MiMeDB: Showing metabocard for Heptanoyl-CoA (MMDBc0048643)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:05:53 UTC

Update Date

2024-04-30 20:37:01 UTC

Metabolite ID

MMDBc0048643

Metabolite Identification

Common Name

Heptanoyl-CoA

Description

Heptanoyl-CoA is an acyl-CoA with the C-7 fatty acid Acyl chain moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304302200052D          

104106  0  0  1  0            999 V2000
  -12.1591    4.5863    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8735    4.1738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8735    3.3488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.1591    3.7613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1591    2.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1591    2.1113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4446    3.3488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0321    4.0633    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7301    2.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1004    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3599    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0157    3.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6454    4.0861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3012    2.1113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5867    3.3488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5867    4.1738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2425    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4433    2.9363    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288    3.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288    4.1738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3846    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2999    3.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    4.0861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6702    4.0861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854    2.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8710    3.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    4.0861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2412    4.0861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5267    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4420    3.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8545    4.0633    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5880    2.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -18.5893    2.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.2438    2.0216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -23.2015    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -24.0084    2.1431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  -17.7374    4.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END


  Mrv1652304302200052D          

104106  0  0  1  0            999 V2000
  -12.1591    4.5863    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8735    4.1738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8735    3.3488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.1591    3.7613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1591    2.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1591    2.1113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4446    3.3488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  -17.7374    4.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -16.7425    4.4803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  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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 99103  1  0  0  0  0
103104  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048643

> <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])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C2N=C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([H])OP(=O)(O[H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H48N7O17P3S/c1-4-5-6-7-8-19(37)56-12-11-30-18(36)9-10-31-26(40)23(39)28(2,3)14-49-55(46,47)52-54(44,45)48-13-17-22(51-53(41,42)43)21(38)27(50-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,38-39H,4-14H2,1-3H3,(H,30,36)(H,31,40)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,21-,22-,23+,27-/m1/s1

> <INCHI_KEY>
CHVYGJMBUXUTSX-SVHODSNWSA-N

> <FORMULA>
C28H48N7O17P3S

> <MOLECULAR_WEIGHT>
879.71

> <EXACT_MASS>
879.204025282

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
82.16405958848577

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
-3.40280860614796

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776186

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398175

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.63

> <JCHEM_REFRACTIVITY>
195.23890000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heptanoyl-coa

> <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     -22.697   8.561   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0     -24.031   7.791   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -24.031   6.251   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0     -22.697   7.021   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0     -22.697   5.481   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -22.697   3.941   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0     -21.363   6.251   0.000  0.00  0.00           N+0
HETATM    8  H   UNK     0     -20.593   7.585   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0     -20.030   5.481   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0     -20.721   4.105   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0     -19.338   4.105   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0     -18.696   6.251   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0     -18.005   7.627   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0     -19.387   7.627   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0     -17.362   5.481   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -17.362   3.941   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0     -16.029   6.251   0.000  0.00  0.00           N+0
HETATM   18  H   UNK     0     -16.029   7.791   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0     -14.695   5.481   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0     -15.386   4.105   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0     -14.004   4.105   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0     -13.361   6.251   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0     -12.670   7.627   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0     -14.052   7.627   0.000  0.00  0.00           H+0
HETATM   25  S   UNK     0     -12.028   5.481   0.000  0.00  0.00           S+0
HETATM   26  C   UNK     0     -10.694   6.251   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -10.694   7.791   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -9.360   5.481   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0     -10.051   4.105   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -8.669   4.105   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      -8.026   6.251   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      -7.335   7.627   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -8.718   7.627   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0      -6.693   5.481   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      -7.384   4.105   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.002   4.105   0.000  0.00  0.00           H+0
HETATM   37  C   UNK     0      -5.359   6.251   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0      -4.668   7.627   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.050   7.627   0.000  0.00  0.00           H+0
HETATM   40  C   UNK     0      -4.025   5.481   0.000  0.00  0.00           C+0
HETATM   41  H   UNK     0      -4.717   4.105   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.334   4.105   0.000  0.00  0.00           H+0
HETATM   43  C   UNK     0      -2.692   6.251   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0      -1.922   4.917   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.358   7.021   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.462   7.585   0.000  0.00  0.00           H+0
HETATM   47  C   UNK     0     -25.364   5.481   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -26.134   6.815   0.000  0.00  0.00           C+0
HETATM   49  H   UNK     0     -24.801   7.585   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0     -26.904   8.149   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0     -27.468   6.045   0.000  0.00  0.00           H+0
HETATM   52  C   UNK     0     -24.594   4.147   0.000  0.00  0.00           C+0
HETATM   53  H   UNK     0     -25.928   3.377   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0     -23.824   2.814   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0     -23.261   4.917   0.000  0.00  0.00           H+0
HETATM   56  C   UNK     0     -26.698   4.711   0.000  0.00  0.00           C+0
HETATM   57  H   UNK     0     -28.145   4.184   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0     -27.225   3.264   0.000  0.00  0.00           H+0
HETATM   59  O   UNK     0     -28.032   5.481   0.000  0.00  0.00           O+0
HETATM   60  P   UNK     0     -29.365   4.711   0.000  0.00  0.00           P+0
HETATM   61  O   UNK     0     -30.135   6.045   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0     -28.595   3.377   0.000  0.00  0.00           O+0
HETATM   63  H   UNK     0     -29.420   2.077   0.000  0.00  0.00           H+0
HETATM   64  O   UNK     0     -30.699   3.941   0.000  0.00  0.00           O+0
HETATM   65  P   UNK     0     -32.033   4.711   0.000  0.00  0.00           P+0
HETATM   66  O   UNK     0     -31.263   6.045   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0     -32.803   3.377   0.000  0.00  0.00           O+0
HETATM   68  H   UNK     0     -34.343   3.377   0.000  0.00  0.00           H+0
HETATM   69  O   UNK     0     -33.366   5.481   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0     -34.700   4.711   0.000  0.00  0.00           C+0
HETATM   71  H   UNK     0     -35.922   3.774   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0     -33.277   4.122   0.000  0.00  0.00           H+0
HETATM   73  C   UNK     0     -36.034   5.481   0.000  0.00  0.00           C+0
HETATM   74  H   UNK     0     -34.742   6.320   0.000  0.00  0.00           H+0
HETATM   75  O   UNK     0     -37.441   4.855   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0     -38.471   5.999   0.000  0.00  0.00           C+0
HETATM   77  H   UNK     0     -39.310   7.291   0.000  0.00  0.00           H+0
HETATM   78  N   UNK     0     -40.003   5.838   0.000  0.00  0.00           N+0
HETATM   79  C   UNK     0     -41.033   6.983   0.000  0.00  0.00           C+0
HETATM   80  H   UNK     0     -41.485   8.455   0.000  0.00  0.00           H+0
HETATM   81  N   UNK     0     -42.440   6.356   0.000  0.00  0.00           N+0
HETATM   82  C   UNK     0     -42.279   4.825   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0     -40.773   4.505   0.000  0.00  0.00           C+0
HETATM   84  N   UNK     0     -40.297   3.040   0.000  0.00  0.00           N+0
HETATM   85  C   UNK     0     -41.327   1.896   0.000  0.00  0.00           C+0
HETATM   86  H   UNK     0     -40.851   0.431   0.000  0.00  0.00           H+0
HETATM   87  N   UNK     0     -42.834   2.216   0.000  0.00  0.00           N+0
HETATM   88  C   UNK     0     -43.309   3.680   0.000  0.00  0.00           C+0
HETATM   89  N   UNK     0     -44.816   4.001   0.000  0.00  0.00           N+0
HETATM   90  H   UNK     0     -45.292   5.465   0.000  0.00  0.00           H+0
HETATM   91  H   UNK     0     -45.846   2.856   0.000  0.00  0.00           H+0
HETATM   92  C   UNK     0     -37.701   7.333   0.000  0.00  0.00           C+0
HETATM   93  H   UNK     0     -36.732   8.530   0.000  0.00  0.00           H+0
HETATM   94  O   UNK     0     -38.327   8.740   0.000  0.00  0.00           O+0
HETATM   95  H   UNK     0     -38.958  10.145   0.000  0.00  0.00           H+0
HETATM   96  C   UNK     0     -36.195   7.013   0.000  0.00  0.00           C+0
HETATM   97  H   UNK     0     -37.339   5.982   0.000  0.00  0.00           H+0
HETATM   98  O   UNK     0     -35.050   8.043   0.000  0.00  0.00           O+0
HETATM   99  P   UNK     0     -33.586   7.567   0.000  0.00  0.00           P+0
HETATM  100  O   UNK     0     -34.062   6.103   0.000  0.00  0.00           O+0
HETATM  101  O   UNK     0     -33.110   9.032   0.000  0.00  0.00           O+0
HETATM  102  H   UNK     0     -31.603   9.352   0.000  0.00  0.00           H+0
HETATM  103  O   UNK     0     -32.121   7.091   0.000  0.00  0.00           O+0
HETATM  104  H   UNK     0     -31.253   8.363   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   47                                             
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                                                            
CONECT   47    3   48   52   56                                             
CONECT   48   47   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48                                                            
CONECT   52   47   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52                                                            
CONECT   56   47   57   58   59                                             
CONECT   57   56                                                            
CONECT   58   56                                                            
CONECT   59   56   60                                                       
CONECT   60   59   61   62   64                                             
CONECT   61   60                                                            
CONECT   62   60   63                                                       
CONECT   63   62                                                            
CONECT   64   60   65                                                       
CONECT   65   64   66   67   69                                             
CONECT   66   65                                                            
CONECT   67   65   68                                                       
CONECT   68   67                                                            
CONECT   69   65   70                                                       
CONECT   70   69   71   72   73                                             
CONECT   71   70                                                            
CONECT   72   70                                                            
CONECT   73   70   74   75   96                                             
CONECT   74   73                                                            
CONECT   75   73   76                                                       
CONECT   76   75   77   78   92                                             
CONECT   77   76                                                            
CONECT   78   76   79   83                                                  
CONECT   79   78   80   81                                                  
CONECT   80   79                                                            
CONECT   81   79   82                                                       
CONECT   82   81   83   88                                                  
CONECT   83   82   78   84                                                  
CONECT   84   83   85                                                       
CONECT   85   84   86   87                                                  
CONECT   86   85                                                            
CONECT   87   85   88                                                       
CONECT   88   87   82   89                                                  
CONECT   89   88   90   91                                                  
CONECT   90   89                                                            
CONECT   91   89                                                            
CONECT   92   76   93   94   96                                             
CONECT   93   92                                                            
CONECT   94   92   95                                                       
CONECT   95   94                                                            
CONECT   96   92   73   97   98                                             
CONECT   97   96                                                            
CONECT   98   96   99                                                       
CONECT   99   98  100  101  103                                             
CONECT  100   99                                                            
CONECT  101   99  102                                                       
CONECT  102  101                                                            
CONECT  103   99  104                                                       
CONECT  104  103                                                            
MASTER        0    0    0    0    0    0    0    0  104    0  212    0
END

Synonyms

Value	Source
3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-4-[(3-{[2-(heptanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate)	ChEBI
C7:0-CoA	ChEBI
Enanthyl-CoA	ChEBI
Enanthyl-coenzyme A	ChEBI
3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-4-[(3-{[2-(heptanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphoric acid)	Generator
3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-4-[(3-{[2-(heptanoylsulphanyl)ethyl]amino}-3-oxopropyl)amino]-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate)	Generator
3'-Phosphoadenosine 5'-(3-{(3R)-3-hydroxy-4-[(3-{[2-(heptanoylsulphanyl)ethyl]amino}-3-oxopropyl)amino]-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphoric acid)	Generator

Molecular Formula

C₂₈H₄₈N₇O₁₇P₃S

Average Mass

879.71

Monoisotopic Mass

879.204025282

IUPAC Name

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

Traditional Name

heptanoyl-coa

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])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C2N=C([H])N=C3N([H])[H])[C@]([H])(O[H])[C@]1([H])OP(=O)(O[H])O[H]

InChI Identifier

InChI=1S/C28H48N7O17P3S/c1-4-5-6-7-8-19(37)56-12-11-30-18(36)9-10-31-26(40)23(39)28(2,3)14-49-55(46,47)52-54(44,45)48-13-17-22(51-53(41,42)43)21(38)27(50-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,38-39H,4-14H2,1-3H3,(H,30,36)(H,31,40)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,21-,22-,23+,27-/m1/s1

InChI Key

CHVYGJMBUXUTSX-SVHODSNWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2,3,4-saturated 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

medium-chain fatty acyl-CoA (CHEBI:37283 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.61 g/L	ALOGPS
logP	0.25	ALOGPS
logP	-3.4	ChemAxon
logS	-2.4	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	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	195.24 m³·mol⁻¹	ChemAxon
Polarizability	82.16 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	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum

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	611.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	470.3
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	451.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	492.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	399.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	151.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1650.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	947.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	287.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	151.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	241.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	161.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	123.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	295.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	418.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	102.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	234.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	733.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	726.5

Retention Indices

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

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

Name	SMPDB/PathBank	Species
Quorum sensing: Alkylquinolones Biosynthesis (pqsABCDE Operon Activation)		Escherichia coli Pseudomonas aeruginosa Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Mycobacterium marinum M Pseudomonas aeruginosa PA7 Acinetobacter sp. ADP1 Escherichia coli CFT073 Myxococcus xanthus DK 1622 Ochrobactrum anthropi Bacillus subtilis Pseudomonas stutzeri Mycobacterium tuberculosis Klebsiella pneumoniae Bacillus cereus Pseudomonas fluorescens Pf-5 Streptomyces griseus subsp. griseus NBRC 13350 Mycobacterium tuberculosis CDC1551 Bacillus amyloliquefaciens Salmonella enterica Staphylococcus aureus Clostridium sporogenes Rhodospirillum rubrum ATCC 11170 Aromatoleum aromaticum EbN1 Saccharopolyspora erythraea NRRL 2338 Streptomyces avermitilis MA-4680 Shewanella denitrificans OS217 Acinetobacter baumannii Bacillus cereus AH187 (F4810/72) Bacillus halodurans C-125 Alkalihalobacillus pseudofirmus OF4 Bacillus timonensis 10403023 Bacteroides caccae Bacteroides cellulosilyticus Bacteroides fragilis Bacteroides thetaiotaomicron Bacteroides thetaiotaomicron VPI-5482 Bacteroides vulgatus Bacteroides xylanisolvens XB1A Brevibacillus brevis NBRC 100599 Clostridium botulinum Dysgonomonas gadei ATCC BAA-286 Lactobacillus paracasei Methylobacterium nodulans Ochrobactrum anthropi ATCC 49188 Ochrobactrum intermedium LMG 3301 Pelobacter carbinolicus Comamonas testosteroni Burkholderia cepacia Pseudomonas fluorescens Pseudomonas mendocina Pseudomonas putida Pseudomonas syringae Xanthomonas campestris Bradyrhizobium japonicum Mesorhizobium loti Sinorhizobium meliloti Methylococcus capsulatus Moraxella catarrhalis Neisseria flavescens Neisseria gonorrhoeae Neisseria mucosa Acidiphilium cryptum Chromobacterium violaceum Proteus mirabilis Shigella boydii Shigella dysenteriae Shigella flexneri Shigella sonnei Aeromonas hydrophila Vibrio cholerae Vibrio vulnificus Bacteroides uniformis Desulfovibrio salexigens Acidithiobacillus ferrooxidans Cytophaga hutchinsonii Capnocytophaga sputigena Rhodopseudomonas palustris Chlorobium phaeobacteroides Leuconostoc mesenteroides Staphylococcus epidermidis Deinococcus radiodurans Bacillus licheniformis Priestia megaterium Bacillus mycoides Bacillus pumilus Bacillus thuringiensis Weissella confusa Lactobacillus coryniformis Cellulomonas flavigena Mycobacterium avium Methanosphaera stadtmanae Xylella fastidiosa Roseobacter denitrificans Staphylococcus lugdunensis Neisseria subflava Staphylococcus saprophyticus Thiobacillus denitrificans Stenotrophomonas maltophilia Actinosynnema mirum Burkholderia vietnamiensis Sodalis glossinidius Enterobacter cancerogenus Bacillus clausii Bacillus pseudofirmus Methanocaldococcus fervens Clostridium methylpentosum Achromobacter xylosoxidans Burkholderia multivorans Burkholderia cenocepacia Methylibium petroleiphilum Syntrophobacter fumaroxidans Citrobacter youngae Leuconostoc kimchii Burkholderia ambifaria Alicycliphilus denitrificans Desulfovibrio magneticus Shewanella denitrificans Methylocella silvestris Escherichia albertii Bacteroides nordii Geobacter lovleyi Bacteroides intestinalis Bacteroides fluxus Bacteroides oleiciplenus Bacteroides faecis Agrobacterium tumefaciens Bacteroides helcogenes Dysgonomonas gadei Fusobacterium nucleatum Klebsiella variicola Lactobacillus ruminis Leuconostoc citreum Rothia dentocariosa Achromobacter xylosoxidans A8 Acinetobacter baumannii SDF Acinetobacter baumannii ACICU Acinetobacter baumannii AB0057 Acinetobacter baumannii AB307-0294 Actinobacillus pleuropneumoniae serovar 5b str. L20 Actinobacillus pleuropneumoniae serovar 3 str. JL03 Actinobacillus pleuropneumoniae serovar 7 str. AP76 Aeromonas hydrophila subsp. hydrophila ATCC 7966 Agrobacterium tumefaciens str. C58 Bacillus cereus ATCC 10987 Bacillus megaterium QM B1551 Bacillus thuringiensis serovar konkukian str. 97-27 Bacillus licheniformis ATCC 14580 Bacillus clausii KSM-K16 Bacillus amyloliquefaciens FZB42 Bacillus pumilus SAFR-032 Bacillus cereus AH820 Bacillus cereus G9842 Bacillus cereus Q1 Priestia megaterium DSM 319 Bacillus subtilis subsp. spizizenii str. W23 Bacillus amyloliquefaciens DSM 7 Bartonella quintana str. Toulouse Bradyrhizobium japonicum USDA 110 Citrobacter koseri ATCC BAA-895 Clostridium botulinum A str. Hall Clostridium botulinum A2 str. Kyoto Clostridium botulinum Ba4 str. 657 Cronobacter sakazakii ATCC BAA-894 Delftia acidovorans SPH-1 Dyadobacter fermentans DSM 18053 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli APEC O1 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Kytococcus sedentarius DSM 20547 Laribacter hongkongensis HLHK9 Leuconostoc mesenteroides subsp. mesenteroides ATCC 8293 Lysinibacillus sphaericus C3-41 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Micrococcus luteus NCTC 2665 Mycobacterium avium subsp. paratuberculosis K-10 Mycobacterium avium 104 Neisseria gonorrhoeae FA 1090 Neisseria meningitidis MC58 Neisseria meningitidis Z2491 Neisseria meningitidis FAM18 Neisseria gonorrhoeae NCCP11945 Escherichia coli 042 Acinetobacter calcoaceticus PHEA-2 Edwardsiella tarda FL6-60 Pediococcus pentosaceus ATCC 25745 Proteus mirabilis HI4320 Pseudomonas putida KT2440 Pseudomonas fluorescens Pf0-1 Pseudomonas stutzeri A1501 Pseudomonas fluorescens SBW25 Pseudomonas putida GB-1 Rhizobium leguminosarum bv. viciae 3841 Rhizobium leguminosarum bv. trifolii WSM2304 Rhodococcus erythropolis PR4 Rothia dentocariosa ATCC 17931 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella sonnei Ss046 Shigella dysenteriae Sd197 Shigella flexneri 5 str. 8401 Spirosoma linguale DSM 74 Staphylococcus aureus subsp. aureus Mu50 Staphylococcus aureus subsp. aureus COL Staphylococcus aureus subsp. aureus MRSA252 Staphylococcus epidermidis RP62A Staphylococcus epidermidis ATCC 12228 Staphylococcus haemolyticus JCSC1435 Staphylococcus saprophyticus subsp. saprophyticus ATCC 15305 Staphylococcus aureus subsp. aureus NCTC 8325 Stenotrophomonas maltophilia K279a Stenotrophomonas maltophilia R551-3 Streptococcus oralis Uo5 Vibrio parahaemolyticus RIMD 2210633 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Bacteroides cellulosilyticus DSM 14838 Bacteroides fluxus YIT 12057 Bacteroides intestinalis DSM 17393 Bacteroides nordii CL02T12C05 Bacteroides oleiciplenus YIT 12058 Bacteroides uniformis ATCC 8492 Bacteroides xylanisolvens SD CC 1b Bacteroides sp. 1_1_14 Bacteroides sp. 1_1_30 Bacteroides sp. 2_1_22 Bacteroides sp. D2 Bacteroides sp. D20 Bacteroides sp. D22 Odoribacter laneus YIT 12061 Spirosoma linguale Chlorobium limicola Cetobacterium somerae ATCC BAA-474 Fusobacterium nucleatum subsp. animalis 4_8 Fusobacterium nucleatum subsp. animalis 7_1 Fusobacterium nucleatum subsp. animalis D11 Fusobacterium periodonticum 1_1_41FAA Bartonella quintana Beijerinckia indica Bradyrhizobium elkanii Methylobacterium mesophilicum Methylobacterium mesophilicum SR1.6/6 Rhizobium etli Azorhizobium caulinodans Xanthobacter autotrophicus Rickettsia rickettsii Alcaligenes faecalis Burkholderia cepacia GG4 Lautropia mirabilis Lautropia mirabilis ATCC 51599 Laribacter hongkongensis Eikenella corrodens Eikenella corrodens ATCC 23834 Kingella oralis Kingella oralis ATCC 51147 Neisseria cinerea ATCC 14685 Neisseria elongata Neisseria elongata subsp. glycolytica ATCC 29315 Neisseria macacae Neisseria macacae ATCC 33926 Neisseria meningitidis Neisseria mucosa ATCC 25996 Neisseria subflava NJ9703 Nitrosospira multiformis Methyloversatilis universalis Methyloversatilis universalis FAM5 Campylobacter hyointestinalis Aeromonas caviae Aeromonas media Aeromonas veronii Allochromatium vinosum Cedecea davisae Cedecea davisae DSM 4568 Citrobacter amalonaticus Citrobacter amalonaticus Y19 Citrobacter freundii Citrobacter youngae ATCC 29220 Escherichia albertii TW07627 Klebsiella aerogenes Salmonella Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Tatumella ptyseos Tatumella ptyseos ATCC 33301 Edwardsiella tarda Edwardsiella tarda ATCC 23685 Hafnia alvei Hafnia alvei ATCC 51873 Morganella morganii Morganella morganii subsp. morganii KT Providencia alcalifaciens DSM 30120 Providencia rustigianii DSM 4541 Providencia stuartii ATCC 25827 Serratia marcescens subsp. marcescens Db11 Yersinia enterocolitica Yersinia pestis Yersinia pseudotuberculosis Plesiomonas shigelloides 302-73 Legionella pneumophila Actinobacillus pleuropneumoniae Aggregatibacter aphrophilus Acinetobacter pittii Acinetobacter haemolyticus Acinetobacter johnsonii Acinetobacter johnsonii SH046 Acinetobacter junii SH205 Francisella tularensis Grimontia hollisae CIP 101886 Vibrio fluvialis Vibrio fluvialis PG41 Vibrio parahaemolyticus Vibrio mimicus Brachyspira pilosicoli B2904 Gordonia terrae C-6 Rhodococcus erythropolis Brevibacterium casei Brevibacterium casei S18 Brevibacterium linens Microbacterium oleivorans Kocuria palustris PEL Cellulosimicrobium cellulans Propionibacterium Streptomyces avermitilis Thermomonospora curvata Bacillus altitudinis Bacillus infantis NRRL B-14911 Bacillus firmus DS1 Lysinibacillus sphaericus Aneurinibacillus aneurinilyticus Aneurinibacillus aneurinilyticus ATCC 12856 Paenibacillus lactis 154 Exiguobacterium aurantiacum Lactobacillus ruminis ATCC 25644 Lactobacillus coryniformis subsp. coryniformis CECT 5711 Pediococcus acidilactici DSM 20284 Pediococcus pentosaceus Leuconostoc mesenteroides subsp. cremoris ATCC 19254 Weissella cibaria Weissella paramesenteroides Weissella paramesenteroides ATCC 33313 Streptomyces coelicolor A3(2) Bordetella pertussis Tohama I Bordetella parapertussis 12822 Ralstonia eutropha H16 Xanthomonas campestris pv. campestris str. ATCC 33913 Xanthomonas campestris pv. campestris str. B100 Xanthomonas campestris pv. campestris str. 8004 Vibrio cholerae M66-2 Vibrio cholerae O1 biovar El Tor str. N16961 Shewanella frigidimarina NCIMB 400 Bacillus cytotoxicus NVH 391-98 Lactobacillus ruminis ATCC 27782 Leuconostoc citreum KM20 Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 Amycolatopsis mediterranei U32 Arthrobacter sp. FB24 Arthrobacter aurescens TC1 Arthrobacter chlorophenolicus A6 Beutenbergia cavernae DSM 12333 Catenulispora acidiphila DSM 44928 Cellulomonas flavigena DSM 20109 Clavibacter michiganensis subsp. michiganensis NCPPB 382 Conexibacter woesei DSM 14684 Deinococcus radiodurans R1 Deinococcus proteolyticus MRP Exiguobacterium sibiricum 255-15 Exiguobacterium sp. AT1b Frankia alni ACN14a Frankia sp. EuI1c Gordonia bronchialis DSM 43247 Intrasporangium calvum DSM 43043 Kineococcus radiotolerans SRS30216 Kribbella flavida DSM 17836 Leuconostoc kimchii IMSNU 11154 Macrococcus caseolyticus JCSC5402 Meiothermus ruber DSM 1279 Mycobacterium bovis AF2122/97 Mycobacterium ulcerans Agy99 Mycobacterium vanbaalenii PYR-1 Mycobacterium bovis BCG str. Pasteur 1173P2 Mycobacterium tuberculosis H37Ra Mycobacterium abscessus ATCC 19977 Mycobacterium sp. Spyr1 Mycobacterium sp. JDM601 Mycobacterium canettii CIPT 140010059 Nakamurella multipartita DSM 44233 Nocardia farcinica IFM 10152 Thermobaculum terrenum ATCC BAA-798 Pseudonocardia dioxanivorans CB1190 Renibacterium salmoninarum ATCC 33209 Rhodococcus opacus B4 Rhodococcus jostii RHA1 Rhodococcus equi 103S Rubrobacter xylanophilus DSM 9941 Saccharomonospora viridis DSM 43017 Salinispora tropica CNB-440 Sanguibacter keddieii DSM 10542 Sphaerobacter thermophilus DSM 20745 Stackebrandtia nassauensis DSM 44728 Staphylococcus carnosus subsp. carnosus TM300 Streptomyces scabiei 87.22 Streptomyces violaceusniger Tu 4113 Streptosporangium roseum DSM 43021 Thermobispora bispora DSM 43833 Thermomonospora curvata DSM 43183 Tsukamurella paurometabola DSM 20162 Xylanimonas cellulosilytica DSM 15894 Aspergillus nomiae NRRL 13137 Aspergillus novofumigatus Aspergillus novofumigatus IBT 16806 Aspergillus parasiticus SU-1 Aspergillus phoenicis Aspergillus sclerotioniger Aspergillus glaucus Aspergillus aculeatus ATCC 16872 Aspergillus leporis Aspergillus oryzae RIB40 Aspergillus terreus NIH2624 Aspergillus wentii Aspergillus clavatus NRRL 1 Aspergillus fischeri NRRL 181 Aspergillus fumigatus A1163 Aspergillus fumigatus Af293 Aspergillus calidoustus Aspergillus nidulans FGSC A4 Aspergillus taichungensis Aspergillus tamarii Aspergillus thermomutatus Aspergillus ustus Aspergillus violaceofuscus Aspergillus viridinutans Penicillium brasilianum Penicillium chermesinum Penicillium citrinum Penicillium concentricum Penicillium daleae Penicillium decumbens Penicillium griseofulvum Penicillium hordei Penicillium italicum Penicillium oxalicum Penicillium polonicum Penicillium steckii Penicillium thymicola Penicillium vulpinum Verticillium alfalfae VaMs.102 Trichoderma arundinaceum Trichoderma asperellum Trichoderma atroviride IMI 206040 Trichoderma citrinoviride Trichoderma harzianum Trichoderma longibrachiatum Trichoderma parareesei Trichoderma reesei QM6a Trichoderma virens Trichoderma virens Gv29-8 Fusarium acutatum Fusarium fujikuroi IMI 58289 Fusarium mangiferae Fusarium nygamai Fusarium proliferatum ET1 Fusarium subglutinans Fusarium verticillioides 7600 Fusarium heterosporum Fusarium equiseti Fusarium oxysporum Fo5176 Fusarium oxysporum f. sp. lycopersici 4287 Fusarium austroamericanum Fusarium graminearum PH-1 Fusarium poae Fusarium pseudograminearum CS3096 Fusarium sporotrichioides Fusarium vanettenii Fusarium vanettenii 77-13-4 Fusarium tricinctum Paraburkholderia graminis C4D1M Mycolicibacterium fortuitum subsp. fortuitum DSM 46621 = ATCC 6841 Rhodococcus hoagii ATCC 33707 Acidipropionibacterium acidipropionici ATCC 4875 Cutibacterium granulosum DSM 20700 Leuconostoc mesenteroides subsp. cremoris Bacteroides helcogenes P 36-108 Klebsiella aerogenes KCTC 2190 Acaryochloris marina MBIC11017 Acidiphilium cryptum JF-5 Acidiphilium multivorum AIU301 Acidithiobacillus ferrooxidans ATCC 23270 Acidobacterium capsulatum ATCC 51196 Acidovorax citrulli AAC00-1 Acidovorax sp. JS42 Acidovorax ebreus TPSY Aeromonas salmonicida subsp. salmonicida A449 Agrobacterium vitis S4 Agrobacterium radiobacter K84 Rhodoferax ferrireducens T118 Alcanivorax borkumensis SK2 Alicycliphilus denitrificans K601 Vibrio fischeri MJ11 Aliivibrio salmonicida LFI1238 Alkalilimnicola ehrlichii MLHE-1 Anabaena variabilis ATCC 29413 Anaeromyxobacter dehalogenans 2CP-C Anaeromyxobacter sp. Fw109-5 Anaeromyxobacter sp. K Anaeromyxobacter dehalogenans 2CP-1 Azorhizobium caulinodans ORS 571 Azotobacter vinelandii DJ Bartonella bacilliformis KC583 Bartonella tribocorum CIP 105476 Bartonella grahamii as4aup Beijerinckia indica subsp. indica ATCC 9039 Bordetella petrii DSM 12804 Bordetella avium 197N Brachyspira hyodysenteriae WA1 Brachyspira murdochii DSM 12563 Brachyspira pilosicoli 95/1000 Bradyrhizobium sp. ORS278 Bradyrhizobium sp. BTAi1 Brucella melitensis bv. 1 str. 16M Brucella abortus bv. 1 str. 9-941 Brucella ovis ATCC 25840 Brucella canis ATCC 23365 Brucella suis ATCC 23445 Brucella abortus S19 Brucella melitensis ATCC 23457 Brucella microti CCM 4915 Burkholderia mallei ATCC 23344 Burkholderia pseudomallei 1710b Burkholderia sp. 383 Burkholderia xenovorans LB400 Burkholderia ambifaria AMMD Burkholderia mallei NCTC 10229 Burkholderia pseudomallei 1106a Burkholderia vietnamiensis G4 Burkholderia cenocepacia MC0-3 Burkholderia ambifaria MC40-6 Burkholderia phymatum STM815 Burkholderia phytofirmans PsJN Burkholderia cenocepacia J2315 Burkholderia rhizoxinica HKI 454 Candidatus Koribacter versatilis Ellin345 Caulobacter crescentus CB15 Caulobacter crescentus NA1000 Caulobacter segnis ATCC 21756 Chitinophaga pinensis DSM 2588 Chlorobium tepidum TLS Chlorobium phaeobacteroides DSM 266 Chlorobium limicola DSM 245 Chromohalobacter salexigens DSM 3043 Citrobacter rodentium ICC168 Colwellia psychrerythraea 34H Coxiella burnetii RSA 493 Coxiella burnetii Dugway 5J108-111 Cronobacter turicensis z3032 Cupriavidus metallidurans CH34 Cupriavidus taiwanensis LMG 19424 Cupriavidus necator N-1 Cyanothece sp. ATCC 51142 Cyanothece sp. PCC 8801 Cyanothece sp. PCC 7424 Cytophaga hutchinsonii ATCC 33406 Deinococcus deserti VCD115 Desulfovibrio magneticus RS-1 Desulfovibrio salexigens DSM 2638 Dichelobacter nodosus VCS1703A Dickeya dadantii Ech703 Dickeya zeae Ech1591 Dickeya dadantii Ech586 Dickeya dadantii 3937 Dinoroseobacter shibae DFL 12 Edwardsiella ictaluri 93-146 Enterobacter sp. 638 Enterobacter cloacae SCF1 Erwinia tasmaniensis Et1/99 Erwinia amylovora CFBP1430 Erwinia billingiae Eb661 Erythrobacter litoralis HTCC2594 Ferrimonas balearica DSM 9799 Francisella tularensis subsp. holarctica LVS Geobacter lovleyi SZ Gluconacetobacter diazotrophicus PAl 5 Gluconobacter oxydans 621H Gramella forsetii KT0803 Granulibacter bethesdensis CGDNIH1 Haemophilus parasuis SH0165 Hahella chejuensis KCTC 2396 Haliangium ochraceum DSM 14365 Halorhodospira halophila SL1 Halothiobacillus neapolitanus c2 Herminiimonas arsenicoxydans Herpetosiphon aurantiacus DSM 785 Hyphomonas neptunium ATCC 15444 Idiomarina loihiensis L2TR Jannaschia sp. CCS1 Janthinobacterium sp. Marseille Klebsiella pneumoniae 342 Leadbetterella byssophila DSM 17132 Legionella pneumophila subsp. pneumophila str. Philadelphia 1 Legionella pneumophila str. Lens Legionella longbeachae NSW150 Leptothrix cholodnii SP-6 Magnetospirillum magneticum AMB-1 Maricaulis maris MCS10 Marinobacter aquaeolei VT8 Marinomonas mediterranea MMB-1 Marinomonas posidonica IVIA-Po-181 Methanocaldococcus fervens AG86 Methylibium petroleiphilum PM1 Methylobacillus flagellatus KT Methylobacterium chloromethanicum CM4 Methylobacterium nodulans ORS 2060 Methylobacterium extorquens AM1 Methylobacterium extorquens DM4 Methylocella silvestris BL2 Methylotenera mobilis JLW8 Methylovorus glucosetrophus SIP3-4 Microbacterium testaceum StLB037 Microcystis aeruginosa NIES-843 Neisseria meningitidis alpha14 Neisseria lactamica 020-06 Nitrobacter winogradskyi Nb-255 Nitrobacter hamburgensis X14 Nitrosococcus oceani ATCC 19707 Nitrosococcus halophilus Nc4 Nitrosomonas eutropha C91 Nitrosospira multiformis ATCC 25196 Nostoc sp. PCC 7120 Nostoc punctiforme PCC 73102 Novosphingobium aromaticivorans DSM 12444 Bordetella bronchiseptica RB50 Haemophilus ducreyi 35000HP Xanthomonas axonopodis pv. citri str. 306 Nitrosomonas europaea ATCC 19718 Chromobacterium violaceum ATCC 12472 Bdellovibrio bacteriovorus HD100 Sodalis glossinidius str. 'morsitans' Synechococcus sp. JA-2-3B'a(2-13) Rickettsia rickettsii str. 'Sheila Smith' Sorangium cellulosum 'So ce 56' Opitutus terrae PB90-1 Alteromonas macleodii str. 'Deep ecotype' Gemmatimonas aurantiaca T-27 Thermus scotoductus SA-01 Rhodobacter capsulatus SB1003 Pantoea ananatis LMG 20103 Paracoccus denitrificans PD1222 Parvibaculum lavamentivorans DS-1 Pasteurella multocida subsp. multocida str. Pm70 Pectobacterium atrosepticum SCRI1043 Pectobacterium carotovorum subsp. carotovorum PC1 Pedobacter heparinus DSM 2366 Pelobacter carbinolicus DSM 2380 Pelodictyon phaeoclathratiforme BU-1 Phenylobacterium zucineum HLK1 Photobacterium profundum SS9 Photorhabdus luminescens subsp. laumondii TTO1 Photorhabdus asymbiotica subsp. asymbiotica ATCC 43949 Pirellula staleyi DSM 6068 Planctomyces limnophilus DSM 3776 Polaromonas sp. JS666 Polaromonas naphthalenivorans CJ2 Polynucleobacter necessarius subsp. asymbioticus QLW-P1DMWA-1 Prosthecochloris aestuarii DSM 271 Pseudoalteromonas haloplanktis TAC125 Pseudomonas syringae pv. tomato str. DC3000 Pseudomonas syringae pv. phaseolicola 1448A Pseudomonas syringae pv. syringae B728a Pseudomonas entomophila L48 Pseudomonas fulva 12-X Psychrobacter arcticus 273-4 Psychrobacter cryohalolentis K5 Psychromonas ingrahamii 37 Ralstonia solanacearum GMI1000 Rhizobium etli CFN 42 Rhizobium etli CIAT 652 Rhizobium leguminosarum bv. trifolii WSM1325 Rhodopirellula baltica SH 1 Rhodopseudomonas palustris CGA009 Rhodopseudomonas palustris HaA2 Rhodopseudomonas palustris BisB5 Rhodospirillum centenum SW Rickettsia prowazekii str. Madrid E Rickettsia conorii str. Malish 7 Rickettsia typhi str. Wilmington Rickettsia felis URRWXCal2 Rickettsia bellii RML369-C Rickettsia canadensis str. McKiel Rickettsia akari str. Hartford Rickettsia massiliae MTU5 Rickettsia rickettsii str. Iowa Rickettsia africae ESF-5 Rickettsia peacockii str. Rustic Roseiflexus sp. RS-1 Roseobacter denitrificans OCh 114 Roseobacter litoralis Och 149 Ruegeria pomeroyi DSS-3 Ruegeria sp. TM1040 Saccharophagus degradans 2-40 Salmonella enterica subsp. enterica serovar Paratyphi A str. Segniliparus rotundus DSM 44985 Shewanella oneidensis MR-1 Shewanella sp. ANA-3 Shewanella amazonensis SB2B Shewanella sp. W3-18-1 Shewanella baltica OS155 Shewanella loihica PV-4 Shewanella sediminis HAW-EB3 Shewanella pealeana ATCC 700345 Shewanella baltica OS195 Shewanella halifaxensis HAW-EB4 Shewanella woodyi ATCC 51908 Shewanella piezotolerans WP3 Shewanella violacea DSS12 Shigella flexneri 2a str. 301 Shigella boydii Sb227 Shigella boydii CDC 3083-94 Sinorhizobium meliloti 1021 Sinorhizobium medicae WSM419 Sphingobium japonicum UT26S Sphingomonas wittichii RW1 Sphingopyxis alaskensis RB2256 Synechococcus sp. JA-3-3Ab Synechococcus sp. CC9311 Synechococcus sp. PCC 7002 Syntrophobacter fumaroxidans MPOB Syntrophus aciditrophicus SB Teredinibacter turnerae T7901 Thioalkalivibrio sp. K90mix Thiobacillus denitrificans ATCC 25259 Tolumonas auensis DSM 9187 Variovorax paradoxus EPS Verminephrobacter eiseniae EF01-2 Vibrio vulnificus CMCP6 Vibrio vulnificus YJ016 Vibrio splendidus LGP32 Weeksella virosa DSM 16922 Xanthobacter autotrophicus Py2 Xanthomonas oryzae pv. oryzae KACC10331 Xanthomonas campestris pv. vesicatoria str. 85-10 Xanthomonas oryzae pv. oryzae PXO99A Xenorhabdus bovienii SS-2004 Xenorhabdus nematophila ATCC 19061 Xylella fastidiosa 9a5c Xylella fastidiosa Temecula1 Xylella fastidiosa M23 Zymomonas mobilis subsp. pomaceae ATCC 29192 Sphingobacterium paucimobilis HER1398 Neisseria meningitidis serogroup C Atlantibacter hermannii NBRC 105704 Klebsiella michiganensis KCTC 1686 Chania multitudinisentens RB-25

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
MMDBr0025042	Heptanoyl-CoA	Carbon dioxide	3-oxoacyl-[acyl-carrier-protein] synthase 3 protein 2	Synthesis	RHEA	34755880
MMDBr0038832	Heptanoyl-CoA	Heptanoic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880
MMDBr0039012	Heptanoyl-CoA	Heptanoic acid	Thioesterase 1/protease 1/lysophospholipase L1	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
Bacteria/Eubacteria	Actinobacteria	1	Human

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

10140228

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966235

PDB ID

Not Available

ChEBI ID

37283

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Heptanoyl-CoA (MMDBc0048643)

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