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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 21:14:16 UTC

Update Date

2021-09-22 21:14:16 UTC

HMDB ID

HMDB0301803

Secondary Accession Numbers

None

Metabolite Identification

Common Name

13(S)-Hydroperoxylinolenic acid

Description

13(s)-hydroperoxylinolenic acid, also known as 13(S)-hpotre or 13-hpot, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 13(s)-hydroperoxylinolenic acid is considered to be an octadecanoid lipid molecule. 13(s)-hydroperoxylinolenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 13(s)-hydroperoxylinolenic acid can be found in a number of food items such as grass pea, garden tomato (variety), american butterfish, and black crowberry, which makes 13(s)-hydroperoxylinolenic acid a potential biomarker for the consumption of these food products. .

Structure

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

HMDB0301803
     RDKit          3D
13(S)-Hydroperoxylinolenic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
   -8.7252   -0.6930   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5499   -0.2029    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7768    0.8359   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5087    0.7488   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931   -0.4192   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130   -0.1058    0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6836    0.8964   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495    0.7302   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    1.7133   -0.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5981   -1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5064    0.4706   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898   -0.2098   -1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -1.3903   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205   -1.0519   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0859   -0.0505   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971    0.3003    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0310   -0.8793    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0845   -0.3769    1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9478   -1.1500    1.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1810    0.9699    1.7708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8999    0.3813    1.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.3148    2.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5211   -1.6874   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9499    0.0793   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5976   -0.8334    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9749    0.2969    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0298   -1.0737    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3100    1.7789   -0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0665    1.6217   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3152   -0.8068   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2078   -1.2792    0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -1.0159    0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    1.7765   -0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.1658    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313    2.6062   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797    2.4055   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    0.7956    0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703   -0.2570    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087   -0.5747   -2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8207    0.5040   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786   -1.7929   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -2.1730   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -0.5930    0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5985   -1.9831    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4828   -0.4802   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760    0.8943   -1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750    0.8628    0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870    0.9861   -0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4506   -1.6375    1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687   -1.3228   -0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5499    1.6731    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.4049    2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
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 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
 22 52  1  0
M  END

  Mrv0541 02241221382D          

 22 21  0  0  1  0            999 V2000
    2.2836   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -5.0309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2849   -5.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -6.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 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  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301803

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/b9-7-,11-3-,15-12+/t17-/m0/s1

> <INCHI_KEY>
UYQGVDXDXBAABN-FQSPHKRJSA-N

> <FORMULA>
C18H30O4

> <MOLECULAR_WEIGHT>
310.4284

> <EXACT_MASS>
310.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.77882266536244

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
5.278479448

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.711074282435678

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167201738501

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237376144817387

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
92.5011

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13(S)-HpOTrE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301803
     RDKit          3D
13(S)-Hydroperoxylinolenic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
   -8.7252   -0.6930   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5499   -0.2029    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7768    0.8359   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5087    0.7488   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931   -0.4192   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130   -0.1058    0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6836    0.8964   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495    0.7302   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    1.7133   -0.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5981   -1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5064    0.4706   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898   -0.2098   -1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -1.3903   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205   -1.0519   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0859   -0.0505   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971    0.3003    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0310   -0.8793    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0845   -0.3769    1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9478   -1.1500    1.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1810    0.9699    1.7708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8999    0.3813    1.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.3148    2.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5211   -1.6874   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9499    0.0793   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5976   -0.8334    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9749    0.2969    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0298   -1.0737    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3100    1.7789   -0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0665    1.6217   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3152   -0.8068   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2078   -1.2792    0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -1.0159    0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    1.7765   -0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.1658    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313    2.6062   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797    2.4055   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    0.7956    0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703   -0.2570    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087   -0.5747   -2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8207    0.5040   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786   -1.7929   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -2.1730   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -0.5930    0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5985   -1.9831    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4828   -0.4802   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760    0.8943   -1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750    0.8628    0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870    0.9861   -0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4506   -1.6375    1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687   -1.3228   -0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5499    1.6731    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.4049    2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
 22 52  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.263  -4.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.596  -4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.596  -6.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.264  -4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597  -4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931  -4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598  -4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.932  -4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.266  -4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.266  -6.311   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.932  -7.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.932  -8.621   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.598  -9.391   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.598 -10.931   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.932 -11.701   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.265  -8.621   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.265  -7.081   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.931  -6.311   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.597  -7.081   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.597  -8.621   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0301803
HETATM    1  C1  UNL     1      -8.725  -0.693  -0.438  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.550  -0.203   0.402  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.777   0.836  -0.281  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.509   0.749  -0.594  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.693  -0.419  -0.295  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.513  -0.106   0.608  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.684   0.896  -0.105  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.349   0.730  -0.205  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.544   1.713  -0.903  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.743   1.598  -1.026  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.506   0.471  -0.475  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.190  -0.210  -1.651  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.013  -1.390  -1.241  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.121  -1.052  -0.275  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.086  -0.051  -0.871  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.197   0.300   0.074  1.00  0.00           C  
HETATM   17  C17 UNL     1       7.031  -0.879   0.484  1.00  0.00           C  
HETATM   18  C18 UNL     1       8.085  -0.377   1.415  1.00  0.00           C  
HETATM   19  O1  UNL     1       8.948  -1.150   1.932  1.00  0.00           O  
HETATM   20  O2  UNL     1       8.181   0.970   1.771  1.00  0.00           O  
HETATM   21  O3  UNL     1      -3.900   0.381   1.830  1.00  0.00           O  
HETATM   22  O4  UNL     1      -3.476  -0.315   2.850  1.00  0.00           O  
HETATM   23  H1  UNL     1      -8.521  -1.687  -0.890  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.950   0.079  -1.198  1.00  0.00           H  
HETATM   25  H3  UNL     1      -9.598  -0.833   0.233  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.975   0.297   1.331  1.00  0.00           H  
HETATM   27  H5  UNL     1      -7.030  -1.074   0.766  1.00  0.00           H  
HETATM   28  H6  UNL     1      -7.310   1.779  -0.558  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.066   1.622  -1.110  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.315  -0.807  -1.294  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.208  -1.279   0.146  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.905  -1.016   0.789  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.110   1.777  -0.561  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.000  -0.166   0.272  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.031   2.606  -1.357  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.280   2.406  -1.581  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.256   0.796   0.285  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.870  -0.257   0.032  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.409  -0.575  -2.345  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.821   0.504  -2.221  1.00  0.00           H  
HETATM   41  H19 UNL     1       3.479  -1.793  -2.175  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.344  -2.173  -0.870  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.701  -0.593   0.645  1.00  0.00           H  
HETATM   44  H22 UNL     1       4.598  -1.983   0.021  1.00  0.00           H  
HETATM   45  H23 UNL     1       5.483  -0.480  -1.811  1.00  0.00           H  
HETATM   46  H24 UNL     1       4.576   0.894  -1.146  1.00  0.00           H  
HETATM   47  H25 UNL     1       5.875   0.863   0.949  1.00  0.00           H  
HETATM   48  H26 UNL     1       6.887   0.986  -0.499  1.00  0.00           H  
HETATM   49  H27 UNL     1       6.451  -1.637   1.047  1.00  0.00           H  
HETATM   50  H28 UNL     1       7.569  -1.323  -0.377  1.00  0.00           H  
HETATM   51  H29 UNL     1       8.550   1.673   1.156  1.00  0.00           H  
HETATM   52  H30 UNL     1      -2.509  -0.405   2.906  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4    4   28
CONECT    4    5   29
CONECT    5    6   30   31
CONECT    6    7   21   32
CONECT    7    8    8   33
CONECT    8    9   34
CONECT    9   10   10   35
CONECT   10   11   36
CONECT   11   12   37   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   19   20
CONECT   20   51
CONECT   21   22
CONECT   22   52
END

HMDB0301803
     RDKit          3D
13(S)-Hydroperoxylinolenic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
   -8.7252   -0.6930   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5499   -0.2029    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7768    0.8359   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5087    0.7488   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931   -0.4192   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130   -0.1058    0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6836    0.8964   -0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495    0.7302   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    1.7133   -0.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5981   -1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5064    0.4706   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898   -0.2098   -1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -1.3903   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205   -1.0519   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0859   -0.0505   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971    0.3003    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0310   -0.8793    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0845   -0.3769    1.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9478   -1.1500    1.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1810    0.9699    1.7708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8999    0.3813    1.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.3148    2.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5211   -1.6874   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9499    0.0793   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5976   -0.8334    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9749    0.2969    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0298   -1.0737    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3100    1.7789   -0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0665    1.6217   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3152   -0.8068   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2078   -1.2792    0.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -1.0159    0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    1.7765   -0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.1658    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313    2.6062   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797    2.4055   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    0.7956    0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703   -0.2570    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087   -0.5747   -2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8207    0.5040   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786   -1.7929   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -2.1730   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -0.5930    0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5985   -1.9831    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4828   -0.4802   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760    0.8943   -1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750    0.8628    0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870    0.9861   -0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4506   -1.6375    1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687   -1.3228   -0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5499    1.6731    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.4049    2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
 22 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoic acid	ChEBI
(9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoate	ChEBI
13(S)-HPOT	ChEBI
13(S)-HpOTrE	ChEBI
13(S)-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoic acid	ChEBI
13(S)-Hydroperoxylinolenic acid	ChEBI
13-HPOT	ChEBI
13S-HpOTrE	ChEBI
13S-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoic acid	ChEBI
13S-Hydroperoxy-9Z,11E,15Z-octadecatrienoic acid	ChEBI
(9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoate	Generator
(9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoic acid	Generator
13(S)-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoate	Generator
13(S)-Hydroperoxylinolenate	Generator
13S-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoate	Generator
13S-Hydroperoxy-9Z,11E,15Z-octadecatrienoate	Generator
(9Z,11E,13S,15Z)-13-Hydroperoxyoctadeca-9,11,15-trienoate	Generator
13-Hydroperoxy-9,11,15-octadecatrienoic acid	MeSH

Chemical Formula

C₁₈H₃₀O₄

Average Molecular Weight

310.4284

Monoisotopic Molecular Weight

310.214409448

IUPAC Name

(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid

Traditional Name

13(S)-HpOTrE

CAS Registry Number

67597-26-6

SMILES

CC\C=C/C[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/b9-7-,11-3-,15-12+/t17-/m0/s1

InChI Key

UYQGVDXDXBAABN-FQSPHKRJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroperoxy fatty acid
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Hydroperoxide
Carboxylic acid derivative
Alkyl hydroperoxide
Carboxylic acid
Peroxol
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:48905 )
lipid hydroperoxide (CHEBI:48905 )
trienoic fatty acid (CHEBI:48905 )
Hydroperoxy fatty acids (C04785 )
Other Octadecanoids (LMFA02000052 )

Ontology

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
logP	5.46	ALOGPS
logP	5.28	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	92.5 m³·mol⁻¹	ChemAxon
Polarizability	36.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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
AllCCS	[M+H]+	182.971	32859911
AllCCS	[M+H-H2O]+	180.006	32859911
AllCCS	[M+Na]+	186.503	32859911
AllCCS	[M+NH4]+	185.715	32859911
AllCCS	[M-H]-	181.422	32859911
AllCCS	[M+Na-2H]-	182.952	32859911
AllCCS	[M+HCOO]-	184.783	32859911
DeepCCS	[M+H]+	180.319	30932474
DeepCCS	[M-H]-	177.961	30932474
DeepCCS	[M-2H]-	210.848	30932474
DeepCCS	[M+Na]+	186.412	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 10V, Positive-QTOF	splash10-03dl-0295000000-7bceeb67ef82db3c2c75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 20V, Positive-QTOF	splash10-016r-4981000000-0e947fcae49e860e5eac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 40V, Positive-QTOF	splash10-0ldm-9620000000-93f1b98e9f06d2dd75b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 10V, Negative-QTOF	splash10-0a4i-1149000000-565fa404c042d0829423	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 20V, Negative-QTOF	splash10-0aos-3393000000-a59a598dde5117fbff42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 40V, Negative-QTOF	splash10-0a4i-9330000000-8f6b878a5bebf4db37d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 10V, Positive-QTOF	splash10-004i-0591000000-d0bc121c45f15c6aae68	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 20V, Positive-QTOF	splash10-0560-1950000000-9f7031f4e0f47c858c26	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 40V, Positive-QTOF	splash10-05o3-9500000000-cb42787800e5a6ce9cd1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 10V, Negative-QTOF	splash10-0a6r-0096000000-b41fadcfdc13a28d6ea4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 20V, Negative-QTOF	splash10-056r-1190000000-f0708581583845bef578	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13(S)-Hydroperoxylinolenic acid 40V, Negative-QTOF	splash10-052e-9150000000-649b6a690207294ae2e8	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB001431

KNApSAcK ID

Not Available

Chemspider ID

4593698

KEGG Compound ID

C04785

BioCyc ID

CPD-725

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5497123

PDB ID

Not Available

ChEBI ID

48905

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

Not Available

Showing metabocard for 13(S)-Hydroperoxylinolenic acid (HMDB0301803)

MOL for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

3D MOL for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

3D SDF for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

3D-SDF for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

PDB for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

3D PDB for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

SMILES for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

INCHI for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

Structure for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

3D Structure for HMDB0301803 (13(S)-Hydroperoxylinolenic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra