Showing metabocard for octanoic acid (MMDBc0054613)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:21:17 UTC
Update Date2024-04-30 20:54:44 UTC
Metabolite IDMMDBc0054613
Metabolite Identification
Common Nameoctanoic acid
DescriptionCaprylic acid, or octanoic acid, with the structural formula CH3(CH2)6CO2H, is an eight-carbon straight-chain fatty acid and a carboxylic acid. It is an oily Liquid with a slightly unpleasant rancid taste and odor. It is minimally soluble in water. Caprylic acid can be found in numerous foods such as Prunus (Cherry, Plum), pineapple sages, black raspberries, shallots, coconuts and breast milk. Caprylic acid is taken as a dietary supplement. Caprylic acid is used commercially in the production of esters used in perfumery and in the manufacture of dyes. Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities, schools/colleges, industrial facilities, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in greenhouses and garden centers. Caprylic acid, and other fatty acids, affect the hunger hormone ghrelin. Ghrelin must be acylated, where it acquires an -OH group, before it can stimulate the hunger receptors in the hypothalamus. Caprylic acid becomes linked post-translationally to serine at the 3-position by the enzyme ghrelin O-acyltransferase (GOAT), located on the cell membrane of ghrelin cells in the stomach and pancreas (PMID 19896496 ). Caprylic acid affects those with medium-chain acyl-CoA dehydrogenase deficiency (MCAD), which is an inborn error of metabolism, marked by mutations of the gene ACADM. Those affected with MCAD have difficulties converting fatty acids to energy, especially during fasting. As a result, fatty acids build up and cause damage to liver and brain (PMID: 27536022 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fed080422a0>


  Mrv1652303202019022D          

 10  9  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  CHG  1   9  -1
M  END
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3D MOL for #<Metabolite:0x00007fed080422a0>

HMDB0304443
     RDKit          3D
octanoate
 25 24  0  0  0  0  0  0  0  0999 V2000
   -3.6358    0.8442    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7742   -0.1049   -0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098   -0.0509    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5700   -1.0415   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -1.1182   -0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    0.1638   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848   -0.0590   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8730    1.1827   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0949    1.2183    0.0338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    2.3344   -0.6283 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5633    0.2801    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349    1.6548    0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1992    1.2362    1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074   -1.1567    0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    0.1348   -1.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    0.9734    0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350   -0.3613    1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974   -2.0500   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7306   -0.8712   -1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330   -1.8653   -0.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -1.5007    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037    0.4915   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2606    0.9571    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5515   -0.8250   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2117   -0.4665    1.0184 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
M  CHG  1  10  -1
M  END
Download

3D SDF for #<Metabolite:0x00007fed080422a0>


  Mrv1652303202019022D          

 10  9  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  CHG  1   9  -1
M  END
> <DATABASE_ID>
MMDBc0054613

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1

> <INCHI_KEY>
WWZKQHOCKIZLMA-UHFFFAOYSA-M

> <FORMULA>
C8H15O2

> <MOLECULAR_WEIGHT>
143.2035

> <EXACT_MASS>
143.107204724

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.95089976810226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octanoate

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.700033457666666

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.192975275996319

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
51.112700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
octanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fed080422a0>

HMDB0304443
     RDKit          3D
octanoate
 25 24  0  0  0  0  0  0  0  0999 V2000
   -3.6358    0.8442    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7742   -0.1049   -0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098   -0.0509    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5700   -1.0415   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -1.1182   -0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312    0.1638   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848   -0.0590   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8730    1.1827   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0949    1.2183    0.0338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418    2.3344   -0.6283 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5633    0.2801    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349    1.6548    0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1992    1.2362    1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074   -1.1567    0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    0.1348   -1.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    0.9734    0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350   -0.3613    1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974   -2.0500   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7306   -0.8712   -1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3330   -1.8653   -0.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -1.5007    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037    0.4915   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2606    0.9571    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5515   -0.8250   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2117   -0.4665    1.0184 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
M  CHG  1  10  -1
M  END
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PDB for #<Metabolite:0x00007fed080422a0>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007fed080422a0>

COMPND    HMDB0304443
HETATM    1  C1  UNL     1      -3.636   0.844   0.692  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.774  -0.105  -0.065  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.310  -0.051   0.376  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.570  -1.042  -0.456  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.899  -1.118  -0.150  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.631   0.164  -0.354  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.085  -0.059  -0.012  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.873   1.183  -0.194  1.00  0.00           C  
HETATM    9  O1  UNL     1       5.095   1.218   0.034  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.242   2.334  -0.628  1.00  0.00           O1-
HETATM   11  H1  UNL     1      -4.563   0.280   1.004  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.035   1.655   0.017  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.199   1.236   1.616  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.107  -1.157   0.050  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.824   0.135  -1.138  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.910   0.973   0.318  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.235  -0.361   1.448  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.997  -2.050  -0.239  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.731  -0.871  -1.536  1.00  0.00           H  
HETATM   20  H10 UNL     1       1.333  -1.865  -0.871  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.106  -1.501   0.849  1.00  0.00           H  
HETATM   22  H12 UNL     1       1.604   0.492  -1.422  1.00  0.00           H  
HETATM   23  H13 UNL     1       1.261   0.957   0.329  1.00  0.00           H  
HETATM   24  H14 UNL     1       3.552  -0.825  -0.685  1.00  0.00           H  
HETATM   25  H15 UNL     1       3.212  -0.466   1.018  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9    9   10
END
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SMILES for #<Metabolite:0x00007fed080422a0>

CCCCCCCC([O-])=O
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INCHI for #<Metabolite:0x00007fed080422a0>

InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1
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Synonyms
ValueSource
1-HeptanecarboxylateChEBI
CaprilateChEBI
CaprylateChEBI
CH3-[CH2]6-COO(-)ChEBI
N-CaprylateChEBI
N-OctanoateChEBI
N-OctoateChEBI
N-OctylateChEBI
Octanoic acid, ion(1-)ChEBI
OctylateChEBI
1-Heptanecarboxylic acidGenerator
Caprilic acidGenerator
Caprylic acidGenerator
N-Caprylic acidGenerator
N-Octanoic acidGenerator
N-Octoic acidGenerator
N-Octylic acidGenerator
Octanoate, ion(1-)Generator
Octylic acidGenerator
Octanoic acidGenerator
Caprylic acid, 14C-labeledMeSH
Caprylic acid, aluminum saltMeSH
Caprylic acid, ammonia saltMeSH
Caprylic acid, barium saltMeSH
Caprylic acid, cadmium saltMeSH
Caprylic acid, calcium saltMeSH
Caprylic acid, cesium saltMeSH
Caprylic acid, chromium(+2) saltMeSH
Caprylic acid, cobalt saltMeSH
Caprylic acid, copper saltMeSH
Caprylic acid, copper(+2) saltMeSH
Caprylic acid, iridum(+3) saltMeSH
Caprylic acid, iron(+3) saltMeSH
Caprylic acid, lanthanum(+3) saltMeSH
Caprylic acid, lead(+2) saltMeSH
Caprylic acid, lithium saltMeSH
Caprylic acid, manganese saltMeSH
Caprylic acid, nickel(+2) saltMeSH
Caprylic acid, potassium saltMeSH
Caprylic acid, ruthenium(+3) saltMeSH
Caprylic acid, sodium saltMeSH
Caprylic acid, sodium salt, 11C-labeledMeSH
Caprylic acid, tin saltMeSH
Caprylic acid, tin(+2) saltMeSH
Caprylic acid, zinc saltMeSH
Caprylic acid, zirconium saltMeSH
Caprylic acid, zirconium(+4) saltMeSH
Lithium octanoateMeSH
Sodium caprylateMeSH
Sodium octanoateMeSH
Molecular FormulaC8H15O2
Average Mass143.2035
Monoisotopic Mass143.107204724
IUPAC Nameoctanoate
Traditional Nameoctanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCC([O-])=O
InChI Identifier
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1
InChI KeyWWZKQHOCKIZLMA-UHFFFAOYSA-M