MiMeDB: Showing metabocard for (9Z)-hexadecenoyl-CoA (MMDBc0055005)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:42 UTC

Update Date

2022-08-12 20:09:11 UTC

Metabolite ID

MMDBc0055005

Metabolite Identification

Common Name

(9Z)-hexadecenoyl-CoA

Description

palmitoleoyl-CoA(4-), also known as (9Z)-hexadecenoyl-CoA or 16:1-delta9-CoA(4-), belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Based on a literature review a small amount of articles have been published on palmitoleoyl-CoA(4-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 72 74  0  0  1  0            999 V2000
   -8.3543   19.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2315   14.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842   15.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5442   19.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2741   18.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4640   18.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1939   17.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838   17.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1138   16.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   16.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   17.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336   17.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4935   18.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   19.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235   19.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133   19.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   19.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074   16.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774   15.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171   17.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2530   17.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1986   16.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479   15.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7792   15.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2363   18.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0087   16.7232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0973   16.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   18.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4050   17.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1774   16.0782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3588   15.9761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0678   14.2286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1944   17.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8027   16.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576   14.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3334   16.8883    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6078   14.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7968   17.7276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8272   17.0350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   15.1641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3815   16.3603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9898   16.0363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0550   18.1506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0804   17.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5572   15.6318    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7931   19.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7412   15.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3378   13.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   13.7609    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.1194   16.0627    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.1512   14.4131    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.3105   15.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6925   15.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0043   17.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1218   15.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8745   16.4837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6585   16.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581   15.3200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6111   17.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9602   15.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0382   16.5673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1353   15.2379    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.8484   16.4114    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.4982   15.9436    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   18.1264    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6539   16.0995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336   15.7877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5020   16.0721    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8967   15.3024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7574   16.6984    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977   15.0082    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9844   16.3816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 26 22  1  1  0  0  0
 27 18  1  0  0  0  0
 28 17  1  0  0  0  0
 31 26  1  0  0  0  0
 31 30  1  0  0  0  0
 33 29  2  0  0  0  0
 34 29  1  0  0  0  0
 35 32  1  0  0  0  0
 36 30  1  0  0  0  0
 37  2  1  0  0  0  0
 37  3  1  0  0  0  0
 37 23  1  0  0  0  0
 37 32  1  0  0  0  0
 38 33  1  0  0  0  0
 39 20  1  4  0  0  0
 39 27  2  0  0  0  0
 40 19  1  4  0  0  0
 40 35  2  0  0  0  0
 41 24  2  0  0  0  0
 41 33  1  0  0  0  0
 42 24  1  0  0  0  0
 42 34  2  0  0  0  0
 43 25  2  0  0  0  0
 43 29  1  0  0  0  0
 44 25  1  0  0  0  0
 44 34  1  0  0  0  0
 36 44  1  1  0  0  0
 45 27  1  0  0  0  0
 46 28  2  0  0  0  0
 30 47  1  6  0  0  0
 32 48  1  6  0  0  0
 49 35  1  0  0  0  0
 57 22  1  0  0  0  0
 58 23  1  0  0  0  0
 59 26  1  0  0  0  0
 59 36  1  0  0  0  0
 31 60  1  1  0  0  0
 62 50  1  0  0  0  0
 62 51  1  0  0  0  0
 62 52  2  0  0  0  0
 62 60  1  0  0  0  0
 63 53  1  0  0  0  0
 63 54  2  0  0  0  0
 63 57  1  0  0  0  0
 63 61  1  0  0  0  0
 64 55  1  0  0  0  0
 64 56  2  0  0  0  0
 64 58  1  0  0  0  0
 64 61  1  0  0  0  0
 65 21  1  0  0  0  0
 65 28  1  0  0  0  0
 66  9  1  0  0  0  0
 67 10  1  0  0  0  0
 26 68  1  6  0  0  0
 30 69  1  1  0  0  0
 31 70  1  1  0  0  0
 32 71  1  6  0  0  0
 36 72  1  6  0  0  0
M  CHG  4  45  -1  49  -1  50  -1  51  -1
M  END


  Mrv1652306172221392D          

 72 74  0  0  1  0            999 V2000
   -8.3543   19.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2315   14.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842   15.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5442   19.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2741   18.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4640   18.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1939   17.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838   17.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1138   16.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   16.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   17.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336   17.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4935   18.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635   19.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235   19.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133   19.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   19.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074   16.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774   15.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171   17.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2530   17.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1986   16.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479   15.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7792   15.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2363   18.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0087   16.7232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0973   16.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   18.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4050   17.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1774   16.0782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3588   15.9761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0678   14.2286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1944   17.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8027   16.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576   14.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3334   16.8883    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6078   14.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7968   17.7276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8272   17.0350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   15.1641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3815   16.3603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9898   16.0363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0550   18.1506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0804   17.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5572   15.6318    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7931   19.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7412   15.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3378   13.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   13.7609    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.1194   16.0627    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.1512   14.4131    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.3105   15.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6925   15.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0043   17.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1218   15.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8745   16.4837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6585   16.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581   15.3200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6111   17.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9602   15.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0382   16.5673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1353   15.2379    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.8484   16.4114    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.4982   15.9436    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   18.1264    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6539   16.0995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0336   15.7877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5020   16.0721    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8967   15.3024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7574   16.6984    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977   15.0082    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9844   16.3816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 26 22  1  1  0  0  0
 27 18  1  0  0  0  0
 28 17  1  0  0  0  0
 31 26  1  0  0  0  0
 31 30  1  0  0  0  0
 33 29  2  0  0  0  0
 34 29  1  0  0  0  0
 35 32  1  0  0  0  0
 36 30  1  0  0  0  0
 37  2  1  0  0  0  0
 37  3  1  0  0  0  0
 37 23  1  0  0  0  0
 37 32  1  0  0  0  0
 38 33  1  0  0  0  0
 39 20  1  4  0  0  0
 39 27  2  0  0  0  0
 40 19  1  4  0  0  0
 40 35  2  0  0  0  0
 41 24  2  0  0  0  0
 41 33  1  0  0  0  0
 42 24  1  0  0  0  0
 42 34  2  0  0  0  0
 43 25  2  0  0  0  0
 43 29  1  0  0  0  0
 44 25  1  0  0  0  0
 44 34  1  0  0  0  0
 36 44  1  1  0  0  0
 45 27  1  0  0  0  0
 46 28  2  0  0  0  0
 30 47  1  6  0  0  0
 32 48  1  6  0  0  0
 49 35  1  0  0  0  0
 57 22  1  0  0  0  0
 58 23  1  0  0  0  0
 59 26  1  0  0  0  0
 59 36  1  0  0  0  0
 31 60  1  1  0  0  0
 62 50  1  0  0  0  0
 62 51  1  0  0  0  0
 62 52  2  0  0  0  0
 62 60  1  0  0  0  0
 63 53  1  0  0  0  0
 63 54  2  0  0  0  0
 63 57  1  0  0  0  0
 63 61  1  0  0  0  0
 64 55  1  0  0  0  0
 64 56  2  0  0  0  0
 64 58  1  0  0  0  0
 64 61  1  0  0  0  0
 65 21  1  0  0  0  0
 65 28  1  0  0  0  0
 66  9  1  0  0  0  0
 67 10  1  0  0  0  0
 26 68  1  6  0  0  0
 30 69  1  1  0  0  0
 31 70  1  1  0  0  0
 32 71  1  6  0  0  0
 36 72  1  6  0  0  0
M  CHG  4  45  -1  49  -1  50  -1  51  -1
M  END
> <DATABASE_ID>
MMDBc0055005

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=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/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h9-10,24-26,30-32,36,47-48H,4-8,11-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/p-4/b10-9-/t26-,30-,31-,32+,36-/m1/s1

> <INCHI_KEY>
QBYOCCWNZAOZTL-MDMKAECGSA-J

> <FORMULA>
C37H60N7O17P3S

> <MOLECULAR_WEIGHT>
999.9

> <EXACT_MASS>
999.300119988

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
97.8634453259701

> <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-[(9Z)-hexadec-9-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanecarboximidate

> <JCHEM_LOGP>
0.49865842963956714

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8864429258961048

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.819156882648989

> <JCHEM_PKA_STRONGEST_BASIC>
6.431293194740966

> <JCHEM_POLAR_SURFACE_AREA>
381.9300000000001

> <JCHEM_REFRACTIVITY>
257.66510000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
33

> <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-[(9Z)-hexadec-9-enoylsulfanyl]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     -15.595  36.455   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.765  26.716   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.437  28.732   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.082  36.164   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.578  34.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.066  34.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.562  32.963   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.050  32.672   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.546  31.217   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.033  30.926   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.025  32.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.529  33.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.521  34.709   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.025  36.164   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.017  37.328   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.505  37.037   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  35.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.560  30.052   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.065  28.597   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.032  32.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.472  33.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.171  31.508   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.609  28.888   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.721  29.487   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.841  33.691   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.683  31.217   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.048  30.344   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.489  35.291   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.023  32.487   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.865  30.013   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.336  29.822   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.593  26.560   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.496  32.039   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.898  31.434   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.081  26.851   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.156  31.525   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.601  27.724   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      27.621  33.091   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0       1.544  31.799   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0       5.577  28.306   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0      26.845  30.539   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      24.248  29.934   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      24.369  33.881   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      22.550  32.178   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0       1.040  29.179   0.000  0.00  0.00           O-1
HETATM   46  O   UNK     0      -1.480  36.455   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      21.917  28.888   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       8.097  25.105   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       5.073  25.687   0.000  0.00  0.00           O-1
HETATM   50  O   UNK     0      17.023  29.984   0.000  0.00  0.00           O-1
HETATM   51  O   UNK     0      17.082  26.904   0.000  0.00  0.00           O-1
HETATM   52  O   UNK     0      15.513  28.414   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      14.359  29.122   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      14.941  32.147   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      13.294  28.753   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      10.966  30.770   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      16.163  30.344   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      11.122  28.597   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      19.807  32.269   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      18.592  28.474   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      13.138  30.926   0.000  0.00  0.00           O+0
HETATM   62  P   UNK     0      17.053  28.444   0.000  0.00  0.00           P+0
HETATM   63  P   UNK     0      14.650  30.635   0.000  0.00  0.00           P+0
HETATM   64  P   UNK     0      12.130  29.761   0.000  0.00  0.00           P+0
HETATM   65  S   UNK     0      -1.984  33.836   0.000  0.00  0.00           S+0
HETATM   66  H   UNK     0     -10.554  30.052   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      -7.529  29.470   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      17.737  30.001   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0      20.341  28.565   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      20.080  31.170   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0       7.089  28.015   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0      22.371  30.579   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   37                                                            
CONECT    3   37                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   66                                                  
CONECT   10    9   11   67                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   28                                                       
CONECT   18   19   27                                                       
CONECT   19   18   40                                                       
CONECT   20   21   39                                                       
CONECT   21   20   65                                                       
CONECT   22   26   57                                                       
CONECT   23   37   58                                                       
CONECT   24   41   42                                                       
CONECT   25   43   44                                                       
CONECT   26   22   31   59   68                                             
CONECT   27   18   39   45                                                  
CONECT   28   17   46   65                                                  
CONECT   29   33   34   43                                                  
CONECT   30   31   36   47   69                                             
CONECT   31   26   30   60   70                                             
CONECT   32   35   37   48   71                                             
CONECT   33   29   38   41                                                  
CONECT   34   29   42   44                                                  
CONECT   35   32   40   49                                                  
CONECT   36   30   44   59   72                                             
CONECT   37    2    3   23   32                                             
CONECT   38   33                                                            
CONECT   39   20   27                                                       
CONECT   40   19   35                                                       
CONECT   41   24   33                                                       
CONECT   42   24   34                                                       
CONECT   43   25   29                                                       
CONECT   44   25   34   36                                                  
CONECT   45   27                                                            
CONECT   46   28                                                            
CONECT   47   30                                                            
CONECT   48   32                                                            
CONECT   49   35                                                            
CONECT   50   62                                                            
CONECT   51   62                                                            
CONECT   52   62                                                            
CONECT   53   63                                                            
CONECT   54   63                                                            
CONECT   55   64                                                            
CONECT   56   64                                                            
CONECT   57   22   63                                                       
CONECT   58   23   64                                                       
CONECT   59   26   36                                                       
CONECT   60   31   62                                                       
CONECT   61   63   64                                                       
CONECT   62   50   51   52   60                                             
CONECT   63   53   54   57   61                                             
CONECT   64   55   56   58   61                                             
CONECT   65   21   28                                                       
CONECT   66    9                                                            
CONECT   67   10                                                            
CONECT   68   26                                                            
CONECT   69   30                                                            
CONECT   70   31                                                            
CONECT   71   32                                                            
CONECT   72   36                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  148    0
END

Synonyms

Value	Source
(9Z)-Hexadecenoyl-CoA	ChEBI
(Z)-Hexadec-9-enoyl-CoA tetraanion	ChEBI
(Z)-Hexadec-9-enoyl-CoA(4-)	ChEBI
(Z)-Hexadec-9-enoyl-coenzyme A tetraanion	ChEBI
(Z)-Hexadec-9-enoyl-coenzyme A(4-)	ChEBI
16:1-delta9-CoA(4-)	ChEBI
9Z-Hexadecenoyl-CoA(4-)	ChEBI
cis-9-Hexadecenoyl-CoA(4-)	ChEBI
Palmitoleoyl-coenzyme A(4-)	ChEBI
Palmitoleyl-CoA tetraanion	ChEBI
16:1-Δ9-CoA(4-)	Generator

Molecular Formula

C₃₇H₆₀N₇O₁₇P₃S

Average Mass

999.9

Monoisotopic Mass

999.300119988

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-[(9Z)-hexadec-9-enoylsulfanyl]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-[(9Z)-hexadec-9-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanecarboximidate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=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/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h9-10,24-26,30-32,36,47-48H,4-8,11-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/p-4/b10-9-/t26-,30-,31-,32+,36-/m1/s1

InChI Key

QBYOCCWNZAOZTL-MDMKAECGSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain fatty 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
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

monounsaturated fatty acyl-CoA(4-) (CHEBI:61540 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.5	ChemAxon
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.43	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	33	ChemAxon
Refractivity	257.67 m³·mol⁻¹	ChemAxon
Polarizability	97.86 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

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0015258	(9Z)-hexadecenoic acid	(9Z)-hexadecenoyl-CoA	Long-chain-fatty-acid--CoA ligase 1	Ligation	RHEA	34755880
MMDBr0015259	(9Z)-hexadecenoic acid	(9Z)-hexadecenoyl-CoA	Long-chain-fatty-acid--CoA ligase 1	Ligation	RHEA	34755880
MMDBr0015544	Fe2+	(9Z)-hexadecenoyl-CoA	Acyl-CoA desaturase 1	Desaturation	RHEA	34755880
MMDBr0015545	Fe2+	(9Z)-hexadecenoyl-CoA	Acyl-CoA desaturase 1	Desaturation	RHEA	34755880
MMDBr0015562	(9Z)-hexadecenoyl-CoA	PC(16:0/16:1(9Z))	Lysophospholipid acyltransferase	Acylation	RHEA	34755880
MMDBr0015563	(9Z)-hexadecenoyl-CoA	PC(16:0/16:1(9Z))	Lysophospholipid acyltransferase	Acylation	RHEA	34755880
MMDBr0015725	(9Z)-hexadecenoyl-CoA	(9Z)-hexadecenoic acid	Thioesterase 1/protease 1/lysophospholipase L1	Hydrolysis	RHEA	34755880
MMDBr0015726	(9Z)-hexadecenoyl-CoA	(9Z)-hexadecenoic acid	Thioesterase 1/protease 1/lysophospholipase L1	Hydrolysis	RHEA	34755880
MMDBr0015829	(9Z)-hexadecenoyl-CoA	PE(18:1(9Z)/16:1(9Z))	Lysophospholipid acyltransferase	Acylation	RHEA	34755880
MMDBr0015830	(9Z)-hexadecenoyl-CoA	PE(18:1(9Z)/16:1(9Z))	Lysophospholipid acyltransferase	Acylation	RHEA	34755880
MMDBr0016006	(9Z)-hexadecenoyl-CoA	1-(9Z-hexadecenoyl)-sn-glycero-3-phosphate	Glycerol-3-phosphate O-acyltransferase 1	Acylation	RHEA	34755880
MMDBr0016007	(9Z)-hexadecenoyl-CoA	1-(9Z-hexadecenoyl)-sn-glycero-3-phosphate	Glycerol-3-phosphate O-acyltransferase 1	Acylation	RHEA	34755880
MMDBr0016116	(9Z)-hexadecenoyl-CoA	(9Z,12Z)-hexadecadienoyl-CoA	Delta(12)-fatty-acid desaturase	Desaturation	RHEA	34755880
MMDBr0038880	(9Z)-hexadecenoyl-CoA	(9Z)-hexadecenoic 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
Eukaryota/Fungi	Ascomycota	1
Bacteria	Proteobacteria	2	Human ; Human feces
Bacteria	nah	2	Human
Eukaryota/Fungi	Mucoromycota	2

Exposure Sources

Source Type	Source Sub-type	Species	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

26332265

KEGG Compound ID

Not Available

BioCyc ID

CPD-10269

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25244393

PDB ID

Not Available

ChEBI ID

61540

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 (9Z)-hexadecenoyl-CoA (MMDBc0055005)

MOL for #<Metabolite:0x000055c79c54bc58>

3D MOL for #<Metabolite:0x000055c79c54bc58>

3D SDF for #<Metabolite:0x000055c79c54bc58>

3D-SDF for #<Metabolite:0x000055c79c54bc58>

PDB for #<Metabolite:0x000055c79c54bc58>

3D PDB for #<Metabolite:0x000055c79c54bc58>

SMILES for #<Metabolite:0x000055c79c54bc58>

INCHI for #<Metabolite:0x000055c79c54bc58>

Structure for #<Metabolite:0x000055c79c54bc58>

3D Structure for #<Metabolite:0x000055c79c54bc58>