Showing metabocard for 2',3'-cGAMP (MMDBc0057098)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-10-17 17:51:43 UTC
Update Date2025-10-07 16:09:48 UTC
Metabolite IDMMDBc0057098
Metabolite Identification
Common Name2',3'-cGAMP
Description2',3'-cGAMP is a cyclic dinucleotide belonging to the class of nucleotide metabolites. Its chemical structure consists of a guanosine and an adenosine moiety linked by a phosphate group, forming a cyclic bond between the 2' position of guanosine and the 5' position of adenosine, with additional phosphodiester linkages. This molecule serves as a potent endogenous agonist of the STING (stimulator of interferon genes) pathway, which is crucial for innate immune activation. Upon binding to STING, 2',3'-cGAMP triggers a cascade of signaling events that culminate in the production of type 1 interferons (IFN-1), thereby enhancing the immune response against pathogens and tumors (PMID:40585794 ). It is particularly significant in the context of certain genetic variants, such as the hSTING-R232H variant, where modified forms like C4'-Me-modified 2',3'-cGAMP demonstrate enhanced immunogenicity, suggesting potential therapeutic applications in infections, cancer, and autoimmune diseases (PMID:40985216 ). Thus, 2',3'-cGAMP and its derivatives represent promising candidates for STING-targeted immunotherapy, especially for patients with specific STING variants that exhibit impaired responses to native 2',3'-cGAMP (PMID:40985216 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fd448888910>


  Mrv1652310172219512D          

 45 51  0  0  1  0            999 V2000
    2.5345   -1.4416    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670   -1.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.5909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9916   -0.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1779   -0.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -1.3703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3750   -1.9589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2386   -2.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -1.4921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973   -0.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3357   -1.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -3.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6364   -3.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1115   -2.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002   -2.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -2.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025    0.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5230    0.5214    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614    1.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294    0.6843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8141    0.9393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2990    0.2718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693   -0.4717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1157   -0.1362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4482   -0.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556   -1.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0690    1.7239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841    2.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0690    3.0588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    2.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    3.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2826    2.8038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2826    1.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    1.5663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    1.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9970    1.5663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    4.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246    1.1788    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.4196   -2.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166   -2.2168    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  1  0  0  0
  6  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
  9 17  1  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  1  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
  1 31  1  0  0  0  0
 25 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 35 40  2  0  0  0  0
 32 40  1  0  0  0  0
 38 41  1  0  0  0  0
 36 42  2  0  0  0  0
 21 43  1  0  0  0  0
  1 44  2  0  0  0  0
  1 45  1  0  0  0  0
M  CHG  2  43  -1  45  -1
M  END
Download

3D MOL for #<Metabolite:0x00007fd448888910>

Download
3D SDF for #<Metabolite:0x00007fd448888910>

  Mrv1652310172219512D          

 45 51  0  0  1  0            999 V2000
    2.5345   -1.4416    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670   -1.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.5909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9916   -0.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1779   -0.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -1.3703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3750   -1.9589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2386   -2.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -1.4921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973   -0.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3357   -1.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500   -3.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6364   -3.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1115   -2.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002   -2.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -2.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025    0.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5230    0.5214    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614    1.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294    0.6843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8141    0.9393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2990    0.2718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693   -0.4717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1157   -0.1362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4482   -0.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556   -1.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0690    1.7239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841    2.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0690    3.0588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    2.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    3.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2826    2.8038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2826    1.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    1.5663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    1.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9970    1.5663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    4.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246    1.1788    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.4196   -2.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166   -2.2168    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  1  0  0  0
  6  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
  9 17  1  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  1  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
  1 31  1  0  0  0  0
 25 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 35 40  2  0  0  0  0
 32 40  1  0  0  0  0
 38 41  1  0  0  0  0
 36 42  2  0  0  0  0
 21 43  1  0  0  0  0
  1 44  2  0  0  0  0
  1 45  1  0  0  0  0
M  CHG  2  43  -1  45  -1
M  END
> <DATABASE_ID>
MMDBc0057098

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP([O-])(=O)O[C@@H]4[C@@H](COP([O-])(=O)O[C@@H]2[C@@H]3O)O[C@H]([C@@H]4O)N2C=NC3=C2N=CN=C3N)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/p-2/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1

> <INCHI_KEY>
XRILCFTWUCUKJR-INFSMZHSSA-L

> <FORMULA>
C20H22N10O13P2

> <MOLECULAR_WEIGHT>
672.402

> <EXACT_MASS>
672.085401964

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
55.61307277709089

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-8-(6-amino-9H-purin-9-yl)-9,18-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.0^{6,10}]octadecane-3,12-bis(olate)

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-5.656936951215268

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1212444586278685

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5225456896880645

> <JCHEM_PKA_STRONGEST_BASIC>
3.9281866265985714

> <JCHEM_POLAR_SURFACE_AREA>
331.02

> <JCHEM_REFRACTIVITY>
139.76110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-8-(6-aminopurin-9-yl)-9,18-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.0^{6,10}]octadecane-3,12-bis(olate)

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for #<Metabolite:0x00007fd448888910>
Download
PDB for #<Metabolite:0x00007fd448888910>
HEADER    PROTEIN                                 17-OCT-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-22         0                                  
HETATM    1  P   UNK     0       4.731  -2.691   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       3.485  -3.596   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.078  -2.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.851  -1.447   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.332  -1.192   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.379  -2.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.700  -3.657   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.445  -5.175   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -1.902  -2.785   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.982  -1.687   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -4.360  -2.374   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.133  -3.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.112  -5.085   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -4.573  -6.527   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -3.055  -6.782   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.075  -5.594   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.614  -4.151   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -6.631  -4.830   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.685  -0.273   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.311   1.134   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0       2.843   0.973   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0       3.101   2.492   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.248   1.904   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.655   1.277   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.120   1.753   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.025   0.507   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.223  -0.881   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.816  -0.254   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.570  -1.159   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.384  -2.412   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.138  -3.317   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0       7.595   3.218   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       6.690   4.464   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       7.595   5.710   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       9.060   5.234   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.394   6.004   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      11.727   5.234   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0      11.727   3.694   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      10.394   2.924   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0       9.060   3.694   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      13.061   2.924   0.000  0.00  0.00           N+0
HETATM   42  O   UNK     0      10.394   7.544   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       1.913   2.200   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0       4.517  -4.216   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       5.258  -4.138   0.000  0.00  0.00           O-1
CONECT    1    2   31   44   45                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    3    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    9                                                  
CONECT   18   13                                                            
CONECT   19    4   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   43                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   24   29                                                  
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30    1                                                       
CONECT   32   25   33   40                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   35   32                                                  
CONECT   41   38                                                            
CONECT   42   36                                                            
CONECT   43   21                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

Download
3D PDB for #<Metabolite:0x00007fd448888910>
Download
SMILES for #<Metabolite:0x00007fd448888910>
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP([O-])(=O)O[C@@H]4[C@@H](COP([O-])(=O)O[C@@H]2[C@@H]3O)O[C@H]([C@@H]4O)N2C=NC3=C2N=CN=C3N)C(=O)N1
Download
INCHI for #<Metabolite:0x00007fd448888910>
InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/p-2/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
Download
Synonyms
ValueSource
2',3'-CGAMPChEBI
2'-3'-Cyclic GMP-AMP(2-)ChEBI
Cyclic g(2'-5')pa(3'-5')p(2-)ChEBI
Molecular FormulaC20H22N10O13P2
Average Mass672.402
Monoisotopic Mass672.085401964
IUPAC Name(1R,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-8-(6-amino-9H-purin-9-yl)-9,18-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.0^{6,10}]octadecane-3,12-bis(olate)
Traditional Name(1R,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-8-(6-aminopurin-9-yl)-9,18-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.0^{6,10}]octadecane-3,12-bis(olate)
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP([O-])(=O)O[C@@H]4[C@@H](COP([O-])(=O)O[C@@H]2[C@@H]3O)O[C@H]([C@@H]4O)N2C=NC3=C2N=CN=C3N)C(=O)N1
InChI Identifier
InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/p-2/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
InChI KeyXRILCFTWUCUKJR-INFSMZHSSA-L