MiMeDB: Showing metabocard for cyclic tetraadenylate (MMDBc0055833)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:08:12 UTC

Update Date

2025-10-07 16:09:24 UTC

Metabolite ID

MMDBc0055833

Metabolite Identification

Common Name

cyclic tetraadenylate

Description

Cyclic tetraadenylate is a cyclic nucleotide that belongs to the class of adenine-based metabolites. Its chemical structure features a cyclic arrangement of four adenosine monophosphate (AMP) units, which are linked by phosphodiester bonds, creating a unique cyclic tetramer. This compound plays a significant role in various biochemical pathways, particularly in the activation of CRISPR-associated nucleases. For instance, cyclic tetraadenylate binding induces dimerization of protein dimers, which is essential for the activation of a CRISPR-associated PIN nuclease (PMID:40794864 ). Additionally, biochemical characterization of CaPN has shown that the CARF domain specifically senses cyclic tetraadenylate, leading to the activation of the PIN domain for effective RNA cleavage (PMID:40794864 ). Moreover, the Csx1 homolog, SyCsx1, functions as a cyclic tetraadenylate-dependent RNase, exhibiting strict specificity for cytosine nucleotides (PMID:36419420 ). These interactions highlight the importance of cyclic tetraadenylate in RNA metabolism and the regulatory mechanisms of CRISPR systems, underscoring its relevance in both molecular biology and biochemistry.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222082D          

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M  CHG  4  65  -1  67  -1  69  -1  71  -1
M  END


  Mrv1652306172222082D          

104116  0  0  1  0            999 V2000
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   13.7254   -5.3766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5506    5.0273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070   -8.3139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842    1.5670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4879   -6.0911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2651    3.7898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -7.0764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6217    0.8525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2504   -5.3766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5506    2.5523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -8.5689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293   -0.6466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7429   -3.8776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0516    4.0447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -7.2340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641   -0.6466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4080   -3.8776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0516    2.7099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7310    1.2249    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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   10.2189   -1.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316   -4.0521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2261   -4.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6461    0.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6840   -5.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5866   -2.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1881    0.8885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4910   -5.2411    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3811    0.7169    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.4151   -1.2072    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3283   -1.2567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5952   -5.8199    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9939   -2.1029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2769    1.2957    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0105   -4.5583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8616    0.0341    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6589   -7.0327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.4849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2067   -3.0393    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2132    2.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 21 61  1  1  0  0  0
 22 62  1  1  0  0  0
 23 63  1  1  0  0  0
 24 64  1  1  0  0  0
 73  1  1  0  0  0  0
 74  3  1  0  0  0  0
 75  2  1  0  0  0  0
 76  4  1  0  0  0  0
 77 13  1  0  0  0  0
 77 37  1  0  0  0  0
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 78 38  1  0  0  0  0
 79 15  1  0  0  0  0
 79 39  1  0  0  0  0
 80 16  1  0  0  0  0
 80 40  1  0  0  0  0
 81 25  1  0  0  0  0
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 85 66  2  0  0  0  0
 85 73  1  0  0  0  0
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 87 75  1  0  0  0  0
 87 84  1  0  0  0  0
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 88 72  2  0  0  0  0
 88 76  1  0  0  0  0
 88 83  1  0  0  0  0
 13 89  1  1  0  0  0
 14 90  1  1  0  0  0
 15 91  1  1  0  0  0
 16 92  1  1  0  0  0
 21 93  1  6  0  0  0
 22 94  1  6  0  0  0
 23 95  1  6  0  0  0
 24 96  1  6  0  0  0
 25 97  1  6  0  0  0
 26 98  1  6  0  0  0
 27 99  1  6  0  0  0
 28100  1  6  0  0  0
 37101  1  1  0  0  0
 38102  1  1  0  0  0
 39103  1  1  0  0  0
 40104  1  1  0  0  0
M  CHG  4  65  -1  67  -1  69  -1  71  -1
M  END
> <DATABASE_ID>
MMDBc0055833

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12COP([O-])(=O)O[C@]3([H])[C@@]([H])(COP([O-])(=O)O[C@]4([H])[C@@]([H])(COP([O-])(=O)O[C@]5([H])[C@@]([H])(COP([O-])(=O)O[C@@]1([H])[C@@]([H])(O)[C@@]([H])(O2)N1C=NC2=C(N)N=CN=C12)O[C@@]([H])(N1C=NC2=C(N)N=CN=C12)[C@]5([H])O)O[C@@]([H])(N1C=NC2=C(N)N=CN=C12)[C@]4([H])O)O[C@@]([H])(N1C=NC2=C(N)N=CN=C12)[C@]3([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C40H48N20O24P4/c41-29-17-33(49-5-45-29)57(9-53-17)37-21(61)25-13(77-37)1-73-85(65,66)82-26-14(78-38(22(26)62)58-10-54-18-30(42)46-6-50-34(18)58)2-75-87(69,70)84-28-16(80-40(24(28)64)60-12-56-20-32(44)48-8-52-36(20)60)4-76-88(71,72)83-27-15(3-74-86(67,68)81-25)79-39(23(27)63)59-11-55-19-31(43)47-7-51-35(19)59/h5-16,21-28,37-40,61-64H,1-4H2,(H,65,66)(H,67,68)(H,69,70)(H,71,72)(H2,41,45,49)(H2,42,46,50)(H2,43,47,51)(H2,44,48,52)/p-4/t13-,14-,15-,16-,21-,22-,23-,24-,25-,26-,27-,28-,37-,38-,39-,40-/m1/s1

> <INCHI_KEY>
MIALYWQLJTUJBG-HKIDEBSPSA-J

> <FORMULA>
C40H44N20O24P4

> <MOLECULAR_WEIGHT>
1312.805

> <EXACT_MASS>
1312.180974688

> <JCHEM_ACCEPTOR_COUNT>
32

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
113.54356636173324

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6R,8R,9R,10S,15R,17R,18R,19S,24R,26R,27R,28S,33R,35R,36R)-8,17,26,35-tetrakis(6-amino-9H-purin-9-yl)-9,18,27,36-tetrahydroxy-3,12,21,30-tetraoxo-2,4,7,11,13,16,20,22,25,29,31,34-dodecaoxa-3lambda5,12lambda5,21lambda5,30lambda5-tetraphosphapentacyclo[31.3.0.0^{6,10}.0^{15,19}.0^{24,28}]hexatriacontane-3,12,21,30-tetrakis(olate)

> <JCHEM_LOGP>
-13.370119819818159

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
13

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.6507450782044075

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.227100160265791

> <JCHEM_PKA_STRONGEST_BASIC>
4.524709107674157

> <JCHEM_POLAR_SURFACE_AREA>
630.6799999999998

> <JCHEM_REFRACTIVITY>
276.67119999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R,8R,9R,10S,15R,17R,18R,19S,24R,26R,27R,28S,33R,35R,36R)-8,17,26,35-tetrakis(6-aminopurin-9-yl)-9,18,27,36-tetrahydroxy-3,12,21,30-tetraoxo-2,4,7,11,13,16,20,22,25,29,31,34-dodecaoxa-3lambda5,12lambda5,21lambda5,30lambda5-tetraphosphapentacyclo[31.3.0.0^{6,10}.0^{15,19}.0^{24,28}]hexatriacontane-3,12,21,30-tetrakis(olate)

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       8.183  -8.708   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.528  -0.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.500  -8.054   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.845   0.263   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.866 -13.979   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.257   2.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.771 -11.370   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.162   5.534   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.904 -14.749   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.487  -2.112   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.541  -6.333   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.124   6.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.474  -9.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.689  -1.683   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.339  -6.762   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.554   1.102   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.534 -15.519   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.717   0.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.311  -8.703   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.494   7.074   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.939 -11.563   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.674  -3.147   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.354  -5.298   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.089   3.118   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.939 -10.023   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.214  -3.147   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.814  -5.298   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.089   1.578   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.200 -16.289   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.053   1.591   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.081 -10.036   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.828   7.844   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.534 -13.979   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.257   0.258   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.771  -8.703   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.494   5.534   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.474 -12.039   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.198  -1.683   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.830  -6.762   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.554   3.594   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       6.200 -17.829   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      -1.593   1.591   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      25.621 -10.036   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      17.828   9.384   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0       4.866 -15.519   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0       0.717   2.925   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      23.311 -11.370   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0      19.162   7.074   0.000  0.00  0.00           N+0
HETATM   49  N   UNK     0       6.200 -13.209   0.000  0.00  0.00           N+0
HETATM   50  N   UNK     0       3.027   1.591   0.000  0.00  0.00           N+0
HETATM   51  N   UNK     0      21.001 -10.036   0.000  0.00  0.00           N+0
HETATM   52  N   UNK     0      17.828   4.764   0.000  0.00  0.00           N+0
HETATM   53  N   UNK     0       8.998 -15.995   0.000  0.00  0.00           N+0
HETATM   54  N   UNK     0       0.241  -1.207   0.000  0.00  0.00           N+0
HETATM   55  N   UNK     0      23.787  -7.238   0.000  0.00  0.00           N+0
HETATM   56  N   UNK     0      15.030   7.550   0.000  0.00  0.00           N+0
HETATM   57  N   UNK     0       8.998 -13.503   0.000  0.00  0.00           N+0
HETATM   58  N   UNK     0       2.733  -1.207   0.000  0.00  0.00           N+0
HETATM   59  N   UNK     0      21.295  -7.238   0.000  0.00  0.00           N+0
HETATM   60  N   UNK     0      15.030   5.058   0.000  0.00  0.00           N+0
HETATM   61  O   UNK     0      12.185 -12.468   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       3.768  -4.393   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      20.260  -4.052   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      11.843   4.023   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       5.505  -7.405   0.000  0.00  0.00           O-1
HETATM   66  O   UNK     0       4.953  -5.845   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      15.197 -10.731   0.000  0.00  0.00           O-1
HETATM   68  O   UNK     0      13.637 -11.284   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0       8.831   2.286   0.000  0.00  0.00           O-1
HETATM   70  O   UNK     0      10.391   2.839   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      18.523  -1.040   0.000  0.00  0.00           O-1
HETATM   72  O   UNK     0      19.075  -2.600   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0       7.152  -7.564   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      15.355  -9.084   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0       8.673   0.639   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      16.876  -0.881   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0       8.569 -10.793   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0       5.444  -0.778   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      18.584  -7.667   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      15.459   2.348   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      12.477 -10.104   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0       6.133  -4.685   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0      17.895  -3.760   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0      11.551   1.658   0.000  0.00  0.00           O+0
HETATM   85  P   UNK     0       6.453  -6.192   0.000  0.00  0.00           P+0
HETATM   86  P   UNK     0      13.983  -9.783   0.000  0.00  0.00           P+0
HETATM   87  P   UNK     0      10.045   1.338   0.000  0.00  0.00           P+0
HETATM   88  P   UNK     0      17.575  -2.253   0.000  0.00  0.00           P+0
HETATM   89  H   UNK     0      10.137  -8.157   0.000  0.00  0.00           H+0
HETATM   90  H   UNK     0       8.079  -2.346   0.000  0.00  0.00           H+0
HETATM   91  H   UNK     0      15.949  -6.099   0.000  0.00  0.00           H+0
HETATM   92  H   UNK     0      13.891  -0.288   0.000  0.00  0.00           H+0
HETATM   93  H   UNK     0      12.311 -10.864   0.000  0.00  0.00           H+0
HETATM   94  H   UNK     0       5.373  -4.520   0.000  0.00  0.00           H+0
HETATM   95  H   UNK     0      18.655  -3.925   0.000  0.00  0.00           H+0
HETATM   96  H   UNK     0      11.717   2.419   0.000  0.00  0.00           H+0
HETATM   97  H   UNK     0      11.220  -8.509   0.000  0.00  0.00           H+0
HETATM   98  H   UNK     0       7.728  -3.428   0.000  0.00  0.00           H+0
HETATM   99  H   UNK     0      16.300  -5.017   0.000  0.00  0.00           H+0
HETATM  100  H   UNK     0      12.808   0.064   0.000  0.00  0.00           H+0
HETATM  101  H   UNK     0      10.563 -13.128   0.000  0.00  0.00           H+0
HETATM  102  H   UNK     0       3.109  -2.772   0.000  0.00  0.00           H+0
HETATM  103  H   UNK     0      20.919  -5.673   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      13.465   4.683   0.000  0.00  0.00           H+0
CONECT    1   13   73                                                       
CONECT    2   14   75                                                       
CONECT    3   15   74                                                       
CONECT    4   16   76                                                       
CONECT    5   45   49                                                       
CONECT    6   46   50                                                       
CONECT    7   47   51                                                       
CONECT    8   48   52                                                       
CONECT    9   53   57                                                       
CONECT   10   54   58                                                       
CONECT   11   55   59                                                       
CONECT   12   56   60                                                       
CONECT   13    1   25   77   89                                             
CONECT   14    2   26   78   90                                             
CONECT   15    3   27   79   91                                             
CONECT   16    4   28   80   92                                             
CONECT   17   29   33   53                                                  
CONECT   18   30   34   54                                                  
CONECT   19   31   35   55                                                  
CONECT   20   32   36   56                                                  
CONECT   21   25   37   61   93                                             
CONECT   22   26   38   62   94                                             
CONECT   23   27   39   63   95                                             
CONECT   24   28   40   64   96                                             
CONECT   25   13   21   81   97                                             
CONECT   26   14   22   82   98                                             
CONECT   27   15   23   83   99                                             
CONECT   28   16   24   84  100                                             
CONECT   29   17   41   45                                                  
CONECT   30   18   42   46                                                  
CONECT   31   19   43   47                                                  
CONECT   32   20   44   48                                                  
CONECT   33   17   49   57                                                  
CONECT   34   18   50   58                                                  
CONECT   35   19   51   59                                                  
CONECT   36   20   52   60                                                  
CONECT   37   21   57   77  101                                             
CONECT   38   22   58   78  102                                             
CONECT   39   23   59   79  103                                             
CONECT   40   24   60   80  104                                             
CONECT   41   29                                                            
CONECT   42   30                                                            
CONECT   43   31                                                            
CONECT   44   32                                                            
CONECT   45    5   29                                                       
CONECT   46    6   30                                                       
CONECT   47    7   31                                                       
CONECT   48    8   32                                                       
CONECT   49    5   33                                                       
CONECT   50    6   34                                                       
CONECT   51    7   35                                                       
CONECT   52    8   36                                                       
CONECT   53    9   17                                                       
CONECT   54   10   18                                                       
CONECT   55   11   19                                                       
CONECT   56   12   20                                                       
CONECT   57    9   33   37                                                  
CONECT   58   10   34   38                                                  
CONECT   59   11   35   39                                                  
CONECT   60   12   36   40                                                  
CONECT   61   21                                                            
CONECT   62   22                                                            
CONECT   63   23                                                            
CONECT   64   24                                                            
CONECT   65   85                                                            
CONECT   66   85                                                            
CONECT   67   86                                                            
CONECT   68   86                                                            
CONECT   69   87                                                            
CONECT   70   87                                                            
CONECT   71   88                                                            
CONECT   72   88                                                            
CONECT   73    1   85                                                       
CONECT   74    3   86                                                       
CONECT   75    2   87                                                       
CONECT   76    4   88                                                       
CONECT   77   13   37                                                       
CONECT   78   14   38                                                       
CONECT   79   15   39                                                       
CONECT   80   16   40                                                       
CONECT   81   25   86                                                       
CONECT   82   26   85                                                       
CONECT   83   27   88                                                       
CONECT   84   28   87                                                       
CONECT   85   65   66   73   82                                             
CONECT   86   67   68   74   81                                             
CONECT   87   69   70   75   84                                             
CONECT   88   71   72   76   83                                             
CONECT   89   13                                                            
CONECT   90   14                                                            
CONECT   91   15                                                            
CONECT   92   16                                                            
CONECT   93   21                                                            
CONECT   94   22                                                            
CONECT   95   23                                                            
CONECT   96   24                                                            
CONECT   97   25                                                            
CONECT   98   26                                                            
CONECT   99   27                                                            
CONECT  100   28                                                            
CONECT  101   37                                                            
CONECT  102   38                                                            
CONECT  103   39                                                            
CONECT  104   40                                                            
MASTER        0    0    0    0    0    0    0    0  104    0  232    0
END

Synonyms

Value	Source
Cyclic tetraadenylic acid	Generator

Molecular Formula

C₄₀H₄₄N₂₀O₂₄P₄

Average Mass

1312.805

Monoisotopic Mass

1312.180974688

IUPAC Name

(1S,6R,8R,9R,10S,15R,17R,18R,19S,24R,26R,27R,28S,33R,35R,36R)-8,17,26,35-tetrakis(6-amino-9H-purin-9-yl)-9,18,27,36-tetrahydroxy-3,12,21,30-tetraoxo-2,4,7,11,13,16,20,22,25,29,31,34-dodecaoxa-3lambda5,12lambda5,21lambda5,30lambda5-tetraphosphapentacyclo[31.3.0.0^{6,10}.0^{15,19}.0^{24,28}]hexatriacontane-3,12,21,30-tetrakis(olate)

Traditional Name

(1S,6R,8R,9R,10S,15R,17R,18R,19S,24R,26R,27R,28S,33R,35R,36R)-8,17,26,35-tetrakis(6-aminopurin-9-yl)-9,18,27,36-tetrahydroxy-3,12,21,30-tetraoxo-2,4,7,11,13,16,20,22,25,29,31,34-dodecaoxa-3lambda5,12lambda5,21lambda5,30lambda5-tetraphosphapentacyclo[31.3.0.0^{6,10}.0^{15,19}.0^{24,28}]hexatriacontane-3,12,21,30-tetrakis(olate)

CAS Registry Number

Not Available

SMILES

[H][C@@]12COP([O-])(=O)O[C@]3([H])[C@@]([H])(COP([O-])(=O)O[C@]4([H])[C@@]([H])(COP([O-])(=O)O[C@]5([H])[C@@]([H])(COP([O-])(=O)O[C@@]1([H])[C@@]([H])(O)[C@@]([H])(O2)N1C=NC2=C(N)N=CN=C12)O[C@@]([H])(N1C=NC2=C(N)N=CN=C12)[C@]5([H])O)O[C@@]([H])(N1C=NC2=C(N)N=CN=C12)[C@]4([H])O)O[C@@]([H])(N1C=NC2=C(N)N=CN=C12)[C@]3([H])O

InChI Identifier

InChI=1S/C40H48N20O24P4/c41-29-17-33(49-5-45-29)57(9-53-17)37-21(61)25-13(77-37)1-73-85(65,66)82-26-14(78-38(22(26)62)58-10-54-18-30(42)46-6-50-34(18)58)2-75-87(69,70)84-28-16(80-40(24(28)64)60-12-56-20-32(44)48-8-52-36(20)60)4-76-88(71,72)83-27-15(3-74-86(67,68)81-25)79-39(23(27)63)59-11-55-19-31(43)47-7-51-35(19)59/h5-16,21-28,37-40,61-64H,1-4H2,(H,65,66)(H,67,68)(H,69,70)(H,71,72)(H2,41,45,49)(H2,42,46,50)(H2,43,47,51)(H2,44,48,52)/p-4/t13-,14-,15-,16-,21-,22-,23-,24-,25-,26-,27-,28-,37-,38-,39-,40-/m1/s1

InChI Key

MIALYWQLJTUJBG-HKIDEBSPSA-J

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-13	ChemAxon
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	4.52	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	32	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	630.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	276.67 m³·mol⁻¹	ChemAxon
Polarizability	113.54 Å³	ChemAxon
Number of Rings	13	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

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	19.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	102.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	756.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	730.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	671.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	157.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	3141.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	144.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	835.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	210.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	201.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	118.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	167.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	225.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	337.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	133.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	311.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	2301.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1201.6

Retention Indices

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Archaea	Crenarchaeota	1
Bacteria/Eubacteria	Deinococcus-thermus	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135563793

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 cyclic tetraadenylate (MMDBc0055833)

MOL for #<Metabolite:0x00007f9aa2b9a110>

3D MOL for #<Metabolite:0x00007f9aa2b9a110>

3D SDF for #<Metabolite:0x00007f9aa2b9a110>

3D-SDF for #<Metabolite:0x00007f9aa2b9a110>

PDB for #<Metabolite:0x00007f9aa2b9a110>

3D PDB for #<Metabolite:0x00007f9aa2b9a110>

SMILES for #<Metabolite:0x00007f9aa2b9a110>

INCHI for #<Metabolite:0x00007f9aa2b9a110>

Structure for #<Metabolite:0x00007f9aa2b9a110>

3D Structure for #<Metabolite:0x00007f9aa2b9a110>