MiMeDB: Showing metabocard for Heptadecanoyl Coenzyme A (MMDBc0048645)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:05:56 UTC

Update Date

2025-10-07 16:08:12 UTC

Metabolite ID

MMDBc0048645

Metabolite Identification

Common Name

Heptadecanoyl Coenzyme A

Description

Heptadecanoyl Coenzyme A is a fatty acyl-CoA derivative, belonging to the chemical class of acyl-CoA thioesters. It features a long-chain fatty acid with a 17-carbon backbone, linked to coenzyme A via a thioester bond, which facilitates its role in various metabolic pathways. The chemical structure includes a hydrophobic hydrocarbon chain, which is crucial for its function in lipid metabolism. Heptadecanoyl Coenzyme A is involved in the synthesis and degradation of fatty acids, playing a role in the β-oxidation pathway, where it is utilized for energy production. Additionally, it may participate in the biosynthesis of complex lipids and signaling molecules. Recent studies have identified heptadecanoyl Coenzyme A as a significant metabolite in different species, with one study reporting its presence at a notable concentration (13.5%) in S. (PMID:37365525 ). This highlights its potential importance in metabolic profiling and understanding lipid-related processes in various biological systems.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304302200052D          

130132  0  0  1  0            999 V2000
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127129  1  0  0  0  0
127130  2  0  0  0  0
M  CHG  4  91  -1  95  -1 128  -1 129  -1
M  END


  Mrv1652304302200052D          

130132  0  0  1  0            999 V2000
   11.2743    2.0262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5598    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5598    0.7887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2743    1.2012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2743    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2743   -0.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9888    0.7887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4013    1.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3330   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   13.0475    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1322    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1322   -0.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1909   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9314   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2756    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6459    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9054    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7046    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.7632    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   20.1922    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2769    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9066   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.6472   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.9914    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3616    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.6211    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.7059    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3356   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0761   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4203    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7906    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0501    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1348    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7645   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5051   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.8493    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2195    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4790    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.5637    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1935   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.9340   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.2782    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6485    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.9079    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.9927    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6224   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.3629   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.7071    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0774    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.3369    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.4216    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0514   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.7919   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.1361    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5486    0.0742    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.8506    1.2012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.7236    1.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8454    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4329    1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1473    1.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0204    1.8051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7184    0.6781    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2579   -0.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5434   -0.7508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6704   -1.0528    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9723    0.0742    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1309   -0.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -0.3185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4164    0.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7020   -0.0363    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.2895    0.6781    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.1145   -0.7508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875   -0.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8215    0.8255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
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120122  1  6  0  0  0
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126127  1  0  0  0  0
127128  1  0  0  0  0
127129  1  0  0  0  0
127130  2  0  0  0  0
M  CHG  4  91  -1  95  -1 128  -1 129  -1
M  END
> <DATABASE_ID>
MMDBc0048645

> <DATABASE_NAME>
MIME

> <SMILES>
[H]O[C@@]([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C(N=C([H])N=C23)N([H])[H])[C@]([H])(O[H])[C@]1([H])OP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C38H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-29(47)66-22-21-40-28(46)19-20-41-36(50)33(49)38(2,3)24-59-65(56,57)62-64(54,55)58-23-27-32(61-63(51,52)53)31(48)37(60-27)45-26-44-30-34(39)42-25-43-35(30)45/h25-27,31-33,37,48-49H,4-24H2,1-3H3,(H,40,46)(H,41,50)(H,54,55)(H,56,57)(H2,39,42,43)(H2,51,52,53)/p-4/t27-,31-,32-,33+,37-/m1/s1

> <INCHI_KEY>
DRABUZIHHACUPI-DUPKZGIXSA-J

> <FORMULA>
C38H64N7O17P3S

> <MOLECULAR_WEIGHT>
1015.95

> <EXACT_MASS>
1015.331420116

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
130

> <JCHEM_AVERAGE_POLARIZABILITY>
102.399465251067

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(2-{[2-(heptadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxy)phosphonate

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
1.0428780438520424

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776186

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398224

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
374.95

> <JCHEM_REFRACTIVITY>
236.7621000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
35

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(2-{[2-(heptadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-22         0                                  
HETATM    1  H   UNK     0      21.045   3.782   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      19.712   3.012   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      19.712   1.472   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      21.045   2.242   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      21.045   0.702   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      21.045  -0.838   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      22.379   1.472   0.000  0.00  0.00           N+0
HETATM    8  H   UNK     0      23.149   2.806   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      23.713   0.702   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      23.022  -0.674   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0      24.404  -0.674   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      25.046   1.472   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      25.738   2.848   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      24.355   2.848   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      26.380   0.702   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      26.380  -0.838   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      27.714   1.472   0.000  0.00  0.00           N+0
HETATM   18  H   UNK     0      27.714   3.012   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      29.047   0.702   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      28.356  -0.674   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      29.739  -0.674   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      30.381   1.472   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      31.072   2.848   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      29.690   2.848   0.000  0.00  0.00           H+0
HETATM   25  S   UNK     0      31.715   0.702   0.000  0.00  0.00           S+0
HETATM   26  C   UNK     0      33.049   1.472   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      33.049   3.012   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      34.382   0.702   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.691  -0.674   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      35.073  -0.674   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      35.716   1.472   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      36.407   2.848   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      35.025   2.848   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0      37.050   0.702   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      36.358  -0.674   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      37.741  -0.674   0.000  0.00  0.00           H+0
HETATM   37  C   UNK     0      38.383   1.472   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0      39.074   2.848   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      37.692   2.848   0.000  0.00  0.00           H+0
HETATM   40  C   UNK     0      39.717   0.702   0.000  0.00  0.00           C+0
HETATM   41  H   UNK     0      39.026  -0.674   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      40.408  -0.674   0.000  0.00  0.00           H+0
HETATM   43  C   UNK     0      41.051   1.472   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0      41.742   2.848   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      40.359   2.848   0.000  0.00  0.00           H+0
HETATM   46  C   UNK     0      42.384   0.702   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0      41.693  -0.674   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      43.075  -0.674   0.000  0.00  0.00           H+0
HETATM   49  C   UNK     0      43.718   1.472   0.000  0.00  0.00           C+0
HETATM   50  H   UNK     0      44.409   2.848   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      43.027   2.848   0.000  0.00  0.00           H+0
HETATM   52  C   UNK     0      45.052   0.702   0.000  0.00  0.00           C+0
HETATM   53  H   UNK     0      44.360  -0.674   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      45.743  -0.674   0.000  0.00  0.00           H+0
HETATM   55  C   UNK     0      46.385   1.472   0.000  0.00  0.00           C+0
HETATM   56  H   UNK     0      47.076   2.848   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      45.694   2.848   0.000  0.00  0.00           H+0
HETATM   58  C   UNK     0      47.719   0.702   0.000  0.00  0.00           C+0
HETATM   59  H   UNK     0      47.028  -0.674   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      48.410  -0.674   0.000  0.00  0.00           H+0
HETATM   61  C   UNK     0      49.053   1.472   0.000  0.00  0.00           C+0
HETATM   62  H   UNK     0      49.744   2.848   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      48.362   2.848   0.000  0.00  0.00           H+0
HETATM   64  C   UNK     0      50.386   0.702   0.000  0.00  0.00           C+0
HETATM   65  H   UNK     0      49.695  -0.674   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      51.077  -0.674   0.000  0.00  0.00           H+0
HETATM   67  C   UNK     0      51.720   1.472   0.000  0.00  0.00           C+0
HETATM   68  H   UNK     0      52.411   2.848   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0      51.029   2.848   0.000  0.00  0.00           H+0
HETATM   70  C   UNK     0      53.054   0.702   0.000  0.00  0.00           C+0
HETATM   71  H   UNK     0      52.363  -0.674   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0      53.745  -0.674   0.000  0.00  0.00           H+0
HETATM   73  C   UNK     0      54.387   1.472   0.000  0.00  0.00           C+0
HETATM   74  H   UNK     0      55.157   0.138   0.000  0.00  0.00           H+0
HETATM   75  H   UNK     0      55.721   2.242   0.000  0.00  0.00           H+0
HETATM   76  H   UNK     0      53.617   2.806   0.000  0.00  0.00           H+0
HETATM   77  C   UNK     0      18.378   0.702   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      17.608   2.036   0.000  0.00  0.00           C+0
HETATM   79  H   UNK     0      18.942   2.806   0.000  0.00  0.00           H+0
HETATM   80  H   UNK     0      16.838   3.370   0.000  0.00  0.00           H+0
HETATM   81  H   UNK     0      16.274   1.266   0.000  0.00  0.00           H+0
HETATM   82  C   UNK     0      19.148  -0.632   0.000  0.00  0.00           C+0
HETATM   83  H   UNK     0      17.814  -1.402   0.000  0.00  0.00           H+0
HETATM   84  H   UNK     0      19.918  -1.965   0.000  0.00  0.00           H+0
HETATM   85  H   UNK     0      20.482   0.138   0.000  0.00  0.00           H+0
HETATM   86  C   UNK     0      17.044  -0.068   0.000  0.00  0.00           C+0
HETATM   87  H   UNK     0      15.597  -0.595   0.000  0.00  0.00           H+0
HETATM   88  H   UNK     0      16.518  -1.515   0.000  0.00  0.00           H+0
HETATM   89  O   UNK     0      15.711   0.702   0.000  0.00  0.00           O+0
HETATM   90  P   UNK     0      14.377  -0.068   0.000  0.00  0.00           P+0
HETATM   91  O   UNK     0      13.607   1.266   0.000  0.00  0.00           O-1
HETATM   92  O   UNK     0      15.147  -1.402   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0      13.043  -0.838   0.000  0.00  0.00           O+0
HETATM   94  P   UNK     0      11.710  -0.068   0.000  0.00  0.00           P+0
HETATM   95  O   UNK     0      12.480   1.266   0.000  0.00  0.00           O-1
HETATM   96  O   UNK     0      10.940  -1.402   0.000  0.00  0.00           O+0
HETATM   97  O   UNK     0      10.376   0.702   0.000  0.00  0.00           O+0
HETATM   98  C   UNK     0       9.042  -0.068   0.000  0.00  0.00           C+0
HETATM   99  H   UNK     0       8.351  -1.444   0.000  0.00  0.00           H+0
HETATM  100  H   UNK     0       9.733  -1.444   0.000  0.00  0.00           H+0
HETATM  101  C   UNK     0       7.709   0.702   0.000  0.00  0.00           C+0
HETATM  102  H   UNK     0       9.000   1.541   0.000  0.00  0.00           H+0
HETATM  103  O   UNK     0       6.302   0.076   0.000  0.00  0.00           O+0
HETATM  104  C   UNK     0       5.271   1.220   0.000  0.00  0.00           C+0
HETATM  105  H   UNK     0       4.433   2.512   0.000  0.00  0.00           H+0
HETATM  106  N   UNK     0       3.740   1.059   0.000  0.00  0.00           N+0
HETATM  107  C   UNK     0       2.970  -0.274   0.000  0.00  0.00           C+0
HETATM  108  H   UNK     0       3.596  -1.681   0.000  0.00  0.00           H+0
HETATM  109  N   UNK     0       1.463   0.046   0.000  0.00  0.00           N+0
HETATM  110  C   UNK     0       1.302   1.577   0.000  0.00  0.00           C+0
HETATM  111  C   UNK     0       0.057   2.483   0.000  0.00  0.00           C+0
HETATM  112  N   UNK     0       0.217   4.014   0.000  0.00  0.00           N+0
HETATM  113  C   UNK     0       1.624   4.640   0.000  0.00  0.00           C+0
HETATM  114  H   UNK     0       1.785   6.172   0.000  0.00  0.00           H+0
HETATM  115  N   UNK     0       2.870   3.735   0.000  0.00  0.00           N+0
HETATM  116  C   UNK     0       2.709   2.204   0.000  0.00  0.00           C+0
HETATM  117  N   UNK     0      -1.350   1.856   0.000  0.00  0.00           N+0
HETATM  118  H   UNK     0      -2.596   2.761   0.000  0.00  0.00           H+0
HETATM  119  H   UNK     0      -1.511   0.325   0.000  0.00  0.00           H+0
HETATM  120  C   UNK     0       6.041   2.554   0.000  0.00  0.00           C+0
HETATM  121  H   UNK     0       7.010   3.751   0.000  0.00  0.00           H+0
HETATM  122  O   UNK     0       5.415   3.961   0.000  0.00  0.00           O+0
HETATM  123  H   UNK     0       4.784   5.366   0.000  0.00  0.00           H+0
HETATM  124  C   UNK     0       7.548   2.234   0.000  0.00  0.00           C+0
HETATM  125  H   UNK     0       6.403   1.203   0.000  0.00  0.00           H+0
HETATM  126  O   UNK     0       8.692   3.264   0.000  0.00  0.00           O+0
HETATM  127  P   UNK     0      10.157   2.788   0.000  0.00  0.00           P+0
HETATM  128  O   UNK     0       9.681   1.324   0.000  0.00  0.00           O-1
HETATM  129  O   UNK     0      10.633   4.253   0.000  0.00  0.00           O-1
HETATM  130  O   UNK     0      11.621   2.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   77                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   41   42   43                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   40   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52   56   57   58                                             
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58   55   59   60   61                                             
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   58   62   63   64                                             
CONECT   62   61                                                            
CONECT   63   61                                                            
CONECT   64   61   65   66   67                                             
CONECT   65   64                                                            
CONECT   66   64                                                            
CONECT   67   64   68   69   70                                             
CONECT   68   67                                                            
CONECT   69   67                                                            
CONECT   70   67   71   72   73                                             
CONECT   71   70                                                            
CONECT   72   70                                                            
CONECT   73   70   74   75   76                                             
CONECT   74   73                                                            
CONECT   75   73                                                            
CONECT   76   73                                                            
CONECT   77    3   78   82   86                                             
CONECT   78   77   79   80   81                                             
CONECT   79   78                                                            
CONECT   80   78                                                            
CONECT   81   78                                                            
CONECT   82   77   83   84   85                                             
CONECT   83   82                                                            
CONECT   84   82                                                            
CONECT   85   82                                                            
CONECT   86   77   87   88   89                                             
CONECT   87   86                                                            
CONECT   88   86                                                            
CONECT   89   86   90                                                       
CONECT   90   89   91   92   93                                             
CONECT   91   90                                                            
CONECT   92   90                                                            
CONECT   93   90   94                                                       
CONECT   94   93   95   96   97                                             
CONECT   95   94                                                            
CONECT   96   94                                                            
CONECT   97   94   98                                                       
CONECT   98   97   99  100  101                                             
CONECT   99   98                                                            
CONECT  100   98                                                            
CONECT  101   98  102  103  124                                             
CONECT  102  101                                                            
CONECT  103  101  104                                                       
CONECT  104  103  105  106  120                                             
CONECT  105  104                                                            
CONECT  106  104  107  116                                                  
CONECT  107  106  108  109                                                  
CONECT  108  107                                                            
CONECT  109  107  110                                                       
CONECT  110  109  111  116                                                  
CONECT  111  110  112  117                                                  
CONECT  112  111  113                                                       
CONECT  113  112  114  115                                                  
CONECT  114  113                                                            
CONECT  115  113  116                                                       
CONECT  116  115  106  110                                                  
CONECT  117  111  118  119                                                  
CONECT  118  117                                                            
CONECT  119  117                                                            
CONECT  120  104  121  122  124                                             
CONECT  121  120                                                            
CONECT  122  120  123                                                       
CONECT  123  122                                                            
CONECT  124  120  101  125  126                                             
CONECT  125  124                                                            
CONECT  126  124  127                                                       
CONECT  127  126  128  129  130                                             
CONECT  128  127                                                            
CONECT  129  127                                                            
CONECT  130  127                                                            
MASTER        0    0    0    0    0    0    0    0  130    0  264    0
END

Synonyms

Value	Source
Heptadecanoyl-CoA	ChEBI
Heptadecanoyl-coenzyme A(4-)	ChEBI

Molecular Formula

C₃₈H₆₄N₇O₁₇P₃S

Average Mass

1015.95

Monoisotopic Mass

1015.331420116

IUPAC Name

(3R)-3-[(2-{[2-(heptadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxy)phosphonate

Traditional Name

(3R)-3-[(2-{[2-(heptadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxyphosphonate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C(N=C([H])N=C23)N([H])[H])[C@]([H])(O[H])[C@]1([H])OP([O-])([O-])=O

InChI Identifier

InChI=1S/C38H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-29(47)66-22-21-40-28(46)19-20-41-36(50)33(49)38(2,3)24-59-65(56,57)62-64(54,55)58-23-27-32(61-63(51,52)53)31(48)37(60-27)45-26-44-30-34(39)42-25-43-35(30)45/h25-27,31-33,37,48-49H,4-24H2,1-3H3,(H,40,46)(H,41,50)(H,54,55)(H,56,57)(H2,39,42,43)(H2,51,52,53)/p-4/t27-,31-,32-,33+,37-/m1/s1

InChI Key

DRABUZIHHACUPI-DUPKZGIXSA-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

long-chain fatty acyl-CoA(4-) (CHEBI:74307 )
saturated fatty acyl-CoA(4-) (CHEBI:74307 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.84 g/L	ALOGPS
logP	3.57	ALOGPS
logP	1.04	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	374.95 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	236.76 m³·mol⁻¹	ChemAxon
Polarizability	102.4 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

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	286.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	90.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	861.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1048.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	939.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	121.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	4794.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	205.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	307.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	645.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	42.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	152.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	284.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	8.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	79.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	319.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	557.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	2314.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1785.4

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Not Available

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
MMDBr0020968	Glycerol 3-phosphate	1-Heptadecanoyl-Glycero-3-Phosphate	Glycerol-3-phosphate acyltransferase	Acylation	PathBank	31602464
MMDBr0020993	LPA(18:1(11Z)/0:0)	PA(18:1(11Z)/17:0)	1-acyl-sn-glycerol-3-phosphate acyltransferase	Acylation	PathBank	31602464

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

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
Human Feces	Detected but not Quantified									HMDB

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

29368261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71581236

PDB ID

Not Available

ChEBI ID

74307

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Finocchiaro G, Taroni F, Rocchi M, Martin AL, Colombo I, Tarelli GT, DiDonato S: cDNA cloning, sequence analysis, and chromosomal localization of the gene for human carnitine palmitoyltransferase. Proc Natl Acad Sci U S A. 1991 Jan 15;88(2):661-5. doi: 10.1073/pnas.88.2.661. [PubMed:1988962 ]
Naito E, Ozasa H, Ikeda Y, Tanaka K: Molecular cloning and nucleotide sequence of complementary DNAs encoding human short chain acyl-coenzyme A dehydrogenase and the study of the molecular basis of human short chain acyl-coenzyme A dehydrogenase deficiency. J Clin Invest. 1989 May;83(5):1605-13. doi: 10.1172/JCI114058. [PubMed:2565344 ]
Mashek DG, Bornfeldt KE, Coleman RA, Berger J, Bernlohr DA, Black P, DiRusso CC, Farber SA, Guo W, Hashimoto N, Khodiyar V, Kuypers FA, Maltais LJ, Nebert DW, Renieri A, Schaffer JE, Stahl A, Watkins PA, Vasiliou V, Yamamoto TT: Revised nomenclature for the mammalian long-chain acyl-CoA synthetase gene family. J Lipid Res. 2004 Oct;45(10):1958-61. doi: 10.1194/jlr.E400002-JLR200. Epub 2004 Aug 1. [PubMed:15292367 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Heptadecanoyl Coenzyme A (MMDBc0048645)

MOL for #<Metabolite:0x00007f9af0dd6e08>

3D MOL for #<Metabolite:0x00007f9af0dd6e08>

3D SDF for #<Metabolite:0x00007f9af0dd6e08>

3D-SDF for #<Metabolite:0x00007f9af0dd6e08>

PDB for #<Metabolite:0x00007f9af0dd6e08>

3D PDB for #<Metabolite:0x00007f9af0dd6e08>

SMILES for #<Metabolite:0x00007f9af0dd6e08>

INCHI for #<Metabolite:0x00007f9af0dd6e08>

Structure for #<Metabolite:0x00007f9af0dd6e08>

3D Structure for #<Metabolite:0x00007f9af0dd6e08>