MiMeDB: Showing metabocard for Guanosine 2',3'-cyclic phosphate (MMDBc0000647)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:52 UTC

Update Date

2024-04-30 19:33:24 UTC

Metabolite ID

MMDBc0000647

Metabolite Identification

Common Name

Guanosine 2',3'-cyclic phosphate

Description

Guanosine 2',3'-cyclic phosphate, also known as 2’,3’-cyclic GMP, is a cyclic guanosine derivative that is a precursor to 3'-GMP. The enzyme 2'3'-cyclic-nucleotide 2'-phosphodiesterase (E.C. 3.1.4.16) catalyses the hydrolysis of both 2',3'-cyclic AMP and 2',3'-cyclic GMP into 3'-AMP and 3'-GMP, respectively, at the 3'-terminal of RNA. 2',3'-cyclic phosphate termini are produced, as either intermediates or final products, during RNA cleavage by many different endoribonucleases. The enzyme RNA 3'-phosphate cyclase also converts the 3'-terminal phosphate in RNA into the 2',3'-cyclic phosphodiester in the ATP-dependent reaction which involves formation of the covalent cyclase-AMP and the RNA-N3' pp5' A intermediates (PMID: 10397337 ). This enzyme could be involved in the maintenance of cyclic ends in tRNA splicing intermediates or in the cyclization of the 3' end of U6 snRNA (PMID: 9184239 ). Guanosine-2',3'-cyclic phosphate is capable of blocking DNA synthesis in vitro (PMID: 7528887 ). 2', 3'-cGMP seems to preferentially stimulate mature T-cells while 3', 5'-cGMP preferentially acts on B-cells (PMID: 163786 ).

Structure

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

HMDB0011629
     RDKit          3D
Guanosine 2',3'-cyclic phosphate
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.0040   -2.0199    0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5741   -0.6923   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162    0.1843   -0.4270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996    1.4563   -0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0421    2.3159   -1.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    1.8248   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2146    2.9664   -0.7830 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160    2.7670   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    1.4895   -0.1269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494    0.9457    0.2395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4890    0.1321    1.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7934   -0.3564    1.4248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9504   -1.5140    2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.6004    2.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1468   -0.7349   -0.0197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3955   -0.2444   -0.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752    0.1953   -1.9144 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5631   -0.9641   -2.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066    1.5343   -2.2674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046    0.5610   -1.9045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.0076   -0.7782 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9099    0.9025   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752   -0.3631    0.1070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551   -2.2021    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732   -2.7936   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815    3.5573   -0.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034    1.7245    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    0.4716    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -1.1396    3.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143   -1.8389    2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5597   -3.3856    2.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -1.8332   -0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4932    1.4518   -3.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -0.7427   -1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.0475    0.4172 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
  4  6  1  0
  6  7  1  0
  7  8  2  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
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  1  0
 23  2  1  0
 22  6  2  0
 21 10  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 19 33  1  0
 21 34  1  6
 23 35  1  0
M  END


  Mrv0541 02241201482D          

 23 26  0  0  1  0            999 V2000
   11.3888  -18.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042  -18.2974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3888  -19.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1033  -18.1399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042  -19.6323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8178  -19.3774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1033  -19.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8178  -18.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1193  -18.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1033  -20.6149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5323  -18.1399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0191  -17.3042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7302  -16.0009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3481  -16.5476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0194  -16.4197    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1980  -17.2252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1982  -16.3406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4871  -17.6439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8093  -15.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1376  -14.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0824  -16.8491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8692  -17.0972    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.2609  -17.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  9  2  1  0  0  0  0
 12  2  1  1  0  0  0
  5  3  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  8  6  2  0  0  0  0
  7  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 14 12  1  0  0  0  0
 16 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 13 19  1  1  0  0  0
 16 15  1  0  0  0  0
 15 17  1  6  0  0  0
 16 18  1  6  0  0  0
 22 17  1  0  0  0  0
 20 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  2  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000647

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(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>
UASRYODFRYWBRC-UUOKFMHZSA-N

> <FORMULA>
C10H12N5O7P

> <MOLECULAR_WEIGHT>
345.2053

> <EXACT_MASS>
345.047434275

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
29.106434045453927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-1.61

> <JCHEM_LOGP>
-2.3973771412686973

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.9818642383631335

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6988539991839868

> <JCHEM_PKA_STRONGEST_BASIC>
2.644189521168459

> <JCHEM_POLAR_SURFACE_AREA>
170.51999999999998

> <JCHEM_REFRACTIVITY>
71.28160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011629
     RDKit          3D
Guanosine 2',3'-cyclic phosphate
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.0040   -2.0199    0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5741   -0.6923   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162    0.1843   -0.4270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996    1.4563   -0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0421    2.3159   -1.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    1.8248   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2146    2.9664   -0.7830 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160    2.7670   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    1.4895   -0.1269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494    0.9457    0.2395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4890    0.1321    1.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7934   -0.3564    1.4248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9504   -1.5140    2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.6004    2.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1468   -0.7349   -0.0197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3955   -0.2444   -0.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752    0.1953   -1.9144 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5631   -0.9641   -2.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066    1.5343   -2.2674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046    0.5610   -1.9045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.0076   -0.7782 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9099    0.9025   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752   -0.3631    0.1070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551   -2.2021    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732   -2.7936   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815    3.5573   -0.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034    1.7245    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    0.4716    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -1.1396    3.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143   -1.8389    2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5597   -3.3856    2.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -1.8332   -0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4932    1.4518   -3.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -0.7427   -1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.0475    0.4172 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
  4  6  1  0
  6  7  1  0
  7  8  2  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
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  1  0
 23  2  1  0
 22  6  2  0
 21 10  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 19 33  1  0
 21 34  1  6
 23 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.259 -34.631   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      19.795 -34.155   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      21.259 -36.171   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      22.593 -33.861   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      19.795 -36.647   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      23.927 -36.171   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      22.593 -36.941   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.927 -34.631   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.889 -35.401   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      22.593 -38.481   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      25.260 -33.861   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      18.702 -32.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.163 -29.868   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      19.316 -30.889   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.836 -30.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.170 -32.154   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.303 -30.502   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      15.843 -32.935   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      18.311 -28.336   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.057 -27.441   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.220 -31.452   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      14.689 -31.915   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      13.554 -32.955   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    9   12                                                  
CONECT    3    1    5    7                                                  
CONECT    4    1    8                                                       
CONECT    5    3    9                                                       
CONECT    6    8    7                                                       
CONECT    7    3    6   10                                                  
CONECT    8    4    6   11                                                  
CONECT    9    2    5                                                       
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    2   14   16                                                  
CONECT   13   14   15   19                                                  
CONECT   14   12   13                                                       
CONECT   15   13   16   17                                                  
CONECT   16   12   15   18                                                  
CONECT   17   15   22                                                       
CONECT   18   16   22                                                       
CONECT   19   13   20                                                       
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22   17   21   23   18                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0011629
HETATM    1  N1  UNL     1       4.004  -2.020   0.257  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.574  -0.692  -0.028  1.00  0.00           C  
HETATM    3  N2  UNL     1       4.516   0.184  -0.427  1.00  0.00           N  
HETATM    4  C2  UNL     1       4.200   1.456  -0.716  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.042   2.316  -1.094  1.00  0.00           O  
HETATM    6  C3  UNL     1       2.876   1.825  -0.588  1.00  0.00           C  
HETATM    7  N3  UNL     1       2.215   2.966  -0.783  1.00  0.00           N  
HETATM    8  C4  UNL     1       0.916   2.767  -0.505  1.00  0.00           C  
HETATM    9  N4  UNL     1       0.724   1.489  -0.127  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.549   0.946   0.239  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.489   0.132   1.379  1.00  0.00           O  
HETATM   12  C6  UNL     1      -1.793  -0.356   1.425  1.00  0.00           C  
HETATM   13  C7  UNL     1      -1.950  -1.514   2.359  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.173  -2.600   2.044  1.00  0.00           O  
HETATM   15  C8  UNL     1      -2.147  -0.735  -0.020  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.395  -0.244  -0.266  1.00  0.00           O  
HETATM   17  P1  UNL     1      -3.275   0.195  -1.914  1.00  0.00           P  
HETATM   18  O5  UNL     1      -3.563  -0.964  -2.813  1.00  0.00           O  
HETATM   19  O6  UNL     1      -4.207   1.534  -2.267  1.00  0.00           O  
HETATM   20  O7  UNL     1      -1.605   0.561  -1.905  1.00  0.00           O  
HETATM   21  C9  UNL     1      -1.117  -0.008  -0.778  1.00  0.00           C  
HETATM   22  C10 UNL     1       1.910   0.903  -0.172  1.00  0.00           C  
HETATM   23  N5  UNL     1       2.275  -0.363   0.107  1.00  0.00           N  
HETATM   24  H1  UNL     1       4.355  -2.202   1.218  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.973  -2.794  -0.464  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.181   3.557  -0.593  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.303   1.724   0.443  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.437   0.472   1.787  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.797  -1.140   3.392  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.014  -1.839   2.309  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.560  -3.386   2.549  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.127  -1.833  -0.158  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.493   1.452  -3.227  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.315  -0.743  -1.079  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.549  -1.048   0.417  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3    3   23
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   22   22
CONECT    7    8    8
CONECT    8    9   26
CONECT    9   10   22
CONECT   10   11   21   27
CONECT   11   12
CONECT   12   13   15   28
CONECT   13   14   29   30
CONECT   14   31
CONECT   15   16   21   32
CONECT   16   17
CONECT   17   18   18   19   20
CONECT   19   33
CONECT   20   21
CONECT   21   34
CONECT   22   23
CONECT   23   35
END

HMDB0011629
     RDKit          3D
Guanosine 2',3'-cyclic phosphate
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.0040   -2.0199    0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5741   -0.6923   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162    0.1843   -0.4270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996    1.4563   -0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0421    2.3159   -1.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    1.8248   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2146    2.9664   -0.7830 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160    2.7670   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    1.4895   -0.1269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494    0.9457    0.2395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4890    0.1321    1.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7934   -0.3564    1.4248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9504   -1.5140    2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.6004    2.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1468   -0.7349   -0.0197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3955   -0.2444   -0.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752    0.1953   -1.9144 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5631   -0.9641   -2.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066    1.5343   -2.2674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046    0.5610   -1.9045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.0076   -0.7782 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9099    0.9025   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752   -0.3631    0.1070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551   -2.2021    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732   -2.7936   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815    3.5573   -0.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034    1.7245    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    0.4716    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -1.1396    3.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143   -1.8389    2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5597   -3.3856    2.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -1.8332   -0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4932    1.4518   -3.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146   -0.7427   -1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -1.0475    0.4172 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
  4  6  1  0
  6  7  1  0
  7  8  2  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
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  1  0
 23  2  1  0
 22  6  2  0
 21 10  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 19 33  1  0
 21 34  1  6
 23 35  1  0
M  END

Synonyms

Value	Source
Cyclic guanosine 2',3'-monophosphate	ChEBI
Guanosine 2',3'-cyclic monophosphate	ChEBI
Guanosine cyclic 2',3'-(hydrogen phosphate)	ChEBI
Guanosine cyclic-2',3'-monophosphate	ChEBI
O(2'),O(3')-Hydroxyphosphoryl-guanosine	ChEBI
Cyclic guanosine 2',3'-monophosphoric acid	Generator
Guanosine 2',3'-cyclic monophosphoric acid	Generator
Guanosine cyclic 2',3'-(hydrogen phosphoric acid)	Generator
Guanosine cyclic-2',3'-monophosphoric acid	Generator
Guanosine 2',3'-cyclic phosphoric acid	Generator
2',3'-Cyclic GMP, lithium salt	MeSH, HMDB
2',3'-Cyclic GMP, monosodium salt	MeSH, HMDB
Guanosine cyclic 2,3 monophosphate	MeSH, HMDB
2',3'-Cyclic GMP, sodium salt	MeSH, HMDB
Guanosine cyclic 2',3'-monophosphate	MeSH, HMDB
Guanosine 2',3'-cyclic phosphate	ChEBI
2',3'-Cyclic GMP	MeSH

Molecular Formula

C₁₀H₁₂N₅O₇P

Average Mass

345.2053

Monoisotopic Mass

345.047434275

IUPAC Name

9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one

Traditional Name

9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12

InChI Identifier

InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(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

UASRYODFRYWBRC-UUOKFMHZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 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

2',3'-cyclic purine nucleotides

Alternative Parents

Substituents

2',3'-cyclic purine ribonucleotide
Ribonucleoside 3'-phosphate
Imidazopyrimidine
Purine
Hydroxypyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Organic phosphoric acid derivative
Azole
1,3_dioxaphospholane
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2',3'-cyclic purine nucleotide (CHEBI:28181 )
2',3'-Cyclic nucleotides (C06194 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.53 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.7	ChemAxon
pKa (Strongest Basic)	2.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.28 m³·mol⁻¹	ChemAxon
Polarizability	29.11 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

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-01x1-3972000000-df2552fc3c7b33d5fbfb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-01x1-3972000000-df2552fc3c7b33d5fbfb	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01c3-3933000000-4fe05159f55ac562ab6a	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5962000000-2fa436cbb4e5959d639d	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1904000000-8fb2afe37dd02a6d845e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-ca072c32c08d839446b3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-2900000000-950846db10c3ea5bf17a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6x-0409000000-7560a795a4081c2a83ae	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-5678b133858684f7c137	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc3-6900000000-860a8c5cf0d45d6b0444	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-361a2474138028086bb3	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0903000000-946cd7b17d2fe5f36ad6	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1922000000-4f6eb6f377248f3ec6d4	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-9ebf2bf873fdea0ab0a5	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-0629000000-1f736274756361159764	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3900000000-fdd7fdc6c2d094787d5b	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	485.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	308.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	110.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	269.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	311.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	241.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	613.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	762.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	636.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	141.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	314.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	155.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	57.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	386.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	659.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	48.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	192.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	712.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	594.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard non polar	2025-10-23	1967.46
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_2	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3[NH]C(N)=NC4=O)[C@@H]2O1	standard non polar	2025-10-23	1563.15
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_3	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O)O[C@H]31)C=N2	standard non polar	2025-10-23	2879.85
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_4	C[Si](C)(C)N1C(N)=NC(=O)C2=C1N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O)O[C@H]31)C=N2	standard non polar	2025-10-23	2515.99
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_5	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard non polar	2025-10-23	1575.72
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_6	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O)O[C@H]31)C=N2	standard non polar	2025-10-23	2564.89
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_7	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard non polar	2025-10-23	2192.01
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_8	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@H]31)C=N2	standard non polar	2025-10-23	2907.34
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_9	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3N([Si](C)(C)C)C(N)=NC4=O)[C@@H]2O1	standard non polar	2025-10-23	2702.26
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_10	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O)O[C@H]31)C=N2)[Si](C)(C)C	standard non polar	2025-10-23	1708.02
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_11	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@H]4OP(=O)(O)O[C@H]43)C=N2)N1[Si](C)(C)C	standard non polar	2025-10-23	2196.04
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_12	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@H]31)C=N2	standard non polar	2025-10-23	2323.24
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_13	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard non polar	2025-10-23	2428.0
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_14	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard non polar	2025-10-23	2120.83
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_15	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@H]4OP(=O)(O)O[C@H]43)C=N2)N1[Si](C)(C)C	standard non polar	2025-10-23	2612.78
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_16	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)[C@@H]2O1	standard non polar	2025-10-23	1735.74
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_17	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@H]4OP(=O)(O[Si](C)(C)C)O[C@H]43)C=N2)N1[Si](C)(C)C	standard non polar	2025-10-23	1738.07
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_18	C[Si](C)(C)N(C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@H]4OP(=O)(O)O[C@H]43)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2124.03
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_19	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard non polar	2025-10-23	2140.73
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_20	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@H]4OP(=O)(O[Si](C)(C)C)O[C@H]43)C=N2)N1[Si](C)(C)C	standard non polar	2025-10-23	1929.85
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_21	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard non polar	2025-10-23	1640.42
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_22	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)[C@@H]2O1	standard non polar	2025-10-23	1515.57
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_23	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard non polar	2025-10-23	2898.59
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard polar	2025-10-23	1949.71
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_2	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3[NH]C(N)=NC4=O)[C@@H]2O1	standard polar	2025-10-23	2670.36
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_3	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O)O[C@H]31)C=N2	standard polar	2025-10-23	2114.05
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_4	C[Si](C)(C)N1C(N)=NC(=O)C2=C1N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O)O[C@H]31)C=N2	standard polar	2025-10-23	1489.56
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_5	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard polar	2025-10-23	2363.9
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_6	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O)O[C@H]31)C=N2	standard polar	2025-10-23	1742.6
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_7	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard polar	2025-10-23	2244.67
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_8	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@H]31)C=N2	standard polar	2025-10-23	2689.42
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_9	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3N([Si](C)(C)C)C(N)=NC4=O)[C@@H]2O1	standard polar	2025-10-23	2237.57
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_10	C[Si](C)(C)N(C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@H]3OP(=O)(O)O[C@H]31)C=N2)[Si](C)(C)C	standard polar	2025-10-23	2983.91
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_11	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@H]4OP(=O)(O)O[C@H]43)C=N2)N1[Si](C)(C)C	standard polar	2025-10-23	1696.6
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_12	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@H]3OP(=O)(O[Si](C)(C)C)O[C@H]31)C=N2	standard polar	2025-10-23	3525.71
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_13	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard polar	2025-10-23	2140.6
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_14	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard polar	2025-10-23	634.937
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_15	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@H]4OP(=O)(O)O[C@H]43)C=N2)N1[Si](C)(C)C	standard polar	2025-10-23	2043.05
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_16	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)[C@@H]2O1	standard polar	2025-10-23	1957.2
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_17	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@H]4OP(=O)(O[Si](C)(C)C)O[C@H]43)C=N2)N1[Si](C)(C)C	standard polar	2025-10-23	1848.99
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_18	C[Si](C)(C)N(C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@H]4OP(=O)(O)O[C@H]43)C=N2)N1[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2458.34
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_19	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard polar	2025-10-23	2477.26
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_20	C[Si](C)(C)NC1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@H]4OP(=O)(O[Si](C)(C)C)O[C@H]43)C=N2)N1[Si](C)(C)C	standard polar	2025-10-23	2883.45
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_21	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O)O[C@H]12	standard polar	2025-10-23	2378.72
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_22	C[Si](C)(C)OP1(=O)O[C@@H]2[C@@H](CO)O[C@@H](N3C=NC4=C3N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC4=O)[C@@H]2O1	standard polar	2025-10-23	1289.9
Gas Chromatography	Guanosine 2',3'-cyclic phosphate_TMS_23	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC3=O)[C@@H]2OP(=O)(O[Si](C)(C)C)O[C@H]12	standard polar	2025-10-23	2250.41

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193538	2',3'-cyclic-nucleotide 3'-phosphodiesterase	Enzyme	P09543	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
MMDBr0026034	Guanosine 2',3'-cyclic phosphate	Guanosine 2'-phosphate	2',3'-cyclic-nucleotide 3'-phosphodiesterase	Formation of 2'-nucleotide products from 2',3'-cyclic substrates	RHEA	34755880
MMDBr0026049	Guanosine 2',3'-cyclic phosphate	Guanosine 3'-phosphate	2',3'-cyclic-nucleotide 2'-phosphodiesterase	Hydrolysis of nucleotide; Dephosphorylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0011629

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028329

KNApSAcK ID

Not Available

Chemspider ID

83792

KEGG Compound ID

C06194

BioCyc ID

CPD-3709

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481125

PDB ID

Not Available

ChEBI ID

28181

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Diamantstein T, Ulmer A: Effect of cyclic nucleotides on DNA synthesis in mouse lymphoid cells. Immunol Commun. 1975;4(1):51-62. doi: 10.3109/08820137509055761. [PubMed:163786 ]
Hamada K, Yokoro K: Blocking of DNA synthesis in vitro by a guanosine 2',3'-cyclic phosphate: a possible mechanism of chromosome aberrations induced by U5 snRNA. Mutat Res. 1995 Jan;326(1):71-82. doi: 10.1016/0027-5107(94)00159-3. [PubMed:7528887 ]
Genschik P, Billy E, Swianiewicz M, Filipowicz W: The human RNA 3'-terminal phosphate cyclase is a member of a new family of proteins conserved in Eucarya, Bacteria and Archaea. EMBO J. 1997 May 15;16(10):2955-67. doi: 10.1093/emboj/16.10.2955. [PubMed:9184239 ]
Filipowicz W, Billy E, Drabikowski K, Genschik P: Cyclases of the 3'-terminal phosphate in RNA: a new family of RNA processing enzymes conserved in eucarya, bacteria and archaea. Acta Biochim Pol. 1998;45(4):895-906. [PubMed:10397337 ]
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 ]

Showing metabocard for Guanosine 2',3'-cyclic phosphate (MMDBc0000647)

MOL for #<Metabolite:0x00007f2e1c051ad0>

3D MOL for #<Metabolite:0x00007f2e1c051ad0>

3D SDF for #<Metabolite:0x00007f2e1c051ad0>

3D-SDF for #<Metabolite:0x00007f2e1c051ad0>

PDB for #<Metabolite:0x00007f2e1c051ad0>

3D PDB for #<Metabolite:0x00007f2e1c051ad0>

SMILES for #<Metabolite:0x00007f2e1c051ad0>

INCHI for #<Metabolite:0x00007f2e1c051ad0>

Structure for #<Metabolite:0x00007f2e1c051ad0>

3D Structure for #<Metabolite:0x00007f2e1c051ad0>