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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-05-01 17:30:31 UTC

Update Date

2022-09-22 17:44:09 UTC

HMDB ID

HMDB0060055

Secondary Accession Numbers

HMDB60055

Metabolite Identification

Common Name

Tetranor 12-HETE

Description

12(S)-HETE is a product of arachidonic acid metabolism through the 12-lipoxygenase pathway. It is primarily found in platelets, leukocytes, and to a lesser extent in smooth muscle cells. It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix. tetranor-12(S)-HETE is the major β-oxidation product resulting from peroxisomal metabolism of 12(S)-HETE in numerous tissues, and Lewis lung carcinoma cells. No biological function has yet been determined for tetranor-12(S)-HETE. Some data indicate it may play a role in controlling the inflammatory response in injured corneas.4 In some diseases (e.g., Zellweger’s Syndrome) peroxisomal abnormalities result in the inability of cells to metabolize 12(S)-HETE, which may be responsible for symptoms of the disease. The tetranor derivative of 12(S)-HETE is available as a research tool for the elucidation of the metabolic fate of its parent compound. (http://www.caymanchem.com)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0060055
     RDKit          3D
Tetranor 12-HETE
 45 44  0  0  0  0  0  0  0  0999 V2000
   -6.7974    1.3234    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2506    0.5494   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7145   -0.8021   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946   -0.7475    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020    0.0423    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809    0.0308    1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -0.4610    1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116   -1.0726   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -0.2621   -0.5001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9689   -0.8071   -1.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5955   -0.3860    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.3621    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -0.4786    0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074   -0.4609    0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5911   -0.3216   -0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4367    0.9544   -0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6342    0.8152   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6012    0.1033   -0.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7081    1.4599    1.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9007    1.2512    0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3622    1.0816    1.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5784    2.4122    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0881    0.3747   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656    1.0923   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2893   -1.2484   -1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4785   -1.4941    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370   -1.7911    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9068   -0.3818    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877   -0.3002   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976    1.0976    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141    0.4685    2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4964   -0.4115    2.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919   -1.1203   -0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539   -2.1362    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    0.7851   -0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.1013   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957   -0.4920    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533   -0.2513   -1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352   -0.5862    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9815   -0.5583    1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7878   -0.3264   -1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2508   -1.1901   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237    1.1368   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    1.8275   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542    1.7447    1.5932 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END


  Mrv0541 05011310302D          

 19 18  0  0  1  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.5230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.5230    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060055

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C[C@H](O)\C=C\C=C/CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O3/c1-2-3-4-5-6-9-12-15(17)13-10-7-8-11-14-16(18)19/h6-10,13,15,17H,2-5,11-12,14H2,1H3,(H,18,19)/b8-7-,9-6-,13-10+/t15-/m0/s1

> <INCHI_KEY>
KBOVKDIBOBQLRS-ONCCEEIJSA-N

> <FORMULA>
C16H26O3

> <MOLECULAR_WEIGHT>
266.3758

> <EXACT_MASS>
266.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.641528654612802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z,6E,8S,10Z)-8-hydroxyhexadeca-4,6,10-trienoic acid

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
3.940006740666666

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720826441527002

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.642085972493471

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6087107962500968

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
81.9489

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,6E,8S,10Z)-8-hydroxyhexadeca-4,6,10-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060055
     RDKit          3D
Tetranor 12-HETE
 45 44  0  0  0  0  0  0  0  0999 V2000
   -6.7974    1.3234    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2506    0.5494   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7145   -0.8021   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946   -0.7475    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020    0.0423    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809    0.0308    1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -0.4610    1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116   -1.0726   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -0.2621   -0.5001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9689   -0.8071   -1.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5955   -0.3860    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.3621    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -0.4786    0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074   -0.4609    0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5911   -0.3216   -0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4367    0.9544   -0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6342    0.8152   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6012    0.1033   -0.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7081    1.4599    1.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9007    1.2512    0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3622    1.0816    1.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5784    2.4122    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0881    0.3747   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656    1.0923   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2893   -1.2484   -1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4785   -1.4941    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370   -1.7911    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9068   -0.3818    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877   -0.3002   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976    1.0976    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141    0.4685    2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4964   -0.4115    2.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919   -1.1203   -0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539   -2.1362    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    0.7851   -0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.1013   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957   -0.4920    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533   -0.2513   -1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352   -0.5862    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9815   -0.5583    1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7878   -0.3264   -1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2508   -1.1901   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237    1.1368   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    1.8275   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542    1.7447    1.5932 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END

HEADER    PROTEIN                                 01-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.645  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.311   0.976   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.977   0.206   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.311   2.516   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.977   3.286   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.977   4.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.644   5.596   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.310   4.826   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.310   3.286   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.976   2.516   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.357   3.286   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.976   0.976   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                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0060055
HETATM    1  C1  UNL     1      -6.797   1.323   0.628  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.251   0.549  -0.522  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.714  -0.802  -0.149  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.595  -0.748   0.845  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.402   0.042   0.332  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.381   0.031   1.371  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.174  -0.461   1.241  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.712  -1.073  -0.010  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.502  -0.262  -0.500  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.969  -0.807  -1.705  1.00  0.00           O  
HETATM   11  C10 UNL     1       1.596  -0.386   0.477  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.859  -0.362   0.026  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.983  -0.479   0.929  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.207  -0.461   0.529  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.591  -0.322  -0.879  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.437   0.954  -0.978  1.00  0.00           C  
HETATM   17  C16 UNL     1       7.634   0.815  -0.114  1.00  0.00           C  
HETATM   18  O2  UNL     1       8.601   0.103  -0.482  1.00  0.00           O  
HETATM   19  O3  UNL     1       7.708   1.460   1.101  1.00  0.00           O  
HETATM   20  H1  UNL     1      -7.901   1.251   0.728  1.00  0.00           H  
HETATM   21  H2  UNL     1      -6.362   1.082   1.605  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.578   2.412   0.442  1.00  0.00           H  
HETATM   23  H4  UNL     1      -7.088   0.375  -1.242  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.466   1.092  -1.094  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.289  -1.248  -1.085  1.00  0.00           H  
HETATM   26  H7  UNL     1      -6.478  -1.494   0.213  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.237  -1.791   0.995  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.907  -0.382   1.844  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.088  -0.300  -0.636  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.798   1.098   0.155  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.614   0.468   2.371  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.496  -0.411   2.107  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.392  -1.120  -0.841  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.354  -2.136   0.178  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.249   0.785  -0.644  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.189  -0.101  -2.363  1.00  0.00           H  
HETATM   37  H18 UNL     1       1.396  -0.492   1.512  1.00  0.00           H  
HETATM   38  H19 UNL     1       2.953  -0.251  -1.032  1.00  0.00           H  
HETATM   39  H20 UNL     1       3.735  -0.586   2.007  1.00  0.00           H  
HETATM   40  H21 UNL     1       5.982  -0.558   1.316  1.00  0.00           H  
HETATM   41  H22 UNL     1       4.788  -0.326  -1.598  1.00  0.00           H  
HETATM   42  H23 UNL     1       6.251  -1.190  -1.124  1.00  0.00           H  
HETATM   43  H24 UNL     1       6.724   1.137  -2.037  1.00  0.00           H  
HETATM   44  H25 UNL     1       5.867   1.827  -0.630  1.00  0.00           H  
HETATM   45  H26 UNL     1       6.854   1.745   1.593  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7    7   31
CONECT    7    8   32
CONECT    8    9   33   34
CONECT    9   10   11   35
CONECT   10   36
CONECT   11   12   12   37
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15   40
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   18   19
CONECT   19   45
END

HMDB0060055
     RDKit          3D
Tetranor 12-HETE
 45 44  0  0  0  0  0  0  0  0999 V2000
   -6.7974    1.3234    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2506    0.5494   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7145   -0.8021   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946   -0.7475    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020    0.0423    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809    0.0308    1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -0.4610    1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116   -1.0726   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -0.2621   -0.5001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9689   -0.8071   -1.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5955   -0.3860    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.3621    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -0.4786    0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074   -0.4609    0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5911   -0.3216   -0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4367    0.9544   -0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6342    0.8152   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6012    0.1033   -0.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7081    1.4599    1.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9007    1.2512    0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3622    1.0816    1.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5784    2.4122    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0881    0.3747   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656    1.0923   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2893   -1.2484   -1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4785   -1.4941    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370   -1.7911    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9068   -0.3818    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0877   -0.3002   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976    1.0976    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141    0.4685    2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4964   -0.4115    2.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919   -1.1203   -0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539   -2.1362    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    0.7851   -0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.1013   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957   -0.4920    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533   -0.2513   -1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352   -0.5862    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9815   -0.5583    1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7878   -0.3264   -1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2508   -1.1901   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237    1.1368   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    1.8275   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542    1.7447    1.5932 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4Z,8S,10Z)-8-Hydroxyhexadeca-4,6,10-trienoate	Generator

Chemical Formula

C₁₆H₂₆O₃

Average Molecular Weight

266.3758

Monoisotopic Molecular Weight

266.188194698

IUPAC Name

(4Z,6E,8S,10Z)-8-hydroxyhexadeca-4,6,10-trienoic acid

Traditional Name

(4Z,6E,8S,10Z)-8-hydroxyhexadeca-4,6,10-trienoic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C[C@H](O)\C=C\C=C/CCC(O)=O

InChI Identifier

InChI=1S/C16H26O3/c1-2-3-4-5-6-9-12-15(17)13-10-7-8-11-14-16(18)19/h6-10,13,15,17H,2-5,11-12,14H2,1H3,(H,18,19)/b8-7-,9-6-,13-10+/t15-/m0/s1

InChI Key

KBOVKDIBOBQLRS-ONCCEEIJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Membrane (HMDB: HMDB0060055)

Source

Exogenous

Exogenous (HMDB: HMDB0060055)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	4.86	ALOGPS
logP	3.94	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	81.95 m³·mol⁻¹	ChemAxon
Polarizability	31.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.842	31661259
DarkChem	[M-H]-	170.978	31661259
DeepCCS	[M+H]+	174.363	30932474
DeepCCS	[M-H]-	172.005	30932474
DeepCCS	[M-2H]-	204.891	30932474
DeepCCS	[M+Na]+	180.457	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.4	32859911
AllCCS	[M-H]-	170.3	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	172.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.05 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4216 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2671.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	340.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	730.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	490.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1583.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	550.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1406.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	538.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	348.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	399.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetranor 12-HETE	CCCCC\C=C/C[C@H](O)\C=C\C=C/CCC(O)=O	3641.4	Standard polar	33892256
Tetranor 12-HETE	CCCCC\C=C/C[C@H](O)\C=C\C=C/CCC(O)=O	2104.3	Standard non polar	33892256
Tetranor 12-HETE	CCCCC\C=C/C[C@H](O)\C=C\C=C/CCC(O)=O	2223.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetranor 12-HETE,1TMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\CCC(=O)O)O[Si](C)(C)C	2336.3	Semi standard non polar	33892256
Tetranor 12-HETE,1TMS,isomer #2	CCCCC/C=C\C[C@H](O)/C=C/C=C\CCC(=O)O[Si](C)(C)C	2258.6	Semi standard non polar	33892256
Tetranor 12-HETE,2TMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2334.1	Semi standard non polar	33892256
Tetranor 12-HETE,1TBDMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C	2590.9	Semi standard non polar	33892256
Tetranor 12-HETE,1TBDMS,isomer #2	CCCCC/C=C\C[C@H](O)/C=C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C	2494.5	Semi standard non polar	33892256
Tetranor 12-HETE,2TBDMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2805.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetranor 12-HETE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-4930000000-b2a70aea1a00f4359802	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetranor 12-HETE GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9224000000-32c60c2987341cfc0b09	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetranor 12-HETE GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetranor 12-HETE GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 10V, Positive-QTOF	splash10-0002-0090000000-8f374bed5d96909bb7b7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 20V, Positive-QTOF	splash10-000t-6490000000-b8d80acba819222c8895	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 40V, Positive-QTOF	splash10-0fr6-9300000000-85d452033f8ba084a156	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 10V, Negative-QTOF	splash10-014i-0090000000-5f03823d3028f3da0c48	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 20V, Negative-QTOF	splash10-00kb-0190000000-913d691aab64c36775ba	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 40V, Negative-QTOF	splash10-0a4l-9720000000-0332cdcf1604a119f5a4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 10V, Positive-QTOF	splash10-0002-1590000000-883acdbaec563f48ea59	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 20V, Positive-QTOF	splash10-0ar0-7910000000-69b222e1f3d29f942d70	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 40V, Positive-QTOF	splash10-0ar0-9300000000-26b1b96aecb6f76ac99a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 10V, Negative-QTOF	splash10-014i-0090000000-8bbd564c705da51c5333	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 20V, Negative-QTOF	splash10-066s-1490000000-4531abd414815f25e339	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetranor 12-HETE 40V, Negative-QTOF	splash10-0ab9-7910000000-35fdd941a9b246367352	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00031 +/- 0.000031 uM	Adult (>18 years old)	Both	Normal	20671299	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15730832

PDB ID

Not Available

ChEBI ID

89569

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Tetranor 12-HETE (HMDB0060055)

MOL for HMDB0060055 (Tetranor 12-HETE)

3D MOL for HMDB0060055 (Tetranor 12-HETE)

3D SDF for HMDB0060055 (Tetranor 12-HETE)

3D-SDF for HMDB0060055 (Tetranor 12-HETE)

PDB for HMDB0060055 (Tetranor 12-HETE)

3D PDB for HMDB0060055 (Tetranor 12-HETE)

SMILES for HMDB0060055 (Tetranor 12-HETE)

INCHI for HMDB0060055 (Tetranor 12-HETE)

Structure for HMDB0060055 (Tetranor 12-HETE)

3D Structure for HMDB0060055 (Tetranor 12-HETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra