Showing NP-Card for Caproic acid (NP0000312)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-17 17:37:51 UTC
NP-MRD IDNP0000312
Secondary Accession NumbersNone
Natural Product Identification
Common NameCaproic acid
DescriptionCaproic acid, also known as hexanoic acid or C6:0, Is a medium-chain fatty acid. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides. Caproic acid is a colourless oily liquid that smells like cheese with an overlying waxy or barnyard odor like that of goats or other barnyard animals. Its name comes from the Latin word capra, meaning "goat". Two other fatty acids are named after goats: Caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15% of the fat in goat's milk. Caproic acid is a fatty acid found naturally in various animal fats and oils. While generally more abundant in animals, caproic acid is found in all organisms ranging from bacteria to plants to animals. Caproic acid is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo fruit its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. Industrially, the primary use of caproic acid is in the manufacture of its esters for use as artificial flavors and in the manufacture of hexyl derivatives, such as hexylphenols. Caproic acid has been associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a relatively volatile organic compound, caproic acid has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000312 (Caproic acid)

  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 NP0000312 (Caproic acid)

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 NP0000312 (Caproic acid)

  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>
NP0000312

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000312 (Caproic acid)

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 NP0000312 (Caproic acid)

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 NP0000312 (Caproic acid)

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 NP0000312 (Caproic acid)

CCCCCC(O)=O
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INCHI for NP0000312 (Caproic acid)

InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
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Synonyms
Chemical FormulaC6H12O2
Average Mass116.1583 Da
Monoisotopic Mass116.08373 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Ganoderma lucidumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-4.00 to -3.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point202.00 to 203.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility10.3 mg/mLNot Available
LogP1.92Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility9.72 g/LALOGPS
logP1.88ALOGPS
logP1.81ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)5.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.07 m³·mol⁻¹ChemAxon
Polarizability13.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000535
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004034
KNApSAcK IDC00001218
Chemspider ID8552
KEGG Compound IDC01585
BioCyc IDHEXANOATE
BiGG IDNot Available
Wikipedia LinkHexanoic_acid
METLIN ID5520
PubChem Compound8892
PDB IDNot Available
ChEBI ID30776
Good Scents IDrw1008541
References
General References
  1. Jakobs C, Sweetman L, Nyhan WL: Hydroxy acid metabolites of branched-chain amino acids in amniotic fluid. Clin Chim Acta. 1984 Jul 16;140(2):157-66. [PubMed:6467607 ]
  2. Epps JM, Phillips JO, Mestecky J: IgA-mediated clearance and tissue deposition of dinitrophenylated human serum albumin at various DNP:HSA ratios. Mol Immunol. 1988 Aug;25(8):731-8. [PubMed:3185569 ]
  3. Varani J, Orr W, Ward PA: Cell-associated proteases affect tumour cell migration in vitro. J Cell Sci. 1979 Apr;36:241-52. [PubMed:457809 ]
  4. Nilsen SL, Castellino FJ: Expression of human plasminogen in Drosophila Schneider S2 cells. Protein Expr Purif. 1999 Jun;16(1):136-43. [PubMed:10336871 ]
  5. Varani J, Orr W, Ward PA: Comparison of cell attachment and caseinolytic activities of five tumour cell types. J Cell Sci. 1978 Dec;34:133-44. [PubMed:748334 ]
  6. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81. [PubMed:6740214 ]
  7. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]