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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 04:42:27 UTC

Update Date

2022-03-07 03:17:57 UTC

HMDB ID

HMDB0062619

Secondary Accession Numbers

HMDB62619

Metabolite Identification

Common Name

(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid

Description

(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid, also known as Hepoxilin a3 or 8-EH-2, is classified as a member of the Hepoxilins. Hepoxilins are eicosanoids containing an oxirane group attached to the fatty acyl chain. (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid is considered to be practically insoluble (in water) and acidic

Structure

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


  Mrv1652303231705422D          

 33 33  0  0  1  0            999 V2000
  -10.3342    4.9204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3342    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3342    7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0487    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0487    8.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7631    7.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9052    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9052    4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4763    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4763    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    6.1579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    5.3329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1194    4.5360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    6.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7214    4.5360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    3.6829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934    4.0954    0.0000 C   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  1  0  0  0  0
  6  8  2  0  0  0  0
  2  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 17  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0062619
     RDKit          3D
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid
 56 56  0  0  0  0  0  0  0  0999 V2000
    8.0267   -0.0794    0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7371   -0.8511   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3100   -0.0340   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1288    0.8280   -1.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7921    0.2446   -1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744   -0.4310   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499    0.0104    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7766    1.1639    0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.6615    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267    0.0368    1.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047   -0.7193    0.5816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1511   -1.4337    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2829   -0.9199    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5830   -1.5963    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -1.9191    1.8501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -0.6195   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7807   -1.2913   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9139   -0.8489    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0054    0.3554    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8205    1.4913    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2440    1.1754    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4928    0.1560   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3635   -0.7472   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7684    0.1740   -1.9361 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4439    0.9110    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1276   -0.0677    1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7959   -0.6511    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821   -1.2556   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -1.7766   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563   -0.7362   -2.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2004    0.5838   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267    1.3152   -2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    1.7579   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6114   -0.5489   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092    1.0003   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947   -1.3146    0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -0.5454    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546    1.8331    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    1.7944   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772    1.3859    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9991   -1.4134    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1546   -2.3947   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    0.0171    1.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -2.4994   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -1.0711    2.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0704   -0.4779   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    0.3705    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -2.2236   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8378   -1.4473   -0.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    0.0148    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519    0.7812    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7284    2.3528    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3202    1.8830   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6501    0.8084    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7637    2.1205   -0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0937    0.8552   -2.1920 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 11  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 11 41  1  1
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END


  Mrv1652303231705422D          

 33 33  0  0  1  0            999 V2000
  -10.3342    4.9204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3342    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3342    7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0487    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0487    8.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7631    7.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9052    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9052    4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4763    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4763    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    6.1579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    5.3329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1194    4.5360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    6.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7214    4.5360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    3.6829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934    4.0954    0.0000 C   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  1  0  0  0  0
  6  8  2  0  0  0  0
  2  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 17  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062619

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18?,19-/m0/s1

> <INCHI_KEY>
SGTUOBURCVMACZ-NSIHWEAISA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.84931104354597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
4.574270298999999

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.834272608307948

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676900472679159

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8712891629033512

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
99.7198

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062619
     RDKit          3D
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid
 56 56  0  0  0  0  0  0  0  0999 V2000
    8.0267   -0.0794    0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7371   -0.8511   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3100   -0.0340   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1288    0.8280   -1.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7921    0.2446   -1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744   -0.4310   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499    0.0104    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7766    1.1639    0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.6615    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267    0.0368    1.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047   -0.7193    0.5816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1511   -1.4337    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2829   -0.9199    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5830   -1.5963    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -1.9191    1.8501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -0.6195   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7807   -1.2913   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9139   -0.8489    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0054    0.3554    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8205    1.4913    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2440    1.1754    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4928    0.1560   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3635   -0.7472   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7684    0.1740   -1.9361 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4439    0.9110    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1276   -0.0677    1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7959   -0.6511    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821   -1.2556   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -1.7766   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563   -0.7362   -2.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2004    0.5838   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267    1.3152   -2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    1.7579   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6114   -0.5489   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092    1.0003   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947   -1.3146    0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -0.5454    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546    1.8331    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    1.7944   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772    1.3859    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9991   -1.4134    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1546   -2.3947   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    0.0171    1.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -2.4994   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -1.0711    2.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0704   -0.4779   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    0.3705    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -2.2236   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8378   -1.4473   -0.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    0.0148    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519    0.7812    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7284    2.3528    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3202    1.8830   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6501    0.8084    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7637    2.1205   -0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0937    0.8552   -2.1920 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 11  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 11 41  1  1
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0     -19.290   9.185   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0     -17.957   9.955   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.957  11.495   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -19.290  12.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -19.290  13.805   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -20.624  14.575   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -20.624  16.115   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0     -21.958  13.805   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -16.623   9.185   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0     -16.623   7.645   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0     -15.289   9.955   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.956   9.185   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0     -15.289   8.415   0.000  0.00  0.00           H+0
HETATM   14  O   UNK     0     -13.956   7.645   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0     -12.622   9.955   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0     -12.622  11.495   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0     -11.288   9.185   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0     -11.288   7.645   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -9.955   9.955   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -9.556   8.467   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0      -9.185  11.288   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.415   9.955   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -8.813   8.467   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      -7.081   9.185   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.081   7.645   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      -8.415   6.875   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0      -5.747   6.875   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      -5.747   5.335   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      -4.414   7.645   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.080   6.875   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.746   7.645   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.413   6.875   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.921   7.645   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   19   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

COMPND    HMDB0062619
HETATM    1  C1  UNL     1       8.027  -0.079   0.693  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.737  -0.851  -0.572  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.310  -0.034  -1.720  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.129   0.828  -1.636  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.792   0.245  -1.359  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.574  -0.431  -0.092  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.650   0.010   0.783  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.777   1.164   0.610  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.322   0.661   0.651  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.027   0.037   1.860  1.00  0.00           O  
HETATM   11  C10 UNL     1       1.105  -0.719   0.582  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.151  -1.434   0.351  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.283  -0.920   0.798  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.583  -1.596   0.595  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.094  -1.919   1.850  1.00  0.00           O  
HETATM   16  C14 UNL     1      -3.501  -0.619  -0.133  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.781  -1.291  -0.331  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.914  -0.849   0.161  1.00  0.00           C  
HETATM   19  C17 UNL     1      -6.005   0.355   0.954  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.820   1.491   0.456  1.00  0.00           C  
HETATM   21  C19 UNL     1      -8.244   1.175   0.260  1.00  0.00           C  
HETATM   22  C20 UNL     1      -8.493   0.156  -0.763  1.00  0.00           C  
HETATM   23  O3  UNL     1      -9.364  -0.747  -0.599  1.00  0.00           O  
HETATM   24  O4  UNL     1      -7.768   0.174  -1.936  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.444   0.911   0.502  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.128  -0.068   1.368  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.796  -0.651   1.283  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.782  -1.256  -0.881  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.193  -1.777  -0.369  1.00  0.00           H  
HETATM   30  H6  UNL     1       7.156  -0.736  -2.599  1.00  0.00           H  
HETATM   31  H7  UNL     1       8.200   0.584  -2.073  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.027   1.315  -2.669  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.312   1.758  -0.996  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.611  -0.549  -2.179  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.009   1.000  -1.631  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.095  -1.315   0.246  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.525  -0.545   1.736  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.955   1.833   1.501  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.908   1.794  -0.254  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.577   1.386   0.264  1.00  0.00           H  
HETATM   41  H17 UNL     1       1.999  -1.413   0.619  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.155  -2.395  -0.193  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.258   0.017   1.326  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.410  -2.499  -0.024  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.021  -1.071   2.391  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.070  -0.478  -1.184  1.00  0.00           H  
HETATM   47  H23 UNL     1      -3.490   0.370   0.292  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.813  -2.224  -0.925  1.00  0.00           H  
HETATM   49  H25 UNL     1      -6.838  -1.447  -0.020  1.00  0.00           H  
HETATM   50  H26 UNL     1      -6.502   0.015   1.948  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.052   0.781   1.335  1.00  0.00           H  
HETATM   52  H28 UNL     1      -6.728   2.353   1.191  1.00  0.00           H  
HETATM   53  H29 UNL     1      -6.320   1.883  -0.473  1.00  0.00           H  
HETATM   54  H30 UNL     1      -8.650   0.808   1.238  1.00  0.00           H  
HETATM   55  H31 UNL     1      -8.764   2.121  -0.040  1.00  0.00           H  
HETATM   56  H32 UNL     1      -7.094   0.855  -2.192  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   11   40
CONECT   10   11
CONECT   11   12   41
CONECT   12   13   13   42
CONECT   13   14   43
CONECT   14   15   16   44
CONECT   15   45
CONECT   16   17   46   47
CONECT   17   18   18   48
CONECT   18   19   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0062619
     RDKit          3D
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid
 56 56  0  0  0  0  0  0  0  0999 V2000
    8.0267   -0.0794    0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7371   -0.8511   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3100   -0.0340   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1288    0.8280   -1.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7921    0.2446   -1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744   -0.4310   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499    0.0104    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7766    1.1639    0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.6615    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267    0.0368    1.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047   -0.7193    0.5816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1511   -1.4337    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2829   -0.9199    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5830   -1.5963    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -1.9191    1.8501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -0.6195   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7807   -1.2913   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9139   -0.8489    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0054    0.3554    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8205    1.4913    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2440    1.1754    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4928    0.1560   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3635   -0.7472   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7684    0.1740   -1.9361 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4439    0.9110    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1276   -0.0677    1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7959   -0.6511    1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821   -1.2556   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -1.7766   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563   -0.7362   -2.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2004    0.5838   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267    1.3152   -2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    1.7579   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6114   -0.5489   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092    1.0003   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947   -1.3146    0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -0.5454    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546    1.8331    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    1.7944   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772    1.3859    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9991   -1.4134    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1546   -2.3947   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    0.0171    1.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -2.4994   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -1.0711    2.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0704   -0.4779   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4897    0.3705    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -2.2236   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8378   -1.4473   -0.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    0.0148    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519    0.7812    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7284    2.3528    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3202    1.8830   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6501    0.8084    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7637    2.1205   -0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0937    0.8552   -2.1920 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 11  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 11 41  1  1
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoate	Kegg
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic acid	Generator
Hepoxilin a	MeSH
8-EH-2	MeSH
Hexophilin a3	MeSH
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid	MeSH
HXA3 CPD	MeSH
Hepoxilin a3	KEGG

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.472

Monoisotopic Molecular Weight

336.23005951

IUPAC Name

(5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid

Traditional Name

(5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18?,19-/m0/s1

InChI Key

SGTUOBURCVMACZ-NSIHWEAISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hepoxilins

Alternative Parents

Substituents

Hepoxilin
Medium-chain hydroxy acid
Medium-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Epoxy fatty acids (C04849 )
Hepoxilins (C04849 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062619)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0094 g/l	ALOGPS
LogP	5.57	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.57	ALOGPS
logP	4.57	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	99.72 m³·mol⁻¹	ChemAxon
Polarizability	39.85 Å³	ChemAxon
Number of Rings	1	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]+	187.897	31661259
DarkChem	[M-H]-	185.386	31661259
DeepCCS	[M+H]+	195.081	30932474
DeepCCS	[M-H]-	193.256	30932474
DeepCCS	[M-2H]-	226.499	30932474
DeepCCS	[M+Na]+	200.687	30932474
AllCCS	[M+H]+	192.0	32859911
AllCCS	[M+H-H2O]+	189.2	32859911
AllCCS	[M+NH4]+	194.6	32859911
AllCCS	[M+Na]+	195.3	32859911
AllCCS	[M-H]-	190.1	32859911
AllCCS	[M+Na-2H]-	191.8	32859911
AllCCS	[M+HCOO]-	193.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	7.5 minutes	32390414
Predicted by Siyang on May 30, 2022	16.7552 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2982.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	189.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	769.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	517.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	134.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1676.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	589.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1569.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	543.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	442.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	342.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	339.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid	[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC	4187.0	Standard polar	33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid	[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC	2485.7	Standard non polar	33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid	[H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC	2620.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TMS,isomer #1	CCCCC/C=C\CC1O[C@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C	2637.7	Semi standard non polar	33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TMS,isomer #2	CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C	2738.1	Semi standard non polar	33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,2TMS,isomer #1	CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2689.9	Semi standard non polar	33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TBDMS,isomer #1	CCCCC/C=C\CC1O[C@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2898.3	Semi standard non polar	33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TBDMS,isomer #2	CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2981.7	Semi standard non polar	33892256
(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,2TBDMS,isomer #1	CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3168.3	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 - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0403-4973000000-68b05a5879abdd2702ca	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (2 TMS) - 70eV, Positive	splash10-00fs-9504200000-b478b5ac38b9ea248120	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Positive-QTOF	splash10-014i-0119000000-f183a896d40b122d34a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Positive-QTOF	splash10-0100-3923000000-55a8fa7b860b76630757	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Positive-QTOF	splash10-05tf-9320000000-806f2e69b92eec98be14	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Negative-QTOF	splash10-000i-0029000000-babbe7e5cbfec6729e52	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Negative-QTOF	splash10-014r-1849000000-46fca9cc7712fb3e7876	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Negative-QTOF	splash10-0a4l-9510000000-19c94ffaa2521c24fe09	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Negative-QTOF	splash10-000i-0009000000-4284d12526c896900597	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Negative-QTOF	splash10-000i-0697000000-b6393912f77c76528f02	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Negative-QTOF	splash10-0035-2961000000-b6e6a2b7949fd45ad206	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Positive-QTOF	splash10-014r-2229000000-797f9fb3ace53b814b60	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Positive-QTOF	splash10-0kxr-7986000000-202c1560017bfda5161a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Positive-QTOF	splash10-00pi-9300000000-94a32c143312056553eb	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04849

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hepoxilin

METLIN ID

Not Available

PubChem Compound

5280743

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

C04849

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
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 ]
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Showing metabocard for (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid (HMDB0062619)

MOL for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

3D MOL for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

3D SDF for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

3D-SDF for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

PDB for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

3D PDB for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

SMILES for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

INCHI for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

Structure for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

3D Structure for HMDB0062619 ((5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra