MiMeDB: Showing metabocard for (10E,12Z)-9-HODE (MMDBc0000790)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 21:51:52 UTC

Update Date

2024-04-30 19:33:42 UTC

Metabolite ID

MMDBc0000790

Metabolite Identification

Common Name

(10E,12Z)-9-HODE

Description

(10E,12Z)-9-HODE, also known as 9-Hydroxy-10E,12Z-octadecadienoic acid or 9-Hydroxylinoleic acid, 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)-9-HODE is considered to be practically insoluble (in water) and acidic. (10E,12Z)-9-HODE is an octadecanoid lipid molecule

Structure

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

HMDB0062652
     RDKit          3D
(10E,12Z)-9-HODE
 53 52  0  0  0  0  0  0  0  0999 V2000
    6.9212    0.1734   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7421   -0.7983   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424   -1.2060    1.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9132   -0.1623    2.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    0.6421    1.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988    1.4323    0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8449    1.3071   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.3391   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    0.1968   -1.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373   -0.8599   -1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -2.0441   -0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -0.2357   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524    1.0105   -1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.7688   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    0.8813    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    0.3860   -1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6654   -0.4928   -1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713    0.0845   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7191    0.5147    0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1365    1.6590    1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1185   -0.2989    1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4744    0.1422    0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5539   -0.0735   -1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133    1.1971   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215   -1.7495   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9777   -0.4298   -0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562   -1.6981    1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289   -2.0569    1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020   -0.6794    3.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8023    0.4716    2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564    0.0694    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    1.3845    2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4622    2.2164    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221    1.9622   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -0.3357    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105    0.8432   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -1.0329   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689   -2.0448    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9534   -0.9817   -0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -0.0180    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556    0.7179   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135    1.6548   -1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    2.1418    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888    2.6582   -0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5678    1.5314    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.0303    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -0.1885   -1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7478    1.2521   -1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753   -1.4336   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9800   -0.9437   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6882   -0.7005   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2309    0.9432   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7545   -0.7414    2.5404 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
 10 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  0
  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

      
  Mrv1652311101716532D          

 25 24  0  0  0  0            999 V2000
    2.8065    5.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    4.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    2.8578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6644    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8078    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5223    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6657    2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6657    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000790

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+

> <INCHI_KEY>
NPDSHTNEKLQQIJ-ZJHFMPGASA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.451

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.42721081023866

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.191065727333333

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677864657474

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745528848431

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759708475080179

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.03429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062652
     RDKit          3D
(10E,12Z)-9-HODE
 53 52  0  0  0  0  0  0  0  0999 V2000
    6.9212    0.1734   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7421   -0.7983   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424   -1.2060    1.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9132   -0.1623    2.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    0.6421    1.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988    1.4323    0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8449    1.3071   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.3391   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    0.1968   -1.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373   -0.8599   -1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -2.0441   -0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -0.2357   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524    1.0105   -1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.7688   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    0.8813    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    0.3860   -1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6654   -0.4928   -1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713    0.0845   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7191    0.5147    0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1365    1.6590    1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1185   -0.2989    1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4744    0.1422    0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5539   -0.0735   -1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133    1.1971   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215   -1.7495   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9777   -0.4298   -0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562   -1.6981    1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289   -2.0569    1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020   -0.6794    3.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8023    0.4716    2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564    0.0694    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    1.3845    2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4622    2.2164    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221    1.9622   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -0.3357    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105    0.8432   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -1.0329   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689   -2.0448    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9534   -0.9817   -0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -0.0180    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556    0.7179   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135    1.6548   -1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    2.1418    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888    2.6582   -0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5678    1.5314    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.0303    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -0.1885   -1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7478    1.2521   -1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753   -1.4336   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9800   -0.9437   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6882   -0.7005   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2309    0.9432   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7545   -0.7414    2.5404 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
 10 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  0
  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                                 10-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-NOV-17         0                                  
HETATM    1  H   UNK     0       5.239  10.725   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.573   9.955   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.906  10.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.906  12.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.240  13.035   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.240  14.575   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.574  15.345   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.573   8.415   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       5.239   7.645   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       9.240   8.415   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       6.573   5.335   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0062652
HETATM    1  C1  UNL     1       6.921   0.173  -0.183  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.742  -0.798  -0.197  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.342  -1.206   1.173  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.913  -0.162   2.114  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.708   0.642   1.808  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.699   1.432   0.592  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.845   1.307  -0.401  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.789   0.339  -0.398  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.917   0.197  -1.383  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.137  -0.860  -1.244  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.350  -2.044  -0.756  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.175  -0.236  -0.302  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.652   1.010  -1.011  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.668   1.769  -0.238  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.874   0.881   0.043  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.487   0.386  -1.214  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.665  -0.493  -1.085  1.00  0.00           C  
HETATM   18  C17 UNL     1      -6.871   0.085  -0.453  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.719   0.515   0.924  1.00  0.00           C  
HETATM   20  O2  UNL     1      -7.137   1.659   1.308  1.00  0.00           O  
HETATM   21  O3  UNL     1      -6.118  -0.299   1.867  1.00  0.00           O  
HETATM   22  H1  UNL     1       7.474   0.142   0.772  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.554  -0.073  -1.058  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.513   1.197  -0.400  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.122  -1.750  -0.698  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.978  -0.430  -0.868  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.256  -1.698   1.630  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.629  -2.057   1.068  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.702  -0.679   3.104  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.802   0.472   2.356  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.756   0.069   1.940  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.633   1.384   2.692  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.462   2.216   0.459  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.922   1.962  -1.282  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.659  -0.336   0.432  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.011   0.843  -2.232  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.560  -1.033  -2.249  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.469  -2.045   0.230  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.953  -0.982  -0.142  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.682  -0.018   0.660  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.956   0.718  -2.036  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.713   1.655  -1.107  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.212   2.142   0.700  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.989   2.658  -0.804  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.568   1.531   0.614  1.00  0.00           H  
HETATM   46  H25 UNL     1      -3.526   0.030   0.673  1.00  0.00           H  
HETATM   47  H26 UNL     1      -3.730  -0.189  -1.838  1.00  0.00           H  
HETATM   48  H27 UNL     1      -4.748   1.252  -1.888  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.375  -1.434  -0.493  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.980  -0.944  -2.070  1.00  0.00           H  
HETATM   51  H30 UNL     1      -7.688  -0.700  -0.563  1.00  0.00           H  
HETATM   52  H31 UNL     1      -7.231   0.943  -1.104  1.00  0.00           H  
HETATM   53  H32 UNL     1      -6.755  -0.741   2.540  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    7   33
CONECT    7    8   34
CONECT    8    9    9   35
CONECT    9   10   36
CONECT   10   11   12   37
CONECT   11   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

HMDB0062652
     RDKit          3D
(10E,12Z)-9-HODE
 53 52  0  0  0  0  0  0  0  0999 V2000
    6.9212    0.1734   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7421   -0.7983   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424   -1.2060    1.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9132   -0.1623    2.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    0.6421    1.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988    1.4323    0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8449    1.3071   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.3391   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    0.1968   -1.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373   -0.8599   -1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499   -2.0441   -0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -0.2357   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524    1.0105   -1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.7688   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    0.8813    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4868    0.3860   -1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6654   -0.4928   -1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713    0.0845   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7191    0.5147    0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1365    1.6590    1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1185   -0.2989    1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4744    0.1422    0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5539   -0.0735   -1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133    1.1971   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215   -1.7495   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9777   -0.4298   -0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562   -1.6981    1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289   -2.0569    1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020   -0.6794    3.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8023    0.4716    2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564    0.0694    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    1.3845    2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4622    2.2164    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221    1.9622   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -0.3357    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105    0.8432   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -1.0329   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689   -2.0448    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9534   -0.9817   -0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -0.0180    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556    0.7179   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135    1.6548   -1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    2.1418    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888    2.6582   -0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5678    1.5314    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.0303    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298   -0.1885   -1.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7478    1.2521   -1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753   -1.4336   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9800   -0.9437   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6882   -0.7005   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2309    0.9432   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7545   -0.7414    2.5404 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
 10 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  0
  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

Synonyms

Value	Source
(10E,12Z)-9-HODE	ChEBI
9-Hydroxy-10E,12Z-octadecadienoic acid	ChEBI
9-Hydroxy-trans-10,cis-12-octadecadienoic acid	ChEBI
9-Hydroxy-10E,12Z-octadecadienoate	Generator
9-Hydroxy-trans-10,cis-12-octadecadienoate	Generator
9-Hydroxylinoleic acid	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomer	MeSH
Dimorphecolic acid	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomer	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomer	MeSH
9-OH-18:2DElta(10t,12t)	MeSH
9-Hydroxy-10,12-octadecadienoic acid	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomer	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomer	MeSH
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomer	MeSH
(10E,12Z)-9-hydroxy-10,12-octadecadienoic acid	SMPDB, HMDB
9-hydroxy-10E,12Z-octadecadienoic acid	SMPDB, HMDB, ChEBI
9-hydroxy-(10E,12Z)-octadeca-10,12-dienoic acid	SMPDB, HMDB
9-hydroxy-10(E),12(Z)-octadecadienoic acid	SMPDB, HMDB
9-hydroxy-10-trans-12-cis-octadecadienoic acid	SMPDB, HMDB
9-hydroxy-trans-10-cis-12-octadecadienoic acid	SMPDB, HMDB
9-hydroxyoctadeca-10,12-dienoic acid	SMPDB, HMDB
9-(E,Z)-HODE	SMPDB, HMDB
9-HODE	SMPDB, HMDB
9-hydroxylinoleic acid	SMPDB, HMDB, MeSH
(10E,12Z)-9-HODE	SMPDB, HMDB, ChEBI

Molecular Formula

C₁₈H₃₂O₃

Average Mass

296.451

Monoisotopic Mass

296.23514489

IUPAC Name

(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

Traditional Name

(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+

InChI Key

NPDSHTNEKLQQIJ-ZJHFMPGASA-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:72651 )
Other Octadecanoids (LMFA02000151 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	5.88	ALOGPS
logP	5.19	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.68	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	37.43 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0062652

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

9-Hydroxyoctadecadienoic acid

METLIN ID

Not Available

PubChem Compound

5282944

PDB ID

Not Available

ChEBI ID

72651

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. 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 (10E,12Z)-9-HODE (MMDBc0000790)

MOL for #<Metabolite:0x00007f9228ae1868>

3D MOL for #<Metabolite:0x00007f9228ae1868>

3D SDF for #<Metabolite:0x00007f9228ae1868>

3D-SDF for #<Metabolite:0x00007f9228ae1868>

PDB for #<Metabolite:0x00007f9228ae1868>

3D PDB for #<Metabolite:0x00007f9228ae1868>

SMILES for #<Metabolite:0x00007f9228ae1868>

INCHI for #<Metabolite:0x00007f9228ae1868>

Structure for #<Metabolite:0x00007f9228ae1868>

3D Structure for #<Metabolite:0x00007f9228ae1868>