MiMeDB: Showing metabocard for 13-L-Hydroperoxylinoleic acid (MMDBc0049803)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:42:56 UTC

Update Date

2024-04-30 20:38:58 UTC

Metabolite ID

MMDBc0049803

Metabolite Identification

Common Name

13-L-Hydroperoxylinoleic acid

Description

13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-lipoxygenase pathway (EC 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group) (PMID: 9082450 ).

Structure

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

HMDB0003871
     RDKit          3D
13-L-Hydroperoxylinoleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.0755    0.1669   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3418    1.4230   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1865    1.3343    0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985    0.5385    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -0.8925   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454   -1.7005   -0.4013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0019   -1.7004    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960   -0.6909    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469   -0.6603    1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8762    0.2764    1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9010    1.3832    0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    1.4824   -0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903    1.7406    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9871    0.7494    1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1038   -0.6293    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550   -0.6859   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3840   -0.2655   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0761   -0.4073   -1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6148    0.1986   -2.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843   -1.1948   -1.6783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235   -3.0275   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -3.4443   -1.7816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9545   -0.2145   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1972    0.4090   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9276   -0.5952    0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0817    2.1239    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1011    2.0058   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5674    0.8990    1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8281    2.3788    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2202    0.6942    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766    1.0380   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8981   -0.9642   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -1.3376    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895   -1.3885   -1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -2.4433    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0480   -0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -1.4695    2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974    0.1771    2.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0309    1.4281    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130    2.3353    1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808    0.5133   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    2.2868   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    1.9553   -0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    2.7397    0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5865    0.7710    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0955    1.1043    1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.0287    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5555   -1.2763    1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4654   -0.0705   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -1.7556   -0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4267    0.8202    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8974   -0.8305    0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8522   -1.2018   -2.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681   -3.1456   -2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  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
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 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


  Mrv1652305251817432D          

 22 21  0  0  0  0            999 V2000
 9990.2888 9987.3755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9989.5754 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8600 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.1446 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.3202 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.6056 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8908 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.1762 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.4616 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.7470 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.0322 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.3176 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6030 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.8864 9987.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6030 9988.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0042 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7196 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4330 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1484 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8637 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2888 9986.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0042 9986.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  1 21  1  6  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049803

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7-,15-12+/t17-/m0/s1

> <INCHI_KEY>
JDSRHVWSAMTSSN-IRQZEAMPSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.4443

> <EXACT_MASS>
312.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.13716024232122

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.76

> <JCHEM_LOGP>
5.640401104666667

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712374089551586

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167201984285

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2368076090774425

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
91.38449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-HpODE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003871
     RDKit          3D
13-L-Hydroperoxylinoleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.0755    0.1669   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3418    1.4230   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1865    1.3343    0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985    0.5385    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -0.8925   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454   -1.7005   -0.4013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0019   -1.7004    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960   -0.6909    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469   -0.6603    1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8762    0.2764    1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9010    1.3832    0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    1.4824   -0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903    1.7406    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9871    0.7494    1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1038   -0.6293    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550   -0.6859   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3840   -0.2655   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0761   -0.4073   -1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6148    0.1986   -2.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843   -1.1948   -1.6783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235   -3.0275   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -3.4443   -1.7816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9545   -0.2145   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1972    0.4090   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9276   -0.5952    0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0817    2.1239    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1011    2.0058   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5674    0.8990    1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8281    2.3788    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2202    0.6942    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766    1.0380   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8981   -0.9642   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -1.3376    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895   -1.3885   -1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -2.4433    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0480   -0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -1.4695    2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974    0.1771    2.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0309    1.4281    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130    2.3353    1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808    0.5133   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    2.2868   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    1.9553   -0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    2.7397    0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5865    0.7710    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0955    1.1043    1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.0287    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5555   -1.2763    1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4654   -0.0705   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -1.7556   -0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4267    0.8202    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8974   -0.8305    0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8522   -1.2018   -2.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681   -3.1456   -2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  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
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 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                                 25-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-18         0                                  
HETATM    1  C   UNK     0    8648.5398643.101   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8647.2078643.871   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8645.8728643.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8644.5378643.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8642.9988643.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8641.6648643.101   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8640.3308643.871   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8638.9968643.101   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8637.6628643.871   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8636.3288643.101   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8634.9938643.871   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8633.6608643.101   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8632.3268643.871   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8630.9888643.101   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8632.3268645.410   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8649.8748643.871   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8651.2108643.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8652.5428643.871   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8653.8778643.101   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8655.2128643.871   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8648.5398641.562   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8649.8748640.790   0.000  0.00  0.00           O+0
CONECT    1    2   16   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0003871
HETATM    1  C1  UNL     1      -7.076   0.167  -0.667  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.342   1.423  -0.350  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.187   1.334   0.569  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.999   0.539   0.181  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.286  -0.892  -0.046  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.045  -1.701  -0.401  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.002  -1.700   0.603  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.096  -0.691   0.597  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.047  -0.660   1.581  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.876   0.276   1.652  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.901   1.383   0.711  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.073   1.482  -0.163  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.390   1.741   0.400  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.987   0.749   1.337  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.104  -0.629   0.779  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.955  -0.686  -0.453  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.384  -0.266  -0.272  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.076  -0.407  -1.595  1.00  0.00           C  
HETATM   19  O1  UNL     1       6.615   0.199  -2.575  1.00  0.00           O  
HETATM   20  O2  UNL     1       8.184  -1.195  -1.678  1.00  0.00           O  
HETATM   21  O3  UNL     1      -3.523  -3.027  -0.543  1.00  0.00           O  
HETATM   22  O4  UNL     1      -3.407  -3.444  -1.782  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.955  -0.215  -1.700  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.197   0.409  -0.629  1.00  0.00           H  
HETATM   25  H3  UNL     1      -6.928  -0.595   0.104  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.082   2.124   0.162  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.101   2.006  -1.290  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.567   0.899   1.549  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.828   2.379   0.854  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.220   0.694   0.983  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.577   1.038  -0.744  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.898  -0.964  -0.992  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.785  -1.338   0.809  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.690  -1.389  -1.386  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.884  -2.443   1.363  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.211   0.048  -0.161  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.014  -1.470   2.347  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.597   0.177   2.483  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.031   1.428   0.069  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.813   2.335   1.365  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.181   0.513  -0.794  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.905   2.287  -0.965  1.00  0.00           H  
HETATM   43  H21 UNL     1       4.157   1.955  -0.430  1.00  0.00           H  
HETATM   44  H22 UNL     1       3.362   2.740   0.962  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.586   0.771   2.359  1.00  0.00           H  
HETATM   46  H24 UNL     1       5.095   1.104   1.464  1.00  0.00           H  
HETATM   47  H25 UNL     1       3.103  -1.029   0.496  1.00  0.00           H  
HETATM   48  H26 UNL     1       4.555  -1.276   1.572  1.00  0.00           H  
HETATM   49  H27 UNL     1       4.465  -0.071  -1.245  1.00  0.00           H  
HETATM   50  H28 UNL     1       4.974  -1.756  -0.801  1.00  0.00           H  
HETATM   51  H29 UNL     1       6.427   0.820   0.040  1.00  0.00           H  
HETATM   52  H30 UNL     1       6.897  -0.831   0.524  1.00  0.00           H  
HETATM   53  H31 UNL     1       8.852  -1.202  -2.441  1.00  0.00           H  
HETATM   54  H32 UNL     1      -2.568  -3.146  -2.205  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   21   34
CONECT    7    8    8   35
CONECT    8    9   36
CONECT    9   10   10   37
CONECT   10   11   38
CONECT   11   12   39   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

HMDB0003871
     RDKit          3D
13-L-Hydroperoxylinoleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.0755    0.1669   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3418    1.4230   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1865    1.3343    0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985    0.5385    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -0.8925   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454   -1.7005   -0.4013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0019   -1.7004    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960   -0.6909    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469   -0.6603    1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8762    0.2764    1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9010    1.3832    0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    1.4824   -0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903    1.7406    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9871    0.7494    1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1038   -0.6293    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550   -0.6859   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3840   -0.2655   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0761   -0.4073   -1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6148    0.1986   -2.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843   -1.1948   -1.6783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235   -3.0275   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -3.4443   -1.7816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9545   -0.2145   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1972    0.4090   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9276   -0.5952    0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0817    2.1239    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1011    2.0058   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5674    0.8990    1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8281    2.3788    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2202    0.6942    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5766    1.0380   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8981   -0.9642   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -1.3376    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895   -1.3885   -1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -2.4433    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111    0.0480   -0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -1.4695    2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974    0.1771    2.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0309    1.4281    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130    2.3353    1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808    0.5133   -0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    2.2868   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    1.9553   -0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    2.7397    0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5865    0.7710    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0955    1.1043    1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.0287    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5555   -1.2763    1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4654   -0.0705   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -1.7556   -0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4267    0.8202    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8974   -0.8305    0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8522   -1.2018   -2.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681   -3.1456   -2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  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
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 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
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoate	ChEBI
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid	ChEBI
13S-Hydroperoxy-9Z,11E-octadecadienoic acid	ChEBI
13(S)-HPODE	Kegg
13S-Hydroperoxy-9Z,11E-octadecadienoate	Generator
13-L-Hydroperoxylinoleate	Generator
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid	HMDB
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoate	HMDB
(13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoate	HMDB
(13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoic acid	HMDB
13(S)-Hydroperoxy-9Z,11E-octadecadienoate	HMDB
13(S)-Hydroperoxy-9Z,11E-octadecadienoic acid	HMDB
13(S)-Hydroperoxylinoleic acid	HMDB
13-HPOD	HMDB
13-Hpode	HMDB
13-L-Hydroperoxy-9-cis,11-trans-octadecadienoate	HMDB
13-L-Hydroperoxy-9-cis,11-trans-octadecadienoic acid	HMDB
13-L-Hydroperoxy-cis-9,trans-11-octadecadienoate	HMDB
13-L-Hydroperoxy-cis-9,trans-11-octadecadienoic acid	HMDB
Hpode	HMDB
Linoleic acid 13(S)-hydroperoxide	HMDB
13-Hydroperoxy-9,11-octadecadienoic acid	HMDB
13-Hydroperoxy-9,11-octadecadienoic acid, (Z,e)-isomer	HMDB

Molecular Formula

C₁₈H₃₂O₄

Average Mass

312.4443

Monoisotopic Mass

312.230059512

IUPAC Name

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

Traditional Name

13-HpODE

CAS Registry Number

33964-75-9

SMILES

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

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7-,15-12+/t17-/m0/s1

InChI Key

JDSRHVWSAMTSSN-IRQZEAMPSA-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:15655 )
Hydroperoxy fatty acids (C04717 )
Other Octadecanoids (LMFA02000034 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0033 g/L	ALOGPS
logP	5.76	ALOGPS
logP	5.64	ChemAxon
logS	-5	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	15	ChemAxon
Refractivity	91.38 m³·mol⁻¹	ChemAxon
Polarizability	37.14 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	splash10-00lv-5930000000-8cce9b35b53a054c4f06	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00v0-9833000000-b058eeece5c0d35efc4d	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0192000000-8901325cb7e062b9df46	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fr2-4690000000-a7a0479469a6409a29c6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05g4-9520000000-94dc42e5d4d562d9e058	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0049000000-f858b43abe2e420068f4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01oy-2292000000-43fbe3658909492d215d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9340000000-9de0efa9f8357ac365c9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0029000000-6109e2991a8f70f9b092	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1291000000-7a8262a60fa6aac089ac	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01vt-9180000000-ecc5c55edc141deff801	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0491000000-14168164306c962c44e2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01tj-2960000000-0d34e09e6afa84c664c0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-9300000000-e52ec41d50c5aa80e190	2021-09-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

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
MMDBp0192585	Arachidonate 15-lipoxygenase B	Unknown	O15296	Homo sapiens
MMDBp0192589	Arachidonate 15-lipoxygenase	Unknown	P16050	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004772	13-L-Hydroperoxylinoleic acid	Pelargonic acid	Not Available	VMH	11408659 11686005
MMDBr0009725	Linoleic acid	13-L-Hydroperoxylinoleic acid	arachidonate 15-lipoxygenase	VMH; KEGG	30371894
MMDBr0009726	13-L-Hydroperoxylinoleic acid	(9Z,11E)-13-HODE	glutathione peroxidase 1	VMH	30371894
MMDBr0009727	13-L-Hydroperoxylinoleic acid	13-Oxy Radical-Octadecadienoate	Not Available	VMH	30371894

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	1	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
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.00601	0.0055			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215

External Links

HMDB ID

HMDB0003871

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

13-HYDROPEROXYOCTADECA-911-DIENOATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280720

PDB ID

Not Available

ChEBI ID

15655

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kuhn H: Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)XY-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)XY-9Z,11E-octadecadienoic acid. Prog Lipid Res. 1996 Sep;35(3):203-26. doi: 10.1016/s0163-7827(96)00008-2. [PubMed:9082450 ]

Showing metabocard for 13-L-Hydroperoxylinoleic acid (MMDBc0049803)

MOL for #<Metabolite:0x00007feca5a601a0>

3D MOL for #<Metabolite:0x00007feca5a601a0>

3D SDF for #<Metabolite:0x00007feca5a601a0>

3D-SDF for #<Metabolite:0x00007feca5a601a0>

PDB for #<Metabolite:0x00007feca5a601a0>

3D PDB for #<Metabolite:0x00007feca5a601a0>

SMILES for #<Metabolite:0x00007feca5a601a0>

INCHI for #<Metabolite:0x00007feca5a601a0>

Structure for #<Metabolite:0x00007feca5a601a0>

3D Structure for #<Metabolite:0x00007feca5a601a0>