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Showing NP-Card for Heptanoic acid (NP0001296)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:12 UTC
NP-MRD IDNP0001296
Secondary Accession NumbersNone
Natural Product Identification
Common NameHeptanoic acid
DescriptionHeptanoic acid, or C7:0 Also known as enanthic acid or heptylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides Heptanoic acid is an oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether. Its name derives from the Latin oenanthe which is in turn derived from the Ancient Greek oinos "wine" and anthos "blossom." Heptanoic acid is used in the preparation of esters, such as ethyl enanthate, which are used in fragrances and as artificial flavors. The triglyceride ester of heptanoic acid is the triheptanoin, which is used in certain medical conditions as a nutritional supplement.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001296 (Heptanoic acid)


  Mrv1652305271900152D          

  9  8  0  0  0  0            999 V2000
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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
  7  9  2  0  0  0  0
M  END
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3D MOL for NP0001296 (Heptanoic acid)

HMDB0000666
     RDKit          3D
Heptanoic acid
 23 22  0  0  0  0  0  0  0  0999 V2000
   -3.0619   -0.1642   -0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.8127   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0885    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    0.9475    0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317    0.1566    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7040   -1.1317    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432   -0.9461   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425   -2.0039   -1.0387 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.2366   -1.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564   -0.9984   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9308    0.3296   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3050   -0.5764    0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    1.1432   -1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    1.6832   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728   -0.8460   -0.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953   -0.1261    1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0140    1.8567    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8147    1.2850   -0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    0.7350    1.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7773   -0.0362    2.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4387   -1.5897    1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803   -1.8882    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2045    1.0321   -0.5738 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  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
M  END
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3D SDF for NP0001296 (Heptanoic acid)


  Mrv1652305271900152D          

  9  8  0  0  0  0            999 V2000
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001296

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)

> <INCHI_KEY>
MNWFXJYAOYHMED-UHFFFAOYSA-N

> <FORMULA>
C7H14O2

> <MOLECULAR_WEIGHT>
130.1849

> <EXACT_MASS>
130.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.331230708854507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
heptanoic acid

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.2554647926666664

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.147893056329631

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
35.6746

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heptanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0001296 (Heptanoic acid)

HMDB0000666
     RDKit          3D
Heptanoic acid
 23 22  0  0  0  0  0  0  0  0999 V2000
   -3.0619   -0.1642   -0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.8127   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0885    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    0.9475    0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317    0.1566    1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7040   -1.1317    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432   -0.9461   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425   -2.0039   -1.0387 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.2366   -1.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564   -0.9984   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9308    0.3296   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3050   -0.5764    0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    1.1432   -1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    1.6832   -0.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728   -0.8460   -0.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953   -0.1261    1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0140    1.8567    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8147    1.2850   -0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    0.7350    1.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7773   -0.0362    2.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4387   -1.5897    1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803   -1.8882    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2045    1.0321   -0.5738 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  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
M  END
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PDB for NP0001296 (Heptanoic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   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    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0001296 (Heptanoic acid)

COMPND    HMDB0000666
HETATM    1  C1  UNL     1      -3.062  -0.164  -0.840  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.906   0.813  -0.629  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.906   0.089   0.260  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.299   0.948   0.550  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.232   0.157   1.439  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.704  -1.132   0.809  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.443  -0.946  -0.441  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.843  -2.004  -1.039  1.00  0.00           O  
HETATM    9  O2  UNL     1       2.762   0.237  -1.053  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.656  -0.998  -1.430  1.00  0.00           H  
HETATM   11  H2  UNL     1      -3.931   0.330  -1.301  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.305  -0.576   0.168  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.460   1.143  -1.571  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.350   1.683  -0.105  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.573  -0.846  -0.234  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.395  -0.126   1.232  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.014   1.857   1.136  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.815   1.285  -0.366  1.00  0.00           H  
HETATM   19  H10 UNL     1       2.160   0.735   1.664  1.00  0.00           H  
HETATM   20  H11 UNL     1       0.777  -0.036   2.440  1.00  0.00           H  
HETATM   21  H12 UNL     1       2.439  -1.590   1.539  1.00  0.00           H  
HETATM   22  H13 UNL     1       0.880  -1.888   0.715  1.00  0.00           H  
HETATM   23  H14 UNL     1       3.204   1.032  -0.574  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    8    9
CONECT    9   23
END
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SMILES for NP0001296 (Heptanoic acid)

CCCCCCC(O)=O
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INCHI for NP0001296 (Heptanoic acid)

InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
CH3-[CH2]5-COOHChEBI
Enanthic acidChEBI
Enanthylic acidChEBI
HeptansaeureChEBI
Heptoic acidChEBI
Heptylic acidChEBI
N-Heptanoic acidChEBI
N-Heptoic acidChEBI
N-Heptylic acidChEBI
Oenanthic acidChEBI
Oenanthylic acidChEBI
OenanthsaeureChEBI
EnanthateGenerator
EnanthylateGenerator
HeptoateGenerator
HeptylateGenerator
N-HeptanoateGenerator
N-HeptoateGenerator
N-HeptylateGenerator
OenanthateGenerator
OenanthylateGenerator
HeptanoateGenerator
1-HexanecarboxylateHMDB
1-Hexanecarboxylic acidHMDB
Chemical FormulaC7H14O2
Average Mass130.1849 Da
Monoisotopic Mass130.09938 Da
IUPAC Nameheptanoic acid
Traditional Nameheptanoic acid
CAS Registry Number111-14-8
SMILES
CCCCCCC(O)=O
InChI Identifier
InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)
InChI KeyMNWFXJYAOYHMED-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 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 NameSourceReference
Ajania fastigiataLOTUS Database
AmaranthusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arachis hypogaeaFooDB
Artemisia macrocephalaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
CarideaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chenopodium quinoaFooDB
CichlidaeFooDB
Cinnamomum aromaticumFooDB
Citrus reticulataFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
ColumbaFooDB
ColumbidaeFooDB
CoregonusFooDB
Crassostrea virginicaFooDB
Cucurbita maximaFooDB
Daphne papyraceaLOTUS Database
Dromaius novaehollandiaeFooDB
Elettaria cardamomumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Erigeron philadelphicusLOTUS Database
Evernia prunastriLOTUS Database
Fumaria vaillantiiLOTUS Database
Gallus gallusFooDB
Glehnia littoralisLOTUS Database
Glycine maxFooDB
Glycyrrhiza glabraLOTUS Database
HippoglossusFooDB
Homo sapiensLOTUS Database
Hoplostethus atlanticusFooDB
Ictalurus punctatusFooDB
Lagopus mutaFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
LeporidaeFooDB
Lepus timidusFooDB
Linum usitatissimumFooDB
Malus pumilaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Notopterygium franchetiiLOTUS Database
Numida meleagrisFooDB
Nuphar luteaFooDB
OdocoileusFooDB
Oecophylla smaragdinaLOTUS Database
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
OryctolagusFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Ovis ariesFooDB
Panicum miliaceumFooDB
PectinidaeFooDB
Pelargonium graveolensLOTUS Database
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
PinusFooDB
Polygala senegaLOTUS Database
Rhododendron sichotenseLOTUS Database
Salmo salarFooDB
Salvia rosmarinusFooDB
Saussurea involucrataLOTUS Database
Scutellaria baicalensisLOTUS Database
SiluriformesFooDB
Solanum tuberosumFooDB
Sorghum bicolorFooDB
Stenodus leucichthysFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Thunnus albacaresFooDB
TriticumFooDB
Triticum aestivumKNApSAcK Database
Triticum speltaFooDB
Triticum turanicumFooDB
Vitis viniferaLOTUS Database
Zea mays L.FooDB
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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-7.5 °CNot Available
Boiling Point222.00 to 223.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.82 mg/mLNot Available
LogP2.42Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility2.98 g/LALOGPS
logP2.41ALOGPS
logP2.26ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)5.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.67 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000666
DrugBank IDDB02938
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008051
KNApSAcK IDC00053307
Chemspider ID7803
KEGG Compound IDC17714
BioCyc IDCPD-7619
BiGG IDNot Available
Wikipedia LinkHeptanoic_acid
METLIN ID5636
PubChem Compound8094
PDB IDNot Available
ChEBI ID45571
Good Scents IDrw1008501
References
General References
  1. Jones PM, Butt YM, Bennett MJ: Effects of odd-numbered medium-chain fatty acids on the accumulation of long-chain 3-hydroxy-fatty acids in long-chain L-3-hydroxyacyl CoA dehydrogenase and mitochondrial trifunctional protein deficient skin fibroblasts. Mol Genet Metab. 2004 Feb;81(2):96-9. [PubMed:14741189 ]
  2. Grislain L, Gele P, Bromet N, Luijten W, Volland JP, Mocaer E, Kamoun A: Metabolism of amineptine in rat, dog and man. Eur J Drug Metab Pharmacokinet. 1990 Oct-Dec;15(4):339-45. [PubMed:2088771 ]
  3. Buccellati C, Sala A, Rossoni G, Capra V, Rovati GE, Di Gennaro A, Folco G, Colli S, Casagrande C: Pharmacological characterization of 2NTX-99 [4-methoxy-N1-(4-trans-nitrooxycyclohexyl)-N3-(3-pyridinylmethyl)-1,3-benzenedica rboxamide], a potential antiatherothrombotic agent with antithromboxane and nitric oxide donor activity in platelet and vascular preparations. J Pharmacol Exp Ther. 2006 May;317(2):830-7. Epub 2006 Jan 6. [PubMed:16399881 ]
  4. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  5. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]