MiMeDB: Showing metabocard for 9,10-DHOME (MMDBc0000433)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:39 UTC

Update Date

2024-04-30 19:32:23 UTC

Metabolite ID

MMDBc0000433

Metabolite Identification

Common Name

9,10-DHOME

Description

9,10-Dihydroxy-12-octadecenoic acid (CAS: 263399-34-4), also known as 9,10-DHOME, is a derivative of linoleic acid diol and has been reported to be toxic in human's tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10-EpOME. 9,10-EpOME act as a protoxin, with the corresponding epoxide hydrolase metabolite 9,10-DHOME, specifically exerting toxicity. Both 9,10-EpOME and 9,10-DHOME are shown to have neutrophil chemotactic activity. 9,10-DHOME suppresses the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation (PMID: 12021203 , 12127265 , 17435320 ). 9,10-DHOME is found in fruits and can be isolated from the seeds of Cucurbita pepo.

Structure

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

HMDB0004704
     RDKit          3D
9,10-DHOME
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.4871   -1.0787    1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7460   -0.1327    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3953   -0.8017   -0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639    0.0995   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3372    0.5948   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5314   -0.5806   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.7937   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.1313   -1.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4165    0.7001   -1.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6050    1.3871   -0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7198   -0.2785   -1.4282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6236   -1.2272   -0.4338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0672    0.3673   -1.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.3525   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225    0.8609    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.2654    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115    0.1808    0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607   -0.9498    0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2806   -0.6068    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8358    0.4776    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9766    0.9746    1.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1783    1.0216    2.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3856   -0.5961    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8601   -1.3729    2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8184   -1.9964    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4024    0.7466    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8571    0.2237    1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3689   -1.0493   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8881   -1.7740   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3798   -0.4892   -2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2830    0.9334   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9905    1.3307   -1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633    1.1810    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9261   -1.3362    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7969   -1.7197   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.9779   -2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763   -0.4263   -2.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071    1.4917   -2.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743    1.0829    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -0.9128   -2.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -0.9745    0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8021   -0.4735   -1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814    0.8203   -2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    1.7954   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094    2.1908   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278    1.7128    1.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5432    0.6097    1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5401   -0.4763    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2097   -1.2024    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1601    1.0039    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709    0.5415   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773   -1.8591    0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -1.2978    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9290   -1.5275    0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -0.3441   -0.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033    0.5632    3.3274 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  1  0
 14 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  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END


  Mrv1652307191923432D          

 22 21  0  0  0  0            999 V2000
10002.223710002.4998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.938710002.0878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.652110002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.367410002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.192110002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.907610002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.623110002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.336410002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.051810002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.767310002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.938710001.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.509110002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.794210002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.079710002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.365010002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.650410002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.935710002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.221010002.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.506410002.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.789710002.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.506410003.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.223710003.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  1 22  1  1  0  0  0
  2  3  1  0  0  0  0
  2 11  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 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  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000433

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7-/t16-,17-/m1/s1

> <INCHI_KEY>
XEBKSQSGNGRGDW-GJWDQICYSA-N

> <FORMULA>
C18H34O4

> <MOLECULAR_WEIGHT>
314.466

> <EXACT_MASS>
314.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.63282950605321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.322176317

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.874418489893223

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6153253509261605

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148519607080268

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
90.43319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004704
     RDKit          3D
9,10-DHOME
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.4871   -1.0787    1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7460   -0.1327    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3953   -0.8017   -0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639    0.0995   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3372    0.5948   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5314   -0.5806   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.7937   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.1313   -1.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4165    0.7001   -1.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6050    1.3871   -0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7198   -0.2785   -1.4282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6236   -1.2272   -0.4338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0672    0.3673   -1.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.3525   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225    0.8609    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.2654    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115    0.1808    0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607   -0.9498    0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2806   -0.6068    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8358    0.4776    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9766    0.9746    1.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1783    1.0216    2.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3856   -0.5961    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8601   -1.3729    2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8184   -1.9964    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4024    0.7466    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8571    0.2237    1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3689   -1.0493   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8881   -1.7740   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3798   -0.4892   -2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2830    0.9334   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9905    1.3307   -1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633    1.1810    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9261   -1.3362    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7969   -1.7197   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.9779   -2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763   -0.4263   -2.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071    1.4917   -2.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743    1.0829    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -0.9128   -2.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -0.9745    0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8021   -0.4735   -1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814    0.8203   -2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    1.7954   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094    2.1908   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278    1.7128    1.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5432    0.6097    1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5401   -0.4763    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2097   -1.2024    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1601    1.0039    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709    0.5415   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773   -1.8591    0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -1.2978    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9290   -1.5275    0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -0.3441   -0.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033    0.5632    3.3274 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  1  0
 14 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  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8670.8178671.333   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8672.1528670.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8673.4848671.333   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.8198670.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8676.3598670.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8677.6948671.333   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8679.0308670.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8680.3618671.333   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8681.6978670.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8683.0328671.333   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8672.1528669.023   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8669.4848670.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.1498671.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.8158670.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.4818671.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.1478670.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.8138671.333   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.4798670.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8660.1458671.333   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8658.8078670.564   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8660.1458672.872   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8670.8178672.872   0.000  0.00  0.00           O+0
CONECT    1    2   12   22                                                  
CONECT    2    1    3   11                                                  
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                                                            
CONECT   11    2                                                            
CONECT   12    1   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                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0004704
HETATM    1  C1  UNL     1      -7.487  -1.079   1.869  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.746  -0.133   0.950  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.395  -0.802  -0.364  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.664   0.100  -1.295  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.337   0.595  -0.696  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.531  -0.581  -0.427  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.356  -0.794  -0.971  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.739   0.131  -1.905  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.416   0.700  -1.443  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.605   1.387  -0.264  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.720  -0.279  -1.428  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.624  -1.227  -0.434  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.067   0.367  -1.561  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.447   1.352  -0.523  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.522   0.861   0.874  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.512  -0.265   1.066  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.911   0.181   0.685  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.861  -0.950   0.886  1.00  0.00           C  
HETATM   19  C17 UNL     1       7.281  -0.607   0.531  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.836   0.478   1.342  1.00  0.00           C  
HETATM   21  O3  UNL     1       8.977   0.975   1.080  1.00  0.00           O  
HETATM   22  O4  UNL     1       7.178   1.022   2.422  1.00  0.00           O  
HETATM   23  H1  UNL     1      -8.386  -0.596   2.302  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.860  -1.373   2.757  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.818  -1.996   1.332  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.402   0.747   0.788  1.00  0.00           H  
HETATM   27  H5  UNL     1      -5.857   0.224   1.501  1.00  0.00           H  
HETATM   28  H6  UNL     1      -7.369  -1.049  -0.850  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.888  -1.774  -0.207  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.380  -0.489  -2.191  1.00  0.00           H  
HETATM   31  H9  UNL     1      -6.283   0.933  -1.620  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.990   1.331  -1.405  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.563   1.181   0.249  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.926  -1.336   0.272  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.797  -1.720  -0.734  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.321   0.978  -2.259  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.476  -0.426  -2.880  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.107   1.492  -2.191  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.374   1.083   0.272  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.643  -0.913  -2.395  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.113  -0.975   0.358  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.802  -0.474  -1.645  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.081   0.820  -2.598  1.00  0.00           H  
HETATM   44  H22 UNL     1       3.437   1.795  -0.835  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.709   2.191  -0.549  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.928   1.713   1.500  1.00  0.00           H  
HETATM   47  H25 UNL     1       1.543   0.610   1.257  1.00  0.00           H  
HETATM   48  H26 UNL     1       3.540  -0.476   2.159  1.00  0.00           H  
HETATM   49  H27 UNL     1       3.210  -1.202   0.573  1.00  0.00           H  
HETATM   50  H28 UNL     1       5.160   1.004   1.371  1.00  0.00           H  
HETATM   51  H29 UNL     1       4.971   0.541  -0.357  1.00  0.00           H  
HETATM   52  H30 UNL     1       5.577  -1.859   0.282  1.00  0.00           H  
HETATM   53  H31 UNL     1       5.873  -1.298   1.959  1.00  0.00           H  
HETATM   54  H32 UNL     1       7.929  -1.528   0.627  1.00  0.00           H  
HETATM   55  H33 UNL     1       7.321  -0.344  -0.561  1.00  0.00           H  
HETATM   56  H34 UNL     1       7.303   0.563   3.327  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   11   38
CONECT   10   39
CONECT   11   12   13   40
CONECT   12   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   50   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   21   22
CONECT   22   56
END

HMDB0004704
     RDKit          3D
9,10-DHOME
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.4871   -1.0787    1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7460   -0.1327    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3953   -0.8017   -0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639    0.0995   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3372    0.5948   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5314   -0.5806   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.7937   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.1313   -1.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4165    0.7001   -1.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6050    1.3871   -0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7198   -0.2785   -1.4282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6236   -1.2272   -0.4338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0672    0.3673   -1.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474    1.3525   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225    0.8609    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -0.2654    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115    0.1808    0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607   -0.9498    0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2806   -0.6068    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8358    0.4776    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9766    0.9746    1.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1783    1.0216    2.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3856   -0.5961    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8601   -1.3729    2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8184   -1.9964    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4024    0.7466    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8571    0.2237    1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3689   -1.0493   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8881   -1.7740   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3798   -0.4892   -2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2830    0.9334   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9905    1.3307   -1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633    1.1810    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9261   -1.3362    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7969   -1.7197   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.9779   -2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763   -0.4263   -2.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071    1.4917   -2.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743    1.0829    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -0.9128   -2.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -0.9745    0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8021   -0.4735   -1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814    0.8203   -2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    1.7954   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094    2.1908   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278    1.7128    1.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5432    0.6097    1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5401   -0.4763    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2097   -1.2024    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1601    1.0039    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709    0.5415   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773   -1.8591    0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -1.2978    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9290   -1.5275    0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -0.3441   -0.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033    0.5632    3.3274 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  1  0
 14 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  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

Synonyms

Value	Source
(12Z)-9,10-Dihydroxy-12-octadecenoic acid	HMDB
9,10-DiHOME	HMDB
9,10-Dihydroxy-12Z-octadecenoic acid	HMDB
9,10-Dihydroxy-12-octadecenoic acid	HMDB
(9R,10R)-Dihydroxy-12(Z)-octadecenoic acid	HMDB
(R,R)-9,10-Dihydroxy-cis-12-octadecenoic acid	HMDB
9,10-DHOME	HMDB

Molecular Formula

C₁₈H₃₄O₄

Average Mass

314.466

Monoisotopic Mass

314.245709575

IUPAC Name

(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid

Traditional Name

(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7-/t16-,17-/m1/s1

InChI Key

XEBKSQSGNGRGDW-GJWDQICYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.32	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	90.43 m³·mol⁻¹	ChemAxon
Polarizability	38.63 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-1292000000-0f3e5b9fbea53aa0e2e1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9620000000-60b31b5845c6de3eb91f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0api-9100000000-bbf0c5a646e02e8c1a10	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-1ac21b756268fbd2f688	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0978000000-11ea0f921e4c12485b9f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pka-6920000000-1aad2280930e1660cd08	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
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	Data Source	Reference
MMDBr0004669	9,10-Epoxyoctadecenoic acid	9,10-DHOME	epoxide hydrolase 2, cytoplasmic	VMH; KEGG	30371894
MMDBr0004670	9,10-Epoxyoctadecenoic acid	9,10-DHOME	epoxide hydrolase 1, microsomal (xenobiotic)	VMH	10933884
MMDBr0004673	9,10-DHOME	9-Hydroxy-10-O-D-Glucuronoside-12Z-Octadecenoate	UDP glucuronosyltransferase 1 family, polypeptide A8	VMH	10933884
MMDBr0004674	9,10-DHOME	9-Hydroxy-10-O-D-Glucuronoside-12Z-Octadecenoate	UDP glucuronosyltransferase 1 family, polypeptide A10	VMH	10933884
MMDBr0004678	9,10-DHOME	10-Hydroxy-Octadec-12Z-Enoate-9-Beta-D-Glucuronide	UDP glucuronosyltransferase 1 family, polypeptide A8	VMH	10933884
MMDBr0004679	9,10-DHOME	10-Hydroxy-Octadec-12Z-Enoate-9-Beta-D-Glucuronide	UDP glucuronosyltransferase 1 family, polypeptide A10	VMH	10933884

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
Bacteria	Firmicutes	2	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.0297	0.011	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.0605	0.0038	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.0605	0.00382	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	18953024
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00049	0.00044	uM	Adult (>18 years old)	Both	Normal	HMDB	John W. Newman, USDA ARS Western Human Nutrition Research Center, Davis CA (personal communication - March 2, 2009)
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0004704

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023415

KNApSAcK ID

Not Available

Chemspider ID

26324121

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25320862

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
Lecka-Czernik B, Moerman EJ, Grant DF, Lehmann JM, Manolagas SC, Jilka RL: Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation. Endocrinology. 2002 Jun;143(6):2376-84. doi: 10.1210/endo.143.6.8834. [PubMed:12021203 ]
Ha J, Dobretsov M, Kurten RC, Grant DF, Stimers JR: Effect of linoleic acid metabolites on Na(+)/K(+) pump current in N20.1 oligodendrocytes: role of membrane fluidity. Toxicol Appl Pharmacol. 2002 Jul 1;182(1):76-83. doi: 10.1006/taap.2002.9435. [PubMed:12127265 ]
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 ]
Thompson DA, Hammock BD: Dihydroxyoctadecamonoenoate esters inhibit the neutrophil respiratory burst. J Biosci. 2007 Mar;32(2):279-91. doi: 10.1007/s12038-007-0028-x. [PubMed:17435320 ]
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.
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 9,10-DHOME (MMDBc0000433)

MOL for #<Metabolite:0x00007f4704934688>

3D MOL for #<Metabolite:0x00007f4704934688>

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Structure for #<Metabolite:0x00007f4704934688>

3D Structure for #<Metabolite:0x00007f4704934688>