruno GA, Messina M, Ferri M, Pescarmona GP: Serum DHEAS levels correlate with platelet cGMP in normal women. J Endocrinol Invest. 2001 Nov;24(10):RC28-30. doi: 10.1007/BF03343922. [PubMed:11765058 ]
Barani J, Gottsater A, Mattiasson I, Lindblad B: Platelet and leukocyte activation during aortoiliac angiography and angioplasty. Eur J Vasc Endovasc Surg. 2002 Mar;23(3):220-5. doi: 10.1053/ejvs.2001.1594. [PubMed:11914008 ]
Kotikoski H, Moilanen E, Vapaatalo H, Aine E: Biochemical markers of the L-arginine-nitric oxide pathway in the aqueous humour in glaucoma patients. Acta Ophthalmol Scand. 2002 Apr;80(2):191-5. doi: 10.1034/j.1600-0420.2002.800214.x. [PubMed:11952488 ]
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Engelhardt T, Galley HF, MacLennan FM, Webster NR: Saliva cyclic GMP increases during anaesthesia. Br J Anaesth. 2002 Oct;89(4):635-7. doi: 10.1093/bja/aef229. [PubMed:12393367 ]
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Showing metabocard for Cyclic GMP (MMDBc0029763)

MOL for #<Metabolite:0x00007f92321c46e0>

3D MOL for #<Metabolite:0x00007f92321c46e0>

3D SDF for #<Metabolite:0x00007f92321c46e0>

3D-SDF for #<Metabolite:0x00007f92321c46e0>

PDB for #<Metabolite:0x00007f92321c46e0>

3D PDB for #<Metabolite:0x00007f92321c46e0>

SMILES for #<Metabolite:0x00007f92321c46e0>

INCHI for #<Metabolite:0x00007f92321c46e0>

Structure for #<Metabolite:0x00007f92321c46e0>

3D Structure for #<Metabolite:0x00007f92321c46e0>