Hmdb loader

Showing metabocard for 9,10-DHOME (HMDB0004704)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-14 01:38:14 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004704
Secondary Accession Numbers
  • HMDB0031679
  • HMDB04704
  • HMDB31679
Metabolite Identification
Common Name9,10-DHOME
Description9,10-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
Data?1582752313
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004704 (9,10-DHOME)


  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
Download

3D MOL for HMDB0004704 (9,10-DHOME)

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
Download

3D SDF for HMDB0004704 (9,10-DHOME)


  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>
HMDB0004704

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0004704 (9,10-DHOME)

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
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PDB for HMDB0004704 (9,10-DHOME)

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
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3D PDB for HMDB0004704 (9,10-DHOME)

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
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SMILES for HMDB0004704 (9,10-DHOME)

CCCCC\C=C/C[C@@H](O)[C@H](O)CCCCCCCC(O)=O
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INCHI for HMDB0004704 (9,10-DHOME)

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
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(12Z)-9,10-Dihydroxy-12-octadecenoic acidHMDB
9,10-DiHOMEHMDB
9,10-Dihydroxy-12Z-octadecenoic acidHMDB
9,10-Dihydroxy-12-octadecenoic acidHMDB
(9R,10R)-Dihydroxy-12(Z)-octadecenoic acidHMDB
(R,R)-9,10-Dihydroxy-cis-12-octadecenoic acidHMDB
9,10-DHOMEHMDB
Chemical FormulaC18H34O4
Average Molecular Weight314.466
Monoisotopic Molecular Weight314.245709575
IUPAC Name(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid
Traditional Name(9R,10R,12Z)-9,10-dihydroxyoctadec-12-enoic acid
CAS Registry Number125356-86-7
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 KeyXEBKSQSGNGRGDW-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP5.18ALOGPS
logP4.32ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity90.43 m³·mol⁻¹ChemAxon
Polarizability38.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+192.54630932474
DeepCCS[M-H]-190.18830932474
DeepCCS[M-2H]-223.07530932474
DeepCCS[M+Na]+198.6430932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 9.15 minutes32390414
Predicted by Siyang on May 30, 202215.4528 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.42 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid41.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2786.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid267.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid188.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid181.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid474.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid731.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid590.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)126.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1431.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid545.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1584.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid472.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid413.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate349.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA303.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water8.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9,10-DHOMECCCCC\C=C/C[C@@H](O)[C@H](O)CCCCCCCC(O)=O3890.9Standard polar33892256
9,10-DHOMECCCCC\C=C/C[C@@H](O)[C@H](O)CCCCCCCC(O)=O2368.0Standard non polar33892256
9,10-DHOMECCCCC\C=C/C[C@@H](O)[C@H](O)CCCCCCCC(O)=O2507.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9,10-DHOME,1TMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)CCCCCCCC(=O)O2527.6Semi standard non polar33892256
9,10-DHOME,1TMS,isomer #2CCCCC/C=C\C[C@@H](O)[C@@H](CCCCCCCC(=O)O)O[Si](C)(C)C2520.8Semi standard non polar33892256
9,10-DHOME,1TMS,isomer #3CCCCC/C=C\C[C@@H](O)[C@H](O)CCCCCCCC(=O)O[Si](C)(C)C2539.1Semi standard non polar33892256
9,10-DHOME,2TMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@@H](CCCCCCCC(=O)O)O[Si](C)(C)C2541.3Semi standard non polar33892256
9,10-DHOME,2TMS,isomer #2CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)CCCCCCCC(=O)O[Si](C)(C)C2552.6Semi standard non polar33892256
9,10-DHOME,2TMS,isomer #3CCCCC/C=C\C[C@@H](O)[C@@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2545.2Semi standard non polar33892256
9,10-DHOME,3TMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2546.0Semi standard non polar33892256
9,10-DHOME,1TBDMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CCCCCCCC(=O)O2753.1Semi standard non polar33892256
9,10-DHOME,1TBDMS,isomer #2CCCCC/C=C\C[C@@H](O)[C@@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2758.1Semi standard non polar33892256
9,10-DHOME,1TBDMS,isomer #3CCCCC/C=C\C[C@@H](O)[C@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2783.7Semi standard non polar33892256
9,10-DHOME,2TBDMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3029.3Semi standard non polar33892256
9,10-DHOME,2TBDMS,isomer #2CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3039.0Semi standard non polar33892256
9,10-DHOME,2TBDMS,isomer #3CCCCC/C=C\C[C@@H](O)[C@@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3021.8Semi standard non polar33892256
9,10-DHOME,3TBDMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3281.6Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0605 +/- 0.00382 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.0605 +/- 0.0038 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified0.0297 +/- 0.011 uMAdult (>18 years old)Both
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00049 +/- 0.00044 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023415
KNApSAcK IDNot Available
Chemspider ID26324121
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25320862
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE2047
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:12021203 ]
  2. 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. [PubMed:12127265 ]
  3. Thompson DA, Hammock BD: Dihydroxyoctadecamonoenoate esters inhibit the neutrophil respiratory burst. J Biosci. 2007 Mar;32(2):279-91. [PubMed:17435320 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. 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 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. 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 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.