MiMeDB: Showing metabocard for (E)-3-(indol-3-yl)acryloyl-CoA (MMDBc0055013)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:50 UTC

Update Date

2025-10-07 16:08:51 UTC

Metabolite ID

MMDBc0055013

Metabolite Identification

Common Name

(E)-3-(indol-3-yl)acryloyl-CoA

Description

(E)-3-(indol-3-yl)acryloyl-CoA is a thioester compound belonging to the class of acyl-CoA derivatives. There is limited literature available on this metabolite, indicating that further research may be needed to fully understand its biological significance and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 68 72  0  0  1  0            999 V2000
   -1.4052   -6.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461   -6.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2742   -7.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7591   -8.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4537   -7.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4236   -8.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6661   -7.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9124   -8.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -7.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -7.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0702   -7.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8239   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3335   -9.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3119   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3335   -8.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1182   -8.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6031   -8.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6491   -7.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2450   -7.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1394   -7.0512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069   -7.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2257   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4028   -7.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5605   -7.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1182   -9.5122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5628   -8.6553    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -9.3312   -6.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -7.3867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -8.3566    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.2137    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -4.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -4.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -3.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -2.6617    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.7994    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -4.1048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4913   -8.1335    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7523   -7.1269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8262   -9.1034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -1.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.4794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -6.7156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    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  2  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  2  0  0  0  0
 19  5  2  0  0  0  0
 19 18  1  0  0  0  0
 20  6  2  0  0  0  0
 20 19  1  0  0  0  0
 21 14  1  1  0  0  0
 22  9  1  0  0  0  0
 23  8  1  0  0  0  0
 26 21  1  0  0  0  0
 26 25  1  0  0  0  0
 28 24  2  0  0  0  0
 29 24  1  0  0  0  0
 30 27  1  0  0  0  0
 31 25  1  0  0  0  0
 32  1  1  0  0  0  0
 32  2  1  0  0  0  0
 32 15  1  0  0  0  0
 32 27  1  0  0  0  0
 33 28  1  0  0  0  0
 34 11  1  4  0  0  0
 34 22  2  0  0  0  0
 35 10  1  4  0  0  0
 35 30  2  0  0  0  0
 36 13  1  0  0  0  0
 36 20  1  0  0  0  0
 37 16  2  0  0  0  0
 37 28  1  0  0  0  0
 38 16  1  0  0  0  0
 38 29  2  0  0  0  0
 39 17  2  0  0  0  0
 39 24  1  0  0  0  0
 40 17  1  0  0  0  0
 40 29  1  0  0  0  0
 31 40  1  1  0  0  0
 41 22  1  0  0  0  0
 42 23  2  0  0  0  0
 25 43  1  6  0  0  0
 27 44  1  6  0  0  0
 45 30  1  0  0  0  0
 53 14  1  0  0  0  0
 54 15  1  0  0  0  0
 55 21  1  0  0  0  0
 55 31  1  0  0  0  0
 26 56  1  1  0  0  0
 58 46  1  0  0  0  0
 58 47  1  0  0  0  0
 58 48  2  0  0  0  0
 58 56  1  0  0  0  0
 59 49  1  0  0  0  0
 59 50  2  0  0  0  0
 59 53  1  0  0  0  0
 59 57  1  0  0  0  0
 60 51  1  0  0  0  0
 60 52  2  0  0  0  0
 60 54  1  0  0  0  0
 60 57  1  0  0  0  0
 61 12  1  0  0  0  0
 61 23  1  0  0  0  0
 62  7  1  0  0  0  0
 63  8  1  0  0  0  0
 21 64  1  6  0  0  0
 25 65  1  1  0  0  0
 26 66  1  1  0  0  0
 27 67  1  6  0  0  0
 31 68  1  6  0  0  0
M  CHG  4  41  -1  45  -1  46  -1  47  -1
M  END


  Mrv1652306172221392D          

 68 72  0  0  1  0            999 V2000
   -1.4052   -6.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461   -6.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2742   -7.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7591   -8.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4537   -7.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4236   -8.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6661   -7.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9124   -8.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -7.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -7.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0702   -7.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8239   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3335   -9.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3119   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3335   -8.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1182   -8.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6031   -8.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6491   -7.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2450   -7.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1394   -7.0512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069   -7.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2257   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4028   -7.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5605   -7.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1182   -9.5122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5628   -8.6553    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -9.3312   -6.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -7.3867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -8.3566    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.2137    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -4.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -4.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -3.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -2.6617    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.7994    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -4.1048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4913   -8.1335    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7523   -7.1269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8262   -9.1034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -1.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.4794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -6.7156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    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  2  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  2  0  0  0  0
 19  5  2  0  0  0  0
 19 18  1  0  0  0  0
 20  6  2  0  0  0  0
 20 19  1  0  0  0  0
 21 14  1  1  0  0  0
 22  9  1  0  0  0  0
 23  8  1  0  0  0  0
 26 21  1  0  0  0  0
 26 25  1  0  0  0  0
 28 24  2  0  0  0  0
 29 24  1  0  0  0  0
 30 27  1  0  0  0  0
 31 25  1  0  0  0  0
 32  1  1  0  0  0  0
 32  2  1  0  0  0  0
 32 15  1  0  0  0  0
 32 27  1  0  0  0  0
 33 28  1  0  0  0  0
 34 11  1  4  0  0  0
 34 22  2  0  0  0  0
 35 10  1  4  0  0  0
 35 30  2  0  0  0  0
 36 13  1  0  0  0  0
 36 20  1  0  0  0  0
 37 16  2  0  0  0  0
 37 28  1  0  0  0  0
 38 16  1  0  0  0  0
 38 29  2  0  0  0  0
 39 17  2  0  0  0  0
 39 24  1  0  0  0  0
 40 17  1  0  0  0  0
 40 29  1  0  0  0  0
 31 40  1  1  0  0  0
 41 22  1  0  0  0  0
 42 23  2  0  0  0  0
 25 43  1  6  0  0  0
 27 44  1  6  0  0  0
 45 30  1  0  0  0  0
 53 14  1  0  0  0  0
 54 15  1  0  0  0  0
 55 21  1  0  0  0  0
 55 31  1  0  0  0  0
 26 56  1  1  0  0  0
 58 46  1  0  0  0  0
 58 47  1  0  0  0  0
 58 48  2  0  0  0  0
 58 56  1  0  0  0  0
 59 49  1  0  0  0  0
 59 50  2  0  0  0  0
 59 53  1  0  0  0  0
 59 57  1  0  0  0  0
 60 51  1  0  0  0  0
 60 52  2  0  0  0  0
 60 54  1  0  0  0  0
 60 57  1  0  0  0  0
 61 12  1  0  0  0  0
 61 23  1  0  0  0  0
 62  7  1  0  0  0  0
 63  8  1  0  0  0  0
 21 64  1  6  0  0  0
 25 65  1  1  0  0  0
 26 66  1  1  0  0  0
 27 67  1  6  0  0  0
 31 68  1  6  0  0  0
M  CHG  4  41  -1  45  -1  46  -1  47  -1
M  END
> <DATABASE_ID>
MMDBc0055013

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)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/C32H43N8O17P3S/c1-32(2,27(44)30(45)35-10-9-22(41)34-11-12-61-23(42)8-7-18-13-36-20-6-4-3-5-19(18)20)15-54-60(51,52)57-59(49,50)53-14-21-26(56-58(46,47)48)25(43)31(55-21)40-17-39-24-28(33)37-16-38-29(24)40/h3-8,13,16-17,21,25-27,31,36,43-44H,9-12,14-15H2,1-2H3,(H,34,41)(H,35,45)(H,49,50)(H,51,52)(H2,33,37,38)(H2,46,47,48)/p-4/b8-7+/t21-,25-,26-,27+,31-/m1/s1

> <INCHI_KEY>
LQFMEOXXQRDBPP-BTOWARJYSA-J

> <FORMULA>
C32H39N8O17P3S

> <MOLECULAR_WEIGHT>
932.69

> <EXACT_MASS>
932.138868315

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
85.16605684618222

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <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)-2-hydroxy-N-{2-[(2-{[(2E)-3-(1H-indol-3-yl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanecarboximidate

> <JCHEM_LOGP>
-1.5541416350425972

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8917159666369727

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8202024196606379

> <JCHEM_PKA_STRONGEST_BASIC>
4.161768832410413

> <JCHEM_POLAR_SURFACE_AREA>
397.7200000000001

> <JCHEM_REFRACTIVITY>
233.61130000000003

> <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]-2-hydroxy-N-{2-[(2-{[(2E)-3-(1H-indol-3-yl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-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      -2.623 -11.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.686 -11.792   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -24.779 -13.697   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -25.684 -14.942   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -23.247 -13.857   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -25.057 -16.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -19.910 -14.835   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -18.503 -15.461   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.299 -13.720   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.892 -14.346   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.198 -14.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -14.605 -14.277   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -21.156 -17.280   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.061  -2.789   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.316 -10.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -21.156 -15.740   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -22.621 -15.264   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -23.526 -16.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.185  -1.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.545 -14.625   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -17.257 -14.556   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.555  -1.114   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.650  -2.359   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.994 -13.162   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.239 -14.067   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.155 -11.631   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       4.924   5.923   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0     -11.952 -13.999   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      -6.646 -13.441   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0     -22.621 -17.756   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0     -10.384 -16.157   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0     -17.418 -13.025   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       4.095  -1.114   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -2.587 -13.789   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -5.078 -15.599   0.000  0.00  0.00           O-1
HETATM   46  O   UNK     0      -0.049  -3.938   0.000  0.00  0.00           O-1
HETATM   47  O   UNK     0       2.240  -5.999   0.000  0.00  0.00           O-1
HETATM   48  O   UNK     0       0.065  -6.113   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -1.241  -6.471   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -3.051  -3.980   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -1.699  -7.501   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -4.762  -7.823   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -0.900  -4.320   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -3.070  -9.194   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       0.185  -0.344   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       2.126  -3.824   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -3.392  -6.131   0.000  0.00  0.00           O+0
HETATM   58  P   UNK     0       1.095  -4.969   0.000  0.00  0.00           P+0
HETATM   59  P   UNK     0      -2.146  -5.226   0.000  0.00  0.00           P+0
HETATM   60  P   UNK     0      -3.231  -7.662   0.000  0.00  0.00           P+0
HETATM   61  S   UNK     0     -15.850 -15.183   0.000  0.00  0.00           S+0
HETATM   62  H   UNK     0     -20.071 -13.303   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0     -18.342 -16.993   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.426  -3.405   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.254  -2.486   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.174  -0.895   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      -5.400 -12.536   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.171   0.373   0.000  0.00  0.00           H+0
CONECT    1   32                                                            
CONECT    2   32                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   19                                                       
CONECT    6    4   20                                                       
CONECT    7    8   18   62                                                  
CONECT    8    7   23   63                                                  
CONECT    9   10   22                                                       
CONECT   10    9   35                                                       
CONECT   11   12   34                                                       
CONECT   12   11   61                                                       
CONECT   13   18   36                                                       
CONECT   14   21   53                                                       
CONECT   15   32   54                                                       
CONECT   16   37   38                                                       
CONECT   17   39   40                                                       
CONECT   18    7   13   19                                                  
CONECT   19    5   18   20                                                  
CONECT   20    6   19   36                                                  
CONECT   21   14   26   55   64                                             
CONECT   22    9   34   41                                                  
CONECT   23    8   42   61                                                  
CONECT   24   28   29   39                                                  
CONECT   25   26   31   43   65                                             
CONECT   26   21   25   56   66                                             
CONECT   27   30   32   44   67                                             
CONECT   28   24   33   37                                                  
CONECT   29   24   38   40                                                  
CONECT   30   27   35   45                                                  
CONECT   31   25   40   55   68                                             
CONECT   32    1    2   15   27                                             
CONECT   33   28                                                            
CONECT   34   11   22                                                       
CONECT   35   10   30                                                       
CONECT   36   13   20                                                       
CONECT   37   16   28                                                       
CONECT   38   16   29                                                       
CONECT   39   17   24                                                       
CONECT   40   17   29   31                                                  
CONECT   41   22                                                            
CONECT   42   23                                                            
CONECT   43   25                                                            
CONECT   44   27                                                            
CONECT   45   30                                                            
CONECT   46   58                                                            
CONECT   47   58                                                            
CONECT   48   58                                                            
CONECT   49   59                                                            
CONECT   50   59                                                            
CONECT   51   60                                                            
CONECT   52   60                                                            
CONECT   53   14   59                                                       
CONECT   54   15   60                                                       
CONECT   55   21   31                                                       
CONECT   56   26   58                                                       
CONECT   57   59   60                                                       
CONECT   58   46   47   48   56                                             
CONECT   59   49   50   53   57                                             
CONECT   60   51   52   54   57                                             
CONECT   61   12   23                                                       
CONECT   62    7                                                            
CONECT   63    8                                                            
CONECT   64   21                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   27                                                            
CONECT   68   31                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

Synonyms

Not Available

Molecular Formula

C₃₂H₃₉N₈O₁₇P₃S

Average Mass

932.69

Monoisotopic Mass

932.138868315

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)-2-hydroxy-N-{2-[(2-{[(2E)-3-(1H-indol-3-yl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-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]-2-hydroxy-N-{2-[(2-{[(2E)-3-(1H-indol-3-yl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanecarboximidate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)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/C32H43N8O17P3S/c1-32(2,27(44)30(45)35-10-9-22(41)34-11-12-61-23(42)8-7-18-13-36-20-6-4-3-5-19(18)20)15-54-60(51,52)57-59(49,50)53-14-21-26(56-58(46,47)48)25(43)31(55-21)40-17-39-24-28(33)37-16-38-29(24)40/h3-8,13,16-17,21,25-27,31,36,43-44H,9-12,14-15H2,1-2H3,(H,34,41)(H,35,45)(H,49,50)(H,51,52)(H2,33,37,38)(H2,46,47,48)/p-4/b8-7+/t21-,25-,26-,27+,31-/m1/s1

InChI Key

LQFMEOXXQRDBPP-BTOWARJYSA-J

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Indole or derivatives
Indole
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Benzenoid
Alkyl phosphate
Substituted pyrrole
Pyrimidine
Phosphoric acid ester
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Pyrrole
Imidazole
Azole
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary alcohol
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-1.6	ChemAxon
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	397.72 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	233.61 m³·mol⁻¹	ChemAxon
Polarizability	85.17 Å³	ChemAxon
Number of Rings	5	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

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank	Species

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
MMDBr0038882	(E)-3-(indol-3-yl)acryloyl-CoA	(E)-3-(indol-3-yl)acrylic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

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
Bacteria/Eubacteria	Firmicutes	1	Human vaginal secretion

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

134819956

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 (E)-3-(indol-3-yl)acryloyl-CoA (MMDBc0055013)

MOL for #<Metabolite:0x00007f2acbbe6ae8>

3D MOL for #<Metabolite:0x00007f2acbbe6ae8>

3D SDF for #<Metabolite:0x00007f2acbbe6ae8>

3D-SDF for #<Metabolite:0x00007f2acbbe6ae8>

PDB for #<Metabolite:0x00007f2acbbe6ae8>

3D PDB for #<Metabolite:0x00007f2acbbe6ae8>

SMILES for #<Metabolite:0x00007f2acbbe6ae8>

INCHI for #<Metabolite:0x00007f2acbbe6ae8>

Structure for #<Metabolite:0x00007f2acbbe6ae8>

3D Structure for #<Metabolite:0x00007f2acbbe6ae8>