Np mrd loader

Showing NP-Card for Hydroxyoctanoic acid (NP0001194)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:54 UTC
NP-MRD IDNP0001194
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxyoctanoic acid
DescriptionHydroxyoctanoic acid medium chain substrate of the 2-hydroxy acid oxidases associated with the 3 distinct human 2-hydroxy acid oxidase genes, HAOX1, HAOX2, and HAOX3. (PMID: 10777549 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001194 (Hydroxyoctanoic acid)


  Mrv1652305271900162D          

 11 10  0  0  0  0            999 V2000
   26.3604  -12.6931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7893  -11.8681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -10.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9314  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2169  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5025  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6458  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7879  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3604  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0734  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0001194 (Hydroxyoctanoic acid)

HMDB0000711
     RDKit          3D
Hydroxyoctanoic acid
 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.5402   -0.1620   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635    0.5225   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650   -0.2793   -0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.4066   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -0.3243   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    0.4212   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.2810   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925   -1.5644    0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    0.5047    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2656    1.7115   -0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367   -0.0827    0.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5643   -1.1658   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5002   -0.2523   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3974    0.4695   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1994    1.5594   -0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2902    0.5622    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -1.3080   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.3397   -1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.4620    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    1.4553   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -1.3022    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -0.5827   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696    0.4802    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    1.4388   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -0.2853   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -2.2702   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9047    0.2059    1.0834 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
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0001194 (Hydroxyoctanoic acid)


  Mrv1652305271900162D          

 11 10  0  0  0  0            999 V2000
   26.3604  -12.6931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7893  -11.8681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -10.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9314  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2169  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5025  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6458  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7879  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3604  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0734  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)

> <INCHI_KEY>
JKRDADVRIYVCCY-UHFFFAOYSA-N

> <FORMULA>
C8H16O3

> <MOLECULAR_WEIGHT>
160.2108

> <EXACT_MASS>
160.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.007170726296977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxyoctanoic acid

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.828967537

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.284148892109581

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.422499319236623

> <JCHEM_PKA_STRONGEST_BASIC>
-3.797528711914386

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.767799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyoctanoate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001194 (Hydroxyoctanoic acid)

HMDB0000711
     RDKit          3D
Hydroxyoctanoic acid
 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.5402   -0.1620   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635    0.5225   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650   -0.2793   -0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.4066   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -0.3243   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    0.4212   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.2810   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925   -1.5644    0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    0.5047    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2656    1.7115   -0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367   -0.0827    0.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5643   -1.1658   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5002   -0.2523   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3974    0.4695   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1994    1.5594   -0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2902    0.5622    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -1.3080   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.3397   -1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.4620    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    1.4553   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -1.3022    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -0.5827   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696    0.4802    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    1.4388   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -0.2853   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -2.2702   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9047    0.2059    1.0834 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
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
M  END
Download

PDB for NP0001194 (Hydroxyoctanoic 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  O   UNK     0      49.206 -23.694   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      51.873 -22.154   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      50.540 -19.844   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      46.539 -22.154   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.205 -21.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.871 -22.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.872 -21.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.537 -21.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.206 -22.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      41.204 -22.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.540 -21.384   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    5    7                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8                                                       
CONECT    7    4    9                                                       
CONECT    8    6   10                                                       
CONECT    9    1    7   11                                                  
CONECT   10    8                                                            
CONECT   11    2    3    9                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for NP0001194 (Hydroxyoctanoic acid)

COMPND    HMDB0000711
HETATM    1  C1  UNL     1      -4.540  -0.162  -0.567  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.263   0.523  -0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.065  -0.279  -0.578  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.800   0.407  -0.124  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.436  -0.324  -0.544  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.660   0.421  -0.054  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.938  -0.281  -0.456  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.992  -1.564   0.072  1.00  0.00           O  
HETATM    9  C8  UNL     1       4.062   0.505   0.104  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.266   1.711  -0.198  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.937  -0.083   0.993  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.564  -1.166  -0.143  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.500  -0.252  -1.663  1.00  0.00           H  
HETATM   14  H3  UNL     1      -5.397   0.469  -0.288  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.199   1.559  -0.504  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.290   0.562   0.987  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.143  -1.308  -0.173  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.137  -0.340  -1.682  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.806   0.462   0.976  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.830   1.455  -0.490  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.436  -1.302   0.020  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.492  -0.583  -1.600  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.670   0.480   1.053  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.657   1.439  -0.463  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.077  -0.285  -1.561  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.009  -2.270  -0.608  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.905   0.206   1.083  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    9   25
CONECT    8   26
CONECT    9   10   10   11
CONECT   11   27
END
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SMILES for NP0001194 (Hydroxyoctanoic acid)

CCCCCCC(O)C(O)=O
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INCHI for NP0001194 (Hydroxyoctanoic acid)

InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
2-Hydroxycaprylic acidChEBI
alpha-Hydroxyoctanoic acidChEBI
2-HydroxycaprylateGenerator
a-HydroxyoctanoateGenerator
a-Hydroxyoctanoic acidGenerator
alpha-HydroxyoctanoateGenerator
Α-hydroxyoctanoateGenerator
Α-hydroxyoctanoic acidGenerator
HydroxyoctanoateGenerator
2-HydroxyoctanoateHMDB
2-Hydroxyoctanoic acidHMDB
a-Hydroxy-N-caprylateHMDB
a-Hydroxy-N-caprylic acidHMDB
a-HydroxycaprylateHMDB
a-Hydroxycaprylic acidHMDB
alpha-Hydroxy-N-caprylateHMDB
alpha-Hydroxy-N-caprylic acidHMDB
alpha-HydroxycaprylateHMDB
alpha-Hydroxycaprylic acidHMDB
DL-2-HydroxycaprylateHMDB
DL-2-Hydroxycaprylic acidHMDB
DL-2-HydroxyoctanoateHMDB
DL-2-Hydroxyoctanoic acidHMDB
alpha-HCA acidHMDB
2-Hydroxy caprylateHMDB
Chemical FormulaC8H16O3
Average Mass160.2108 Da
Monoisotopic Mass160.10994 Da
IUPAC Name2-hydroxyoctanoic acid
Traditional Namehydroxyoctanoate
CAS Registry Number617-73-2
SMILES
CCCCCCC(O)C(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
InChI KeyJKRDADVRIYVCCY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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 NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
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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
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point70 °CNot Available
Boiling Point289.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility927 mg/mLNot Available
LogP1.960 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility11.2 g/LALOGPS
logP1.8ALOGPS
logP1.83ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.42ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity41.77 m³·mol⁻¹ChemAxon
Polarizability18.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000711
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022197
KNApSAcK IDNot Available
Chemspider ID84994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5679
PubChem Compound94180
PDB IDNot Available
ChEBI ID86543
Good Scents IDrw1447721
References
General References
  1. Jones JM, Morrell JC, Gould SJ: Identification and characterization of HAOX1, HAOX2, and HAOX3, three human peroxisomal 2-hydroxy acid oxidases. J Biol Chem. 2000 Apr 28;275(17):12590-7. [PubMed:10777549 ]
  2. Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. [PubMed:2044590 ]
  3. Al-Bawab A, Friberg SE: Phase behavior of the alpha-hydroxyoctanoic acid/Laureth 4/white oil/water system and preliminary evaluation of the phase changes during evaporation of its emulsion. J Cosmet Sci. 2002 May-Jun;53(3):151-64. [PubMed:12053206 ]
  4. Selezneva KS, Isakov VA, Eller KI, Goriainov SV, Kirillova OO, Sentsova TB: [Isomeric specific analysis of hydroxyeicosatetraenoic acid in blood samples from obese patients with non-alcoholic and alcoholic steatohepatitis]. Vopr Pitan. 2014;83(5):12-9. [PubMed:25816621 ]
  5. Veurink M, Mangioris G, Kaufmann B, Asmus L, Hennig M, Heiligenhaus A, Gurny R, Moller M, Pournaras CJ: Development of an intravitreal peptide (BQ123) sustained release system based on poly(2-hydroxyoctanoic acid) aiming at a retinal vasodilator response. J Ocul Pharmacol Ther. 2014 Aug;30(6):517-23. doi: 10.1089/jop.2013.0117. Epub 2014 May 19. [PubMed:24978907 ]
  6. Veurink M, Asmus L, Hennig M, Kaufmann B, Bagnewski L, Heiligenhaus A, Mendrinos E, Pournaras CJ, Gurny R, Moller M: Design and in vitro assessment of L-lactic acid-based copolymers as prodrug and carrier for intravitreal sustained L-lactate release to reverse retinal arteriolar occlusions. Eur J Pharm Sci. 2013 May 13;49(2):233-40. doi: 10.1016/j.ejps.2013.02.021. Epub 2013 Mar 14. [PubMed:23500039 ]