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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:22:47 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060465

Secondary Accession Numbers

HMDB60465

Metabolite Identification

Common Name

cyclic GMP-AMP

Description

cyclic GMP-AMP belongs to the class of organic compounds known as (3'->5')-cyclic dinucleotides and analogues. These are cyclic compounds consisting of two ribose moieties connected by two 5',3'-phosphodiester bonds to form a cycle. Each ribose unit is N-linked to a nucleic base or an analogue thereof. Some natural (3'->5')-cyclic dinucleotides include c-di-AMP. Synthetic derivatives are generally more elaborated molecules in which one or the two nucleobase moieties, and/or sugar residues, and/or phosphodiester linkers have been modified. Based on a literature review a significant number of articles have been published on cyclic GMP-AMP.

Structure

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


  Mrv0541 05161318222D          

 45 51  0  0  0  0            999 V2000
    0.9475   -0.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7876    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690   -3.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7295   -4.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0056    4.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -1.2928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2356    1.3805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4599   -4.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2751    4.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -2.3728    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4509    2.4604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2841   -1.5478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4509    1.6354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2545   -4.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -3.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2751    3.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    4.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -2.6277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2356    2.7154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7041    3.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -5.7298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4185    3.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690   -4.4923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -3.2548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -4.7472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    4.8349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    3.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7041    4.5799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -3.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    3.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516   -2.8577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    2.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    5.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5287   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -1.5891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064    0.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    1.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759    0.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9591   -0.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.9603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7205    2.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0911   -1.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6440    1.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -0.8242    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309    0.9119    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22 20  2  0  0  0  0
 23  3  2  0  0  0  0
 23 14  1  0  0  0  0
 24  3  1  0  0  0  0
 24 15  2  0  0  0  0
 25  4  2  0  0  0  0
 25  8  1  0  0  0  0
 26  5  2  0  0  0  0
 26  9  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
 28 17  2  0  0  0  0
 28 20  1  0  0  0  0
 29  4  1  0  0  0  0
 29 15  1  0  0  0  0
 18 29  1  6  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 19 30  1  6  0  0  0
 10 31  1  1  0  0  0
 11 32  1  1  0  0  0
 33 17  1  0  0  0  0
 38  1  1  0  0  0  0
 39  2  1  0  0  0  0
  6 40  1  6  0  0  0
 40 18  1  0  0  0  0
  7 41  1  6  0  0  0
 41 19  1  0  0  0  0
 12 42  1  1  0  0  0
 13 43  1  1  0  0  0
 44 34  1  0  0  0  0
 44 35  2  0  0  0  0
 44 39  1  0  0  0  0
 44 42  1  0  0  0  0
 45 36  1  0  0  0  0
 45 37  2  0  0  0  0
 45 38  1  0  0  0  0
 45 43  1  0  0  0  0
M  END

HMDB0060465
     RDKit          3D
cyclic GMP-AMP
 69 75  0  0  0  0  0  0  0  0999 V2000
   -8.6234    0.3429   -2.0773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2295    0.2981   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1250    0.4039    0.1449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7466    0.3611    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6953    0.4731    2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4074    0.2049    1.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6995    0.1234    2.8610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3967   -0.0292    2.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -0.0505    1.2330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0229   -0.1922    0.4647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2545   -1.2753    0.8657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.0882    0.4202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9828   -1.4060    1.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988   -1.1422    1.1305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -0.1469    2.1716 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.2255   -1.0296    2.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851    0.2287    3.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7099    1.2458    1.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401    1.2920    0.5140 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0810    0.6746   -0.7665 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5337    1.7451   -1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2400    2.0241   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716    1.2295   -2.2186 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5536    2.2863   -3.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1219    0.1405   -3.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571    0.4239   -1.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    0.3519   -0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0615    0.9615    0.6715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4633    2.0948   -0.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2064    0.0546   -1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -0.5183   -0.2082 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1224   -1.0567   -0.5284 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4876   -2.3477   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -2.5153   -0.7730 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2150   -1.3301   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4399   -0.9382   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4671   -1.9016   -1.8167 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5780    0.3588   -1.9959 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5831    1.2534   -1.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3973    0.8453   -1.3625 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868   -0.4201   -1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    0.6947    0.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2527    0.4168    1.9854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4561    0.0926    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9308    0.1467   -0.5686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9676    0.2654   -2.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9490    1.3454    2.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6034   -0.1211    3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2260   -0.2706   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793   -1.7949   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -2.5121    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2783   -0.9342    2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    0.9037    3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    2.3861    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113   -0.0821   -0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336    2.6643   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.3173   -2.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -0.7983   -3.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054    0.8220    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687    1.1342    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    2.7874    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -1.2592    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8673   -3.1606    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2853   -2.7937   -2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4112   -1.6929   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7439    2.3026   -2.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231    1.3419    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1201    0.8315    2.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2330    0.0642   -1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  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
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 20 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 31 42  1  0
 42 43  1  0
  9 44  1  0
 44 45  1  0
 45  2  1  0
 44  6  2  0
 28 10  1  0
 41 32  1  0
 27 12  1  0
 41 35  1  0
 42 19  1  0
  1 46  1  0
  5 47  1  0
  8 48  1  0
 10 49  1  6
 12 50  1  6
 13 51  1  0
 13 52  1  0
 17 53  1  0
 19 54  1  6
 20 55  1  1
 21 56  1  0
 21 57  1  0
 25 58  1  0
 27 59  1  6
 28 60  1  1
 29 61  1  0
 31 62  1  1
 33 63  1  0
 37 64  1  0
 37 65  1  0
 39 66  1  0
 42 67  1  6
 43 68  1  0
 45 69  1  0
M  END


  Mrv0541 05161318222D          

 45 51  0  0  0  0            999 V2000
    0.9475   -0.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7876    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690   -3.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7295   -4.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0056    4.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -1.2928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2356    1.3805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4599   -4.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2751    4.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -2.3728    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4509    2.4604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2841   -1.5478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4509    1.6354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2545   -4.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -3.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2751    3.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    4.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -2.6277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2356    2.7154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7041    3.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -5.7298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4185    3.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690   -4.4923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -3.2548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -4.7472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    4.8349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    3.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7041    4.5799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -3.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    3.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516   -2.8577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    2.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    5.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5287   -0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -1.5891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064    0.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    1.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759    0.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9591   -0.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.9603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7205    2.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0911   -1.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6440    1.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -0.8242    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309    0.9119    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22 20  2  0  0  0  0
 23  3  2  0  0  0  0
 23 14  1  0  0  0  0
 24  3  1  0  0  0  0
 24 15  2  0  0  0  0
 25  4  2  0  0  0  0
 25  8  1  0  0  0  0
 26  5  2  0  0  0  0
 26  9  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
 28 17  2  0  0  0  0
 28 20  1  0  0  0  0
 29  4  1  0  0  0  0
 29 15  1  0  0  0  0
 18 29  1  6  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 19 30  1  6  0  0  0
 10 31  1  1  0  0  0
 11 32  1  1  0  0  0
 33 17  1  0  0  0  0
 38  1  1  0  0  0  0
 39  2  1  0  0  0  0
  6 40  1  6  0  0  0
 40 18  1  0  0  0  0
  7 41  1  6  0  0  0
 41 19  1  0  0  0  0
 12 42  1  1  0  0  0
 13 43  1  1  0  0  0
 44 34  1  0  0  0  0
 44 35  2  0  0  0  0
 44 39  1  0  0  0  0
 44 42  1  0  0  0  0
 45 36  1  0  0  0  0
 45 37  2  0  0  0  0
 45 38  1  0  0  0  0
 45 43  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060465

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-10(31)12-6(40-18)1-38-45(36,37)43-13-7(2-39-44(34,35)42-12)41-19(11(13)32)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)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1

> <INCHI_KEY>
RFCBNSCSPXMEBK-INFSMZHSSA-N

> <FORMULA>
C20H24N10O13P2

> <MOLECULAR_WEIGHT>
674.4113

> <EXACT_MASS>
674.099953928

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
59.035293219493425

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6R,8R,9R,10S,15R,17R,18R)-8-(6-amino-9H-purin-9-yl)-3,9,12,18-tetrahydroxy-17-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione

> <ALOGPS_LOGP>
-1.44

> <JCHEM_LOGP>
-5.852629134916542

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1327767454763733

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5313504010565184

> <JCHEM_PKA_STRONGEST_BASIC>
5.232984672011395

> <JCHEM_POLAR_SURFACE_AREA>
326.3500000000001

> <JCHEM_REFRACTIVITY>
152.5856

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,8R,9R,10S,15R,17R,18R)-8-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-17-(6-hydroxy-2-imino-3H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060465
     RDKit          3D
cyclic GMP-AMP
 69 75  0  0  0  0  0  0  0  0999 V2000
   -8.6234    0.3429   -2.0773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2295    0.2981   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1250    0.4039    0.1449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7466    0.3611    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6953    0.4731    2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4074    0.2049    1.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6995    0.1234    2.8610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3967   -0.0292    2.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -0.0505    1.2330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0229   -0.1922    0.4647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2545   -1.2753    0.8657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.0882    0.4202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9828   -1.4060    1.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988   -1.1422    1.1305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -0.1469    2.1716 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.2255   -1.0296    2.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851    0.2287    3.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7099    1.2458    1.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401    1.2920    0.5140 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0810    0.6746   -0.7665 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5337    1.7451   -1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2400    2.0241   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716    1.2295   -2.2186 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5536    2.2863   -3.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1219    0.1405   -3.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571    0.4239   -1.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    0.3519   -0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0615    0.9615    0.6715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4633    2.0948   -0.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2064    0.0546   -1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -0.5183   -0.2082 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1224   -1.0567   -0.5284 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4876   -2.3477   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -2.5153   -0.7730 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2150   -1.3301   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4399   -0.9382   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4671   -1.9016   -1.8167 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5780    0.3588   -1.9959 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5831    1.2534   -1.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3973    0.8453   -1.3625 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868   -0.4201   -1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    0.6947    0.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2527    0.4168    1.9854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4561    0.0926    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9308    0.1467   -0.5686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9676    0.2654   -2.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9490    1.3454    2.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6034   -0.1211    3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2260   -0.2706   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793   -1.7949   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -2.5121    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2783   -0.9342    2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    0.9037    3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    2.3861    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113   -0.0821   -0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336    2.6643   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.3173   -2.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -0.7983   -3.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054    0.8220    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687    1.1342    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    2.7874    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -1.2592    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8673   -3.1606    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2853   -2.7937   -2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4112   -1.6929   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7439    2.3026   -2.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231    1.3419    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1201    0.8315    2.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2330    0.0642   -1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  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
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 20 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 31 42  1  0
 42 43  1  0
  9 44  1  0
 44 45  1  0
 45  2  1  0
 44  6  2  0
 28 10  1  0
 41 32  1  0
 27 12  1  0
 41 35  1  0
 42 19  1  0
  1 46  1  0
  5 47  1  0
  8 48  1  0
 10 49  1  6
 12 50  1  6
 13 51  1  0
 13 52  1  0
 17 53  1  0
 19 54  1  6
 20 55  1  1
 21 56  1  0
 21 57  1  0
 25 58  1  0
 27 59  1  6
 28 60  1  1
 29 61  1  0
 31 62  1  1
 33 63  1  0
 37 64  1  0
 37 65  1  0
 39 66  1  0
 42 67  1  6
 43 68  1  0
 45 69  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       1.769  -1.269   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.070   1.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.809  -6.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.228  -7.616   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.610   7.779   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.799  -2.413   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.040   2.577   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.858  -8.386   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.980   8.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.264  -4.429   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.575   4.593   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.264  -2.889   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.575   3.053   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.475  -9.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.858  -6.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.980   7.009   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.314   9.319   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.799  -4.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.040   5.069   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.648   7.009   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -0.475 -10.696   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      11.981   6.239   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      -1.809  -8.386   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -0.475  -6.076   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       2.323  -8.861   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       6.516   9.025   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       9.314   6.239   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      10.648   8.549   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       2.323  -6.370   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       6.516   6.533   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       5.510  -5.334   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.329   5.498   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.314  10.859   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.454  -1.485   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       7.491  -2.966   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.385   1.648   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.347   3.130   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       1.448   0.237   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       7.390  -0.074   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.894  -3.659   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       6.945   3.823   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       5.770  -2.569   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.069   2.733   0.000  0.00  0.00           O+0
HETATM   44  P   UNK     0       6.915  -1.539   0.000  0.00  0.00           P+0
HETATM   45  P   UNK     0       1.924   1.702   0.000  0.00  0.00           P+0
CONECT    1    6   38                                                       
CONECT    2    7   39                                                       
CONECT    3   23   24                                                       
CONECT    4   25   29                                                       
CONECT    5   26   30                                                       
CONECT    6    1   12   40                                                  
CONECT    7    2   13   41                                                  
CONECT    8   14   15   25                                                  
CONECT    9   16   17   26                                                  
CONECT   10   12   18   31                                                  
CONECT   11   13   19   32                                                  
CONECT   12    6   10   42                                                  
CONECT   13    7   11   43                                                  
CONECT   14    8   21   23                                                  
CONECT   15    8   24   29                                                  
CONECT   16    9   27   30                                                  
CONECT   17    9   28   33                                                  
CONECT   18   10   29   40                                                  
CONECT   19   11   30   41                                                  
CONECT   20   22   27   28                                                  
CONECT   21   14                                                            
CONECT   22   20                                                            
CONECT   23    3   14                                                       
CONECT   24    3   15                                                       
CONECT   25    4    8                                                       
CONECT   26    5    9                                                       
CONECT   27   16   20                                                       
CONECT   28   17   20                                                       
CONECT   29    4   15   18                                                  
CONECT   30    5   16   19                                                  
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33   17                                                            
CONECT   34   44                                                            
CONECT   35   44                                                            
CONECT   36   45                                                            
CONECT   37   45                                                            
CONECT   38    1   45                                                       
CONECT   39    2   44                                                       
CONECT   40    6   18                                                       
CONECT   41    7   19                                                       
CONECT   42   12   44                                                       
CONECT   43   13   45                                                       
CONECT   44   34   35   39   42                                             
CONECT   45   36   37   38   43                                             
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

COMPND    HMDB0060465
HETATM    1  N1  UNL     1      -8.623   0.343  -2.077  1.00  0.00           N  
HETATM    2  C1  UNL     1      -8.229   0.298  -0.854  1.00  0.00           C  
HETATM    3  N2  UNL     1      -9.125   0.404   0.145  1.00  0.00           N  
HETATM    4  C2  UNL     1      -8.747   0.361   1.433  1.00  0.00           C  
HETATM    5  O1  UNL     1      -9.695   0.473   2.419  1.00  0.00           O  
HETATM    6  C3  UNL     1      -7.407   0.205   1.712  1.00  0.00           C  
HETATM    7  N3  UNL     1      -6.699   0.123   2.861  1.00  0.00           N  
HETATM    8  C4  UNL     1      -5.397  -0.029   2.552  1.00  0.00           C  
HETATM    9  N4  UNL     1      -5.227  -0.050   1.233  1.00  0.00           N  
HETATM   10  C5  UNL     1      -4.023  -0.192   0.465  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.255  -1.275   0.866  1.00  0.00           O  
HETATM   12  C6  UNL     1      -1.974  -1.088   0.420  1.00  0.00           C  
HETATM   13  C7  UNL     1      -0.983  -1.406   1.543  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.299  -1.142   1.130  1.00  0.00           O  
HETATM   15  P1  UNL     1       1.163  -0.147   2.172  1.00  0.00           P  
HETATM   16  O4  UNL     1       2.226  -1.030   2.835  1.00  0.00           O  
HETATM   17  O5  UNL     1       0.085   0.229   3.457  1.00  0.00           O  
HETATM   18  O6  UNL     1       1.710   1.246   1.556  1.00  0.00           O  
HETATM   19  C8  UNL     1       2.540   1.292   0.514  1.00  0.00           C  
HETATM   20  C9  UNL     1       2.081   0.675  -0.767  1.00  0.00           C  
HETATM   21  C10 UNL     1       1.534   1.745  -1.721  1.00  0.00           C  
HETATM   22  O7  UNL     1       0.240   2.024  -1.243  1.00  0.00           O  
HETATM   23  P2  UNL     1      -0.872   1.229  -2.219  1.00  0.00           P  
HETATM   24  O8  UNL     1      -1.554   2.286  -3.076  1.00  0.00           O  
HETATM   25  O9  UNL     1      -0.122   0.140  -3.281  1.00  0.00           O  
HETATM   26  O10 UNL     1      -2.057   0.424  -1.368  1.00  0.00           O  
HETATM   27  C11 UNL     1      -1.831   0.352  -0.008  1.00  0.00           C  
HETATM   28  C12 UNL     1      -3.062   0.962   0.671  1.00  0.00           C  
HETATM   29  O11 UNL     1      -3.463   2.095  -0.003  1.00  0.00           O  
HETATM   30  O12 UNL     1       3.206   0.055  -1.338  1.00  0.00           O  
HETATM   31  C13 UNL     1       3.837  -0.518  -0.208  1.00  0.00           C  
HETATM   32  N5  UNL     1       5.122  -1.057  -0.528  1.00  0.00           N  
HETATM   33  C14 UNL     1       5.488  -2.348  -0.378  1.00  0.00           C  
HETATM   34  N6  UNL     1       6.762  -2.515  -0.773  1.00  0.00           N  
HETATM   35  C15 UNL     1       7.215  -1.330  -1.177  1.00  0.00           C  
HETATM   36  C16 UNL     1       8.440  -0.938  -1.674  1.00  0.00           C  
HETATM   37  N7  UNL     1       9.467  -1.902  -1.817  1.00  0.00           N  
HETATM   38  N8  UNL     1       8.578   0.359  -1.996  1.00  0.00           N  
HETATM   39  C17 UNL     1       7.583   1.253  -1.850  1.00  0.00           C  
HETATM   40  N9  UNL     1       6.397   0.845  -1.363  1.00  0.00           N  
HETATM   41  C18 UNL     1       6.187  -0.420  -1.023  1.00  0.00           C  
HETATM   42  C19 UNL     1       3.906   0.695   0.700  1.00  0.00           C  
HETATM   43  O13 UNL     1       4.253   0.417   1.985  1.00  0.00           O  
HETATM   44  C20 UNL     1      -6.456   0.093   0.701  1.00  0.00           C  
HETATM   45  N10 UNL     1      -6.931   0.147  -0.569  1.00  0.00           N  
HETATM   46  H1  UNL     1      -7.968   0.265  -2.884  1.00  0.00           H  
HETATM   47  H2  UNL     1      -9.949   1.345   2.845  1.00  0.00           H  
HETATM   48  H3  UNL     1      -4.603  -0.121   3.267  1.00  0.00           H  
HETATM   49  H4  UNL     1      -4.226  -0.271  -0.605  1.00  0.00           H  
HETATM   50  H5  UNL     1      -1.779  -1.795  -0.415  1.00  0.00           H  
HETATM   51  H6  UNL     1      -1.066  -2.512   1.703  1.00  0.00           H  
HETATM   52  H7  UNL     1      -1.278  -0.934   2.484  1.00  0.00           H  
HETATM   53  H8  UNL     1      -0.564   0.904   3.090  1.00  0.00           H  
HETATM   54  H9  UNL     1       2.728   2.386   0.281  1.00  0.00           H  
HETATM   55  H10 UNL     1       1.311  -0.082  -0.684  1.00  0.00           H  
HETATM   56  H11 UNL     1       2.134   2.664  -1.664  1.00  0.00           H  
HETATM   57  H12 UNL     1       1.474   1.317  -2.729  1.00  0.00           H  
HETATM   58  H13 UNL     1      -0.421  -0.798  -3.122  1.00  0.00           H  
HETATM   59  H14 UNL     1      -0.905   0.822   0.324  1.00  0.00           H  
HETATM   60  H15 UNL     1      -2.869   1.134   1.749  1.00  0.00           H  
HETATM   61  H16 UNL     1      -3.710   2.787   0.676  1.00  0.00           H  
HETATM   62  H17 UNL     1       3.187  -1.259   0.270  1.00  0.00           H  
HETATM   63  H18 UNL     1       4.867  -3.161   0.004  1.00  0.00           H  
HETATM   64  H19 UNL     1       9.285  -2.794  -2.291  1.00  0.00           H  
HETATM   65  H20 UNL     1      10.411  -1.693  -1.434  1.00  0.00           H  
HETATM   66  H21 UNL     1       7.744   2.303  -2.127  1.00  0.00           H  
HETATM   67  H22 UNL     1       4.723   1.342   0.264  1.00  0.00           H  
HETATM   68  H23 UNL     1       5.120   0.831   2.267  1.00  0.00           H  
HETATM   69  H24 UNL     1      -6.233   0.064  -1.334  1.00  0.00           H  
CONECT    1    2    2   46
CONECT    2    3   45
CONECT    3    4    4
CONECT    4    5    6
CONECT    5   47
CONECT    6    7   44   44
CONECT    7    8    8
CONECT    8    9   48
CONECT    9   10   44
CONECT   10   11   28   49
CONECT   11   12
CONECT   12   13   27   50
CONECT   13   14   51   52
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   53
CONECT   18   19
CONECT   19   20   42   54
CONECT   20   21   30   55
CONECT   21   22   56   57
CONECT   22   23
CONECT   23   24   24   25   26
CONECT   25   58
CONECT   26   27
CONECT   27   28   59
CONECT   28   29   60
CONECT   29   61
CONECT   30   31
CONECT   31   32   42   62
CONECT   32   33   41
CONECT   33   34   34   63
CONECT   34   35
CONECT   35   36   36   41
CONECT   36   37   38
CONECT   37   64   65
CONECT   38   39   39
CONECT   39   40   66
CONECT   40   41   41
CONECT   42   43   67
CONECT   43   68
CONECT   44   45
CONECT   45   69
END

HMDB0060465
     RDKit          3D
cyclic GMP-AMP
 69 75  0  0  0  0  0  0  0  0999 V2000
   -8.6234    0.3429   -2.0773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2295    0.2981   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1250    0.4039    0.1449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7466    0.3611    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6953    0.4731    2.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4074    0.2049    1.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6995    0.1234    2.8610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3967   -0.0292    2.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -0.0505    1.2330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0229   -0.1922    0.4647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2545   -1.2753    0.8657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.0882    0.4202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9828   -1.4060    1.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988   -1.1422    1.1305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -0.1469    2.1716 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.2255   -1.0296    2.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851    0.2287    3.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7099    1.2458    1.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401    1.2920    0.5140 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0810    0.6746   -0.7665 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5337    1.7451   -1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2400    2.0241   -1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716    1.2295   -2.2186 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5536    2.2863   -3.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1219    0.1405   -3.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571    0.4239   -1.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    0.3519   -0.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0615    0.9615    0.6715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4633    2.0948   -0.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2064    0.0546   -1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -0.5183   -0.2082 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1224   -1.0567   -0.5284 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4876   -2.3477   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -2.5153   -0.7730 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2150   -1.3301   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4399   -0.9382   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4671   -1.9016   -1.8167 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5780    0.3588   -1.9959 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5831    1.2534   -1.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3973    0.8453   -1.3625 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868   -0.4201   -1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    0.6947    0.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2527    0.4168    1.9854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4561    0.0926    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9308    0.1467   -0.5686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9676    0.2654   -2.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9490    1.3454    2.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6034   -0.1211    3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2260   -0.2706   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793   -1.7949   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -2.5121    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2783   -0.9342    2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    0.9037    3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    2.3861    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113   -0.0821   -0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336    2.6643   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.3173   -2.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -0.7983   -3.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054    0.8220    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687    1.1342    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098    2.7874    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -1.2592    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8673   -3.1606    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2853   -2.7937   -2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4112   -1.6929   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7439    2.3026   -2.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231    1.3419    0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1201    0.8315    2.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2330    0.0642   -1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  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
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 20 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 31 42  1  0
 42 43  1  0
  9 44  1  0
 44 45  1  0
 45  2  1  0
 44  6  2  0
 28 10  1  0
 41 32  1  0
 27 12  1  0
 41 35  1  0
 42 19  1  0
  1 46  1  0
  5 47  1  0
  8 48  1  0
 10 49  1  6
 12 50  1  6
 13 51  1  0
 13 52  1  0
 17 53  1  0
 19 54  1  6
 20 55  1  1
 21 56  1  0
 21 57  1  0
 25 58  1  0
 27 59  1  6
 28 60  1  1
 29 61  1  0
 31 62  1  1
 33 63  1  0
 37 64  1  0
 37 65  1  0
 39 66  1  0
 42 67  1  6
 43 68  1  0
 45 69  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3',5'-Cyclic GMP-AMP	ChEBI
c[g(3',5')PA(3',5')p]	ChEBI
Cyclic guanosine monophosphate-adenosine monophosphate	HMDB
Cyclic GMP-AMP	ChEBI

Chemical Formula

C₂₀H₂₄N₁₀O₁₃P₂

Average Molecular Weight

674.4113

Monoisotopic Molecular Weight

674.099953928

IUPAC Name

(1S,6R,8R,9R,10S,15R,17R,18R)-8-(6-amino-9H-purin-9-yl)-3,9,12,18-tetrahydroxy-17-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione

Traditional Name

(1S,6R,8R,9R,10S,15R,17R,18R)-8-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-17-(6-hydroxy-2-imino-3H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione

CAS Registry Number

Not Available

SMILES

NC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N1

InChI Identifier

InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-10(31)12-6(40-18)1-38-45(36,37)43-13-7(2-39-44(34,35)42-12)41-19(11(13)32)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)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1

InChI Key

RFCBNSCSPXMEBK-INFSMZHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (3'->5')-cyclic dinucleotides and analogues. These are cyclic compounds consisting of two ribose moieties connected by two 5',3'-phosphodiester bonds to form a cycle. Each ribose unit is N-linked to a nucleic base or an analogue thereof. Some natural (3'->5')-cyclic dinucleotides include c-di-AMP. Synthetic derivatives are generally more elaborated molecules in which one or the two nucleobase moieties, and/or sugar residues, and/or phosphodiester linkers have been modified.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(3'->5')-dinucleotides and analogues

Sub Class

(3'->5')-cyclic dinucleotides and analogues

Direct Parent

(3'->5')-cyclic dinucleotides and analogues

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenyl ribonucleotide (CHEBI:71580 )
guanyl ribonucleotide (CHEBI:71580 )
cyclic purine dinucleotide (CHEBI:71580 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060465)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.63 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.53	ChemAxon
pKa (Strongest Basic)	5.23	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	326.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	152.59 m³·mol⁻¹	ChemAxon
Polarizability	59.04 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	219.597	30932474
DeepCCS	[M-H]-	217.705	30932474
DeepCCS	[M-2H]-	251.197	30932474
DeepCCS	[M+Na]+	225.203	30932474
AllCCS	[M+H]+	230.3	32859911
AllCCS	[M+H-H2O]+	229.6	32859911
AllCCS	[M+NH4]+	230.9	32859911
AllCCS	[M+Na]+	231.1	32859911
AllCCS	[M-H]-	219.5	32859911
AllCCS	[M+Na-2H]-	221.1	32859911
AllCCS	[M+HCOO]-	223.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.76 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2252 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	842.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	229.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	50.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	315.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	1058.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	633.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	124.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	743.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	254.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	702.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	485.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	578.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cyclic GMP-AMP	NC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N1	5719.0	Standard polar	33892256
cyclic GMP-AMP	NC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N1	4008.8	Standard non polar	33892256
cyclic GMP-AMP	NC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N1	6326.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gc0-0319301000-0466348f50e6b25729c4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Positive-QTOF	splash10-0f79-0900002000-500d12b8f6a2b29fb675	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Positive-QTOF	splash10-0f79-0900000000-621bf6b5958fba42a56d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Positive-QTOF	splash10-0f79-0900000000-db0aaf099bc43157bfe1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Negative-QTOF	splash10-0fl0-0900006000-8179017d1e14a0ce3aa1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Negative-QTOF	splash10-0f89-0900000000-046bf98314f0af856365	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Negative-QTOF	splash10-0a59-1900000000-632e05e32dc84b550b91	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Positive-QTOF	splash10-0fb9-0800009000-fc0c083268395937e122	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Positive-QTOF	splash10-0udi-0900000000-1216c13c790913404c23	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Positive-QTOF	splash10-0udr-0900001000-bd55df92f9536dc82210	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Negative-QTOF	splash10-00di-0400009000-2b3d59fd6896b5caf843	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Negative-QTOF	splash10-0089-0800019000-812b8ac2a8bdc2a6f211	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Negative-QTOF	splash10-003r-1900212000-5ecec1e36632bfe46595	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9356547

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11181459

PDB ID

Not Available

ChEBI ID

71580

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Cyclic GMP-AMP synthase

General function:: Not Available
Specific function:: Nucleotidyltransferase that catalyzes formation of cyclic GMP-AMP (cGAMP) from ATP and GTP and exhibits antiviral activity. Has antiviral activity by acting as a key cytosolic DNA sensor, the presence of DNA in the cytoplasm being a danger signal that triggers the immune responses. Binds cytosolic DNA directly, leading to activation and synthesis of cGAMP, a second messenger that binds to and activates TMEM173/STING, thereby triggering type-I interferon production.
Gene Name:: MB21D1
Uniprot ID:: Q8N884
Molecular weight:: 58813.885

Reactions

Adenosine triphosphate + Guanosine triphosphate → Pyrophosphate + cyclic GMP-AMP	details

Showing metabocard for cyclic GMP-AMP (HMDB0060465)

MOL for HMDB0060465 (cyclic GMP-AMP)

3D MOL for HMDB0060465 (cyclic GMP-AMP)

3D SDF for HMDB0060465 (cyclic GMP-AMP)

3D-SDF for HMDB0060465 (cyclic GMP-AMP)

PDB for HMDB0060465 (cyclic GMP-AMP)

3D PDB for HMDB0060465 (cyclic GMP-AMP)

SMILES for HMDB0060465 (cyclic GMP-AMP)

INCHI for HMDB0060465 (cyclic GMP-AMP)

Structure for HMDB0060465 (cyclic GMP-AMP)

3D Structure for HMDB0060465 (cyclic GMP-AMP)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions