MiMeDB: Showing metabocard for (2E,4E)-hexadienoyl-CoA (MMDBc0054797)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:34:59 UTC

Update Date

2022-08-12 20:09:05 UTC

Metabolite ID

MMDBc0054797

Metabolite Identification

Common Name

(2E,4E)-hexadienoyl-CoA

Description

trans,trans-2,4-hexadienoyl-CoA(4-), also known as (2E,4E)-hexadienoyl-CoA, belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms. Based on a literature review a small amount of articles have been published on trans,trans-2,4-hexadienoyl-CoA(4-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221352D          

 64 66  0  0  1  0            999 V2000
    3.0038   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5383   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8883   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5749   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    8.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   12.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0280    6.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3874    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5711    8.2834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1409   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6931    5.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8768    8.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.3248    8.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   14.0584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.4468    5.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6069    6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4643    7.2914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5330    4.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2843   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1142    5.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2743    6.8511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9394    5.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7999    6.5377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409   15.2959    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.5685   13.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6973    8.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   14.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   15.2959    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -10.3312    9.3648    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -11.4353   10.5910    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -10.2701   10.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5547   10.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7297    9.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2527   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6027   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    9.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6574    7.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4963    9.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   10.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8832    9.9779    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1422    9.9334    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.1709    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   14.4709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5749   15.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   15.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6143    9.1072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1725    8.7760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1533    7.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   13.6459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2882    7.2482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 16 12  1  1  0  0  0
 17  8  1  0  0  0  0
 18  7  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 27  2  1  0  0  0  0
 27  3  1  0  0  0  0
 27 13  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 10  1  4  0  0  0
 29 17  2  0  0  0  0
 30  9  1  4  0  0  0
 30 25  2  0  0  0  0
 31 14  2  0  0  0  0
 31 23  1  0  0  0  0
 32 14  1  0  0  0  0
 32 24  2  0  0  0  0
 33 15  2  0  0  0  0
 33 19  1  0  0  0  0
 34 15  1  0  0  0  0
 34 24  1  0  0  0  0
 26 34  1  1  0  0  0
 35 17  1  0  0  0  0
 36 18  2  0  0  0  0
 20 37  1  6  0  0  0
 22 38  1  6  0  0  0
 39 25  1  0  0  0  0
 47 12  1  0  0  0  0
 48 13  1  0  0  0  0
 49 16  1  0  0  0  0
 49 26  1  0  0  0  0
 21 50  1  1  0  0  0
 52 40  1  0  0  0  0
 52 41  1  0  0  0  0
 52 42  2  0  0  0  0
 52 50  1  0  0  0  0
 53 43  1  0  0  0  0
 53 44  2  0  0  0  0
 53 47  1  0  0  0  0
 53 51  1  0  0  0  0
 54 45  1  0  0  0  0
 54 46  2  0  0  0  0
 54 48  1  0  0  0  0
 54 51  1  0  0  0  0
 55 11  1  0  0  0  0
 55 18  1  0  0  0  0
 56  4  1  0  0  0  0
 57  5  1  0  0  0  0
 58  6  1  0  0  0  0
 59  7  1  0  0  0  0
 16 60  1  6  0  0  0
 20 61  1  1  0  0  0
 21 62  1  1  0  0  0
 22 63  1  6  0  0  0
 26 64  1  6  0  0  0
M  CHG  4  35  -1  39  -1  40  -1  41  -1
M  END


  Mrv1652306172221352D          

 64 66  0  0  1  0            999 V2000
    3.0038   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5383   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8883   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5749   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    8.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   12.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0280    6.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3874    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5711    8.2834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1409   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6931    5.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8768    8.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.3248    8.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   14.0584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.4468    5.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6069    6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4643    7.2914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5330    4.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2843   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1142    5.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2743    6.8511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9394    5.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7999    6.5377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409   15.2959    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.5685   13.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6973    8.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   14.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   15.2959    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -10.3312    9.3648    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -11.4353   10.5910    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -10.2701   10.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5547   10.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7297    9.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2527   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6027   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    9.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6574    7.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4963    9.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   10.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8832    9.9779    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1422    9.9334    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.1709    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   14.4709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5749   15.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   15.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6143    9.1072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1725    8.7760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1533    7.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   13.6459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2882    7.2482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 16 12  1  1  0  0  0
 17  8  1  0  0  0  0
 18  7  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 27  2  1  0  0  0  0
 27  3  1  0  0  0  0
 27 13  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 10  1  4  0  0  0
 29 17  2  0  0  0  0
 30  9  1  4  0  0  0
 30 25  2  0  0  0  0
 31 14  2  0  0  0  0
 31 23  1  0  0  0  0
 32 14  1  0  0  0  0
 32 24  2  0  0  0  0
 33 15  2  0  0  0  0
 33 19  1  0  0  0  0
 34 15  1  0  0  0  0
 34 24  1  0  0  0  0
 26 34  1  1  0  0  0
 35 17  1  0  0  0  0
 36 18  2  0  0  0  0
 20 37  1  6  0  0  0
 22 38  1  6  0  0  0
 39 25  1  0  0  0  0
 47 12  1  0  0  0  0
 48 13  1  0  0  0  0
 49 16  1  0  0  0  0
 49 26  1  0  0  0  0
 21 50  1  1  0  0  0
 52 40  1  0  0  0  0
 52 41  1  0  0  0  0
 52 42  2  0  0  0  0
 52 50  1  0  0  0  0
 53 43  1  0  0  0  0
 53 44  2  0  0  0  0
 53 47  1  0  0  0  0
 53 51  1  0  0  0  0
 54 45  1  0  0  0  0
 54 46  2  0  0  0  0
 54 48  1  0  0  0  0
 54 51  1  0  0  0  0
 55 11  1  0  0  0  0
 55 18  1  0  0  0  0
 56  4  1  0  0  0  0
 57  5  1  0  0  0  0
 58  6  1  0  0  0  0
 59  7  1  0  0  0  0
 16 60  1  6  0  0  0
 20 61  1  1  0  0  0
 21 62  1  1  0  0  0
 22 63  1  6  0  0  0
 26 64  1  6  0  0  0
M  CHG  4  35  -1  39  -1  40  -1  41  -1
M  END
> <DATABASE_ID>
MMDBc0054797

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H42N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h4-7,14-16,20-22,26,37-38H,8-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/p-4/b5-4+,7-6+/t16-,20-,21-,22+,26-/m1/s1

> <INCHI_KEY>
OUDBPEVXTMAWSG-VUJIAKIYSA-J

> <FORMULA>
C27H38N7O17P3S

> <MOLECULAR_WEIGHT>
857.62

> <EXACT_MASS>
857.127969279

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
76.0782089656505

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-4

> <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-[(2E,4E)-hexa-2,4-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanecarboximidate

> <JCHEM_LOGP>
-3.7163003589864707

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8863539937738234

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8191484818493477

> <JCHEM_PKA_STRONGEST_BASIC>
6.443940178475289

> <JCHEM_POLAR_SURFACE_AREA>
381.9300000000001

> <JCHEM_REFRACTIVITY>
212.7484000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <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-[(2E,4E)-hexa-2,4-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanecarboximidate

> <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       5.607  27.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.938  24.702   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.858  24.702   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.273  26.242   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.940  27.012   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.606  26.242   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.272  27.012   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.063  26.242   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.397  27.012   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.062  27.012   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.729  26.242   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -18.399  16.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.398  23.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -26.186  12.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -21.256  10.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -19.733  15.462   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.730  27.012   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.061  26.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -23.694  10.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -22.170  14.944   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -21.140  16.089   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.398  26.242   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -25.101   9.726   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -23.533  11.883   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.064  27.012   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -21.400  13.611   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -14.398  24.702   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0     -25.262   8.194   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      -6.396  26.242   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0     -11.731  26.242   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0     -26.347  10.631   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0     -24.779  12.789   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0     -22.287   9.726   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0     -22.026  12.204   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0      -7.730  28.552   0.000  0.00  0.00           O-1
HETATM   36  O   UNK     0      -1.061  24.702   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -23.702  15.105   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -15.732  27.012   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -13.064  28.552   0.000  0.00  0.00           O-1
HETATM   40  O   UNK     0     -19.285  17.481   0.000  0.00  0.00           O-1
HETATM   41  O   UNK     0     -21.346  19.770   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0     -19.171  19.656   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -17.835  19.876   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -16.295  17.209   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0     -17.272  20.852   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0     -14.192  20.852   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -18.399  17.772   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -15.732  22.392   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -19.894  13.931   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -21.460  17.595   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0     -15.732  19.312   0.000  0.00  0.00           O+0
HETATM   52  P   UNK     0     -20.315  18.625   0.000  0.00  0.00           P+0
HETATM   53  P   UNK     0     -17.065  18.542   0.000  0.00  0.00           P+0
HETATM   54  P   UNK     0     -15.732  20.852   0.000  0.00  0.00           P+0
HETATM   55  S   UNK     0      -2.395  27.012   0.000  0.00  0.00           S+0
HETATM   56  H   UNK     0       4.273  24.702   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.940  28.552   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.606  24.702   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.272  28.552   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0     -19.813  17.000   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0     -22.722  16.382   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0     -20.819  14.582   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0     -13.064  25.472   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0     -22.938  13.530   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   27                                                            
CONECT    3   27                                                            
CONECT    4    1    5   56                                                  
CONECT    5    4    6   57                                                  
CONECT    6    5    7   58                                                  
CONECT    7    6   18   59                                                  
CONECT    8    9   17                                                       
CONECT    9    8   30                                                       
CONECT   10   11   29                                                       
CONECT   11   10   55                                                       
CONECT   12   16   47                                                       
CONECT   13   27   48                                                       
CONECT   14   31   32                                                       
CONECT   15   33   34                                                       
CONECT   16   12   21   49   60                                             
CONECT   17    8   29   35                                                  
CONECT   18    7   36   55                                                  
CONECT   19   23   24   33                                                  
CONECT   20   21   26   37   61                                             
CONECT   21   16   20   50   62                                             
CONECT   22   25   27   38   63                                             
CONECT   23   19   28   31                                                  
CONECT   24   19   32   34                                                  
CONECT   25   22   30   39                                                  
CONECT   26   20   34   49   64                                             
CONECT   27    2    3   13   22                                             
CONECT   28   23                                                            
CONECT   29   10   17                                                       
CONECT   30    9   25                                                       
CONECT   31   14   23                                                       
CONECT   32   14   24                                                       
CONECT   33   15   19                                                       
CONECT   34   15   24   26                                                  
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
CONECT   38   22                                                            
CONECT   39   25                                                            
CONECT   40   52                                                            
CONECT   41   52                                                            
CONECT   42   52                                                            
CONECT   43   53                                                            
CONECT   44   53                                                            
CONECT   45   54                                                            
CONECT   46   54                                                            
CONECT   47   12   53                                                       
CONECT   48   13   54                                                       
CONECT   49   16   26                                                       
CONECT   50   21   52                                                       
CONECT   51   53   54                                                       
CONECT   52   40   41   42   50                                             
CONECT   53   43   44   47   51                                             
CONECT   54   45   46   48   51                                             
CONECT   55   11   18                                                       
CONECT   56    4                                                            
CONECT   57    5                                                            
CONECT   58    6                                                            
CONECT   59    7                                                            
CONECT   60   16                                                            
CONECT   61   20                                                            
CONECT   62   21                                                            
CONECT   63   22                                                            
CONECT   64   26                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

Synonyms

Value	Source
(2E,4E)-Hexadienoyl-CoA	ChEBI
(e,e)-2,4-Hexadienoyl-CoA(4-)	ChEBI
2trans,4trans-Hexadienoyl-CoA(4-)	ChEBI

Molecular Formula

C₂₇H₃₈N₇O₁₇P₃S

Average Mass

857.62

Monoisotopic Mass

857.127969279

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-[(2E,4E)-hexa-2,4-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanecarboximidate

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-[(2E,4E)-hexa-2,4-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanecarboximidate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H42N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h4-7,14-16,20-22,26,37-38H,8-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/p-4/b5-4+,7-6+/t16-,20-,21-,22+,26-/m1/s1

InChI Key

OUDBPEVXTMAWSG-VUJIAKIYSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Medium-chain 2-enoyl 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
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Alkyl phosphate
Organic phosphoric acid derivative
N-acyl-amine
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Imidolactam
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Thiocarboxylic acid ester
Carbothioic s-ester
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Thiocarboxylic acid or derivatives
Sulfenyl compound
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Primary amine
Organic oxide
Amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl-CoA(4-) (CHEBI:84788 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.7	ChemAxon
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.44	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	381.93 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	212.75 m³·mol⁻¹	ChemAxon
Polarizability	76.08 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	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View 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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces

Exposure Sources

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

34999528

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44123412

PDB ID

Not Available

ChEBI ID

84788

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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

Showing metabocard for (2E,4E)-hexadienoyl-CoA (MMDBc0054797)

MOL for #<Metabolite:0x00007fdb1a8c9c48>

3D MOL for #<Metabolite:0x00007fdb1a8c9c48>

3D SDF for #<Metabolite:0x00007fdb1a8c9c48>

3D-SDF for #<Metabolite:0x00007fdb1a8c9c48>

PDB for #<Metabolite:0x00007fdb1a8c9c48>

3D PDB for #<Metabolite:0x00007fdb1a8c9c48>

SMILES for #<Metabolite:0x00007fdb1a8c9c48>

INCHI for #<Metabolite:0x00007fdb1a8c9c48>

Structure for #<Metabolite:0x00007fdb1a8c9c48>

3D Structure for #<Metabolite:0x00007fdb1a8c9c48>