MiMeDB: Showing metabocard for (8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acid (MMDBc0054078)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:51:34 UTC

Update Date

2024-04-30 20:51:08 UTC

Metabolite ID

MMDBc0054078

Metabolite Identification

Common Name

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

Description

(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoic acid, also known as 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>
MMDBc0054078

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₈H₃₂O₄

Average Mass

312.4443

Monoisotopic Mass

312.230059512

IUPAC Name

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

Traditional Name

8-hpode

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9350000000-4e15bb0b555cf5d92267	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ai-9433000000-e85394b12021560acb2c	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0192000000-7eca5d6551b8aca983c3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-6691000000-b4e7f6558dfc08f0dd0b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mx-9320000000-219d5f201f0df81dfbea	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0149000000-d56d9b07eeb49ce0108d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-1593000000-4e1eac881c232d4d1e07	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-9730000000-e33bb1a6043188dba7f5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0049000000-42fc9d02d4a221295450	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-2395000000-d45e2144053745f3888f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvl-7920000000-adcdb588c4cccfe027c3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-1392000000-f38d418ef950fbac5167	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-07yi-9430000000-01ed67322ca41ae82f00	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-069r-9400000000-99a033d79a3ab935a881	2021-09-23	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014554	(9Z,12Z)-octadecadienoic acid	(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acid	Linoleate diol synthase	Oxygenation; Synthesis	RHEA	34755880
MMDBr0014555	(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acid	(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoic acid	Linoleate diol synthase	Synthesis	RHEA	34755880
MMDBr0015054	(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acid	(5S,8R,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoic acid	Psi-producing oxygenase A	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	5	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0004706

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

References

Synthesis Reference

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. doi: 10.1016/0021-9150(95)05702-1. [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 (8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acid (MMDBc0054078)

MOL for #<Metabolite:0x0000564af37809a8>

3D MOL for #<Metabolite:0x0000564af37809a8>

3D SDF for #<Metabolite:0x0000564af37809a8>

3D-SDF for #<Metabolite:0x0000564af37809a8>

PDB for #<Metabolite:0x0000564af37809a8>

3D PDB for #<Metabolite:0x0000564af37809a8>

SMILES for #<Metabolite:0x0000564af37809a8>

INCHI for #<Metabolite:0x0000564af37809a8>

Structure for #<Metabolite:0x0000564af37809a8>

3D Structure for #<Metabolite:0x0000564af37809a8>