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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-21 06:19:33 UTC

Update Date

2022-03-07 03:17:54 UTC

HMDB ID

HMDB0062434

Secondary Accession Numbers

HMDB62434

Metabolite Identification

Common Name

(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid

Description

(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid, also known as 9(S)-HPOD or (9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoate, is classified as a lineolic acid or a Lineolic acid derivative. Lineolic acids 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. (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid is considered to be practically insoluble (in water) and acidic. (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid is an octadecanoid lipid molecule. (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid can be found throughout numerous foods such as Barley, Prunus (Cherry, Plum), Cherimoya, and Prairie turnips

Structure

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

  Mrv1533007131514022D          

 27 26  0  0  1  0            999 V2000
    1.5395    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5408   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 17 22  1  1  0  0  0
 22 21  1  0  0  0  0
 23  6  1  0  0  0  0
 24  8  1  0  0  0  0
 25 11  1  0  0  0  0
 26 14  1  0  0  0  0
 17 27  1  1  0  0  0
M  END

HMDB0062434
     RDKit          3D
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.9058   -0.1574    2.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6211   -0.8424    1.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4684   -0.0839    2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1266   -0.6532    1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9354   -0.6568    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0432    0.7350   -0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    1.3196   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    0.7014   -1.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    1.3678   -1.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493    0.6439   -1.8763 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9909    0.0098   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2716   -0.6862   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476   -1.3759    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -2.0303   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1646   -1.1530   -1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8630   -0.0627   -0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1747    1.0909    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2426    2.0213    0.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8889    3.0732    1.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5550    1.6759    0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553    1.4274   -2.3896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591    0.9034   -3.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2552    0.5498    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6994   -0.9320    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6999    0.3766    2.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5869   -1.8786    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6610   -0.8411    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620    1.0008    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6181   -0.1207    3.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1012   -1.6865    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -0.0306    2.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -1.2657   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -1.2103    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0110    1.2836    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.3733   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019   -0.3080   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9840    2.3811   -1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2335   -0.2352   -2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174   -0.7854   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    0.7358    0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589    0.1055   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728   -1.3839   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -0.6748    0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2424   -2.1628    0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -2.8339   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -2.6911    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6852   -0.7865   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9906   -1.8285   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833    0.3771   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278   -0.4822    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5528    1.6543   -0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    0.9159    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1265    1.3457    1.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552    0.3830   -3.9835 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  2  0
  9 10  1  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
 10 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
  9 37  1  0
 10 38  1  6
 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

  Mrv1533007131514022D          

 27 26  0  0  1  0            999 V2000
    1.5395    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5408   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 17 22  1  1  0  0  0
 22 21  1  0  0  0  0
 23  6  1  0  0  0  0
 24  8  1  0  0  0  0
 25 11  1  0  0  0  0
 26 14  1  0  0  0  0
 17 27  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0062434

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/b8-6-,14-11+/t17-/m1/s1

> <INCHI_KEY>
JGUNZIWGNMQSBM-UINYOVNOSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.45

> <EXACT_MASS>
312.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.05740226768299

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
5.640401104666667

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712374047588172

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745143435034

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236807609084804

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
91.38449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-HpODE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062434
     RDKit          3D
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.9058   -0.1574    2.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6211   -0.8424    1.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4684   -0.0839    2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1266   -0.6532    1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9354   -0.6568    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0432    0.7350   -0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    1.3196   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    0.7014   -1.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    1.3678   -1.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493    0.6439   -1.8763 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9909    0.0098   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2716   -0.6862   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476   -1.3759    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -2.0303   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1646   -1.1530   -1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8630   -0.0627   -0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1747    1.0909    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2426    2.0213    0.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8889    3.0732    1.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5550    1.6759    0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553    1.4274   -2.3896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591    0.9034   -3.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2552    0.5498    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6994   -0.9320    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6999    0.3766    2.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5869   -1.8786    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6610   -0.8411    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620    1.0008    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6181   -0.1207    3.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1012   -1.6865    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -0.0306    2.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -1.2657   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -1.2103    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0110    1.2836    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.3733   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019   -0.3080   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9840    2.3811   -1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2335   -0.2352   -2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174   -0.7854   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    0.7358    0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589    0.1055   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728   -1.3839   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -0.6748    0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2424   -2.1628    0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -2.8339   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -2.6911    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6852   -0.7865   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9906   -1.8285   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833    0.3771   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278   -0.4822    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5528    1.6543   -0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    0.9159    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1265    1.3457    1.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552    0.3830   -3.9835 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  2  0
  9 10  1  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
 10 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
  9 37  1  0
 10 38  1  6
 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                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       2.874  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.206   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.208   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.207  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.542  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.876   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.209  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.543   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.209  -1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -2.461   5.390   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.461   2.310   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.540   3.080   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.127  -0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.540   1.540   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8   23                                                  
CONECT    7    9   10                                                       
CONECT    8    6   11   24                                                  
CONECT    9    7   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14   25                                                  
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17   26                                                  
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   22   27                                             
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   22                                                            
CONECT   22   17   21                                                       
CONECT   23    6                                                            
CONECT   24    8                                                            
CONECT   25   11                                                            
CONECT   26   14                                                            
CONECT   27   17                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0062434
HETATM    1  C1  UNL     1      -7.906  -0.157   2.031  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.621  -0.842   1.577  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.468  -0.084   2.159  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.127  -0.653   1.816  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.935  -0.657   0.319  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.043   0.735  -0.160  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.056   1.320  -0.764  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.791   0.701  -1.024  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.799   1.368  -1.662  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.449   0.644  -1.876  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.991   0.010  -0.596  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.272  -0.686  -1.017  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.948  -1.376   0.144  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.194  -2.030  -0.368  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.165  -1.153  -1.010  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.863  -0.063  -0.349  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.175   1.091   0.241  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.243   2.021   0.769  1.00  0.00           C  
HETATM   19  O1  UNL     1       5.889   3.073   1.316  1.00  0.00           O  
HETATM   20  O2  UNL     1       7.555   1.676   0.628  1.00  0.00           O  
HETATM   21  O3  UNL     1       1.455   1.427  -2.390  1.00  0.00           O  
HETATM   22  O4  UNL     1       1.859   0.903  -3.524  1.00  0.00           O  
HETATM   23  H1  UNL     1      -8.255   0.550   1.268  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.699  -0.932   2.225  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.700   0.377   2.974  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.587  -1.879   1.950  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.661  -0.841   0.464  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.562   1.001   1.916  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.618  -0.121   3.279  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.101  -1.686   2.225  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.359  -0.031   2.331  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.820  -1.266  -0.073  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.057  -1.210   0.003  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.011   1.284   0.006  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.199   2.373  -1.103  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.602  -0.308  -0.714  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.984   2.381  -1.972  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.234  -0.235  -2.553  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.317  -0.785  -0.215  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.143   0.736   0.200  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.959   0.105  -1.379  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.073  -1.384  -1.829  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.082  -0.675   0.959  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.242  -2.163   0.571  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.924  -2.834  -1.139  1.00  0.00           H  
HETATM   46  H24 UNL     1       4.657  -2.691   0.442  1.00  0.00           H  
HETATM   47  H25 UNL     1       4.685  -0.787  -1.987  1.00  0.00           H  
HETATM   48  H26 UNL     1       5.991  -1.829  -1.461  1.00  0.00           H  
HETATM   49  H27 UNL     1       6.583   0.377  -1.131  1.00  0.00           H  
HETATM   50  H28 UNL     1       6.628  -0.482   0.399  1.00  0.00           H  
HETATM   51  H29 UNL     1       4.553   1.654  -0.477  1.00  0.00           H  
HETATM   52  H30 UNL     1       4.553   0.916   1.142  1.00  0.00           H  
HETATM   53  H31 UNL     1       8.127   1.346   1.400  1.00  0.00           H  
HETATM   54  H32 UNL     1       1.155   0.383  -3.983  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    9   36
CONECT    9   10   37
CONECT   10   11   21   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

HMDB0062434
     RDKit          3D
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.9058   -0.1574    2.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6211   -0.8424    1.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4684   -0.0839    2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1266   -0.6532    1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9354   -0.6568    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0432    0.7350   -0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    1.3196   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    0.7014   -1.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    1.3678   -1.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493    0.6439   -1.8763 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9909    0.0098   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2716   -0.6862   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476   -1.3759    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -2.0303   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1646   -1.1530   -1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8630   -0.0627   -0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1747    1.0909    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2426    2.0213    0.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8889    3.0732    1.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5550    1.6759    0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553    1.4274   -2.3896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591    0.9034   -3.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2552    0.5498    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6994   -0.9320    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6999    0.3766    2.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5869   -1.8786    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6610   -0.8411    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620    1.0008    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6181   -0.1207    3.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1012   -1.6865    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -0.0306    2.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -1.2657   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -1.2103    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0110    1.2836    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.3733   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019   -0.3080   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9840    2.3811   -1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2335   -0.2352   -2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174   -0.7854   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    0.7358    0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589    0.1055   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728   -1.3839   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0822   -0.6748    0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2424   -2.1628    0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -2.8339   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -2.6911    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6852   -0.7865   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9906   -1.8285   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833    0.3771   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278   -0.4822    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5528    1.6543   -0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    0.9159    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1265    1.3457    1.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552    0.3830   -3.9835 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  2  0
  9 10  1  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
 10 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
  9 37  1  0
 10 38  1  6
 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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid	ChEBI
(9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoic acid	ChEBI
9(S)-HPOD	ChEBI
(9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoate	Kegg
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoate	Generator
(9S,10E,12Z,15Z)-9-Hydroperoxy-10,12,15-octadecadienoic acid	Generator
9-Hydroperoxy-11,12-octadecadienoic acid	MeSH, HMDB
9-Hydroperoxy-11,12-octadecadienoic acid, (e,Z)-isomer	MeSH, HMDB
9-Hydroperoxy-11,12-octadecadienoic acid, (Z,e)-isomer	MeSH, HMDB
9-HPODE	MeSH, HMDB

Chemical Formula

C₁₈H₃₂O₄

Average Molecular Weight

312.45

Monoisotopic Molecular Weight

312.23005951

IUPAC Name

(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid

Traditional Name

9-HpODE

CAS Registry Number

29774-12-7

SMILES

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

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/b8-6-,14-11+/t17-/m1/s1

InChI Key

JGUNZIWGNMQSBM-UINYOVNOSA-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:34498 )
Other Octadecanoids (C14827 )
Other Octadecanoids (LMFA02000012 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0062434)
Cell membrane (HMDB: HMDB0062434)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0062434)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0062434)

Source

Endogenous

Endogenous (HMDB: HMDB0062434)

Animal

Animal (HMDB: HMDB0062434)

Exogenous

Food

Food (HMDB: HMDB0062434)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Peanut (FooDB: FOOD00016)
Hazelnut (FooDB: FOOD00376)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Exogenous (HMDB: HMDB0062434)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0062434)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0062434)

Lipid metabolism pathway (HMDB: HMDB0062434)

Biochemical process

Lipid transport (HMDB: HMDB0062434)

Role

Biological role

Energy source (HMDB: HMDB0062434)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0037 g/l	ALOGPS
LogP	5.74	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.74	ALOGPS
logP	5.64	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.68	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	38.06 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]+	184.097	31661259
DarkChem	[M-H]-	180.64	31661259
DeepCCS	[M+H]+	187.713	30932474
DeepCCS	[M-H]-	185.318	30932474
DeepCCS	[M-2H]-	219.502	30932474
DeepCCS	[M+Na]+	194.571	30932474
AllCCS	[M+H]+	184.7	32859911
AllCCS	[M+H-H2O]+	181.8	32859911
AllCCS	[M+NH4]+	187.4	32859911
AllCCS	[M+Na]+	188.1	32859911
AllCCS	[M-H]-	182.7	32859911
AllCCS	[M+Na-2H]-	184.3	32859911
AllCCS	[M+HCOO]-	186.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid	[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO	3707.1	Standard polar	33892256
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid	[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO	2344.7	Standard non polar	33892256
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid	[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO	2413.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid,1TMS,isomer #1	CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OO	2611.3	Semi standard non polar	33892256
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid,1TBDMS,isomer #1	CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO	2845.9	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 - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mo-9450000000-9f9ce00144bf1470f46e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-01di-9533000000-12686f18ef669f139867	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic 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 - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Positive-QTOF	splash10-0002-0192000000-4f03d2f2bc968d55402e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Positive-QTOF	splash10-066s-5590000000-fbcb5ed3adc3871bd0fa	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Positive-QTOF	splash10-0536-9320000000-3472d061677ef7793c53	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Negative-QTOF	splash10-03di-0149000000-4a41775c40edba3c555e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Negative-QTOF	splash10-01ox-1693000000-822907c2888d3b6c86e7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Negative-QTOF	splash10-0abc-9730000000-1e8118a529f287df673d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Negative-QTOF	splash10-03di-0059000000-401bcd66b7485f93725e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Negative-QTOF	splash10-03fr-0294000000-545cafa8f501f8c69546	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Negative-QTOF	splash10-0553-5970000000-a710051ee52e3fa925c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Positive-QTOF	splash10-03fr-1392000000-aea7db3f968af10d1725	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Positive-QTOF	splash10-00c0-5940000000-1c5206d809c856cefc97	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Positive-QTOF	splash10-001i-9300000000-065159558ba433dab8cd	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030133

KNApSAcK ID

C00000393

Chemspider ID

Not Available

KEGG Compound ID

C14827

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

34498

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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Showing metabocard for (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid (HMDB0062434)

MOL for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

3D MOL for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

3D SDF for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

3D-SDF for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

PDB for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

3D PDB for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

SMILES for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

INCHI for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

Structure for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

3D Structure for HMDB0062434 ((10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra