MiMeDB: Showing metabocard for (S)-3-hydroxypalmitoyl-CoA (MMDBc0032995)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:30:24 UTC

Update Date

2024-04-20 06:12:19 UTC

Metabolite ID

MMDBc0032995

Metabolite Identification

Common Name

(S)-3-hydroxypalmitoyl-CoA

Description

(S)-3-Hydroxyhexadecanoyl-CoA is a beta-oxidation intermediate derivative of palmitoyl-CoA and the substrate of the enzyme peroxisomal acyl-CoA thioesterase 2 (PTE-2, EC 3.1.2.2), which is localized in the peroxisome. The peroxisomal beta-oxidation system contains two sets of enzymes, one of which is involved in the oxidation of branched chain fatty acids and intermediates in the hepatic bile acid biosynthetic pathway and consists of one or two branched-chain acyl-CoA oxidase(s), a D-specific bifunctional protein and the sterol carrier-like protein x (SCPx). Peroxisomes are cellular organelles present in all eukaryotic cells. They play an indispensable role in the metabolism of a variety of lipids including very long-chain fatty acids, dicarboxylic fatty acids, bile acids, prostaglandins, leukotrienes, thromboxanes, pristanic acid, and xenobiotic fatty acids. (S)-3-Hydroxyhexadecanoyl-CoA may accumulate intracellularly in certain long-chain fatty acid/j-oxidation deficiencies. Succinate-driven synthesis of ATP from ADP and phosphate is progressively inhibited by increasing concentrations of (S)-3-Hydroxyhexadecanoyl-CoA. (PMID: 11673457 , 8739955 , 7662716 ).

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1652308111921472D          

 66 68  0  0  1  0            999 V2000
   30.1517   -9.1181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   29.4843   -8.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8968   -9.9027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.8168   -9.1181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.0718   -9.9027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.3817  -10.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4060  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1488  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6915  -13.5716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9771  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2626  -13.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7199  -11.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9771  -12.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7199  -11.0966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2910  -11.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0054  -10.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4344   -9.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3074   -8.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7199   -9.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1324   -8.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0054   -9.8590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.2909   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1488   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7988   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4488   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9738   -8.6215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9738  -10.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6238   -8.6215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6238  -10.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9738   -9.4465    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.6238   -9.4465    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.0322   -8.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5868  -10.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7618  -11.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4118  -11.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5868  -11.3952    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.5868  -12.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9363   -8.8632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5495   -9.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2719   -8.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2639   -9.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5495  -10.2402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0924   -8.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9784   -9.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2640  -10.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9784  -10.2401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6928   -9.0025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8633  -13.1591    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.5778  -14.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5778  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2922  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0067  -14.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0067  -13.5716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.7212  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4356  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1501  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8645  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5790  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2935  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0080  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7224  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4369  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8657  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1513  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5802  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2946  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 53  1  0  0  0  0
 53 52  1  6  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 64 63  1  0  0  0  0
 63 65  1  0  0  0  0
 65 66  1  0  0  0  0
 62 64  1  0  0  0  0
M  END

      
  Mrv1652308111921472D          

 66 68  0  0  1  0            999 V2000
   30.1517   -9.1181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   29.4843   -8.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8968   -9.9027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.8168   -9.1181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.0718   -9.9027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.3817  -10.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4060  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1488  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6915  -13.5716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9771  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2626  -13.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7199  -11.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9771  -12.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7199  -11.0966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2910  -11.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0054  -10.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4344   -9.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3074   -8.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7199   -9.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1324   -8.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0054   -9.8590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.2909   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1488   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7988   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4488   -9.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9738   -8.6215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9738  -10.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6238   -8.6215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6238  -10.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9738   -9.4465    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.6238   -9.4465    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.0322   -8.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5868  -10.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7618  -11.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4118  -11.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5868  -11.3952    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.5868  -12.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9363   -8.8632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5495   -9.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2719   -8.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2639   -9.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5495  -10.2402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0924   -8.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9784   -9.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2640  -10.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9784  -10.2401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6928   -9.0025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8633  -13.1591    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.5778  -14.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5778  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2922  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0067  -14.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0067  -13.5716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.7212  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4356  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1501  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8645  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5790  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2935  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0080  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7224  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4369  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8657  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1513  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5802  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2946  -13.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 53  1  0  0  0  0
 53 52  1  6  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 64 63  1  0  0  0  0
 63 65  1  0  0  0  0
 65 66  1  0  0  0  0
 62 64  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032995

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C37H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-26,30-32,36,45,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t25-,26+,30+,31+,32-,36+/m0/s1

> <INCHI_KEY>
DEHLMTDDPWDRDR-BCIKBWLNSA-N

> <FORMULA>
C37H66N7O18P3S

> <MOLECULAR_WEIGHT>
1021.942

> <EXACT_MASS>
1021.339788569

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
101.96808599775727

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
-0.6325016881479597

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207347761846

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398228

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
383.8599999999999

> <JCHEM_REFRACTIVITY>
238.1634

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-hydroxypalmitoyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-AUG-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-AUG-19         0                                  
HETATM    1  C   UNK     0      56.283 -17.020   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      55.037 -16.115   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      55.807 -18.485   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      53.791 -17.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      54.267 -18.485   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      56.713 -19.731   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      43.691 -24.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.078 -25.334   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      42.357 -25.334   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      41.024 -24.564   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      39.690 -25.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      42.410 -22.254   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.024 -23.024   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      42.410 -20.714   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      39.743 -20.714   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      41.077 -19.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      43.744 -18.403   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.640 -16.300   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      42.410 -17.633   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      43.180 -16.300   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.077 -18.403   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      39.743 -17.633   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      45.078 -17.633   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      48.158 -17.633   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      51.238 -17.633   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      46.618 -16.093   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      46.618 -19.173   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      49.698 -16.093   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      49.698 -19.173   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      46.618 -17.633   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      49.698 -17.633   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      52.327 -16.545   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      53.362 -19.731   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      51.822 -21.271   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      54.902 -21.271   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      53.362 -21.271   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      53.362 -22.811   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      57.748 -16.545   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      58.892 -17.575   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      58.374 -15.138   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      60.226 -16.805   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      58.892 -19.115   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      59.906 -15.299   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      61.560 -17.575   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      60.226 -19.885   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      61.560 -19.115   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      62.893 -16.805   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      46.411 -24.564   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      47.745 -26.874   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      47.745 -25.334   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      49.079 -24.564   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      50.413 -26.874   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      50.413 -25.334   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      51.746 -24.564   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      53.080 -25.334   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      54.414 -24.564   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      55.747 -25.334   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      57.081 -24.564   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      58.415 -25.334   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      59.748 -24.564   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      61.082 -25.334   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      62.416 -24.564   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      65.083 -24.564   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      63.749 -25.334   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      66.416 -25.334   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      67.750 -24.564   0.000  0.00  0.00           C+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   50                                                       
CONECT   49   50                                                            
CONECT   50   48   49   51                                                  
CONECT   51   50   53                                                       
CONECT   52   53                                                            
CONECT   53   51   52   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   64                                                       
CONECT   63   64   65                                                       
CONECT   64   63   62                                                       
CONECT   65   63   66                                                       
CONECT   66   65                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  136    0
END

Synonyms

Value	Source
(S)-3-Hydroxyhexadecanoyl-CoA	ChEBI
(S)-3-Hydroxyhexadecanoyl-coenzyme A	ChEBI
(S)-3-Hydroxypalmitoyl-coenzyme A	ChEBI

Molecular Formula

C₃₇H₆₆N₇O₁₈P₃S

Average Mass

1021.942

Monoisotopic Mass

1021.339788569

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

β-hydroxypalmitoyl-coa

CAS Registry Number

35106-50-4

SMILES

CCCCCCCCCCCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C37H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-26,30-32,36,45,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t25-,26+,30+,31+,32-,36+/m0/s1

InChI Key

DEHLMTDDPWDRDR-BCIKBWLNSA-N

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
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

long-chain fatty acyl-CoA (CHEBI:27402 )
11,12-saturated fatty acyl-CoA (CHEBI:27402 )
3-hydroxy fatty acyl-CoA (CHEBI:27402 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.14 g/L	ALOGPS
logP	1.68	ALOGPS
logP	-0.63	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	238.16 m³·mol⁻¹	ChemAxon
Polarizability	101.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f80-4907310200-86c6b5f89811ee9c3811	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-1916310000-0d256705c0814e067de7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-1903100000-87dcba0f6aaf3de62a85	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fai-9660222400-23c4c62f477575210f02	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4920311000-647eccb2cf9b9bf41a08	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-8900100000-8e47c83815f1b1592503	2016-09-12	View Spectrum
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

Extracellular
Membrane

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
MMDBr0018716	(2E)-Hexadecenoyl-CoA	Water	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018717	NAD	Hydrogen Ion	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019707	(S)-3-hydroxypalmitoyl-CoA	Water	3-ketoacyl-CoA thiolase, peroxisomal	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0019708	NAD	Hydrogen Ion	3-ketoacyl-CoA thiolase, peroxisomal	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0023315	(S)-3-hydroxypalmitoyl-CoA	(2E)-Hexadecenoyl-CoA	Fatty acid oxidation complex subunit alpha	Aerobic and anaerobic degradation of long-chain fatty acids	PathBank	31602464
MMDBr0023316	(S)-3-hydroxypalmitoyl-CoA	(2E)-Hexadecenoyl-CoA	Fatty acid oxidation complex subunit alpha	Aerobic and anaerobic degradation of long-chain fatty acids	PathBank	31602464
MMDBr0038790	(S)-3-hydroxypalmitoyl-CoA	3-Hydroxyhexadecanoic 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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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

Not Available

KEGG Compound ID

C05258

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966179

PDB ID

Not Available

ChEBI ID

27402

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ventura FV, Ruiter JP, Ijlst L, Almeida IT, Wanders RJ: Inhibition of oxidative phosphorylation by palmitoyl-CoA in digitonin permeabilized fibroblasts: implications for long-chain fatty acid beta-oxidation disorders. Biochim Biophys Acta. 1995 Aug 15;1272(1):14-20. doi: 10.1016/0925-4439(95)00064-b. [PubMed:7662716 ]
Ventura FV, Ruiter JP, Ijlst L, de Almeida IT, Wanders RJ: Inhibitory effect of 3-hydroxyacyl-CoAs and other long-chain fatty acid beta-oxidation intermediates on mitochondrial oxidative phosphorylation. J Inherit Metab Dis. 1996;19(2):161-4. doi: 10.1007/BF01799419. [PubMed:8739955 ]
Hunt MC, Solaas K, Kase BF, Alexson SE: Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism. J Biol Chem. 2002 Jan 11;277(2):1128-38. doi: 10.1074/jbc.M106458200. Epub 2001 Oct 22. [PubMed:11673457 ]

Showing metabocard for (S)-3-hydroxypalmitoyl-CoA (MMDBc0032995)

MOL for #<Metabolite:0x00007fe29c01afc8>

3D MOL for #<Metabolite:0x00007fe29c01afc8>

3D SDF for #<Metabolite:0x00007fe29c01afc8>

3D-SDF for #<Metabolite:0x00007fe29c01afc8>

PDB for #<Metabolite:0x00007fe29c01afc8>

3D PDB for #<Metabolite:0x00007fe29c01afc8>

SMILES for #<Metabolite:0x00007fe29c01afc8>

INCHI for #<Metabolite:0x00007fe29c01afc8>

Structure for #<Metabolite:0x00007fe29c01afc8>

3D Structure for #<Metabolite:0x00007fe29c01afc8>