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Showing NP-Card for cis-4-Octenedioic acid (NP0000111)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 15:41:06 UTC
NP-MRD IDNP0000111
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-4-Octenedioic acid
DescriptionCis-4-Octenedioic acid, also known as (Z)-4-octene-1,8-dioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Cis-4-Octenedioic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000111 (cis-4-Octenedioic acid)

Untitled Document-5
  Mrv1652305271900062D          

 12 11  0  0  0  0            999 V2000
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
  2 11  2  0  0  0  0
  9 12  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000111 (cis-4-Octenedioic acid)

HMDB0004982
     RDKit          3D
cis-4-Octenedioic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
    3.0485    1.3950    0.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    0.5623   -0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.0612   -0.3322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    0.1219   -1.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751   -0.9971   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7047   -0.5610    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059   -0.5314    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -0.9146   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5345    0.2291   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052    0.7328    0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2344    0.2638    1.7567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714    1.7979    0.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430    0.3044    0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    0.9084   -1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -0.3285   -2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0316   -1.8878   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -1.2273   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533   -0.2459    1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716   -0.1801    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3017   -1.6744    0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2450   -1.4555   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403    1.0742   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304   -0.0809   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472    2.6335   -0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0000111 (cis-4-Octenedioic acid)

Untitled Document-5
  Mrv1652305271900062D          

 12 11  0  0  0  0            999 V2000
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
  2 11  2  0  0  0  0
  9 12  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC\C=C/CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-2H,3-6H2,(H,9,10)(H,11,12)/b2-1-

> <INCHI_KEY>
LQVYKEXVMZXOAH-UPHRSURJSA-N

> <FORMULA>
C8H12O4

> <MOLECULAR_WEIGHT>
172.1785

> <EXACT_MASS>
172.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.19659519199825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-oct-4-enedioic acid

> <ALOGPS_LOGP>
0.96

> <JCHEM_LOGP>
1.0178700359999997

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.830491640247016

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.077430055226847

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
43.05760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-4-octenedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000111 (cis-4-Octenedioic acid)

HMDB0004982
     RDKit          3D
cis-4-Octenedioic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
    3.0485    1.3950    0.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    0.5623   -0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.0612   -0.3322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    0.1219   -1.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751   -0.9971   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7047   -0.5610    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059   -0.5314    0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -0.9146   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5345    0.2291   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052    0.7328    0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2344    0.2638    1.7567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714    1.7979    0.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430    0.3044    0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    0.9084   -1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -0.3285   -2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0316   -1.8878   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -1.2273   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533   -0.2459    1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716   -0.1801    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3017   -1.6744    0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2450   -1.4555   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403    1.0742   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304   -0.0809   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472    2.6335   -0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

PDB for NP0000111 (cis-4-Octenedioic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-5                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9                                                            
CONECT   11    2                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0000111 (cis-4-Octenedioic acid)

COMPND    HMDB0004982
HETATM    1  O1  UNL     1       3.048   1.395   0.689  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.295   0.562  -0.213  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.577   0.061  -0.332  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.249   0.122  -1.127  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.375  -0.997  -0.555  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.705  -0.561   0.673  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.606  -0.531   0.816  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.611  -0.915  -0.185  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.534   0.229  -0.557  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.305   0.733   0.597  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.234   0.264   1.757  1.00  0.00           O  
HETATM   12  O4  UNL     1      -4.171   1.798   0.401  1.00  0.00           O  
HETATM   13  H1  UNL     1       5.343   0.304   0.271  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.560   0.908  -1.462  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.718  -0.328  -2.035  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.032  -1.888  -0.402  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.644  -1.227  -1.339  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.353  -0.246   1.507  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.972  -0.180   1.802  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.302  -1.674   0.320  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.245  -1.456  -1.066  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.940   1.074  -1.015  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.230  -0.081  -1.360  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.747   2.633  -0.019  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    7   18
CONECT    7    8   19
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   11   12
CONECT   12   24
END
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SMILES for NP0000111 (cis-4-Octenedioic acid)

OC(=O)CC\C=C/CCC(O)=O
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INCHI for NP0000111 (cis-4-Octenedioic acid)

InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-2H,3-6H2,(H,9,10)(H,11,12)/b2-1-
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View in JSmolView NMR Assignments
Synonyms
ValueSource
cis-4-OctenedioateGenerator
(Z)-4-Octene-1,8-dioateHMDB
(Z)-4-Octene-1,8-dioic acidHMDB
cis-4-Octene-1,8-dioateHMDB
cis-4-Octene-1,8-dioic acidHMDB
Chemical FormulaC8H12O4
Average Mass172.1785 Da
Monoisotopic Mass172.07356 Da
IUPAC Name(4Z)-oct-4-enedioic acid
Traditional Namecis-4-octenedioic acid
CAS Registry Number38561-68-1
SMILES
OC(=O)CC\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-2H,3-6H2,(H,9,10)(H,11,12)/b2-1-
InChI KeyLQVYKEXVMZXOAH-UPHRSURJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
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Dromaius novaehollandiaeFooDB
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Lagopus mutaFooDB
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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
  • Unsaturated fatty acid
  • Dicarboxylic 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 Point96 - 98 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.16 g/LALOGPS
logP0.96ALOGPS
logP1.02ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability17.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004982
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023569
KNApSAcK IDNot Available
Chemspider ID9979870
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7235
PubChem Compound11805205
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wei P, Zhu K, Cao J, Lin X, Shen X, Duan Z, Li C: Relationship between Micromolecules and Quality Changes of Tilapia Fillets after Partial Freezing Treatment with Polyphenols. J Agric Food Chem. 2021 Jul 28;69(29):8213-8226. doi: 10.1021/acs.jafc.1c02035. Epub 2021 Jul 15. [PubMed:34264653 ]
  2. Zeng W, Huang KE, Luo Y, Li DX, Chen W, Yu XQ, Ke XH: Nontargeted urine metabolomics analysis of the protective and therapeutic effects of Citri Reticulatae Chachiensis Pericarpium on high-fat feed-induced hyperlipidemia in rats. Biomed Chromatogr. 2020 Apr;34(4):e4795. doi: 10.1002/bmc.4795. Epub 2020 Feb 12. [PubMed:31967660 ]
  3. Cao J, Mi Y, Shi C, Bian Y, Huang C, Ye Z, Liu L, Miao L: First-line anti-tuberculosis drugs induce hepatotoxicity: A novel mechanism based on a urinary metabolomics platform. Biochem Biophys Res Commun. 2018 Mar 4;497(2):485-491. doi: 10.1016/j.bbrc.2018.02.030. Epub 2018 Feb 15. [PubMed:29454961 ]
  4. Lee SY, Kim M, Jung S, Lee SH, Lee JH: Altered plasma lysophosphatidylcholines and amides in non-obese and non-diabetic subjects with borderline-to-moderate hypertriglyceridemia: a case-control study. PLoS One. 2015 Apr 9;10(4):e0123306. doi: 10.1371/journal.pone.0123306. eCollection 2015. [PubMed:25856314 ]