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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:36:10 UTC

Update Date

2021-09-26 22:57:22 UTC

HMDB ID

HMDB0247599

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-Hydroxylinoleic acid

Description

9-Hydroxylinoleic acid belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Based on a literature review a significant number of articles have been published on 9-Hydroxylinoleic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 9-hydroxylinoleic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 9-Hydroxylinoleic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247599
     RDKit          3D
9-Hydroxylinoleic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    7.9348   -2.2747    0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4259   -0.8734    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431   -0.7628    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    0.6638    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5145    1.0500   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    0.5481   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235   -0.1978    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -0.6240    1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -0.1019    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    0.6579    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    0.9618    1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    1.1521   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013    0.6870   -0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435    1.1189    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8396    0.6757    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9155    1.1466    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225    0.8741   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8441   -0.5818   -1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093   -1.3213   -0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1719   -1.1870   -1.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8497   -2.1914    0.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7837   -2.2936    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1628   -2.7219   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1390   -2.9005    1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2315   -0.2491    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2300   -0.4555    1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4050   -1.1292   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3788   -1.4599    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6779    1.0389    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5903    1.2414   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6120    0.8592   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651    2.1789   -0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8617   -0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585   -0.5406    1.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074   -0.2346    2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735   -1.7477    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.3736   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    0.2129    2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757    0.8383   -1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    2.2746   -0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844   -0.4471   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684    0.9805   -1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    0.8673    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4531    2.2596    0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652    0.8578    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8276   -0.4880    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9553    2.2914    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9210    0.8604    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006    1.4852   -1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9979    1.2249   -1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351   -1.0611   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9358   -0.6961   -2.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4921   -2.9543    0.2687 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  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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
  8 36  1  0
  9 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


  Mrv1533004161505452D          

 21 20  0  0  0  0            999 V2000
   -2.0033    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247599

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC=CCC=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/h6,8,14,19H,2-5,7,9-13,15-16H2,1H3,(H,20,21)

> <INCHI_KEY>
JDOLBVXUTAGQDQ-UHFFFAOYSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.451

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.28827405693208

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxyoctadeca-9,12-dienoic acid

> <ALOGPS_LOGP>
5.82

> <JCHEM_LOGP>
5.595122435333332

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.526696038981873

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.645823138558849

> <JCHEM_PKA_STRONGEST_BASIC>
-4.807753501569601

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.56509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxyoctadeca-9,12-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247599
     RDKit          3D
9-Hydroxylinoleic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    7.9348   -2.2747    0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4259   -0.8734    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431   -0.7628    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    0.6638    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5145    1.0500   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    0.5481   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235   -0.1978    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -0.6240    1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -0.1019    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    0.6579    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    0.9618    1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    1.1521   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013    0.6870   -0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435    1.1189    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8396    0.6757    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9155    1.1466    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225    0.8741   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8441   -0.5818   -1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093   -1.3213   -0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1719   -1.1870   -1.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8497   -2.1914    0.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7837   -2.2936    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1628   -2.7219   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1390   -2.9005    1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2315   -0.2491    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2300   -0.4555    1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4050   -1.1292   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3788   -1.4599    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6779    1.0389    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5903    1.2414   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6120    0.8592   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651    2.1789   -0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8617   -0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585   -0.5406    1.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074   -0.2346    2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735   -1.7477    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.3736   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    0.2129    2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757    0.8383   -1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    2.2746   -0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844   -0.4471   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684    0.9805   -1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    0.8673    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4531    2.2596    0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652    0.8578    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8276   -0.4880    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9553    2.2914    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9210    0.8604    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006    1.4852   -1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9979    1.2249   -1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351   -1.0611   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9358   -0.6961   -2.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4921   -2.9543    0.2687 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  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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
  8 36  1  0
  9 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                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -3.739  11.701   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.406  10.931   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.406   9.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.072   8.621   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.072   7.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.262   6.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.263   2.461   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.932   2.461   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    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0247599
HETATM    1  C1  UNL     1       7.935  -2.275   0.933  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.426  -0.873   0.855  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.143  -0.763   0.050  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.743   0.664   0.052  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.515   1.050  -0.660  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.231   0.548  -0.214  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.924  -0.198   0.801  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.520  -0.624   1.105  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.559  -0.102   0.135  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.438   0.658   0.531  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.575   0.962   1.856  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.366   1.152  -0.480  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.801   0.687  -0.316  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.443   1.119   0.941  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.840   0.676   1.139  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.916   1.147   0.262  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.922   0.874  -1.189  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.844  -0.582  -1.546  1.00  0.00           C  
HETATM   19  C18 UNL     1      -7.009  -1.321  -0.972  1.00  0.00           C  
HETATM   20  O2  UNL     1      -8.172  -1.187  -1.437  1.00  0.00           O  
HETATM   21  O3  UNL     1      -6.850  -2.191   0.104  1.00  0.00           O  
HETATM   22  H1  UNL     1       8.784  -2.294   1.647  1.00  0.00           H  
HETATM   23  H2  UNL     1       8.163  -2.722  -0.033  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.139  -2.901   1.408  1.00  0.00           H  
HETATM   25  H4  UNL     1       8.232  -0.249   0.388  1.00  0.00           H  
HETATM   26  H5  UNL     1       7.230  -0.455   1.857  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.405  -1.129  -0.995  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.379  -1.460   0.395  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.678   1.039   1.100  1.00  0.00           H  
HETATM   30  H9  UNL     1       6.590   1.241  -0.415  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.612   0.859  -1.782  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.465   2.179  -0.626  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.365   0.862  -0.859  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.659  -0.541   1.506  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.307  -0.235   2.120  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.473  -1.748   1.164  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.714  -0.374  -0.911  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.624   0.213   2.550  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.076   0.838  -1.511  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.369   2.275  -0.531  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.784  -0.447  -0.333  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.368   0.981  -1.189  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.807   0.867   1.838  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.453   2.260   0.982  1.00  0.00           H  
HETATM   45  H24 UNL     1      -5.165   0.858   2.229  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.828  -0.488   1.159  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.955   2.291   0.417  1.00  0.00           H  
HETATM   48  H27 UNL     1      -6.921   0.860   0.730  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.301   1.485  -1.812  1.00  0.00           H  
HETATM   50  H29 UNL     1      -6.998   1.225  -1.539  1.00  0.00           H  
HETATM   51  H30 UNL     1      -4.935  -1.061  -1.177  1.00  0.00           H  
HETATM   52  H31 UNL     1      -5.936  -0.696  -2.651  1.00  0.00           H  
HETATM   53  H32 UNL     1      -7.492  -2.954   0.269  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   35   36
CONECT    9   10   10   37
CONECT   10   11   12
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

HMDB0247599
     RDKit          3D
9-Hydroxylinoleic acid
 53 52  0  0  0  0  0  0  0  0999 V2000
    7.9348   -2.2747    0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4259   -0.8734    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431   -0.7628    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    0.6638    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5145    1.0500   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    0.5481   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235   -0.1978    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -0.6240    1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -0.1019    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    0.6579    0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5753    0.9618    1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    1.1521   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013    0.6870   -0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435    1.1189    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8396    0.6757    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9155    1.1466    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225    0.8741   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8441   -0.5818   -1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093   -1.3213   -0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1719   -1.1870   -1.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8497   -2.1914    0.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7837   -2.2936    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1628   -2.7219   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1390   -2.9005    1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2315   -0.2491    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2300   -0.4555    1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4050   -1.1292   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3788   -1.4599    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6779    1.0389    1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5903    1.2414   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6120    0.8592   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651    2.1789   -0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8617   -0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585   -0.5406    1.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3074   -0.2346    2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735   -1.7477    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.3736   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    0.2129    2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757    0.8383   -1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    2.2746   -0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844   -0.4471   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684    0.9805   -1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    0.8673    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4531    2.2596    0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652    0.8578    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8276   -0.4880    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9553    2.2914    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9210    0.8604    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006    1.4852   -1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9979    1.2249   -1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351   -1.0611   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9358   -0.6961   -2.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4921   -2.9543    0.2687 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  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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
  8 36  1  0
  9 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
9-Hydroxylinoleate	Generator
9-Hydroxyoctadeca-9,12-dienoate	HMDB

Chemical Formula

C₁₈H₃₂O₃

Average Molecular Weight

296.451

Monoisotopic Molecular Weight

296.23514489

IUPAC Name

9-hydroxyoctadeca-9,12-dienoic acid

Traditional Name

9-hydroxyoctadeca-9,12-dienoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=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/h6,8,14,19H,2-5,7,9-13,15-16H2,1H3,(H,20,21)

InChI Key

JDOLBVXUTAGQDQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.82	ALOGPS
logP	5.6	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-4.8	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	90.57 m³·mol⁻¹	ChemAxon
Polarizability	36.29 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
DeepCCS	[M+H]+	176.979	30932474
DeepCCS	[M-H]-	173.169	30932474
DeepCCS	[M-2H]-	209.698	30932474
DeepCCS	[M+Na]+	185.794	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	177.9	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.4	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	183.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.9675 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2973.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	369.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	213.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	545.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	948.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	556.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1853.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	582.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1654.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	652.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	528.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	536.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxylinoleic acid	CCCCCC=CCC=C(O)CCCCCCCC(O)=O	3674.0	Standard polar	33892256
9-Hydroxylinoleic acid	CCCCCC=CCC=C(O)CCCCCCCC(O)=O	2218.1	Standard non polar	33892256
9-Hydroxylinoleic acid	CCCCCC=CCC=C(O)CCCCCCCC(O)=O	2364.4	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 - 9-Hydroxylinoleic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9770000000-9a923ede4b6ea8eb3a7d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxylinoleic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxylinoleic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxylinoleic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxylinoleic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxylinoleic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxylinoleic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxylinoleic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - 9-Hydroxylinoleic acid 10V, Positive-QTOF	splash10-004j-1290000000-e2ada0aae0021ae92d09	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxylinoleic acid 20V, Positive-QTOF	splash10-0a4j-9530000000-40ebe25cc89f20a79159	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxylinoleic acid 40V, Positive-QTOF	splash10-0api-9100000000-3832483e5e9a20a6dda1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxylinoleic acid 10V, Negative-QTOF	splash10-0002-0090000000-ac1c086be68f1b68836b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxylinoleic acid 20V, Negative-QTOF	splash10-002b-0590000000-f8755d2c5ff9157b4e5d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxylinoleic acid 40V, Negative-QTOF	splash10-054o-5920000000-d9bc42915ef4c635daad	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73226949

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 9-Hydroxylinoleic acid (HMDB0247599)

MOL for HMDB0247599 (9-Hydroxylinoleic acid)

3D MOL for HMDB0247599 (9-Hydroxylinoleic acid)

3D SDF for HMDB0247599 (9-Hydroxylinoleic acid)

3D-SDF for HMDB0247599 (9-Hydroxylinoleic acid)

PDB for HMDB0247599 (9-Hydroxylinoleic acid)

3D PDB for HMDB0247599 (9-Hydroxylinoleic acid)

SMILES for HMDB0247599 (9-Hydroxylinoleic acid)

INCHI for HMDB0247599 (9-Hydroxylinoleic acid)

Structure for HMDB0247599 (9-Hydroxylinoleic acid)

3D Structure for HMDB0247599 (9-Hydroxylinoleic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra