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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:10:16 UTC

Update Date

2022-03-07 02:56:39 UTC

HMDB ID

HMDB0040611

Secondary Accession Numbers

HMDB40611

Metabolite Identification

Common Name

(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid

Description

(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid, also known as (12E)-9,10-dihydroxy-8-oxooctadec-12-enoate, 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 small amount of articles have been published on (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid.

Structure

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

HMDB0040611
     RDKit          3D
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.4199    2.2867    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2599    1.2794   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219    0.1483   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7629   -0.4586    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116   -1.5970    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6407   -1.1948   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -1.3521    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   -0.9742   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639   -2.2236   -0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -2.7909    0.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646   -2.1682   -1.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -3.5382   -1.9838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -1.5309   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -2.2051   -1.1320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0797   -0.1127   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.2691   -0.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016    1.7151   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    2.5008    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5985    2.1863    1.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315    0.8929    1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2330    0.6877    2.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2325    1.5812    3.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011   -0.4380    2.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7483    3.3189    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3718    2.0273    1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    2.2241    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9791    0.8461    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7686    1.7362   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8420   -0.5852   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5136    0.6162   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5871   -0.8286    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1703    0.3344    1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3293   -2.4080   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4651   -2.0541    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315   -0.7753   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3097   -1.7684    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.5379   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -0.1855   -0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -3.0394   -1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -2.0957    1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4090   -1.7497   -2.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -3.8998   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    0.5304   -1.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    0.2195   -0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -0.0527   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016   -0.3721    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293    1.8327    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925    2.1885   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167    2.6464   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    3.5881    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0948    2.2900    2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4132    2.9848    1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799    1.0232    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7439    0.0124    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8821   -1.0301    3.1466 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  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

  Mrv0541 05061311592D          

 23 22  0  0  0  0            999 V2000
   14.9526   -6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040611

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C\CC(O)C(O)C(=O)CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O5/c1-2-3-4-5-6-9-12-15(19)18(23)16(20)13-10-7-8-11-14-17(21)22/h6,9,15,18-19,23H,2-5,7-8,10-14H2,1H3,(H,21,22)/b9-6+

> <INCHI_KEY>
NIOKCFABUMZUDL-RMKNXTFCSA-N

> <FORMULA>
C18H32O5

> <MOLECULAR_WEIGHT>
328.4437

> <EXACT_MASS>
328.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.537100750824294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12E)-9,10-dihydroxy-8-oxooctadec-12-enoic acid

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.6586111979999996

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.417239908273025

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.278127671534757

> <JCHEM_PKA_STRONGEST_BASIC>
-3.247694723978518

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
90.89729999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12E)-9,10-dihydroxy-8-oxooctadec-12-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040611
     RDKit          3D
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.4199    2.2867    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2599    1.2794   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219    0.1483   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7629   -0.4586    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116   -1.5970    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6407   -1.1948   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -1.3521    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   -0.9742   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639   -2.2236   -0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -2.7909    0.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646   -2.1682   -1.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -3.5382   -1.9838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -1.5309   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -2.2051   -1.1320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0797   -0.1127   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.2691   -0.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016    1.7151   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    2.5008    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5985    2.1863    1.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315    0.8929    1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2330    0.6877    2.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2325    1.5812    3.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011   -0.4380    2.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7483    3.3189    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3718    2.0273    1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    2.2241    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9791    0.8461    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7686    1.7362   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8420   -0.5852   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5136    0.6162   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5871   -0.8286    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1703    0.3344    1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3293   -2.4080   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4651   -2.0541    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315   -0.7753   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3097   -1.7684    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.5379   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -0.1855   -0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -3.0394   -1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -2.0957    1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4090   -1.7497   -2.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -3.8998   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    0.5304   -1.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    0.2195   -0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -0.0527   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016   -0.3721    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293    1.8327    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925    2.1885   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167    2.6464   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    3.5881    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0948    2.2900    2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4132    2.9848    1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799    1.0232    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7439    0.0124    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8821   -1.0301    3.1466 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  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
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  9 39  1  0
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 11 41  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      27.912 -13.035   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.578 -12.265   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.578 -10.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.244  -9.955   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.244  -8.415   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.911  -7.645   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.575  -5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.241  -6.105   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.911  -6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.908  -6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.907  -5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.577  -5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.242  -5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.574  -6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.243  -6.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.576  -6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.909  -5.335   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      21.243  -7.645   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      18.576  -7.645   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.906  -6.105   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.240  -3.795   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      19.909  -3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18   19                                                  
CONECT   16   13   18   20                                                  
CONECT   17   14   21   22                                                  
CONECT   18   15   16   23                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0040611
HETATM    1  C1  UNL     1      -6.420   2.287   0.654  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.260   1.279  -0.136  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.322   0.148  -0.564  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.763  -0.459   0.684  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.812  -1.597   0.407  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.641  -1.195  -0.398  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.430  -1.352   0.118  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.180  -0.974  -0.620  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.364  -2.224  -0.766  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.004  -2.791   0.450  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.765  -2.168  -1.740  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.102  -3.538  -1.984  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.002  -1.531  -1.265  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.010  -2.205  -1.132  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.080  -0.113  -0.945  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.570   0.269  -0.593  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.502   1.715  -0.290  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.695   2.501   0.005  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.598   2.186   1.128  1.00  0.00           C  
HETATM   20  C17 UNL     1       6.331   0.893   1.017  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.233   0.688   2.219  1.00  0.00           C  
HETATM   22  O4  UNL     1       7.232   1.581   3.089  1.00  0.00           O  
HETATM   23  O5  UNL     1       8.001  -0.438   2.316  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.748   3.319   0.443  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.372   2.027   1.712  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.368   2.224   0.252  1.00  0.00           H  
HETATM   27  H4  UNL     1      -7.979   0.846   0.589  1.00  0.00           H  
HETATM   28  H5  UNL     1      -7.769   1.736  -0.991  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.842  -0.585  -1.198  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.514   0.616  -1.196  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.587  -0.829   1.297  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.170   0.334   1.203  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.329  -2.408  -0.174  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.465  -2.054   1.350  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.731  -0.775  -1.395  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.310  -1.768   1.111  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.492  -0.538  -1.567  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.718  -0.185  -0.003  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.074  -3.039  -1.204  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.005  -2.096   1.173  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.409  -1.750  -2.713  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.292  -3.900  -1.071  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.836   0.530  -1.795  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.542   0.219  -0.043  1.00  0.00           H  
HETATM   45  H22 UNL     1       4.180  -0.053  -1.423  1.00  0.00           H  
HETATM   46  H23 UNL     1       3.702  -0.372   0.337  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.729   1.833   0.533  1.00  0.00           H  
HETATM   48  H25 UNL     1       2.992   2.188  -1.202  1.00  0.00           H  
HETATM   49  H26 UNL     1       5.317   2.646  -0.960  1.00  0.00           H  
HETATM   50  H27 UNL     1       4.326   3.588   0.137  1.00  0.00           H  
HETATM   51  H28 UNL     1       5.095   2.290   2.130  1.00  0.00           H  
HETATM   52  H29 UNL     1       6.413   2.985   1.186  1.00  0.00           H  
HETATM   53  H30 UNL     1       7.080   1.023   0.166  1.00  0.00           H  
HETATM   54  H31 UNL     1       5.744   0.012   0.854  1.00  0.00           H  
HETATM   55  H32 UNL     1       7.882  -1.030   3.147  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   11   39
CONECT   10   40
CONECT   11   12   13   41
CONECT   12   42
CONECT   13   14   14   15
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   47   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   22   23
CONECT   23   55
END

HMDB0040611
     RDKit          3D
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.4199    2.2867    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2599    1.2794   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219    0.1483   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7629   -0.4586    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116   -1.5970    0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6407   -1.1948   -0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303   -1.3521    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   -0.9742   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639   -2.2236   -0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -2.7909    0.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646   -2.1682   -1.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -3.5382   -1.9838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -1.5309   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -2.2051   -1.1320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0797   -0.1127   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.2691   -0.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016    1.7151   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    2.5008    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5985    2.1863    1.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315    0.8929    1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2330    0.6877    2.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2325    1.5812    3.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011   -0.4380    2.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7483    3.3189    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3718    2.0273    1.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    2.2241    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9791    0.8461    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7686    1.7362   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8420   -0.5852   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5136    0.6162   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5871   -0.8286    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1703    0.3344    1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3293   -2.4080   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4651   -2.0541    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315   -0.7753   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3097   -1.7684    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.5379   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -0.1855   -0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -3.0394   -1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -2.0957    1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4090   -1.7497   -2.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -3.8998   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    0.5304   -1.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    0.2195   -0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -0.0527   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016   -0.3721    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293    1.8327    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925    2.1885   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167    2.6464   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    3.5881    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0948    2.2900    2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4132    2.9848    1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799    1.0232    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7439    0.0124    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8821   -1.0301    3.1466 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  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoate	Generator
(12E)-9,10-Dihydroxy-8-oxooctadec-12-enoate	HMDB

Chemical Formula

C₁₈H₃₂O₅

Average Molecular Weight

328.4437

Monoisotopic Molecular Weight

328.224974134

IUPAC Name

(12E)-9,10-dihydroxy-8-oxooctadec-12-enoic acid

Traditional Name

(12E)-9,10-dihydroxy-8-oxooctadec-12-enoic acid

CAS Registry Number

142036-13-3

SMILES

CCCCC\C=C\CC(O)C(O)C(=O)CCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O5/c1-2-3-4-5-6-9-12-15(19)18(23)16(20)13-10-7-8-11-14-17(21)22/h6,9,15,18-19,23H,2-5,7-8,10-14H2,1H3,(H,21,22)/b9-6+

InChI Key

NIOKCFABUMZUDL-RMKNXTFCSA-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
Keto fatty acid
Acyloin
Beta-hydroxy ketone
Fatty acid
Unsaturated fatty acid
Monosaccharide
Alpha-hydroxy ketone
1,2-diol
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0040611)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040611)

Source

Endogenous

Endogenous (HMDB: HMDB0040611)

Plant

Plant (HMDB: HMDB0040611)

Animal

Animal (HMDB: HMDB0040611)

Exogenous

Food

Food (HMDB: HMDB0040611)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0040611)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040611)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040611)

Lipid metabolism pathway (HMDB: HMDB0040611)

Cellular process

Cell signaling (HMDB: HMDB0040611)

Biochemical process

Lipid transport (HMDB: HMDB0040611)

Role

Biological role

Energy source (HMDB: HMDB0040611)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040611)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	56 - 57 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.66	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.28	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	90.9 m³·mol⁻¹	ChemAxon
Polarizability	38.54 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	184.605	31661259
DarkChem	[M-H]-	182.168	31661259
DeepCCS	[M+H]+	186.057	30932474
DeepCCS	[M-H]-	183.699	30932474
DeepCCS	[M-2H]-	216.585	30932474
DeepCCS	[M+Na]+	192.15	30932474
AllCCS	[M+H]+	188.5	32859911
AllCCS	[M+H-H2O]+	185.7	32859911
AllCCS	[M+NH4]+	191.0	32859911
AllCCS	[M+Na]+	191.8	32859911
AllCCS	[M-H]-	184.8	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	188.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid	CCCCC\C=C\CC(O)C(O)C(=O)CCCCCCC(O)=O	4138.4	Standard polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid	CCCCC\C=C\CC(O)C(O)C(=O)CCCCCCC(O)=O	2334.2	Standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid	CCCCC\C=C\CC(O)C(O)C(=O)CCCCCCC(O)=O	2491.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C)C(O)C(=O)CCCCCCC(=O)O	2635.3	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TMS,isomer #2	CCCCC/C=C/CC(O)C(O[Si](C)(C)C)C(=O)CCCCCCC(=O)O	2642.3	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TMS,isomer #3	CCCCC/C=C/CC(O)C(O)C(=O)CCCCCCC(=O)O[Si](C)(C)C	2692.4	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TMS,isomer #4	CCCCC/C=C/CC(O)C(O)=C(CCCCCCC(=O)O)O[Si](C)(C)C	2673.4	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TMS,isomer #5	CCCCC/C=C/CC(O)C(O)C(=CCCCCCC(=O)O)O[Si](C)(C)C	2715.1	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)CCCCCCC(=O)O	2664.0	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C)C(O)C(=O)CCCCCCC(=O)O[Si](C)(C)C	2664.2	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #3	CCCCC/C=C/CC(O[Si](C)(C)C)C(O)=C(CCCCCCC(=O)O)O[Si](C)(C)C	2731.8	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #4	CCCCC/C=C/CC(O[Si](C)(C)C)C(O)C(=CCCCCCC(=O)O)O[Si](C)(C)C	2726.2	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #5	CCCCC/C=C/CC(O)C(O[Si](C)(C)C)C(=O)CCCCCCC(=O)O[Si](C)(C)C	2663.2	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #6	CCCCC/C=C/CC(O)C(O[Si](C)(C)C)=C(CCCCCCC(=O)O)O[Si](C)(C)C	2651.6	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #7	CCCCC/C=C/CC(O)C(O[Si](C)(C)C)C(=CCCCCCC(=O)O)O[Si](C)(C)C	2731.5	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #8	CCCCC/C=C/CC(O)C(O)=C(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2668.9	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TMS,isomer #9	CCCCC/C=C/CC(O)C(O)C(=CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2687.5	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)CCCCCCC(=O)O[Si](C)(C)C	2659.5	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(CCCCCCC(=O)O)O[Si](C)(C)C	2694.3	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TMS,isomer #3	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=CCCCCCC(=O)O)O[Si](C)(C)C	2728.7	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TMS,isomer #4	CCCCC/C=C/CC(O[Si](C)(C)C)C(O)=C(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2707.3	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TMS,isomer #5	CCCCC/C=C/CC(O[Si](C)(C)C)C(O)C(=CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2673.5	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TMS,isomer #6	CCCCC/C=C/CC(O)C(O[Si](C)(C)C)=C(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2631.4	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TMS,isomer #7	CCCCC/C=C/CC(O)C(O[Si](C)(C)C)C(=CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2660.6	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2657.6	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2598.4	Standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2660.5	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2601.6	Standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TBDMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O)C(=O)CCCCCCC(=O)O	2872.3	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TBDMS,isomer #2	CCCCC/C=C/CC(O)C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCCCC(=O)O	2899.1	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TBDMS,isomer #3	CCCCC/C=C/CC(O)C(O)C(=O)CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2934.4	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TBDMS,isomer #4	CCCCC/C=C/CC(O)C(O)=C(CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2934.8	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,1TBDMS,isomer #5	CCCCC/C=C/CC(O)C(O)C(=CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2982.4	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCCCC(=O)O	3115.9	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O)C(=O)CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3141.6	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #3	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O)=C(CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3204.7	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #4	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O)C(=CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3188.0	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #5	CCCCC/C=C/CC(O)C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3126.6	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #6	CCCCC/C=C/CC(O)C(O[Si](C)(C)C(C)(C)C)=C(CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3156.4	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #7	CCCCC/C=C/CC(O)C(O[Si](C)(C)C(C)(C)C)C(=CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3179.3	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #8	CCCCC/C=C/CC(O)C(O)=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3157.5	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,2TBDMS,isomer #9	CCCCC/C=C/CC(O)C(O)C(=CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3178.1	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TBDMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3334.1	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TBDMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3409.7	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TBDMS,isomer #3	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3378.0	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TBDMS,isomer #4	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O)=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3441.5	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TBDMS,isomer #5	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O)C(=CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3402.0	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TBDMS,isomer #6	CCCCC/C=C/CC(O)C(O[Si](C)(C)C(C)(C)C)=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3388.1	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,3TBDMS,isomer #7	CCCCC/C=C/CC(O)C(O[Si](C)(C)C(C)(C)C)C(=CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3379.6	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TBDMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3591.8	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TBDMS,isomer #1	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3197.3	Standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TBDMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3541.3	Semi standard non polar	33892256
(9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid,4TBDMS,isomer #2	CCCCC/C=C/CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3245.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4901000000-46b6a4d6b03e57e95d5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00ou-7667490000-eb886c59cd8a5f73e65f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 10V, Positive-QTOF	splash10-03di-0439000000-95e71d8b43ea783084d3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 20V, Positive-QTOF	splash10-03di-4911000000-4a8c9bb116ea31892f1c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 40V, Positive-QTOF	splash10-06r6-9400000000-73a38c20a9251231be75	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 10V, Negative-QTOF	splash10-004i-0609000000-80c22f8f39cc7a5fcf7b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 20V, Negative-QTOF	splash10-0a4i-0911000000-7a590d0c6a34f483142e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 40V, Negative-QTOF	splash10-0a4i-9800000000-a2c3ab40fdf309f851ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 10V, Negative-QTOF	splash10-004i-0309000000-0d6cb6ba74daabd5d281	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 20V, Negative-QTOF	splash10-0adi-2914000000-a68982394eba25e1fb7a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 40V, Negative-QTOF	splash10-0abc-9600000000-bda82705339e02b12be4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 10V, Positive-QTOF	splash10-03fu-0439000000-0aaf110656ad98f0300f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 20V, Positive-QTOF	splash10-0bt9-9821000000-8e9da5fc0d3f826e72dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid 40V, Positive-QTOF	splash10-067i-9200000000-986e10d4ae86f7af94a3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB020402

KNApSAcK ID

Not Available

Chemspider ID

35014972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752865

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

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 ]
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Showing metabocard for (9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid (HMDB0040611)

MOL for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

3D MOL for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

3D SDF for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

3D-SDF for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

PDB for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

3D PDB for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

SMILES for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

INCHI for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

Structure for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

3D Structure for HMDB0040611 ((9R,10S,12Z)-9,10-Dihydroxy-8-oxo-12-octadecenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra