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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 02:09:29 UTC

Update Date

2022-03-07 03:17:55 UTC

HMDB ID

HMDB0062479

Secondary Accession Numbers

HMDB62479

Metabolite Identification

Common Name

10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid

Description

(8Z)-10-hydroxy-10-[(3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain (8Z)-10-hydroxy-10-[(3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

  Mrv1652303231703092D          

 33 33  0  0  1  0            999 V2000
   -8.9052    4.9204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9052    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3342    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0487    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7631    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4776    3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7631    4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4763    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    3.6829    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
   -6.7618    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    5.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    5.3329    0.0000 C   0  0  0  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  1  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
  2  1  1  4  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  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  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  6  0  0  0
 22 24  1  1  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

HMDB0062479
     RDKit          3D
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
    7.4401   -0.0238    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562    0.9837    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5338    0.6619   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004   -0.5891   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4700   -0.8367   -1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051   -0.8692    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101   -0.0356    0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4690    1.0050   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    0.7400   -0.0279 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4203    0.7007    1.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4520   -0.4884    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114   -0.9663    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321   -2.1848   -0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -0.0186   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.9398   -0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    1.1204    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    0.9905    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864    0.0657    1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2037   -0.2603    1.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1432    0.5288    0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0272    0.3297   -0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3002   -1.1174   -1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4805   -1.5158   -1.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2254   -1.9470   -1.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4890    0.3793    2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4846   -0.1211    0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8940   -0.9821    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2351    1.9597    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    1.1761    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0320    1.5132   -1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5858    0.6667   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5916   -2.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5344   -1.5035   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735   -0.2087   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -1.8804   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.5841    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -0.1196    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016    1.2752   -1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.9537    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    1.1944   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0731   -1.2731    1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850   -1.2597    0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074   -2.0150   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -0.1036   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180    1.6525   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674    2.1808    1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886    0.4727    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7135    1.7101    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -0.5943    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3090   -1.3454    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5577   -0.1686    2.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1111    1.6162    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1838    0.2200    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8255    0.9601   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0588    0.5551   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3994   -2.9481   -1.2584 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  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 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  6
 11 41  1  0
 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

  Mrv1652303231703092D          

 33 33  0  0  1  0            999 V2000
   -8.9052    4.9204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9052    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3342    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0487    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7631    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4776    3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7631    4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1908    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4763    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    3.6829    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
   -6.7618    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    5.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    5.3329    0.0000 C   0  0  0  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  1  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
  2  1  1  4  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  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  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  6  0  0  0
 22 24  1  1  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>
HMDB0062479

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(CCCC(O)=O)=C([H])C\C([H])=C(\[H])C([H])(O)C1([H])O[C@@]1([H])C\C([H])=C(\[H])CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/b7-6?,12-9-,14-11-/t17?,18-,20?/m0/s1

> <INCHI_KEY>
DWNBPRRXEVJMPO-OLCCVTJXSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.86180224988401

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
4.730177758999999

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.747890205027268

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840400463

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3464728245471864

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
99.5658

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062479
     RDKit          3D
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
    7.4401   -0.0238    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562    0.9837    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5338    0.6619   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004   -0.5891   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4700   -0.8367   -1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051   -0.8692    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101   -0.0356    0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4690    1.0050   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    0.7400   -0.0279 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4203    0.7007    1.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4520   -0.4884    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114   -0.9663    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321   -2.1848   -0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -0.0186   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.9398   -0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    1.1204    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    0.9905    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864    0.0657    1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2037   -0.2603    1.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1432    0.5288    0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0272    0.3297   -0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3002   -1.1174   -1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4805   -1.5158   -1.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2254   -1.9470   -1.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4890    0.3793    2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4846   -0.1211    0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8940   -0.9821    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2351    1.9597    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    1.1761    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0320    1.5132   -1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5858    0.6667   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5916   -2.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5344   -1.5035   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735   -0.2087   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -1.8804   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.5841    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -0.1196    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016    1.2752   -1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.9537    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    1.1944   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0731   -1.2731    1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850   -1.2597    0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074   -2.0150   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -0.1036   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180    1.6525   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674    2.1808    1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886    0.4727    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7135    1.7101    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -0.5943    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3090   -1.3454    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5577   -0.1686    2.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1111    1.6162    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1838    0.2200    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8255    0.9601   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0588    0.5551   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3994   -2.9481   -1.2584 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  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 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  6
 11 41  1  0
 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     -16.623   9.185   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0     -16.623   7.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.957   6.875   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -19.290   7.645   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -20.624   6.875   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -21.958   7.645   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -23.292   6.875   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0     -21.958   9.185   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -15.289   6.875   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0     -15.289   5.335   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0     -13.956   7.645   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.622   6.875   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0     -12.622   5.335   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0     -11.288   7.645   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      -9.955   6.875   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0     -11.288   9.185   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0     -12.622   8.415   0.000  0.00  0.00           H+0
HETATM   18  O   UNK     0     -12.622   9.955   0.000  0.00  0.00           O+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                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   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    HMDB0062479
HETATM    1  C1  UNL     1       7.440  -0.024   1.013  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.656   0.984   0.208  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.534   0.662  -1.222  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.900  -0.589  -1.645  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.470  -0.837  -1.303  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.105  -0.869   0.107  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.210  -0.036   0.603  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.469   1.005  -0.113  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.980   0.740  -0.028  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.420   0.701   1.266  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.452  -0.488   0.572  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.911  -0.966   0.091  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.632  -2.185  -0.590  1.00  0.00           O  
HETATM   14  C12 UNL     1      -1.416  -0.019  -0.897  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.239   0.940  -0.561  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.701   1.120   0.812  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.194   0.991   0.787  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.786   0.066   1.479  1.00  0.00           C  
HETATM   19  C17 UNL     1      -6.204  -0.260   1.614  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.143   0.529   0.786  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.027   0.330  -0.693  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.300  -1.117  -1.019  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.481  -1.516  -1.096  1.00  0.00           O  
HETATM   24  O4  UNL     1      -6.225  -1.947  -1.220  1.00  0.00           O  
HETATM   25  H1  UNL     1       7.489   0.379   2.062  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.485  -0.121   0.687  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.894  -0.982   1.084  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.235   1.960   0.343  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.709   1.176   0.722  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.032   1.513  -1.742  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.586   0.667  -1.654  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.935  -0.592  -2.786  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.534  -1.503  -1.416  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.773  -0.209  -1.938  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.254  -1.880  -1.742  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.563  -1.584   0.788  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.981  -0.120   1.683  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.802   1.275  -1.106  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.615   1.954   0.505  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.402   1.194  -0.848  1.00  0.00           H  
HETATM   41  H17 UNL     1       1.073  -1.273   1.030  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.585  -1.260   0.896  1.00  0.00           H  
HETATM   43  H19 UNL     1      -0.407  -2.015  -1.528  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.105  -0.104  -1.942  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.618   1.653  -1.306  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.467   2.181   1.107  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.289   0.473   1.576  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.713   1.710   0.200  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.107  -0.594   2.071  1.00  0.00           H  
HETATM   50  H26 UNL     1      -6.309  -1.345   1.354  1.00  0.00           H  
HETATM   51  H27 UNL     1      -6.558  -0.169   2.685  1.00  0.00           H  
HETATM   52  H28 UNL     1      -7.111   1.616   1.064  1.00  0.00           H  
HETATM   53  H29 UNL     1      -8.184   0.220   1.095  1.00  0.00           H  
HETATM   54  H30 UNL     1      -7.825   0.960  -1.157  1.00  0.00           H  
HETATM   55  H31 UNL     1      -6.059   0.555  -1.117  1.00  0.00           H  
HETATM   56  H32 UNL     1      -6.399  -2.948  -1.258  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   14   42
CONECT   13   43
CONECT   14   15   15   44
CONECT   15   16   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

HMDB0062479
     RDKit          3D
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid
 56 56  0  0  0  0  0  0  0  0999 V2000
    7.4401   -0.0238    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562    0.9837    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5338    0.6619   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004   -0.5891   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4700   -0.8367   -1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051   -0.8692    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101   -0.0356    0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4690    1.0050   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    0.7400   -0.0279 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4203    0.7007    1.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4520   -0.4884    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114   -0.9663    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321   -2.1848   -0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -0.0186   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.9398   -0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    1.1204    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    0.9905    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864    0.0657    1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2037   -0.2603    1.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1432    0.5288    0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0272    0.3297   -0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3002   -1.1174   -1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4805   -1.5158   -1.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2254   -1.9470   -1.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4890    0.3793    2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4846   -0.1211    0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8940   -0.9821    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2351    1.9597    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    1.1761    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0320    1.5132   -1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5858    0.6667   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5916   -2.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5344   -1.5035   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735   -0.2087   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -1.8804   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -1.5841    0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -0.1196    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016    1.2752   -1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.9537    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    1.1944   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0731   -1.2731    1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850   -1.2597    0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074   -2.0150   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -0.1036   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180    1.6525   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674    2.1808    1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886    0.4727    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7135    1.7101    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -0.5943    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3090   -1.3454    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5577   -0.1686    2.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1111    1.6162    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1838    0.2200    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8255    0.9601   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0588    0.5551   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3994   -2.9481   -1.2584 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  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 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  6
 11 41  1  0
 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
(8Z)-10-Hydroxy-10-[(3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoate	Generator
10-Hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoate	Generator
10-Hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acid	HMDB
EPHETA	HMDB
erythro-Hepoxilin b3	HMDB
Hepoxilin b	HMDB
Hepoxilin b3	HMDB
threo-Hepoxilin b3	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.472

Monoisotopic Molecular Weight

336.23005951

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]C(CCCC(O)=O)=C([H])C\C([H])=C(\[H])C([H])(O)C1([H])O[C@@]1([H])C\C([H])=C(\[H])CCCCC

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/b7-6?,12-9-,14-11-/t17?,18-,20?/m0/s1

InChI Key

DWNBPRRXEVJMPO-OLCCVTJXSA-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

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0062479)

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	0.0092 g/l	ALOGPS
LogP	5.11	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.11	ALOGPS
logP	4.73	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-3.3	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	99.57 m³·mol⁻¹	ChemAxon
Polarizability	39.86 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]+	189.784	31661259
DarkChem	[M-H]-	186.233	31661259
DeepCCS	[M+H]+	194.477	30932474
DeepCCS	[M-H]-	192.652	30932474
DeepCCS	[M-2H]-	225.896	30932474
DeepCCS	[M+Na]+	200.083	30932474
AllCCS	[M+H]+	192.2	32859911
AllCCS	[M+H-H2O]+	189.5	32859911
AllCCS	[M+NH4]+	194.8	32859911
AllCCS	[M+Na]+	195.5	32859911
AllCCS	[M-H]-	190.1	32859911
AllCCS	[M+Na-2H]-	191.8	32859911
AllCCS	[M+HCOO]-	193.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid	[H]C(CCCC(O)=O)=C([H])C\C([H])=C(\[H])C([H])(O)C1([H])O[C@@]1([H])C\C([H])=C(\[H])CCCCC	4202.6	Standard polar	33892256
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid	[H]C(CCCC(O)=O)=C([H])C\C([H])=C(\[H])C([H])(O)C1([H])O[C@@]1([H])C\C([H])=C(\[H])CCCCC	2418.9	Standard non polar	33892256
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid	[H]C(CCCC(O)=O)=C([H])C\C([H])=C(\[H])C([H])(O)C1([H])O[C@@]1([H])C\C([H])=C(\[H])CCCCC	2597.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid,1TMS,isomer #1	CCCCC/C=C\C[C@@H]1OC1C(O)/C=C\CC=CCCCC(=O)O[Si](C)(C)C	2581.9	Semi standard non polar	33892256
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid,1TMS,isomer #2	CCCCC/C=C\C[C@@H]1OC1C(/C=C\CC=CCCCC(=O)O)O[Si](C)(C)C	2620.4	Semi standard non polar	33892256
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid,2TMS,isomer #1	CCCCC/C=C\C[C@@H]1OC1C(/C=C\CC=CCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2608.6	Semi standard non polar	33892256
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid,1TBDMS,isomer #1	CCCCC/C=C\C[C@@H]1OC1C(O)/C=C\CC=CCCCC(=O)O[Si](C)(C)C(C)(C)C	2832.4	Semi standard non polar	33892256
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid,1TBDMS,isomer #2	CCCCC/C=C\C[C@@H]1OC1C(/C=C\CC=CCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2838.6	Semi standard non polar	33892256
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid,2TBDMS,isomer #1	CCCCC/C=C\C[C@@H]1OC1C(/C=C\CC=CCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3097.0	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 - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-07r3-2921000000-2297ca9c8fe2f1e1e7e4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-004i-7509200000-646f9e780523dd7060e7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic 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 - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 10V, Positive-QTOF	splash10-014i-0419000000-8de60f1d7da49d39d629	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 20V, Positive-QTOF	splash10-0629-2901000000-9db5343e48f8cf5dac34	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 40V, Positive-QTOF	splash10-0k9f-9300000000-b9173b0421a1cfd5862d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 10V, Negative-QTOF	splash10-000i-0319000000-57e762a656ee448ceae4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 20V, Negative-QTOF	splash10-0udi-0902000000-aa61e4564104099e78b2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 40V, Negative-QTOF	splash10-0006-9500000000-c97f668aa6ac9dceb4cf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 10V, Negative-QTOF	splash10-000i-0009000000-008540705d491eb4a7df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 20V, Negative-QTOF	splash10-00li-0639000000-f38a8e8a187e067b6199	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 40V, Negative-QTOF	splash10-053v-4912000000-1fc6494ad2303e54a646	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 10V, Positive-QTOF	splash10-014r-2429000000-2e93c0427c47a09346a8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 20V, Positive-QTOF	splash10-014i-8915000000-af317559053eb738b1db	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid 40V, Positive-QTOF	splash10-05po-9200000000-1c8f9c8f16acdde8168b	2021-09-25	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid (HMDB0062479)

MOL for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

3D MOL for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

3D SDF for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

3D-SDF for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

PDB for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

3D PDB for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

SMILES for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

INCHI for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

Structure for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

3D Structure for HMDB0062479 (10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra