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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 05:04:14 UTC

Update Date

2022-03-07 03:17:57 UTC

HMDB ID

HMDB0062637

Secondary Accession Numbers

HMDB62637

Metabolite Identification

Common Name

13-HPODE(1-)

Description

(S)-13-Hydroperoxy-9,11-octadecadienoic acid, also known as 13-hydroperoxyoctadeca-9,11-dienoate, 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. Based on a literature review a significant number of articles have been published on (S)-13-Hydroperoxy-9,11-octadecadienoic acid.

Structure

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

HMDB0244509
     RDKit          3D
13-Hpode
 54 53  0  0  0  0  0  0  0  0999 V2000
   -6.4466    2.2611    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9981    1.4200   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6678   -0.0464   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1615   -0.1770   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174   -1.6018   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037   -1.6211   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866   -0.7953    0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964   -0.5156    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212    0.2949    1.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2946    0.6289    2.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052    0.2176    1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.5735    1.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.1573    1.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6168   -0.4279    0.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553    0.3990   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035    1.0144   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8363   -0.0021   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0868    0.7397   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1121    0.0855   -1.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1319    2.1270   -1.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -1.2468   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581   -2.1797   -2.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1859    1.6884    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    3.0299    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5527    2.8479   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0940    1.5291   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4839    1.7395   -1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1424   -0.6343   -1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0785   -0.3339    0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.4159    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7679    0.1602   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0907   -2.2741   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496   -2.0352    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -2.6715   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545   -0.4120    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568   -0.9280   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6753    0.6516    2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887    1.2488    2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773    1.1243    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -0.3747    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403   -0.0445    2.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -1.4526    2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719   -1.8886    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547   -1.9353    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4856   -1.1447    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028    0.2331    1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7740    1.2376   -0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742   -0.2321   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6562    1.6506   -1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1720    1.6993   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -0.6339   -2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1982   -0.6038   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5214    2.5782   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2874   -3.0787   -2.0005 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  3
  8  9  1  0
  9 10  2  3
 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  0
  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


  Mrv1652305161822382D          

 22 21  0  0  0  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  4  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 11  2  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062637

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(OO)C=CC=CCCCCCCCC(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)

> <INCHI_KEY>
JDSRHVWSAMTSSN-UHFFFAOYSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.45

> <EXACT_MASS>
312.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.964267592989884

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
91.3845

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroperoxyoctadeca-9,11-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244509
     RDKit          3D
13-Hpode
 54 53  0  0  0  0  0  0  0  0999 V2000
   -6.4466    2.2611    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9981    1.4200   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6678   -0.0464   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1615   -0.1770   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174   -1.6018   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037   -1.6211   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866   -0.7953    0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964   -0.5156    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212    0.2949    1.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2946    0.6289    2.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052    0.2176    1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.5735    1.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.1573    1.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6168   -0.4279    0.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553    0.3990   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035    1.0144   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8363   -0.0021   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0868    0.7397   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1121    0.0855   -1.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1319    2.1270   -1.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -1.2468   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581   -2.1797   -2.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1859    1.6884    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    3.0299    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5527    2.8479   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0940    1.5291   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4839    1.7395   -1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1424   -0.6343   -1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0785   -0.3339    0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.4159    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7679    0.1602   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0907   -2.2741   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496   -2.0352    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -2.6715   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545   -0.4120    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568   -0.9280   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6753    0.6516    2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887    1.2488    2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773    1.1243    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -0.3747    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403   -0.0445    2.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -1.4526    2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719   -1.8886    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547   -1.9353    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4856   -1.1447    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028    0.2331    1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7740    1.2376   -0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742   -0.2321   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6562    1.6506   -1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1720    1.6993   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -0.6339   -2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1982   -0.6038   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5214    2.5782   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2874   -3.0787   -2.0005 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  3
  8  9  1  0
  9 10  2  3
 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  0
  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                                 16-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-18         0                                  
HETATM    1  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.072   2.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.406   1.691   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.406   0.151   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.739  -0.619   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.739  -2.159   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.406   4.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.406   6.311   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
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   22                                                  
CONECT   10    9                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   14   21                                                       
CONECT   21   20                                                            
CONECT   22    9                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0062637
HETATM    1  C1  UNL     1      -8.185   0.005   0.486  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.235  -0.672   1.446  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.157  -1.429   0.745  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.273  -0.614  -0.137  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.529   0.467   0.589  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.675   1.202  -0.454  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.774   0.176  -1.027  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.556  -0.060  -0.503  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.758  -1.086  -1.143  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.428  -1.393  -0.714  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.096  -0.778   0.419  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.389  -0.132  -0.033  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.276  -1.171  -0.624  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.624  -0.650  -1.080  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.411  -0.058   0.062  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.753   0.453  -0.396  1.00  0.00           C  
HETATM   17  C17 UNL     1       7.471   1.014   0.818  1.00  0.00           C  
HETATM   18  C18 UNL     1       8.797   1.541   0.479  1.00  0.00           C  
HETATM   19  O1  UNL     1       8.890   2.615  -0.151  1.00  0.00           O  
HETATM   20  O2  UNL     1       9.946   0.873   0.843  1.00  0.00           O  
HETATM   21  O3  UNL     1      -2.907   2.187   0.125  1.00  0.00           O  
HETATM   22  O4  UNL     1      -3.116   3.381  -0.392  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.853  -0.051  -0.570  1.00  0.00           H  
HETATM   24  H2  UNL     1      -9.198  -0.486   0.501  1.00  0.00           H  
HETATM   25  H3  UNL     1      -8.380   1.061   0.795  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.839  -1.415   2.028  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.837   0.034   2.214  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.559  -1.986   1.505  1.00  0.00           H  
HETATM   29  H7  UNL     1      -6.655  -2.236   0.137  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.514  -1.301  -0.586  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.862  -0.203  -0.986  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.818   0.004   1.303  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.204   1.188   1.096  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.326   1.576  -1.274  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.095  -0.398  -1.883  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.246   0.519   0.352  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.186  -1.619  -2.026  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.957  -2.189  -1.245  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.422  -1.555   1.191  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.524  -0.001   0.967  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.100   0.665  -0.751  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.835   0.332   0.879  1.00  0.00           H  
HETATM   43  H21 UNL     1       3.377  -1.997   0.110  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.786  -1.565  -1.564  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.483   0.047  -1.927  1.00  0.00           H  
HETATM   46  H24 UNL     1       5.166  -1.545  -1.500  1.00  0.00           H  
HETATM   47  H25 UNL     1       5.513  -0.838   0.834  1.00  0.00           H  
HETATM   48  H26 UNL     1       4.790   0.745   0.514  1.00  0.00           H  
HETATM   49  H27 UNL     1       6.636   1.217  -1.168  1.00  0.00           H  
HETATM   50  H28 UNL     1       7.318  -0.439  -0.794  1.00  0.00           H  
HETATM   51  H29 UNL     1       6.798   1.733   1.305  1.00  0.00           H  
HETATM   52  H30 UNL     1       7.584   0.148   1.530  1.00  0.00           H  
HETATM   53  H31 UNL     1      10.433   1.096   1.681  1.00  0.00           H  
HETATM   54  H32 UNL     1      -4.062   3.590  -0.239  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

HMDB0244509
     RDKit          3D
13-Hpode
 54 53  0  0  0  0  0  0  0  0999 V2000
   -6.4466    2.2611    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9981    1.4200   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6678   -0.0464   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1615   -0.1770   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174   -1.6018   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037   -1.6211   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866   -0.7953    0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964   -0.5156    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212    0.2949    1.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2946    0.6289    2.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052    0.2176    1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.5735    1.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.1573    1.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6168   -0.4279    0.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553    0.3990   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035    1.0144   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8363   -0.0021   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0868    0.7397   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1121    0.0855   -1.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1319    2.1270   -1.6600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783   -1.2468   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581   -2.1797   -2.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1859    1.6884    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    3.0299    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5527    2.8479   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0940    1.5291   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4839    1.7395   -1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1424   -0.6343   -1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0785   -0.3339    0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.4159    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7679    0.1602   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0907   -2.2741   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496   -2.0352    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -2.6715   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545   -0.4120    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7568   -0.9280   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6753    0.6516    2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887    1.2488    2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773    1.1243    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -0.3747    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403   -0.0445    2.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -1.4526    2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719   -1.8886    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547   -1.9353    0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4856   -1.1447    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028    0.2331    1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7740    1.2376   -0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742   -0.2321   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6562    1.6506   -1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1720    1.6993   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -0.6339   -2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1982   -0.6038   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5214    2.5782   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2874   -3.0787   -2.0005 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  3
  8  9  1  0
  9 10  2  3
 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  0
  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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-13-Hydroperoxy-9,11-octadecadienoate	Generator
13-Hydroperoxyoctadeca-9,11-dienoate	HMDB

Chemical Formula

C₁₈H₃₂O₄

Average Molecular Weight

312.45

Monoisotopic Molecular Weight

312.23005951

IUPAC Name

13-hydroperoxyoctadeca-9,11-dienoic acid

Traditional Name

13-hydroperoxyoctadeca-9,11-dienoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(OO)C=CC=CCCCCCCCC(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)

InChI Key

JDSRHVWSAMTSSN-UHFFFAOYSA-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

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0017 g/l	ALOGPS
LogP	5.85	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	38.96 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
DeepCCS	[M+H]+	180.174	30932474
DeepCCS	[M-H]-	176.187	30932474
DeepCCS	[M-2H]-	212.699	30932474
DeepCCS	[M+Na]+	188.989	30932474
AllCCS	[M+H]+	184.6	32859911
AllCCS	[M+H-H2O]+	181.7	32859911
AllCCS	[M+NH4]+	187.3	32859911
AllCCS	[M+Na]+	188.0	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
13-HPODE(1-)	CCCCCC(OO)C=CC=CCCCCCCCC(O)=O	3855.6	Standard polar	33892256
13-HPODE(1-)	CCCCCC(OO)C=CC=CCCCCCCCC(O)=O	2319.2	Standard non polar	33892256
13-HPODE(1-)	CCCCCC(OO)C=CC=CCCCCCCCC(O)=O	2458.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13-HPODE(1-),1TMS,isomer #1	CCCCCC(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C)OO	2601.5	Semi standard non polar	33892256
13-HPODE(1-),1TBDMS,isomer #1	CCCCCC(C=CC=CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO	2847.9	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 - 13-HPODE(1-) GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lv-5930000000-8cce9b35b53a054c4f06	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-HPODE(1-) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-HPODE(1-) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-HPODE(1-) 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 - 13-HPODE(1-) 10V, Positive-QTOF	splash10-0002-0192000000-8901325cb7e062b9df46	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 20V, Positive-QTOF	splash10-0fr2-4690000000-a7a0479469a6409a29c6	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 40V, Positive-QTOF	splash10-05g4-9520000000-94dc42e5d4d562d9e058	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 10V, Negative-QTOF	splash10-03di-0049000000-f858b43abe2e420068f4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 20V, Negative-QTOF	splash10-01oy-2292000000-43fbe3658909492d215d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 40V, Negative-QTOF	splash10-0a4l-9340000000-9de0efa9f8357ac365c9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 10V, Negative-QTOF	splash10-03di-0029000000-6109e2991a8f70f9b092	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 20V, Negative-QTOF	splash10-01t9-1291000000-7a8262a60fa6aac089ac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 40V, Negative-QTOF	splash10-01vt-9180000000-ecc5c55edc141deff801	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 10V, Positive-QTOF	splash10-01t9-0491000000-14168164306c962c44e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 20V, Positive-QTOF	splash10-01tj-2960000000-0d34e09e6afa84c664c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HPODE(1-) 40V, Positive-QTOF	splash10-0a5c-9300000000-e52ec41d50c5aa80e190	2021-09-22	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1383

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1426

PDB ID

Not Available

ChEBI ID

Not Available

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

Kilty I, Logan A, Vickers PJ: Differential characteristics of human 15-lipoxygenase isozymes and a novel splice variant of 15S-lipoxygenase. Eur J Biochem. 1999 Nov;266(1):83-93. [PubMed:10542053 ]
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 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 13-HPODE(1-) (HMDB0062637)

MOL for HMDB0062637 (13-HPODE(1-))

3D MOL for HMDB0062637 (13-HPODE(1-))

3D SDF for HMDB0062637 (13-HPODE(1-))

3D-SDF for HMDB0062637 (13-HPODE(1-))

PDB for HMDB0062637 (13-HPODE(1-))

3D PDB for HMDB0062637 (13-HPODE(1-))

SMILES for HMDB0062637 (13-HPODE(1-))

INCHI for HMDB0062637 (13-HPODE(1-))

Structure for HMDB0062637 (13-HPODE(1-))

3D Structure for HMDB0062637 (13-HPODE(1-))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra