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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-14 02:00:43 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004706

Secondary Accession Numbers

HMDB04706

Metabolite Identification

Common Name

8(R)-Hydroperoxylinoleic acid

Description

8(R)-hydroperoxylinoleic acid (8(R)-EPODE) is an oxidized product of linoleic acid. Oxidized lipids such as 8(R)-HPODE can decrease cellular proteoglycan metabolism in endothelial monolayers and alter mRNA levels of major specific proteoglycans in a concentration-dependent manner. This may have implications in lipid-mediated disruption of endothelial barrier function and atherosclerosis. (PMID: 8645361 , 9507987 ).

Structure

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

HMDB0004706
     RDKit          3D
8(R)-Hydroperoxylinoleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -8.1428   -0.5854   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0636    0.3956   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2111   -0.3572    0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0831    0.4564    1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1810    0.9430    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504    1.7382    0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8129    1.3904    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456    0.1346   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    0.4101   -1.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543   -0.1073   -1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -0.9835   -0.5801 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0264   -0.2630    0.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033    0.6639   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -0.0649   -0.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8323   -1.1207   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854   -0.7216    0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8609    0.1034    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6800    1.4088    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337    2.2780    0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3617    1.7487   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104   -2.0490   -0.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377   -3.1999   -0.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9738   -0.0022   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6752   -1.2897   -1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4157   -1.1893    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4455    0.6904   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5107    1.2795    0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7237   -1.2245    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7961   -0.8201    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864    1.3295    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5466   -0.0784    2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0200    0.1968   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8502    1.7093   -0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    2.6926    1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180    2.0528    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -0.5516   -0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099   -0.4074    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202    1.0494   -2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    0.1685   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503   -1.5279   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -0.9384    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.4164    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621    1.3554   -0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    1.2795    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334    0.6570   -1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.5360   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1143   -1.9347    0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5058   -1.6495   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011   -0.2812    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0990   -1.6900    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508   -0.5538    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4671    0.2692    1.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7278    0.9678   -1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -3.6577    0.1410 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  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
 11 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
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 22 54  1  0
M  END


  Mrv1652304202019542D          

 22 21  0  0  1  0            999 V2000
   25.7870  -19.4710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5014  -19.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5029  -20.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7884  -21.5335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2160  -20.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9304  -20.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5014  -20.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6449  -20.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7870  -20.2960    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   29.3594  -20.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0739  -20.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0725  -20.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3580  -16.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0725  -16.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3580  -17.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0725  -15.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3580  -20.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3580  -19.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6435  -18.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7884  -20.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6435  -19.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7870  -15.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  9  1  1  6  0  0  0
  3 20  1  0  0  0  0
  4 20  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  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 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 20  1  0  0  0  0
 12 17  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004706

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-11-14-17(22-21)15-12-9-10-13-16-18(19)20/h6-7,11,14,17,21H,2-5,8-10,12-13,15-16H2,1H3,(H,19,20)/b7-6-,14-11-/t17-/m0/s1

> <INCHI_KEY>
RGJSGXNKRWWCOQ-QMEIEYGNSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.4443

> <EXACT_MASS>
312.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.37364291270348

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoic acid

> <ALOGPS_LOGP>
5.68

> <JCHEM_LOGP>
5.640401104666667

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712417628707302

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.448327649852041

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236788539544727

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
91.38449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hpode

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004706
     RDKit          3D
8(R)-Hydroperoxylinoleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -8.1428   -0.5854   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0636    0.3956   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2111   -0.3572    0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0831    0.4564    1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1810    0.9430    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504    1.7382    0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8129    1.3904    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456    0.1346   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    0.4101   -1.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543   -0.1073   -1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -0.9835   -0.5801 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0264   -0.2630    0.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033    0.6639   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -0.0649   -0.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8323   -1.1207   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854   -0.7216    0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8609    0.1034    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6800    1.4088    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337    2.2780    0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3617    1.7487   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104   -2.0490   -0.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377   -3.1999   -0.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9738   -0.0022   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6752   -1.2897   -1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4157   -1.1893    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4455    0.6904   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5107    1.2795    0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7237   -1.2245    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7961   -0.8201    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864    1.3295    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5466   -0.0784    2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0200    0.1968   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8502    1.7093   -0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    2.6926    1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180    2.0528    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -0.5516   -0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099   -0.4074    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202    1.0494   -2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    0.1685   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503   -1.5279   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -0.9384    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.4164    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621    1.3554   -0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    1.2795    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334    0.6570   -1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.5360   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1143   -1.9347    0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5058   -1.6495   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011   -0.2812    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0990   -1.6900    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508   -0.5538    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4671    0.2692    1.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7278    0.9678   -1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -3.6577    0.1410 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  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
 11 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
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 22 54  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0      48.136 -36.346   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      49.469 -35.576   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      58.805 -37.886   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      57.472 -40.196   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      50.803 -37.886   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      52.137 -38.656   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.469 -38.656   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      53.470 -37.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.136 -37.886   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      54.804 -38.656   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      56.138 -37.886   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.802 -38.656   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      45.468 -31.726   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.802 -30.956   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      45.468 -33.266   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      46.802 -29.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      45.468 -37.886   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      45.468 -36.346   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      44.135 -34.036   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      57.472 -38.656   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      44.135 -35.576   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      48.136 -28.646   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1                                                            
CONECT    3   20                                                            
CONECT    4   20                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    1    7   12                                                  
CONECT   10    8   11                                                       
CONECT   11   10   20                                                       
CONECT   12    9   17                                                       
CONECT   13   14   15                                                       
CONECT   14   13   16                                                       
CONECT   15   13   19                                                       
CONECT   16   14   22                                                       
CONECT   17   12   18                                                       
CONECT   18   17   21                                                       
CONECT   19   15   21                                                       
CONECT   20    3    4   11                                                  
CONECT   21   18   19                                                       
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0004706
HETATM    1  C1  UNL     1      -8.143  -0.585  -0.619  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.064   0.396  -0.138  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.211  -0.357   0.822  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.083   0.456   1.413  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.181   0.943   0.295  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.050   1.738   0.768  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.813   1.390   0.572  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.446   0.135  -0.160  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.652   0.410  -1.365  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.554  -0.107  -1.516  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.260  -0.984  -0.580  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.026  -0.263   0.472  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.103   0.664  -0.083  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.114  -0.065  -0.902  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.832  -1.121  -0.159  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.685  -0.722   0.982  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.861   0.103   0.636  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.680   1.409   0.029  1.00  0.00           C  
HETATM   19  O1  UNL     1       5.934   2.278   0.516  1.00  0.00           O  
HETATM   20  O2  UNL     1       7.362   1.749  -1.166  1.00  0.00           O  
HETATM   21  O3  UNL     1       0.510  -2.049  -0.084  1.00  0.00           O  
HETATM   22  O4  UNL     1       0.938  -3.200  -0.464  1.00  0.00           O  
HETATM   23  H1  UNL     1      -8.974  -0.002  -1.032  1.00  0.00           H  
HETATM   24  H2  UNL     1      -7.675  -1.290  -1.348  1.00  0.00           H  
HETATM   25  H3  UNL     1      -8.416  -1.189   0.277  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.445   0.690  -1.023  1.00  0.00           H  
HETATM   27  H5  UNL     1      -7.511   1.279   0.313  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.724  -1.224   0.295  1.00  0.00           H  
HETATM   29  H7  UNL     1      -6.796  -0.820   1.649  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.586   1.329   1.923  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.547  -0.078   2.207  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.020   0.197  -0.461  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.850   1.709  -0.241  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.219   2.693   1.324  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.018   2.053   0.964  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.261  -0.552  -0.341  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.810  -0.407   0.614  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.020   1.049  -2.182  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.073   0.168  -2.465  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.050  -1.528  -1.198  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.503  -0.938   1.211  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.362   0.416   1.060  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.562   1.355  -0.781  1.00  0.00           H  
HETATM   44  H22 UNL     1       3.516   1.279   0.709  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.833   0.657  -1.356  1.00  0.00           H  
HETATM   46  H24 UNL     1       3.632  -0.536  -1.798  1.00  0.00           H  
HETATM   47  H25 UNL     1       4.114  -1.935   0.152  1.00  0.00           H  
HETATM   48  H26 UNL     1       5.506  -1.650  -0.895  1.00  0.00           H  
HETATM   49  H27 UNL     1       5.101  -0.281   1.833  1.00  0.00           H  
HETATM   50  H28 UNL     1       6.099  -1.690   1.416  1.00  0.00           H  
HETATM   51  H29 UNL     1       7.551  -0.554   0.005  1.00  0.00           H  
HETATM   52  H30 UNL     1       7.467   0.269   1.592  1.00  0.00           H  
HETATM   53  H31 UNL     1       7.728   0.968  -1.732  1.00  0.00           H  
HETATM   54  H32 UNL     1       1.557  -3.658   0.141  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   21   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   51   52
CONECT   18   19   19   20
CONECT   20   53
CONECT   21   22
CONECT   22   54
END

HMDB0004706
     RDKit          3D
8(R)-Hydroperoxylinoleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -8.1428   -0.5854   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0636    0.3956   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2111   -0.3572    0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0831    0.4564    1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1810    0.9430    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504    1.7382    0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8129    1.3904    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456    0.1346   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    0.4101   -1.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543   -0.1073   -1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -0.9835   -0.5801 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0264   -0.2630    0.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033    0.6639   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -0.0649   -0.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8323   -1.1207   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854   -0.7216    0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8609    0.1034    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6800    1.4088    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337    2.2780    0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3617    1.7487   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104   -2.0490   -0.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377   -3.1999   -0.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9738   -0.0022   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6752   -1.2897   -1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4157   -1.1893    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4455    0.6904   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5107    1.2795    0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7237   -1.2245    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7961   -0.8201    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864    1.3295    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5466   -0.0784    2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0200    0.1968   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8502    1.7093   -0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    2.6926    1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180    2.0528    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -0.5516   -0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099   -0.4074    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202    1.0494   -2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    0.1685   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503   -1.5279   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -0.9384    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.4164    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621    1.3554   -0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    1.2795    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334    0.6570   -1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.5360   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1143   -1.9347    0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5058   -1.6495   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011   -0.2812    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0990   -1.6900    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508   -0.5538    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4671    0.2692    1.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7278    0.9678   -1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -3.6577    0.1410 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  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
 11 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
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 22 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8R)-8-Hydroperoxylinoleic acid	ChEBI
(9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acid	ChEBI
(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoate	Kegg
(8R)-8-Hydroperoxylinoleate	Generator
(9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoate	Generator
(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acid	Generator
8(R)-Hydroperoxylinoleate	Generator
(R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoate	HMDB
(R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoic acid	HMDB
8(R)-HPODE	HMDB
8-Hpode	HMDB
8-Hydroperoxylinoleic acid	HMDB
8R-Hydroperoxy-9Z,12Z-octadecadienoate	HMDB
8R-Hydroperoxy-9Z,12Z-octadecadienoic acid	HMDB

Chemical Formula

C₁₈H₃₂O₄

Average Molecular Weight

312.4443

Monoisotopic Molecular Weight

312.230059512

IUPAC Name

(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoic acid

Traditional Name

8-hpode

CAS Registry Number

143343-95-7

SMILES

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

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-11-14-17(22-21)15-12-9-10-13-16-18(19)20/h6-7,11,14,17,21H,2-5,8-10,12-13,15-16H2,1H3,(H,19,20)/b7-6-,14-11-/t17-/m0/s1

InChI Key

RGJSGXNKRWWCOQ-QMEIEYGNSA-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

HPODE (CHEBI:34485 )
octadecanoid (CHEBI:34485 )
Other Octadecanoids (C14831 )
Other Octadecanoids (LMFA02000113 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0004706)
Membrane (HMDB: HMDB0004706)

Source

Exogenous

Exogenous (HMDB: HMDB0004706)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004706)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	0.0041 g/L	ALOGPS
logP	5.68	ALOGPS
logP	5.64	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.45	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	15	ChemAxon
Refractivity	91.38 m³·mol⁻¹	ChemAxon
Polarizability	37.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	184.195	31661259
DarkChem	[M-H]-	183.023	31661259
DeepCCS	[M+H]+	187.168	30932474
DeepCCS	[M-H]-	184.81	30932474
DeepCCS	[M-2H]-	217.696	30932474
DeepCCS	[M+Na]+	193.261	30932474
AllCCS	[M+H]+	184.7	32859911
AllCCS	[M+H-H2O]+	181.9	32859911
AllCCS	[M+NH4]+	187.4	32859911
AllCCS	[M+Na]+	188.2	32859911
AllCCS	[M-H]-	182.8	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	186.3	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.	9.33 minutes	32390414
Predicted by Siyang on May 30, 2022	22.2677 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3061.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	402.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	242.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	588.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	942.2 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	597.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1962.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	622.7 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	1721.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	685.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	451.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	493.3 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8(R)-Hydroperoxylinoleic acid	CCCCC\C=C/C\C=C/[C@@H](CCCCCCC(O)=O)OO	3660.8	Standard polar	33892256
8(R)-Hydroperoxylinoleic acid	CCCCC\C=C/C\C=C/[C@@H](CCCCCCC(O)=O)OO	2232.4	Standard non polar	33892256
8(R)-Hydroperoxylinoleic acid	CCCCC\C=C/C\C=C/[C@@H](CCCCCCC(O)=O)OO	2392.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8(R)-Hydroperoxylinoleic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\[C@@H](CCCCCCC(=O)O[Si](C)(C)C)OO	2497.4	Semi standard non polar	33892256
8(R)-Hydroperoxylinoleic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\[C@@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO	2744.4	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 - 8(R)-Hydroperoxylinoleic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9350000000-4e15bb0b555cf5d92267	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8(R)-Hydroperoxylinoleic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00ai-9433000000-e85394b12021560acb2c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8(R)-Hydroperoxylinoleic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8(R)-Hydroperoxylinoleic acid 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 - 8(R)-Hydroperoxylinoleic acid 10V, Positive-QTOF	splash10-0002-0192000000-7eca5d6551b8aca983c3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 20V, Positive-QTOF	splash10-01ba-6691000000-b4e7f6558dfc08f0dd0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 40V, Positive-QTOF	splash10-05mx-9320000000-219d5f201f0df81dfbea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 10V, Negative-QTOF	splash10-03di-0149000000-d56d9b07eeb49ce0108d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 20V, Negative-QTOF	splash10-01ox-1593000000-4e1eac881c232d4d1e07	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 40V, Negative-QTOF	splash10-0a4u-9730000000-e33bb1a6043188dba7f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 10V, Negative-QTOF	splash10-03di-0049000000-42fc9d02d4a221295450	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 20V, Negative-QTOF	splash10-03fr-2395000000-d45e2144053745f3888f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 40V, Negative-QTOF	splash10-0bvl-7920000000-adcdb588c4cccfe027c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 10V, Positive-QTOF	splash10-03fr-1392000000-f38d418ef950fbac5167	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 20V, Positive-QTOF	splash10-07yi-9430000000-01ed67322ca41ae82f00	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(R)-Hydroperoxylinoleic acid 40V, Positive-QTOF	splash10-069r-9400000000-99a033d79a3ab935a881	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB112218

KNApSAcK ID

Not Available

Chemspider ID

4943210

KEGG Compound ID

C14831

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438758

PDB ID

Not Available

ChEBI ID

34485

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

Ramasamy S, Lipke DW, Boissonneault GA, Guo H, Hennig B: Oxidized lipid-mediated alterations in proteoglycan metabolism in cultured pulmonary endothelial cells. Atherosclerosis. 1996 Feb;120(1-2):199-208. [PubMed:8645361 ]
Ramasamy S, Parthasarathy S, Harrison DG: Regulation of endothelial nitric oxide synthase gene expression by oxidized linoleic acid. J Lipid Res. 1998 Feb;39(2):268-76. [PubMed:9507987 ]

Showing metabocard for 8(R)-Hydroperoxylinoleic acid (HMDB0004706)

MOL for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

3D MOL for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

3D SDF for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

3D-SDF for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

PDB for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

3D PDB for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

SMILES for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

INCHI for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

Structure for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

3D Structure for HMDB0004706 (8(R)-Hydroperoxylinoleic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra