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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-14 00:33:07 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004690

Secondary Accession Numbers

HMDB04690

Metabolite Identification

Common Name

Hepoxilin B3

Description

Hepoxilin B3 is a normal human epidermis eicosanoid. Hepoxilin B3 is dramatically elevated in psoriatic lesions. The primary biological action of the hepoxilins appears to relate to their ability to release calcium from intracellular stores through a receptor-mediated action. The receptor is intracellular, and appears to be G-protein coupled. The conversion of hepoxilin into its omega-hydroxy catabolite has recently been demonstrated through the action of an omega-hydroxylase. This enzyme is different from that which oxidizes leukotriene B4, as the former activity is lost when the cell is disrupted, while leukotriene B4-catabolic activity is recovered in both the intact and disrupted cell. Additionally, hepoxilin catabolism is inhibited by CCCP, a mitochondrial uncoupler, while leukotriene catabolism is unaffected. As hepoxilins cause the translocation of calcium from intracellular stores in the endoplasmic reticulum to the mitochondria, it is speculated that hepoxilin omega-oxidation takes place in the mitochondria, and the omega-oxidation product facilitates accumulation of the elevated cytosolic calcium by the mitochondria. (PMID 10692117 , 11851887 , 10086189 ).

Structure

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

HMDB0004690
     RDKit          3D
Hepoxilin B3
 56 56  0  0  0  0  0  0  0  0999 V2000
    7.4255   -2.0368    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4928   -0.6669   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2216    0.1265    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0366   -0.5757   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    0.2775   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    0.4870    1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    0.1405    1.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549   -0.5527    1.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658    0.2092    1.4723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0879   -0.4451    0.8666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6990    0.8177    0.4202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3216    0.8868   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546    2.1690   -1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    0.2304   -1.9528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541    0.6608   -2.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    1.8872   -1.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1851    1.9827   -1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9780    1.0889   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233   -0.3563   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7155   -0.9742    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9574   -0.6718    1.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1621   -1.2406    0.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3889   -2.4714    0.9520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0204   -0.4680    0.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3323   -1.9794    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4038   -2.5310    0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257   -2.6753    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7040   -0.7496   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3426   -0.1393    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1078    0.2497    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3188    1.1044   -0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -0.6093   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991   -1.6098   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9577   -0.0527   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0803    1.2902   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.0092    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281    0.3624    3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4996   -0.8755    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.5135    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456    0.5298    2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571    1.6857    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.3054   -1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    2.7763   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -0.7329   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    0.0272   -3.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980    2.5354   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    2.4772   -1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4962    3.0443   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841    1.4229    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.7427   -1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003   -0.7625   -1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8151   -0.5460    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190   -2.0648    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548   -1.2481    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0769    0.3700    1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3585   -0.8623   -0.8229 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  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  1
 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


  Mrv0541 02231219582D          

 24 24  0  0  1  0            999 V2000
   25.4712  -18.4591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3443  -20.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3443  -24.5362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9153  -24.5362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0587  -19.1736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.8838  -19.1736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.3443  -19.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5983  -19.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3128  -19.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6298  -19.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0272  -19.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9153  -19.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0272  -20.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7417  -20.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9153  -20.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7417  -21.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4562  -22.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2008  -20.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4562  -22.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2008  -21.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9153  -22.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9153  -22.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6298  -23.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6298  -24.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
  6  8  1  1  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004690

> <DATABASE_NAME>
hmdb

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

> <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-YZTVQBIISA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.72251167716722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z)-10-hydroxy-10-[(2R,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>
epheta

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004690
     RDKit          3D
Hepoxilin B3
 56 56  0  0  0  0  0  0  0  0999 V2000
    7.4255   -2.0368    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4928   -0.6669   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2216    0.1265    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0366   -0.5757   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    0.2775   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    0.4870    1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    0.1405    1.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549   -0.5527    1.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658    0.2092    1.4723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0879   -0.4451    0.8666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6990    0.8177    0.4202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3216    0.8868   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546    2.1690   -1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    0.2304   -1.9528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541    0.6608   -2.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    1.8872   -1.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1851    1.9827   -1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9780    1.0889   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233   -0.3563   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7155   -0.9742    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9574   -0.6718    1.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1621   -1.2406    0.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3889   -2.4714    0.9520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0204   -0.4680    0.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3323   -1.9794    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4038   -2.5310    0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257   -2.6753    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7040   -0.7496   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3426   -0.1393    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1078    0.2497    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3188    1.1044   -0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -0.6093   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991   -1.6098   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9577   -0.0527   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0803    1.2902   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.0092    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281    0.3624    3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4996   -0.8755    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.5135    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456    0.5298    2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571    1.6857    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.3054   -1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    2.7763   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -0.7329   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    0.0272   -3.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980    2.5354   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    2.4772   -1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4962    3.0443   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841    1.4229    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.7427   -1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003   -0.7625   -1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8151   -0.5460    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190   -2.0648    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548   -1.2481    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0769    0.3700    1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3585   -0.8623   -0.8229 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  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  1
 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-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      47.546 -34.457   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      45.443 -38.101   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.443 -45.801   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      42.775 -45.801   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      46.776 -35.791   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      48.316 -35.791   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      45.443 -36.561   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.650 -36.561   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      50.984 -35.791   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      44.109 -35.791   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      52.317 -36.561   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.775 -36.561   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      52.317 -38.101   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.651 -38.871   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      42.775 -38.101   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      53.651 -40.411   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      54.985 -41.181   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.441 -38.871   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      54.985 -42.721   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.441 -40.411   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      42.775 -41.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.775 -42.721   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      44.109 -43.491   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.109 -45.031   0.000  0.00  0.00           C+0
CONECT    1    5    6                                                       
CONECT    2    7                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    1    6    7                                                  
CONECT    6    1    5    8                                                  
CONECT    7    2    5   10                                                  
CONECT    8    6    9                                                       
CONECT    9    8   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   15                                                       
CONECT   13   11   14                                                       
CONECT   14   13   16                                                       
CONECT   15   12   18                                                       
CONECT   16   14   17                                                       
CONECT   17   16   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24    3    4   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0004690
HETATM    1  C1  UNL     1       7.425  -2.037   0.532  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.493  -0.667  -0.073  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.222   0.127   0.171  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.037  -0.576  -0.423  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.799   0.277  -0.146  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.544   0.487   1.281  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.490   0.141   1.974  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.355  -0.553   1.340  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.066   0.209   1.472  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.088  -0.445   0.867  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.699   0.818   0.420  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.322   0.887  -1.031  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.055   2.169  -1.437  1.00  0.00           O  
HETATM   14  C12 UNL     1      -1.249   0.230  -1.953  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.454   0.661  -2.314  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.003   1.887  -1.808  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.185   1.983  -1.019  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.978   1.089  -0.544  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.823  -0.356  -0.723  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.715  -0.974   0.705  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.957  -0.672   1.497  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.162  -1.241   0.821  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.389  -2.471   0.952  1.00  0.00           O  
HETATM   24  O4  UNL     1      -8.020  -0.468   0.067  1.00  0.00           O  
HETATM   25  H1  UNL     1       7.332  -1.979   1.633  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.404  -2.531   0.330  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.626  -2.675   0.120  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.704  -0.750  -1.160  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.343  -0.139   0.384  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.108   0.250   1.270  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.319   1.104  -0.334  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.129  -0.609  -1.529  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.899  -1.610  -0.079  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.958  -0.053  -0.752  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.080   1.290  -0.579  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.335   1.009   1.866  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.428   0.362   3.056  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.500  -0.875   0.310  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.230  -1.513   1.937  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.146   0.530   2.527  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.357   1.686   0.733  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.655   0.305  -1.096  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.200   2.776  -0.692  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.946  -0.733  -2.416  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.990   0.027  -3.063  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.198   2.535  -2.764  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.177   2.477  -1.314  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.496   3.044  -0.751  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.884   1.423   0.069  1.00  0.00           H  
HETATM   50  H26 UNL     1      -3.968  -0.743  -1.230  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.800  -0.763  -1.084  1.00  0.00           H  
HETATM   52  H28 UNL     1      -3.815  -0.546   1.148  1.00  0.00           H  
HETATM   53  H29 UNL     1      -4.619  -2.065   0.607  1.00  0.00           H  
HETATM   54  H30 UNL     1      -5.855  -1.248   2.462  1.00  0.00           H  
HETATM   55  H31 UNL     1      -6.077   0.370   1.796  1.00  0.00           H  
HETATM   56  H32 UNL     1      -8.359  -0.862  -0.823  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

HMDB0004690
     RDKit          3D
Hepoxilin B3
 56 56  0  0  0  0  0  0  0  0999 V2000
    7.4255   -2.0368    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4928   -0.6669   -0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2216    0.1265    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0366   -0.5757   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    0.2775   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    0.4870    1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    0.1405    1.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549   -0.5527    1.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658    0.2092    1.4723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0879   -0.4451    0.8666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6990    0.8177    0.4202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3216    0.8868   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546    2.1690   -1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    0.2304   -1.9528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541    0.6608   -2.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    1.8872   -1.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1851    1.9827   -1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9780    1.0889   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233   -0.3563   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7155   -0.9742    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9574   -0.6718    1.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1621   -1.2406    0.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3889   -2.4714    0.9520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0204   -0.4680    0.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3323   -1.9794    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4038   -2.5310    0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257   -2.6753    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7040   -0.7496   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3426   -0.1393    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1078    0.2497    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3188    1.1044   -0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -0.6093   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991   -1.6098   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9577   -0.0527   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0803    1.2902   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349    1.0092    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281    0.3624    3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4996   -0.8755    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.5135    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456    0.5298    2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571    1.6857    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.3054   -1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    2.7763   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -0.7329   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    0.0272   -3.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980    2.5354   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    2.4772   -1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4962    3.0443   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841    1.4229    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.7427   -1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003   -0.7625   -1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8151   -0.5460    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190   -2.0648    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548   -1.2481    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0769    0.3700    1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3585   -0.8623   -0.8229 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  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  1
 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,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid	Kegg
(5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid	Kegg
(5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate	Generator
(5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate	Generator
10-Hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acid	HMDB
EPHETA	HMDB
Hepoxilin b	HMDB
Threo-hepoxilin b3	HMDB
Erythro-hepoxilin b3	HMDB
(5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoate	HMDB
(5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid	HMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate	HMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid	HMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoicacid	HMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate	HMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid	HMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoicacid	HMDB
10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoate	HMDB
10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

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

Traditional Name

epheta

CAS Registry Number

Not Available

SMILES

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

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-YZTVQBIISA-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

long-chain fatty acid (CHEBI:34784 )
epoxy fatty acid (CHEBI:34784 )
trienoic fatty acid (CHEBI:34784 )
hydroxy fatty acid (CHEBI:34784 )
hepoxilin (CHEBI:34784 )
Hepoxilins (C14810 )

Ontology

Not Available

Epidermis (HMDB: HMDB0004690)

Cellular substructure

Membrane (HMDB: HMDB0004690)
Extracellular (HMDB: HMDB0004690)

Organelle

Mitochondrion (HMDB: HMDB0004690)

Source

Exogenous

Exogenous (HMDB: HMDB0004690)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004690)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0092 g/L	ALOGPS
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	39.72 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]+	189.701	31661259
DarkChem	[M-H]-	188.197	31661259
DeepCCS	[M+H]+	194.974	30932474
DeepCCS	[M-H]-	192.443	30932474
DeepCCS	[M-2H]-	226.908	30932474
DeepCCS	[M+Na]+	202.135	30932474
AllCCS	[M+H]+	192.1	32859911
AllCCS	[M+H-H2O]+	189.3	32859911
AllCCS	[M+NH4]+	194.7	32859911
AllCCS	[M+Na]+	195.4	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.32 minutes	32390414
Predicted by Siyang on May 30, 2022	18.8561 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3068.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	337.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	228.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	551.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	890.0 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	549.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1838.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	635.0 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	1699.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	642.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	468.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	351.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	417.8 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hepoxilin B3	CCCCC\C=C/C[C@@H]1O[C@@H]1C(O)\C=C/C\C=C/CCCC(O)=O	3948.1	Standard polar	33892256
Hepoxilin B3	CCCCC\C=C/C[C@@H]1O[C@@H]1C(O)\C=C/C\C=C/CCCC(O)=O	2473.2	Standard non polar	33892256
Hepoxilin B3	CCCCC\C=C/C[C@@H]1O[C@@H]1C(O)\C=C/C\C=C/CCCC(O)=O	2577.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hepoxilin B3,1TMS,isomer #1	CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2617.7	Semi standard non polar	33892256
Hepoxilin B3,1TMS,isomer #2	CCCCC/C=C\C[C@@H]1O[C@@H]1C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2580.3	Semi standard non polar	33892256
Hepoxilin B3,2TMS,isomer #1	CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2617.6	Semi standard non polar	33892256
Hepoxilin B3,1TBDMS,isomer #1	CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2833.9	Semi standard non polar	33892256
Hepoxilin B3,1TBDMS,isomer #2	CCCCC/C=C\C[C@@H]1O[C@@H]1C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2831.2	Semi standard non polar	33892256
Hepoxilin B3,2TBDMS,isomer #1	CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3098.3	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 - Hepoxilin B3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-1900000000-7e176d0aeaf4c4f1ee84	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hepoxilin B3 GC-MS (2 TMS) - 70eV, Positive	splash10-004i-7509200000-646f9e780523dd7060e7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hepoxilin B3 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 - Hepoxilin B3 10V, Positive-QTOF	splash10-014i-0419000000-8de60f1d7da49d39d629	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 20V, Positive-QTOF	splash10-0100-2901000000-2b574e8af2bff160c04a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 40V, Positive-QTOF	splash10-052f-9300000000-171ed87708ea6a95def5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 10V, Negative-QTOF	splash10-000i-0319000000-57e762a656ee448ceae4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 20V, Negative-QTOF	splash10-0udi-0902000000-c21e19e865d525b26795	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 40V, Negative-QTOF	splash10-0006-9500000000-683be61d26516deb4500	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 10V, Positive-QTOF	splash10-0gbi-1219000000-bc47eb0a7064bed6f482	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 20V, Positive-QTOF	splash10-0lel-9546000000-c5d4fbc2b087abf03bdb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 40V, Positive-QTOF	splash10-016u-9200000000-2828e107370bf277debc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 10V, Negative-QTOF	splash10-000i-0109000000-8afa53cdece6f268eab6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 20V, Negative-QTOF	splash10-000i-1915000000-087ec9ceff47ac4d4d80	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin B3 40V, Negative-QTOF	splash10-0006-9430000000-ebabed01fd13ebff372c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Epidermis

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hepoxilin

METLIN ID

7071

PubChem Compound

5283209

PDB ID

Not Available

ChEBI ID

34784

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

Anton R, Vila L: Stereoselective biosynthesis of hepoxilin B3 in human epidermis. J Invest Dermatol. 2000 Mar;114(3):554-9. [PubMed:10692117 ]
Anton R, Camacho M, Puig L, Vila L: Hepoxilin B3 and its enzymatically formed derivative trioxilin B3 are incorporated into phospholipids in psoriatic lesions. J Invest Dermatol. 2002 Jan;118(1):139-46. [PubMed:11851887 ]
Pace-Asciak CR, Reynaud D, Demin P, Nigam S: The hepoxilins. A review. Adv Exp Med Biol. 1999;447:123-32. [PubMed:10086189 ]

Showing metabocard for Hepoxilin B3 (HMDB0004690)

MOL for HMDB0004690 (Hepoxilin B3)

3D MOL for HMDB0004690 (Hepoxilin B3)

3D SDF for HMDB0004690 (Hepoxilin B3)

3D-SDF for HMDB0004690 (Hepoxilin B3)

PDB for HMDB0004690 (Hepoxilin B3)

3D PDB for HMDB0004690 (Hepoxilin B3)

SMILES for HMDB0004690 (Hepoxilin B3)

INCHI for HMDB0004690 (Hepoxilin B3)

Structure for HMDB0004690 (Hepoxilin B3)

3D Structure for HMDB0004690 (Hepoxilin B3)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra