Showing metabocard for Caproic acid (MMDBc0000114)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:36:23 UTC
Update Date2024-09-27 23:51:59 UTC
Metabolite IDMMDBc0000114
Metabolite Identification
Common NameCaproic acid
DescriptionCaproic acid is a colourless oily liquid that smells like cheese. It is a fatty acid found naturally in various animal fats and oils. Caproic acid is a medium chain triglyceride (MCT). MCTs are widely used for parenteral nutrition in individuals requiring supplemental nutrition, and are being more widely used in foods, drugs, and cosmetics (MCTs are essentially non-toxic). It is safe for human dietary consumption up to levels of 1g/kg (PMID: 10685018 ). Caproic acid is found to be associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a volatile organic compound, it has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd5f94fbd58>

  Mrv1652309272007422D          

  8  7  0  0  0  0            999 V2000
   -0.5845   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fd5f94fbd58>

HMDB0000535
     RDKit          3D
Caproic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.5829   -0.2209    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6668    0.8300   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    0.2271   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.3586    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -0.9909    0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878   -0.1074   -0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8324   -0.5330   -0.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4245    1.2172   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    0.0538    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109   -0.2429    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -1.2225   -0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    1.6254    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    1.2915   -1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -0.5686   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.9922   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -1.0585    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.4722    1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.4331    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -1.8922   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950    1.9193    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  END
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3D SDF for #<Metabolite:0x00007fd5f94fbd58>

  Mrv1652309272007422D          

  8  7  0  0  0  0            999 V2000
   -0.5845   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000114

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

> <INCHI_KEY>
FUZZWVXGSFPDMH-UHFFFAOYSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.1583

> <EXACT_MASS>
116.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.269938207309668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexanoic acid

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.8108961276666666

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.090214000852688

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
31.0736

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007fd5f94fbd58>

HMDB0000535
     RDKit          3D
Caproic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.5829   -0.2209    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6668    0.8300   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    0.2271   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.3586    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -0.9909    0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878   -0.1074   -0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8324   -0.5330   -0.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4245    1.2172   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    0.0538    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109   -0.2429    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -1.2225   -0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    1.6254    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    1.2915   -1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -0.5686   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.9922   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -1.0585    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.4722    1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.4331    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -1.8922   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950    1.9193    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  END
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PDB for #<Metabolite:0x00007fd5f94fbd58>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.091  -1.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.241  -0.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.431  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.573  -1.743   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.763  -1.743   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.095  -0.970   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.095   0.567   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -6.428  -1.750   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x00007fd5f94fbd58>

COMPND    HMDB0000535
HETATM    1  C1  UNL     1      -2.583  -0.221   0.280  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.667   0.830  -0.296  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.320   0.227  -0.689  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.325  -0.359   0.502  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.657  -0.991   0.277  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.688  -0.107  -0.238  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.832  -0.533  -0.467  1.00  0.00           O  
HETATM    8  O2  UNL     1       2.425   1.217  -0.483  1.00  0.00           O  
HETATM    9  H1  UNL     1      -3.631   0.054   0.011  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.511  -0.243   1.383  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.411  -1.223  -0.185  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.482   1.625   0.453  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.155   1.292  -1.182  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.578  -0.569  -1.449  1.00  0.00           H  
HETATM   15  H7  UNL     1       0.227   0.992  -1.229  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.386  -1.058   0.986  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.466   0.472   1.253  1.00  0.00           H  
HETATM   18  H10 UNL     1       2.033  -1.433   1.234  1.00  0.00           H  
HETATM   19  H11 UNL     1       1.478  -1.892  -0.382  1.00  0.00           H  
HETATM   20  H12 UNL     1       2.595   1.919   0.220  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7    7    8
CONECT    8   20
END
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SMILES for #<Metabolite:0x00007fd5f94fbd58>

CCCCCC(O)=O
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INCHI for #<Metabolite:0x00007fd5f94fbd58>

InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
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Synonyms
Molecular FormulaC6H12O2
Average Mass116.1583
Monoisotopic Mass116.083729628
IUPAC Namehexanoic acid
Traditional Namehexanoic acid
CAS Registry Number142-62-1
SMILES
CCCCCC(O)=O
InChI Identifier
InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
InChI KeyFUZZWVXGSFPDMH-UHFFFAOYSA-N