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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 23:30:18 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004667

Secondary Accession Numbers

HMDB0006939
HMDB0061708
HMDB0112194
HMDB04667
HMDB06939
HMDB61708

Metabolite Identification

Common Name

13-HODE

Description

13-Hydroxyoctadecadienoic acid (13-HODE) (CAS: 18104-45-5), also known as 13(S)-hydroxy-9Z,11E-octadecadienoic acid or 13(S)-HODE, is the major lipoxygenation product synthesized in the body from linoleic acid. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis. 13-HODE synthesis is enhanced by cyclic AMP. gamma-Linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation (PMID: 9561154 ). 13-HODE is considered an intermediate in linoleic acid metabolism. It is generated from 13(S)-HPODE via the enzyme lipoxygenase (EC 1.13.11.12). 13-HODE has been shown to be involved in cell proliferation and differentiation in a number of systems. 13-HODE is found to be produced by prostate tumours and cell lines and researchers believe that there is a link between linoleic acid metabolism and the development or progression of prostate cancer (PMID: 9367845 ).

Structure

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

HMDB0004667
     RDKit          3D
13-HODE
 53 52  0  0  0  0  0  0  0  0999 V2000
    7.7431   -0.6891    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4549    0.7924    0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    0.9803    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633    0.1769   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    0.3161   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4365   -0.1690    1.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8624   -1.5241    1.2179 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -0.1055    1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9923   -0.1380    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -0.0758    1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -0.1051    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711   -0.2043   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    0.9813   -1.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226    1.0019   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608   -0.2374   -1.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5034   -0.3776   -1.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0768   -0.4642   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9035    0.6586    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7313    0.2686    2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2963   -0.5465    2.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9649    0.8746    2.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8199   -0.8864    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0979   -1.1003    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4369   -1.1372   -0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0562    1.3304    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941    1.1769   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6943    2.0404    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    0.5879    1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -0.9140   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921    0.4787   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    1.3476   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -0.3228   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.3530    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -2.1102    0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191   -0.0287    2.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090   -0.2093   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439    0.0028    2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -0.0643    0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -0.2206   -1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -1.1778   -1.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    1.0017   -2.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    1.8852   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    1.1709   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919    1.9287   -1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -1.1282   -1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8067   -0.3786   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8020   -1.3271   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127    0.4860   -2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7311   -1.4103    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2035   -0.6561   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2428    1.6415    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811    0.6981    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7906    0.5056    1.6546 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  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  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
M  END


  Mrv1652304202019522D          

 21 20  0  0  0  0            999 V2000
10009.876910007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.161410007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.445910007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.621510007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.906810007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.192010007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.477310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.762610007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.047910007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.333110007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.618310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.903710007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.186910007.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.903710008.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.590410007.4857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.305810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.021410007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.734810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.450310007.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.165810007.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.590410006.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  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
 12 14  2  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  6  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
M  END
> <DATABASE_ID>
HMDB0004667

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

> <INCHI_KEY>
HNICUWMFWZBIFP-IRQZEAMPSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.261982452500305

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.191065727333333

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677909269454

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9881674023842

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759706009659333

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.0343

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxyoctadecadienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004667
     RDKit          3D
13-HODE
 53 52  0  0  0  0  0  0  0  0999 V2000
    7.7431   -0.6891    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4549    0.7924    0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    0.9803    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633    0.1769   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    0.3161   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4365   -0.1690    1.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8624   -1.5241    1.2179 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -0.1055    1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9923   -0.1380    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -0.0758    1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -0.1051    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711   -0.2043   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    0.9813   -1.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226    1.0019   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608   -0.2374   -1.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5034   -0.3776   -1.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0768   -0.4642   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9035    0.6586    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7313    0.2686    2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2963   -0.5465    2.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9649    0.8746    2.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8199   -0.8864    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0979   -1.1003    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4369   -1.1372   -0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0562    1.3304    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941    1.1769   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6943    2.0404    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    0.5879    1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -0.9140   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921    0.4787   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    1.3476   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -0.3228   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.3530    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -2.1102    0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191   -0.0287    2.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090   -0.2093   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439    0.0028    2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -0.0643    0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -0.2206   -1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -1.1778   -1.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    1.0017   -2.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    1.8852   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    1.1709   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919    1.9287   -1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -1.1282   -1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8067   -0.3786   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8020   -1.3271   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127    0.4860   -2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7311   -1.4103    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2035   -0.6561   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2428    1.6415    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811    0.6981    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7906    0.5056    1.6546 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  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  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8685.1048681.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8683.7688680.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8682.4328681.409   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8680.8938681.409   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8679.5598680.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8678.2258681.409   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8676.8918680.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.5578681.409   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8674.2238680.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.8888681.409   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8671.5548680.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.2208681.409   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8668.8828680.640   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8670.2208682.948   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8686.4358680.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8687.7718681.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8689.1078680.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8690.4388681.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8691.7748680.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8693.1098681.409   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8686.4358679.099   0.000  0.00  0.00           O+0
CONECT    1    2   15                                                       
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   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0004667
HETATM    1  C1  UNL     1       7.743  -0.689   0.198  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.455   0.792   0.086  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.971   0.980   0.466  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.163   0.177  -0.498  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.693   0.316  -0.193  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.437  -0.169   1.197  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.862  -1.524   1.218  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.002  -0.105   1.608  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.992  -0.138   0.710  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.357  -0.076   1.188  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.403  -0.105   0.411  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.271  -0.204  -1.050  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.936   0.981  -1.687  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.423   1.002  -1.295  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.061  -0.237  -1.752  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.503  -0.378  -1.541  1.00  0.00           C  
HETATM   17  C16 UNL     1      -6.077  -0.464  -0.196  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.903   0.659   0.764  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.731   0.269   2.005  1.00  0.00           C  
HETATM   20  O2  UNL     1      -6.296  -0.547   2.837  1.00  0.00           O  
HETATM   21  O3  UNL     1      -7.965   0.875   2.126  1.00  0.00           O  
HETATM   22  H1  UNL     1       8.820  -0.886   0.329  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.098  -1.100   0.983  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.437  -1.137  -0.781  1.00  0.00           H  
HETATM   25  H4  UNL     1       8.056   1.330   0.838  1.00  0.00           H  
HETATM   26  H5  UNL     1       7.594   1.177  -0.926  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.694   2.040   0.442  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.924   0.588   1.511  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.395  -0.914  -0.376  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.392   0.479  -1.540  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.327   1.348  -0.371  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.177  -0.323  -0.963  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.003   0.353   1.967  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.199  -2.110   0.763  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.719  -0.029   2.644  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.309  -0.209  -0.317  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.544   0.003   2.274  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.427  -0.064   0.858  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.194  -0.221  -1.376  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.652  -1.178  -1.474  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.852   1.002  -2.792  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.485   1.885  -1.221  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.511   1.171  -0.232  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.892   1.929  -1.766  1.00  0.00           H  
HETATM   45  H24 UNL     1      -3.509  -1.128  -1.288  1.00  0.00           H  
HETATM   46  H25 UNL     1      -3.807  -0.379  -2.857  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.802  -1.327  -2.149  1.00  0.00           H  
HETATM   48  H27 UNL     1      -6.013   0.486  -2.120  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.731  -1.410   0.348  1.00  0.00           H  
HETATM   50  H29 UNL     1      -7.203  -0.656  -0.348  1.00  0.00           H  
HETATM   51  H30 UNL     1      -6.243   1.641   0.440  1.00  0.00           H  
HETATM   52  H31 UNL     1      -4.881   0.698   1.244  1.00  0.00           H  
HETATM   53  H32 UNL     1      -8.791   0.506   1.655  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    8   33
CONECT    7   34
CONECT    8    9    9   35
CONECT    9   10   36
CONECT   10   11   11   37
CONECT   11   12   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   20   21
CONECT   21   53
END

HMDB0004667
     RDKit          3D
13-HODE
 53 52  0  0  0  0  0  0  0  0999 V2000
    7.7431   -0.6891    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4549    0.7924    0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    0.9803    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633    0.1769   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    0.3161   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4365   -0.1690    1.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8624   -1.5241    1.2179 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -0.1055    1.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9923   -0.1380    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -0.0758    1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -0.1051    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711   -0.2043   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    0.9813   -1.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226    1.0019   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608   -0.2374   -1.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5034   -0.3776   -1.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0768   -0.4642   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9035    0.6586    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7313    0.2686    2.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2963   -0.5465    2.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9649    0.8746    2.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8199   -0.8864    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0979   -1.1003    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4369   -1.1372   -0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0562    1.3304    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5941    1.1769   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6943    2.0404    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    0.5879    1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -0.9140   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921    0.4787   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    1.3476   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -0.3228   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.3530    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -2.1102    0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191   -0.0287    2.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090   -0.2093   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439    0.0028    2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -0.0643    0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -0.2206   -1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -1.1778   -1.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    1.0017   -2.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    1.8852   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    1.1709   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919    1.9287   -1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -1.1282   -1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8067   -0.3786   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8020   -1.3271   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127    0.4860   -2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7311   -1.4103    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2035   -0.6561   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2428    1.6415    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811    0.6981    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7906    0.5056    1.6546 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  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  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(13S)-Hydroxyoctadecadienoic acid	ChEBI
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid	ChEBI
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid	ChEBI
(13S)-Hydroxyoctadecadienoate	Generator
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate	Generator
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate	Generator
13S-Hydroxyoctadecadienoate	HMDB
13-Hydroxy-9,11-octadecadienoic acid	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomer	HMDB
13-Hydroxyoctadecadienoic acid	HMDB
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomer	HMDB
13(S) HODE	HMDB
13-Hydroxyoctadecadienoate	HMDB
(+)-Coriolic acid	HMDB
(13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acid	HMDB
(9Z,11E,13S)-13-Hydroxyoctadecadienoic acid	HMDB
(S)-Coriolic acid	HMDB
(±)-coriolic acid	HMDB
13-Hydroxy-9(Z),11(e)-octadecadienoic acid	HMDB
13-Hydroxy-9,11-cis,trans-octadecadienoic acid	HMDB
13-Hydroxy-9-cis-11-trans-octadecadienoic acid	HMDB
13-Hydroxy-cis-9-trans-11-octadecadienoic acid	HMDB
13-Hydroxylinoleic acid	HMDB
13-Hydroxyoctadeca-9,11-dienoic acid	HMDB
13S-HODE	HMDB
13S-Hydroxy-9Z,11E-octadecadienoic acid	HMDB
L-13-Hydroxy-cis-9,trans-11-octadecadienoic acid	HMDB
alpha-Artemisolic acid	HMDB
Α-artemisolic acid	HMDB
(9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoate	HMDB
(9Z,11E)-13-HODE	HMDB
(9Z,11E)-13-Hydroxyoctadecadienoic acid	HMDB
FA(18:2(9Z,11E,13-OH))	HMDB
FA(18:2(9Z,11E,13S-OH))	HMDB
13-HODE	HMDB, MeSH

Chemical Formula

C₁₈H₃₂O₃

Average Molecular Weight

296.4449

Monoisotopic Molecular Weight

296.23514489

IUPAC Name

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

Traditional Name

13-hydroxyoctadecadienoic acid

CAS Registry Number

29623-28-7

SMILES

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

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

InChI Key

HNICUWMFWZBIFP-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
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

HODE (CHEBI:34154 )
Other Octadecanoids (C14762 )
Other Octadecanoids (LMFA02000228 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18215696)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0004667)
Saliva (PMID: 22308371)

Organ

Placenta (HMDB: HMDB0004667)

Excreta

Biofluid or Excreta

Urine (PMID: 18215696)
Feces (PMID: 25037050)

Cellular substructure

Membrane (HMDB: HMDB0004667)
Extracellular (HMDB: HMDB0004667)

Source

Exogenous

Exogenous (HMDB: HMDB0004667)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004667)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Autosomal dominant polycystic kidney disease (MarkerDB: MDB00000452)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	183.112	30932474
[M-H]-	Not Available	183.112	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001857

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	5.88	ALOGPS
logP	5.19	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	90.03 m³·mol⁻¹	ChemAxon
Polarizability	37.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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]+	179.86	31661259
DarkChem	[M-H]-	181.452	31661259
DeepCCS	[M+H]+	182.449	30932474
DeepCCS	[M-H]-	180.091	30932474
DeepCCS	[M-2H]-	212.977	30932474
DeepCCS	[M+Na]+	188.542	30932474
AllCCS	[M+H]+	181.1	32859911
AllCCS	[M+H-H2O]+	178.1	32859911
AllCCS	[M+NH4]+	183.8	32859911
AllCCS	[M+Na]+	184.6	32859911
AllCCS	[M-H]-	180.0	32859911
AllCCS	[M+Na-2H]-	181.5	32859911
AllCCS	[M+HCOO]-	183.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	9.12 minutes	32390414
Predicted by Siyang on May 30, 2022	19.7746 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.02 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13-HODE	CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O	3831.2	Standard polar	33892256
13-HODE	CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O	2308.2	Standard non polar	33892256
13-HODE	CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O	2431.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13-HODE,1TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C	2532.1	Semi standard non polar	33892256
13-HODE,1TMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2482.1	Semi standard non polar	33892256
13-HODE,2TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2543.2	Semi standard non polar	33892256
13-HODE,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2782.1	Semi standard non polar	33892256
13-HODE,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2726.1	Semi standard non polar	33892256
13-HODE,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3044.1	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-HODE GC-MS (Non-derivatized) - 70eV, Positive	splash10-054k-6960000000-8cc8c4da0c87c3d65f03	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-HODE GC-MS (2 TMS) - 70eV, Positive	splash10-0fbi-9342100000-19627880cd07ec05cb84	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-HODE 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-HODE 10V, Positive-QTOF	splash10-004j-0090000000-bed7738fb8e72e8df932	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 20V, Positive-QTOF	splash10-0h7j-4490000000-e9f46847d2cc004e1b77	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 40V, Positive-QTOF	splash10-059f-9520000000-57ec0699995e3751af99	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 10V, Negative-QTOF	splash10-0002-0090000000-3ff43b79ccb7acee5d87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 20V, Negative-QTOF	splash10-0002-1190000000-59a7f430444bdc36b530	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 40V, Negative-QTOF	splash10-0a4l-9320000000-2687cbf01f8a4a08925f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 10V, Positive-QTOF	splash10-004i-0490000000-e3207ecec01bdd3e10e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 20V, Positive-QTOF	splash10-01ua-4930000000-a68be67edda5292d6ba1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 40V, Positive-QTOF	splash10-0aor-9600000000-1e60462f1a3dff344af4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 10V, Negative-QTOF	splash10-0002-0090000000-fc43967f64934b080413	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 20V, Negative-QTOF	splash10-002b-1490000000-d60f46720ed576787816	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-HODE 40V, Negative-QTOF	splash10-052f-9330000000-9622ef3fb83ca1fa8e96	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0106 +/- 0.00128 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.0473 +/- 0.00053 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.0582 +/- 0.028 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.230 +/- 0.038 uM	Adult (>18 years old)	Both	Normal	18215696	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0139 +/- 0.0048 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	2162.16 +/- 112.61 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9533182	details
Urine	Detected and Quantified	353.60 +/- 117.12 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9533182	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.310 +/- 0.064 uM	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	18215696	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	467.0 +/- 67.0 umol/mmol creatinine	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	18215696	details

Associated Disorders and Diseases

Disease References

Autosomal dominant polycystic kidney disease
Wang D, Strandgaard S, Borresen ML, Luo Z, Connors SG, Yan Q, Wilcox CS: Asymmetric dimethylarginine and lipid peroxidation products in early autosomal dominant polycystic kidney disease. Am J Kidney Dis. 2008 Feb;51(2):184-91. doi: 10.1053/j.ajkd.2007.09.020. [PubMed:18215696 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

601313 (Autosomal dominant polycystic kidney disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB06926

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

13-Hydroxyoctadecadienoic acid

METLIN ID

Not Available

PubChem Compound

6443013

PDB ID

Not Available

ChEBI ID

34154

Food Biomarker Ontology

Not Available

VMH ID

M00336

MarkerDB ID

MDB00000452

Good Scents ID

Not Available

References

Synthesis Reference

Banks, A.; Keay, J. N.; Smith, J. G. M. Structure of conjugated methyl linoleate hydroperoxide. Nature (London, United Kingdom) (1957), 179 1078.

Material Safety Data Sheet (MSDS)

Not Available

General References

Horrobin DF, Ziboh VA: The importance of linoleic acid metabolites in cancer metastasis and in the synthesis and actions of 13-HODE. Adv Exp Med Biol. 1997;433:291-4. [PubMed:9561154 ]
Spindler SA, Sarkar FH, Sakr WA, Blackburn ML, Bull AW, LaGattuta M, Reddy RG: Production of 13-hydroxyoctadecadienoic acid (13-HODE) by prostate tumors and cell lines. Biochem Biophys Res Commun. 1997 Oct 29;239(3):775-81. [PubMed:9367845 ]
Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 13-HODE (HMDB0004667)

MOL for HMDB0004667 (13-HODE)

3D MOL for HMDB0004667 (13-HODE)

3D SDF for HMDB0004667 (13-HODE)

3D-SDF for HMDB0004667 (13-HODE)

PDB for HMDB0004667 (13-HODE)

3D PDB for HMDB0004667 (13-HODE)

SMILES for HMDB0004667 (13-HODE)

INCHI for HMDB0004667 (13-HODE)

Structure for HMDB0004667 (13-HODE)

3D Structure for HMDB0004667 (13-HODE)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra