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

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-10-17 17:51:43 UTC

Update Date

2022-10-17 17:51:43 UTC

Metabolite ID

MMDBc0057098

Metabolite Identification

Common Name

2',3'-cGAMP

Description

2'-3'-cGAMP(2-), also known as 2',3'-cgamp, belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. Based on a literature review a small amount of articles have been published on 2'-3'-cGAMP(2-).

Structure

MOL SDF PDB SMILES InChI


  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


  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

$$$$

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

Synonyms

Value	Source
2',3'-CGAMP	ChEBI
2'-3'-Cyclic GMP-AMP(2-)	ChEBI
Cyclic g(2'-5')pa(3'-5')p(2-)	ChEBI

Molecular Formula

C₂₀H₂₂N₁₀O₁₃P₂

Average Mass

672.402

Monoisotopic Mass

672.085401964

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 Number

Not 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 Key

XRILCFTWUCUKJR-INFSMZHSSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside 3',5'-bisphosphates

Alternative Parents

Substituents

Purine ribonucleoside 2',5'-bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Pentose-5-phosphate
Pentose phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
Monosaccharide
Pyrimidine
N-substituted imidazole
Imidolactam
Organic phosphoric acid derivative
Azole
Heteroaromatic compound
Imidazole
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Amine
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Primary amine
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:78624 )

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.38 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-5.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.52	ChemAxon
pKa (Strongest Basic)	3.93	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	331.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.76 m³·mol⁻¹	ChemAxon
Polarizability	55.61 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31150585

KEGG Compound ID

Not Available

BioCyc ID

CPD-15224

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86289607

PDB ID

Not Available

ChEBI ID

143093

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

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

MOL for #<Metabolite:0x00005634c2ab16f0>

3D MOL for #<Metabolite:0x00005634c2ab16f0>

3D SDF for #<Metabolite:0x00005634c2ab16f0>

3D-SDF for #<Metabolite:0x00005634c2ab16f0>

PDB for #<Metabolite:0x00005634c2ab16f0>

3D PDB for #<Metabolite:0x00005634c2ab16f0>

SMILES for #<Metabolite:0x00005634c2ab16f0>

INCHI for #<Metabolite:0x00005634c2ab16f0>

Structure for #<Metabolite:0x00005634c2ab16f0>

3D Structure for #<Metabolite:0x00005634c2ab16f0>