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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:22 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012530

Secondary Accession Numbers

HMDB12530

Metabolite Identification

Common Name

11-Hydroxyeicosatetraenoate glyceryl ester

Description

11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853 , 8555273 ).

Structure

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


  Mrv0541 02251208062D          

 28 27  0  0  1  0            999 V2000
   18.1500  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4356  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7211  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -13.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -13.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -12.3445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4342  -11.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -12.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -10.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066   -9.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -9.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -8.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -6.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7198   -7.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -8.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0012530
     RDKit          3D
11-Hydroxyeicosatetraenoate glyceryl ester
 66 65  0  0  0  0  0  0  0  0999 V2000
    5.6080    2.9377    1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6933    3.1919    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7518    2.3684   -1.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0158    0.9527   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2072   -0.1283   -0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0343   -0.1681    0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8724   -0.1867    1.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279   -0.1684    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914   -0.1924    1.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -0.1749    0.7967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0380    0.9401   -0.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -1.3989   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117   -2.6459    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020   -3.6428    0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162   -3.8260    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733   -2.8618   -0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -2.1487   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839   -2.2623    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7798   -2.7111    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4803   -1.7391   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335   -0.4306    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251   -0.1157    1.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1946    0.5817   -0.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3866    1.8783   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6834    2.9018   -0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205    2.6503   -1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8823    2.2050   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5708    1.2794    0.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7619    2.4731    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9534    2.4022    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    3.9186    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6684    3.1385    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6420    4.2977   -0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8180    2.6341   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5985    2.8738   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0668    0.8186   -0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3509    0.6499   -2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129   -1.1187   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2330   -0.1399   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609   -0.1843    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681   -0.2179    2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726   -0.1337   -0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708   -0.2242    2.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3994   -0.1474    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.7667   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -1.3358   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812   -1.2137   -0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -2.7600    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -4.4870    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929   -4.1461    0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -4.8192   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -2.7338   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8519   -1.4588   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445   -1.2153    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123   -2.8241    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3877   -2.7362    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8131   -3.7544   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4634   -2.1426   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8407   -1.5564   -1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0229    1.8916    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0835    2.8849   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8211    3.9082   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    3.2743   -0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9590    3.2399    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2467    2.1457   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3404    0.9462    0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  1
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
M  END


  Mrv0541 02251208062D          

 28 27  0  0  1  0            999 V2000
   18.1500  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4356  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7211  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -13.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -13.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -12.3445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4342  -11.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -12.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -10.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066   -9.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -9.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -8.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -6.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7198   -7.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -8.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012530

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1

> <INCHI_KEY>
SSHLWLAPLZCWOT-XYOZOUKRSA-N

> <FORMULA>
C23H38O5

> <MOLECULAR_WEIGHT>
394.5448

> <EXACT_MASS>
394.271924326

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.88910785704906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.181816846

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.979619367999383

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.278372842011322

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6087117775248538

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
118.49339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012530
     RDKit          3D
11-Hydroxyeicosatetraenoate glyceryl ester
 66 65  0  0  0  0  0  0  0  0999 V2000
    5.6080    2.9377    1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6933    3.1919    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7518    2.3684   -1.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0158    0.9527   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2072   -0.1283   -0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0343   -0.1681    0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8724   -0.1867    1.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279   -0.1684    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914   -0.1924    1.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -0.1749    0.7967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0380    0.9401   -0.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -1.3989   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117   -2.6459    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020   -3.6428    0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162   -3.8260    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733   -2.8618   -0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -2.1487   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839   -2.2623    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7798   -2.7111    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4803   -1.7391   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335   -0.4306    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251   -0.1157    1.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1946    0.5817   -0.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3866    1.8783   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6834    2.9018   -0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205    2.6503   -1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8823    2.2050   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5708    1.2794    0.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7619    2.4731    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9534    2.4022    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    3.9186    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6684    3.1385    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6420    4.2977   -0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8180    2.6341   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5985    2.8738   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0668    0.8186   -0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3509    0.6499   -2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129   -1.1187   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2330   -0.1399   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609   -0.1843    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681   -0.2179    2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726   -0.1337   -0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708   -0.2242    2.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3994   -0.1474    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.7667   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -1.3358   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812   -1.2137   -0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -2.7600    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -4.4870    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929   -4.1461    0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -4.8192   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -2.7338   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8519   -1.4588   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445   -1.2153    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123   -2.8241    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3877   -2.7362    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8131   -3.7544   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4634   -2.1426   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8407   -1.5564   -1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0229    1.8916    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0835    2.8849   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8211    3.9082   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    3.2743   -0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9590    3.2399    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2467    2.1457   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3404    0.9462    0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  1
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      33.880 -26.893   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.546 -27.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.213 -26.893   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.879 -27.663   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.545 -26.893   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.212 -27.663   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.878 -26.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.878 -25.353   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.544 -24.583   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.544 -23.043   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.211 -22.273   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      25.878 -22.273   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.212 -23.043   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.545 -22.273   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.545 -20.733   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.879 -19.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.879 -18.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.545 -17.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.545 -16.113   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.212 -15.343   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.212 -13.803   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      28.545 -13.033   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      25.878 -13.033   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      24.544 -13.803   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.211 -13.033   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.877 -13.803   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      24.544 -15.343   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      23.211 -16.113   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                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0012530
HETATM    1  C1  UNL     1       5.608   2.938   1.137  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.693   3.192   0.153  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.752   2.368  -1.067  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.016   0.953  -1.115  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.207  -0.128  -0.553  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.034  -0.168   0.871  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.872  -0.187   1.483  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.628  -0.168   0.775  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.491  -0.192   1.485  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.203  -0.175   0.797  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.038   0.940  -0.024  1.00  0.00           O  
HETATM   12  C11 UNL     1       1.102  -1.399  -0.111  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.212  -2.646   0.627  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.402  -3.643   0.749  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.916  -3.826   0.156  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.473  -2.862  -0.748  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.576  -2.149  -0.533  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.384  -2.262   0.693  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.780  -2.711   0.398  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.480  -1.739  -0.494  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.634  -0.431   0.148  1.00  0.00           C  
HETATM   22  O2  UNL     1      -5.325  -0.116   1.319  1.00  0.00           O  
HETATM   23  O3  UNL     1      -6.195   0.582  -0.654  1.00  0.00           O  
HETATM   24  C21 UNL     1      -6.387   1.878  -0.135  1.00  0.00           C  
HETATM   25  C22 UNL     1      -5.683   2.902  -0.991  1.00  0.00           C  
HETATM   26  O4  UNL     1      -4.320   2.650  -1.038  1.00  0.00           O  
HETATM   27  C23 UNL     1      -7.882   2.205  -0.140  1.00  0.00           C  
HETATM   28  O5  UNL     1      -8.571   1.279   0.650  1.00  0.00           O  
HETATM   29  H1  UNL     1       4.762   2.473   0.609  1.00  0.00           H  
HETATM   30  H2  UNL     1       5.953   2.402   2.042  1.00  0.00           H  
HETATM   31  H3  UNL     1       5.179   3.919   1.540  1.00  0.00           H  
HETATM   32  H4  UNL     1       7.668   3.139   0.734  1.00  0.00           H  
HETATM   33  H5  UNL     1       6.642   4.298  -0.094  1.00  0.00           H  
HETATM   34  H6  UNL     1       5.818   2.634  -1.735  1.00  0.00           H  
HETATM   35  H7  UNL     1       7.599   2.874  -1.701  1.00  0.00           H  
HETATM   36  H8  UNL     1       8.067   0.819  -0.603  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.351   0.650  -2.198  1.00  0.00           H  
HETATM   38  H10 UNL     1       6.713  -1.119  -0.918  1.00  0.00           H  
HETATM   39  H11 UNL     1       5.233  -0.140  -1.132  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.961  -0.184   1.502  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.868  -0.218   2.593  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.573  -0.134  -0.284  1.00  0.00           H  
HETATM   43  H15 UNL     1       2.571  -0.224   2.558  1.00  0.00           H  
HETATM   44  H16 UNL     1       0.399  -0.147   1.542  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.173   0.767  -0.969  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.028  -1.336  -0.766  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.281  -1.214  -0.766  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.188  -2.760   1.199  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.756  -4.487   1.399  1.00  0.00           H  
HETATM   50  H22 UNL     1      -1.593  -4.146   0.990  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.891  -4.819  -0.456  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.963  -2.734  -1.728  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.852  -1.459  -1.325  1.00  0.00           H  
HETATM   54  H26 UNL     1      -3.444  -1.215   1.104  1.00  0.00           H  
HETATM   55  H27 UNL     1      -2.912  -2.824   1.522  1.00  0.00           H  
HETATM   56  H28 UNL     1      -5.388  -2.736   1.357  1.00  0.00           H  
HETATM   57  H29 UNL     1      -4.813  -3.754  -0.002  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.463  -2.143  -0.860  1.00  0.00           H  
HETATM   59  H31 UNL     1      -4.841  -1.556  -1.411  1.00  0.00           H  
HETATM   60  H32 UNL     1      -6.023   1.892   0.915  1.00  0.00           H  
HETATM   61  H33 UNL     1      -6.084   2.885  -2.013  1.00  0.00           H  
HETATM   62  H34 UNL     1      -5.821   3.908  -0.508  1.00  0.00           H  
HETATM   63  H35 UNL     1      -3.802   3.274  -0.482  1.00  0.00           H  
HETATM   64  H36 UNL     1      -7.959   3.240   0.246  1.00  0.00           H  
HETATM   65  H37 UNL     1      -8.247   2.146  -1.183  1.00  0.00           H  
HETATM   66  H38 UNL     1      -9.340   0.946   0.135  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7    7   40
CONECT    7    8   41
CONECT    8    9    9   42
CONECT    9   10   43
CONECT   10   11   12   44
CONECT   11   45
CONECT   12   13   46   47
CONECT   13   14   14   48
CONECT   14   15   49
CONECT   15   16   50   51
CONECT   16   17   17   52
CONECT   17   18   53
CONECT   18   19   54   55
CONECT   19   20   56   57
CONECT   20   21   58   59
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   25   27   60
CONECT   25   26   61   62
CONECT   26   63
CONECT   27   28   64   65
CONECT   28   66
END

HMDB0012530
     RDKit          3D
11-Hydroxyeicosatetraenoate glyceryl ester
 66 65  0  0  0  0  0  0  0  0999 V2000
    5.6080    2.9377    1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6933    3.1919    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7518    2.3684   -1.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0158    0.9527   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2072   -0.1283   -0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0343   -0.1681    0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8724   -0.1867    1.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279   -0.1684    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914   -0.1924    1.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -0.1749    0.7967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0380    0.9401   -0.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -1.3989   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117   -2.6459    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020   -3.6428    0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162   -3.8260    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733   -2.8618   -0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -2.1487   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839   -2.2623    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7798   -2.7111    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4803   -1.7391   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335   -0.4306    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251   -0.1157    1.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1946    0.5817   -0.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3866    1.8783   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6834    2.9018   -0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205    2.6503   -1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8823    2.2050   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5708    1.2794    0.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7619    2.4731    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9534    2.4022    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    3.9186    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6684    3.1385    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6420    4.2977   -0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8180    2.6341   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5985    2.8738   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0668    0.8186   -0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3509    0.6499   -2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129   -1.1187   -0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2330   -0.1399   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609   -0.1843    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681   -0.2179    2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726   -0.1337   -0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708   -0.2242    2.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3994   -0.1474    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.7667   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -1.3358   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812   -1.2137   -0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -2.7600    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -4.4870    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929   -4.1461    0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -4.8192   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -2.7338   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8519   -1.4588   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4445   -1.2153    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123   -2.8241    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3877   -2.7362    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8131   -3.7544   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4634   -2.1426   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8407   -1.5564   -1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0229    1.8916    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0835    2.8849   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8211    3.9082   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    3.2743   -0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9590    3.2399    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2467    2.1457   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3404    0.9462    0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  1
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-Hydroxyeicosatetraenoic acid glyceryl ester	Generator
(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl-2-glyceryl ester	HMDB
(5Z,8Z,12E,14Z)-11S-Hydroxyeicosatetraenoyl-2-glyceryl ester	HMDB
11-HETE-g	HMDB
2-[(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-glycerol	HMDB
1,3-Dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid	Generator

Chemical Formula

C₂₃H₃₈O₅

Average Molecular Weight

394.5448

Monoisotopic Molecular Weight

394.271924326

IUPAC Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

Traditional Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO

InChI Identifier

InChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1

InChI Key

SSHLWLAPLZCWOT-XYOZOUKRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Endocannabinoids

Sub Class

Not Available

Direct Parent

Endocannabinoids

Alternative Parents

Substituents

2-arachidonoylglycerol-skeleton
Hydroxyeicosapolyenoic acid
Eicosanoid
Fatty alcohol
2-acyl-sn-glycerol
Monoradylglycerol
Monoacylglycerol
Glycerolipid
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.0099 g/L	ALOGPS
logP	4.62	ALOGPS
logP	4.18	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	118.49 m³·mol⁻¹	ChemAxon
Polarizability	45.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	206.055	31661259
DarkChem	[M-H]-	203.85	31661259
DeepCCS	[M+H]+	208.315	30932474
DeepCCS	[M-H]-	205.448	30932474
DeepCCS	[M-2H]-	240.248	30932474
DeepCCS	[M+Na]+	215.476	30932474
AllCCS	[M+H]+	205.2	32859911
AllCCS	[M+H-H2O]+	202.8	32859911
AllCCS	[M+NH4]+	207.3	32859911
AllCCS	[M+Na]+	207.9	32859911
AllCCS	[M-H]-	199.9	32859911
AllCCS	[M+Na-2H]-	202.5	32859911
AllCCS	[M+HCOO]-	205.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-Hydroxyeicosatetraenoate glyceryl ester	CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO	3837.5	Standard polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester	CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO	2776.5	Standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester	CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO	3106.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11-Hydroxyeicosatetraenoate glyceryl ester,1TMS,isomer #1	CCCCC/C=C\C=C\[C@H](C/C=C\C/C=C\CCCC(=O)OC(CO)CO)O[Si](C)(C)C	3182.6	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,1TMS,isomer #2	CCCCC/C=C\C=C\[C@@H](O)C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C	3140.2	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,2TMS,isomer #1	CCCCC/C=C\C=C\[C@H](C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C)O[Si](C)(C)C	3200.6	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,2TMS,isomer #2	CCCCC/C=C\C=C\[C@@H](O)C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C)CO[Si](C)(C)C	3187.3	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,3TMS,isomer #1	CCCCC/C=C\C=C\[C@H](C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C)CO[Si](C)(C)C)O[Si](C)(C)C	3196.3	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,1TBDMS,isomer #1	CCCCC/C=C\C=C\[C@H](C/C=C\C/C=C\CCCC(=O)OC(CO)CO)O[Si](C)(C)C(C)(C)C	3411.5	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,1TBDMS,isomer #2	CCCCC/C=C\C=C\[C@@H](O)C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C(C)(C)C	3357.7	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,2TBDMS,isomer #1	CCCCC/C=C\C=C\[C@H](C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3656.2	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,2TBDMS,isomer #2	CCCCC/C=C\C=C\[C@@H](O)C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	3636.3	Semi standard non polar	33892256
11-Hydroxyeicosatetraenoate glyceryl ester,3TBDMS,isomer #1	CCCCC/C=C\C=C\[C@H](C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3931.8	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 - 11-Hydroxyeicosatetraenoate glyceryl ester GC-MS (3 TMS) - 70eV, Positive	splash10-016s-7296050000-011e66dfb552a34df54a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 10V, Positive-QTOF	splash10-03di-0000900000-c575869144f9867bdc65	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 20V, Positive-QTOF	splash10-03do-0009900000-83bfe115c75e35557114	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 40V, Positive-QTOF	splash10-03e6-0009400000-dee91ea16fe16cc8f25c	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 10V, Positive-QTOF	splash10-03di-0000900000-9f51d2ac31733f26a5d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 20V, Positive-QTOF	splash10-01ox-0009600000-63e6fe070d3a08dec7f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 40V, Positive-QTOF	splash10-000o-0009000000-0b37b0af2169a49a2409	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 10V, Negative-QTOF	splash10-0k96-9007000000-c2b31f587c794f278584	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 20V, Negative-QTOF	splash10-0zfr-9118000000-c387f63afba105336f30	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 40V, Negative-QTOF	splash10-1003-6389000000-6b0c63033b2863336dab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 10V, Positive-QTOF	splash10-0002-0009000000-7af95ca2b5f90947ec62	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 20V, Positive-QTOF	splash10-00dk-0009000000-74867a444b209a7ff6d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 40V, Positive-QTOF	splash10-05i0-0009000000-2eb3c3d4cfdf9069509e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 10V, Positive-QTOF	splash10-014i-0000900000-f48df2712a778cf5e692	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 20V, Positive-QTOF	splash10-014i-0000900000-f48df2712a778cf5e692	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxyeicosatetraenoate glyceryl ester 40V, Positive-QTOF	splash10-0aox-0009300000-2fa39b4f929308f6a25e	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029112

KNApSAcK ID

Not Available

Chemspider ID

30776620

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481455

PDB ID

Not Available

ChEBI ID

171687

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

Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. Epub 2005 Jun 17. [PubMed:15964853 ]
Rosolowsky M, Campbell WB: Synthesis of hydroxyeicosatetraenoic (HETEs) and epoxyeicosatrienoic acids (EETs) by cultured bovine coronary artery endothelial cells. Biochim Biophys Acta. 1996 Jan 19;1299(2):267-77. [PubMed:8555273 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
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 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 11-Hydroxyeicosatetraenoate glyceryl ester (HMDB0012530)

MOL for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D MOL for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D SDF for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D-SDF for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

PDB for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D PDB for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

SMILES for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

INCHI for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

Structure for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D Structure for HMDB0012530 (11-Hydroxyeicosatetraenoate glyceryl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra