MiMeDB: Showing metabocard for 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde (MMDBc0031780)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:02 UTC

Update Date

2022-08-31 18:24:41 UTC

MiMeDB ID

MMDBc0031780

Metabolite Identification

Common Name

3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde

Description

3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde is an intermediate in phenylacetate metabolism. It is a substrate for the enzyme known as Bifunctional protein PaaZ. This enzyme consists of a C-terminal (R)-specific enoyl-CoA hydratase domain (formerly MaoC) that cleaves the phenylacetate ring and produces the highly reactive 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde and an N-terminal NADP-dependent aldehyde dehydrogenase domain that oxidizes the aldehyde to 3-oxo-5,6-dehydrosuberyl-CoA.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10101211192D          

 66 68  0  0  0  0            999 V2000
    9.8906   12.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2406   12.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920   18.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9209   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6367   16.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6367   15.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2077   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   19.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4933   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2090    8.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0656   12.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1829    5.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4622    8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9235    7.8884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9222   16.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3554    7.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8167    6.8964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0097    7.0679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0656   13.6634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0228    6.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6017    7.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3512   14.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2292    7.6108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0656   12.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7765    7.2702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9222   17.3759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3512   14.9009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9366    6.1141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5155    6.2635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2692    8.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0497    7.6971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   19.8509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354   16.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2077   16.1384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643   16.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1523    6.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801   14.0759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6367   13.6634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8670    7.5554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3571    5.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8274    7.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9071   10.2529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0821    8.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6051   10.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9551   10.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2090    9.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801   11.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6772    8.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3966    6.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801    9.9509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6120    6.7708    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.4946    9.5384    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801   10.7759    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788   17.7884    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225   17.3759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   16.5509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4270    7.2295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2975    6.2552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1849    7.0823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3512   13.2509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6785    6.9189    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  9  1  0  0  0  0
 17  6  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  1  0  0  0
 19  7  1  0  0  0  0
 20 12  1  0  0  0  0
 23 18  1  0  0  0  0
 23 22  1  0  0  0  0
 25 21  2  0  0  0  0
 26 21  1  0  0  0  0
 27 24  1  0  0  0  0
 28 22  1  0  0  0  0
 29  1  1  0  0  0  0
 29  2  1  0  0  0  0
 29 14  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31  9  1  4  0  0  0
 31 19  2  0  0  0  0
 32  8  1  4  0  0  0
 32 27  2  0  0  0  0
 33 15  2  0  0  0  0
 33 25  1  0  0  0  0
 34 15  1  0  0  0  0
 34 26  2  0  0  0  0
 35 16  2  0  0  0  0
 35 21  1  0  0  0  0
 36 16  1  0  0  0  0
 36 26  1  0  0  0  0
 28 36  1  1  0  0  0
 37 10  2  0  0  0  0
 38 17  2  0  0  0  0
 39 19  1  0  0  0  0
 40 20  2  0  0  0  0
 22 41  1  6  0  0  0
 24 42  1  1  0  0  0
 43 27  1  0  0  0  0
 51 13  1  0  0  0  0
 52 14  1  0  0  0  0
 53 18  1  0  0  0  0
 53 28  1  0  0  0  0
 23 54  1  6  0  0  0
 56 44  1  0  0  0  0
 56 45  1  0  0  0  0
 56 46  2  0  0  0  0
 56 54  1  0  0  0  0
 57 47  1  0  0  0  0
 57 48  2  0  0  0  0
 57 51  1  0  0  0  0
 57 55  1  0  0  0  0
 58 49  1  0  0  0  0
 58 50  2  0  0  0  0
 58 52  1  0  0  0  0
 58 55  1  0  0  0  0
 59 11  1  0  0  0  0
 59 20  1  0  0  0  0
 60  3  1  0  0  0  0
 61  4  1  0  0  0  0
 18 62  1  6  0  0  0
 22 63  1  1  0  0  0
 23 64  1  1  0  0  0
 24 65  1  1  0  0  0
 28 66  1  6  0  0  0
M  END


  Mrv0541 10101211192D          

 66 68  0  0  0  0            999 V2000
    9.8906   12.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2406   12.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920   18.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9209   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6367   16.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6367   15.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2077   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   19.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4933   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499   17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2090    8.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0656   12.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1829    5.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4622    8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9235    7.8884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9222   16.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643   17.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3554    7.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8167    6.8964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0097    7.0679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0656   13.6634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0228    6.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6017    7.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3512   14.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2292    7.6108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0656   12.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7765    7.2702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9222   17.3759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3512   14.9009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9366    6.1141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5155    6.2635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2692    8.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0497    7.6971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   19.8509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354   16.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2077   16.1384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643   16.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1523    6.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801   14.0759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6367   13.6634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8670    7.5554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3571    5.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8274    7.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9071   10.2529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0821    8.8239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6051   10.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9551   10.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2090    9.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801   11.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6772    8.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3966    6.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801    9.9509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6120    6.7708    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.4946    9.5384    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7801   10.7759    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788   17.7884    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225   17.3759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   16.5509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4270    7.2295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2975    6.2552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1849    7.0823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3512   13.2509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6785    6.9189    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  9  1  0  0  0  0
 17  6  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  1  0  0  0
 19  7  1  0  0  0  0
 20 12  1  0  0  0  0
 23 18  1  0  0  0  0
 23 22  1  0  0  0  0
 25 21  2  0  0  0  0
 26 21  1  0  0  0  0
 27 24  1  0  0  0  0
 28 22  1  0  0  0  0
 29  1  1  0  0  0  0
 29  2  1  0  0  0  0
 29 14  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31  9  1  4  0  0  0
 31 19  2  0  0  0  0
 32  8  1  4  0  0  0
 32 27  2  0  0  0  0
 33 15  2  0  0  0  0
 33 25  1  0  0  0  0
 34 15  1  0  0  0  0
 34 26  2  0  0  0  0
 35 16  2  0  0  0  0
 35 21  1  0  0  0  0
 36 16  1  0  0  0  0
 36 26  1  0  0  0  0
 28 36  1  1  0  0  0
 37 10  2  0  0  0  0
 38 17  2  0  0  0  0
 39 19  1  0  0  0  0
 40 20  2  0  0  0  0
 22 41  1  6  0  0  0
 24 42  1  1  0  0  0
 43 27  1  0  0  0  0
 51 13  1  0  0  0  0
 52 14  1  0  0  0  0
 53 18  1  0  0  0  0
 53 28  1  0  0  0  0
 23 54  1  6  0  0  0
 56 44  1  0  0  0  0
 56 45  1  0  0  0  0
 56 46  2  0  0  0  0
 56 54  1  0  0  0  0
 57 47  1  0  0  0  0
 57 48  2  0  0  0  0
 57 51  1  0  0  0  0
 57 55  1  0  0  0  0
 58 49  1  0  0  0  0
 58 50  2  0  0  0  0
 58 52  1  0  0  0  0
 58 55  1  0  0  0  0
 59 11  1  0  0  0  0
 59 20  1  0  0  0  0
 60  3  1  0  0  0  0
 61  4  1  0  0  0  0
 18 62  1  6  0  0  0
 22 63  1  1  0  0  0
 23 64  1  1  0  0  0
 24 65  1  1  0  0  0
 28 66  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031780

> <DATABASE_NAME>
MIME

> <SMILES>
O=CC\C([H])=C(\[H])CC(=O)CC(=O)SCCN=C(O)CCN=C(O)[C@@](O)([H])C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H44N7O19P3S/c1-29(2,24(42)27(43)32-8-7-19(39)31-9-11-59-20(40)12-17(38)6-4-3-5-10-37)14-52-58(49,50)55-57(47,48)51-13-18-23(54-56(44,45)46)22(41)28(53-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-4,10,15-16,18,22-24,28,41-42H,5-9,11-14H2,1-2H3,(H,31,39)(H,32,43)(H,47,48)(H,49,50)(H2,30,33,34)(H2,44,45,46)/b4-3-/t18-,22-,23-,24+,28-/m1/s1

> <INCHI_KEY>
XYGQIZWAZKPGNV-ZVEAYUPDSA-N

> <FORMULA>
C29H44N7O19P3S

> <MOLECULAR_WEIGHT>
919.681

> <EXACT_MASS>
919.162552487

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
82.38896997748736

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-{2-[(2-{[(5Z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic acid

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
-4.92090695129798

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.6778828235106418

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8251641266959928

> <JCHEM_PKA_STRONGEST_BASIC>
4.7927565159703915

> <JCHEM_POLAR_SURFACE_AREA>
404.75000000000006

> <JCHEM_REFRACTIVITY>
203.4331000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-{2-[(2-{[(5Z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
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HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   56  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   57  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   58  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   59  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   60  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   29                                                            
CONECT    2   29                                                            
CONECT    3    4    5   60                                                  
CONECT    4    3    6   61                                                  
CONECT    5    3   10                                                       
CONECT    6    4   17                                                       
CONECT    7    8   19                                                       
CONECT    8    7   32                                                       
CONECT    9   11   31                                                       
CONECT   10    5   37                                                       
CONECT   11    9   59                                                       
CONECT   12   17   20                                                       
CONECT   13   18   51                                                       
CONECT   14   29   52                                                       
CONECT   15   33   34                                                       
CONECT   16   35   36                                                       
CONECT   17    6   12   38                                                  
CONECT   18   13   23   53   62                                             
CONECT   19    7   31   39                                                  
CONECT   20   12   40   59                                                  
CONECT   21   25   26   35                                                  
CONECT   22   23   28   41   63                                             
CONECT   23   18   22   54   64                                             
CONECT   24   27   29   42   65                                             
CONECT   25   21   30   33                                                  
CONECT   26   21   34   36                                                  
CONECT   27   24   32   43                                                  
CONECT   28   22   36   53   66                                             
CONECT   29    1    2   14   24                                             
CONECT   30   25                                                            
CONECT   31    9   19                                                       
CONECT   32    8   27                                                       
CONECT   33   15   25                                                       
CONECT   34   15   26                                                       
CONECT   35   16   21                                                       
CONECT   36   16   26   28                                                  
CONECT   37   10                                                            
CONECT   38   17                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   22                                                            
CONECT   42   24                                                            
CONECT   43   27                                                            
CONECT   44   56                                                            
CONECT   45   56                                                            
CONECT   46   56                                                            
CONECT   47   57                                                            
CONECT   48   57                                                            
CONECT   49   58                                                            
CONECT   50   58                                                            
CONECT   51   13   57                                                       
CONECT   52   14   58                                                       
CONECT   53   18   28                                                       
CONECT   54   23   56                                                       
CONECT   55   57   58                                                       
CONECT   56   44   45   46   54                                             
CONECT   57   47   48   51   55                                             
CONECT   58   49   50   52   55                                             
CONECT   59   11   20                                                       
CONECT   60    3                                                            
CONECT   61    4                                                            
CONECT   62   18                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   24                                                            
CONECT   66   28                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  136    0
END

Synonyms

Not Available

Chemical Formula

C₂₉H₄₄N₇O₁₉P₃S

Average Molecular Weight

919.681

Monoisotopic Molecular Weight

919.162552487

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-{2-[(2-{[(5Z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic acid

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-{2-[(2-{[(5Z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic acid

CAS Registry Number

Not Available

SMILES

O=CC\C([H])=C(\[H])CC(=O)CC(=O)SCCN=C(O)CCN=C(O)[C@@](O)([H])C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(O)(O)=O

InChI Identifier

InChI=1S/C29H44N7O19P3S/c1-29(2,24(42)27(43)32-8-7-19(39)31-9-11-59-20(40)12-17(38)6-4-3-5-10-37)14-52-58(49,50)55-57(47,48)51-13-18-23(54-56(44,45)46)22(41)28(53-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-4,10,15-16,18,22-24,28,41-42H,5-9,11-14H2,1-2H3,(H,31,39)(H,32,43)(H,47,48)(H,49,50)(H2,30,33,34)(H2,44,45,46)/b4-3-/t18-,22-,23-,24+,28-/m1/s1

InChI Key

XYGQIZWAZKPGNV-ZVEAYUPDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

3-oxo-acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Ribonucleoside 3'-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
1,3-dicarbonyl compound
Organic phosphoric acid derivative
N-substituted imidazole
N-acyl-amine
Alkyl phosphate
Pyrimidine
Imidolactam
Fatty amide
Monosaccharide
Phosphoric acid ester
Imidazole
Heteroaromatic compound
Azole
Alpha-hydrogen aldehyde
Tetrahydrofuran
Thiocarboxylic acid ester
Amino acid or derivatives
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Ketone
Carbothioic s-ester
Sulfenyl compound
Oxacycle
Organoheterocyclic compound
Thiocarboxylic acid or derivatives
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Carbonyl group
Alcohol
Aldehyde
Organic oxide
Primary amine
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
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
Water Solubility	5.04 g/L	ALOGPS
logP	0.38	ALOGPS
logP	-4.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	404.75 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	203.43 m³·mol⁻¹	ChemAxon
Polarizability	82.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1891000202-f3ea3758b79139203398	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-1980100000-e9cc2354ce03c72c2a19	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2950000000-c5adaa148e728c314fba	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-1030-2911021214-5769504ace3c2360ef14	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2910110001-430e565c8cfda0a74027	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-d8acd61364b7aaf8bcef	2015-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

C19946

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56928138

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde (MMDBc0031780)

MOL for #<Metabolite:0x00007f09201d28d0>

3D MOL for #<Metabolite:0x00007f09201d28d0>

3D SDF for #<Metabolite:0x00007f09201d28d0>

3D-SDF for #<Metabolite:0x00007f09201d28d0>

PDB for #<Metabolite:0x00007f09201d28d0>

3D PDB for #<Metabolite:0x00007f09201d28d0>

SMILES for #<Metabolite:0x00007f09201d28d0>

INCHI for #<Metabolite:0x00007f09201d28d0>

Structure for #<Metabolite:0x00007f09201d28d0>

3D Structure for #<Metabolite:0x00007f09201d28d0>