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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-14 00:30:47 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004688

Secondary Accession Numbers

HMDB04688

Metabolite Identification

Common Name

Hepoxilin A3

Description

Hepoxilin A3 is an electrophilic eicosanoids synthesized during arachidonic acid oxidative metabolism, which can participate in the Michael addition reaction with glutathione (GSH, a major cellular antioxidant) catalyzed by the GSH-S-transferase (GST) family. GSH-adducts have been observed with molecules synthesized through the 12-lipoxygenase pathway. (PMID 12432937 ). Hepoxilins have biological actions that appear to have, as their basis, changes in intracellular concentrations of ions including calcium and potassium ions as well as changes in second messenger systems. Recent evidence suggests that the biological actions of the hepoxilins may be receptor-mediated as indicated from data showing the existence of hepoxilin-specific binding proteins in the human neutrophils. Such evidence also implicates the association of G-proteins both in hepoxilin-binding as well as in hepoxilin action. (PMID 7947989 ).

Structure

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

HMDB0004688
     RDKit          3D
Hepoxilin A3
 56 56  0  0  0  0  0  0  0  0999 V2000
   -8.8997    1.4870    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5006    1.6957   -0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0169    0.3201   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6752    0.3679   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6470    0.9805   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5443    0.2031    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -0.3766    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -0.3317    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210   -1.7697    0.3111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6782   -2.5762    1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.3310    0.7514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4759   -1.3677    1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6349    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881    0.3201    1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -0.3288    2.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2660    0.7500    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -0.3530   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647   -0.4509   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478    0.5514    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    1.2715   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759    0.4790   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7459   -0.3616   -2.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6137   -0.1755   -2.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -1.3818   -2.6939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9076    0.5016    0.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6180    1.4813   -0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0527    2.3318    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8524    2.1268    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5942    2.3320   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0121   -0.3167    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7219   -0.0984   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    0.8839   -2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741   -0.6689   -1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9439    2.0313    0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304    1.1129   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    0.1428    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409   -0.9276    2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148    0.0703    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187    0.3317   -0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1926   -2.1903   -0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599   -3.1776    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931   -1.2410    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -0.7237   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6171    1.2218    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3066   -1.0572    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.6471    0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6612    1.1485   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -1.1887   -0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -1.3697   -0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5416    1.2653    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -0.0256    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385    1.9195    0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6821    2.0535   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7391   -0.2052   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0010    1.2007   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2804   -2.3477   -2.7112 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  6
 11 41  1  6
 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
   22.4831  -19.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9106  -15.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0390  -17.7821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1961  -16.4340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4831  -18.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3095  -20.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3095  -20.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6252  -17.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0240  -21.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6252  -16.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7685  -18.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3396  -17.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5950  -19.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1661  -18.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0240  -22.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4515  -18.4965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.6265  -18.4965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9106  -16.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0541  -18.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3396  -18.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5950  -18.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8805  -18.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1976  -18.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9120  -18.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 18  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 11  1  0  0  0  0
  5 23  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 15  1  0  0  0  0
 10 18  1  0  0  0  0
 11 19  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
 16 14  1  1  0  0  0
 14 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 24  1  1  0  0  0
 19 20  2  0  0  0  0
 21 22  2  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004688

> <DATABASE_NAME>
hmdb

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

> <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-CIQDQOFUSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.56639964571616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,9E)-8-hydroxy-10-[(2R,3S)-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>
4.676900472679155

> <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>
HXA3 cpd

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004688
     RDKit          3D
Hepoxilin A3
 56 56  0  0  0  0  0  0  0  0999 V2000
   -8.8997    1.4870    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5006    1.6957   -0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0169    0.3201   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6752    0.3679   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6470    0.9805   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5443    0.2031    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -0.3766    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -0.3317    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210   -1.7697    0.3111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6782   -2.5762    1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.3310    0.7514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4759   -1.3677    1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6349    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881    0.3201    1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -0.3288    2.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2660    0.7500    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -0.3530   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647   -0.4509   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478    0.5514    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    1.2715   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759    0.4790   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7459   -0.3616   -2.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6137   -0.1755   -2.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -1.3818   -2.6939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9076    0.5016    0.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6180    1.4813   -0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0527    2.3318    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8524    2.1268    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5942    2.3320   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0121   -0.3167    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7219   -0.0984   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    0.8839   -2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741   -0.6689   -1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9439    2.0313    0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304    1.1129   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    0.1428    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409   -0.9276    2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148    0.0703    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187    0.3317   -0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1926   -2.1903   -0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599   -3.1776    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931   -1.2410    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -0.7237   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6171    1.2218    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3066   -1.0572    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.6471    0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6612    1.1485   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -1.1887   -0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -1.3697   -0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5416    1.2653    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -0.0256    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385    1.9195    0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6821    2.0535   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7391   -0.2052   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0010    1.2007   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2804   -2.3477   -2.7112 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  6
 11 41  1  6
 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      41.968 -36.837   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.300 -28.367   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      46.739 -33.193   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      33.966 -30.677   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      41.968 -35.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      52.844 -39.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      52.844 -37.607   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.634 -32.217   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      54.178 -39.917   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.634 -30.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      40.635 -34.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.967 -32.987   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.511 -36.837   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      48.843 -35.297   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      54.178 -41.457   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      47.509 -34.527   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      45.969 -34.527   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.300 -29.907   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.301 -35.297   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.967 -34.527   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      51.511 -35.297   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      50.177 -34.527   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      43.302 -34.527   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.636 -35.297   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2   18                                                            
CONECT    3   16   17                                                       
CONECT    4   18                                                            
CONECT    5    1   11   23                                                  
CONECT    6    7    9                                                       
CONECT    7    6   13                                                       
CONECT    8   10   12                                                       
CONECT    9    6   15                                                       
CONECT   10    8   18                                                       
CONECT   11    5   19                                                       
CONECT   12    8   20                                                       
CONECT   13    7   21                                                       
CONECT   14   16   22                                                       
CONECT   15    9                                                            
CONECT   16    3   14   17                                                  
CONECT   17    3   16   24                                                  
CONECT   18    2    4   10                                                  
CONECT   19   11   20                                                       
CONECT   20   12   19                                                       
CONECT   21   13   22                                                       
CONECT   22   14   21                                                       
CONECT   23    5   24                                                       
CONECT   24   17   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0004688
HETATM    1  C1  UNL     1      -8.900   1.487   0.382  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.501   1.696  -0.230  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.017   0.320  -0.589  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.675   0.368  -1.211  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.647   0.980  -0.274  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.544   0.203   0.970  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.455  -0.377   1.378  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.178  -0.332   0.649  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.821  -1.770   0.311  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.678  -2.576   1.439  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.494  -2.331   0.751  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.476  -1.368   1.266  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.227  -0.635   0.478  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.188   0.320   1.069  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.742  -0.329   2.185  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.266   0.750   0.089  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.066  -0.353  -0.408  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.365  -0.451  -0.238  1.00  0.00           C  
HETATM   19  C17 UNL     1       6.148   0.551   0.480  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.161   1.271  -0.349  1.00  0.00           C  
HETATM   21  C19 UNL     1       8.176   0.479  -1.066  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.746  -0.362  -2.172  1.00  0.00           C  
HETATM   23  O3  UNL     1       6.614  -0.176  -2.705  1.00  0.00           O  
HETATM   24  O4  UNL     1       8.519  -1.382  -2.694  1.00  0.00           O  
HETATM   25  H1  UNL     1      -8.908   0.502   0.915  1.00  0.00           H  
HETATM   26  H2  UNL     1      -9.618   1.481  -0.450  1.00  0.00           H  
HETATM   27  H3  UNL     1      -9.053   2.332   1.076  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.852   2.127   0.557  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.594   2.332  -1.126  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.012  -0.317   0.322  1.00  0.00           H  
HETATM   31  H7  UNL     1      -7.722  -0.098  -1.350  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.670   0.884  -2.184  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.274  -0.669  -1.425  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.944   2.031   0.034  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.730   1.113  -0.846  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.486   0.143   1.559  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.541  -0.928   2.342  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.415   0.070   1.391  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.119   0.332  -0.197  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.193  -2.190  -0.637  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.060  -3.178   0.184  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.593  -1.241   2.352  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.148  -0.724  -0.585  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.617   1.222   1.380  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.307  -1.057   1.824  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.787   1.647   0.446  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.661   1.148  -0.802  1.00  0.00           H  
HETATM   48  H24 UNL     1       3.604  -1.189  -0.971  1.00  0.00           H  
HETATM   49  H25 UNL     1       5.896  -1.370  -0.615  1.00  0.00           H  
HETATM   50  H26 UNL     1       5.542   1.265   1.095  1.00  0.00           H  
HETATM   51  H27 UNL     1       6.811  -0.026   1.245  1.00  0.00           H  
HETATM   52  H28 UNL     1       7.738   1.919   0.394  1.00  0.00           H  
HETATM   53  H29 UNL     1       6.682   2.053  -1.003  1.00  0.00           H  
HETATM   54  H30 UNL     1       8.739  -0.205  -0.351  1.00  0.00           H  
HETATM   55  H31 UNL     1       9.001   1.201  -1.374  1.00  0.00           H  
HETATM   56  H32 UNL     1       8.280  -2.348  -2.711  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

HMDB0004688
     RDKit          3D
Hepoxilin A3
 56 56  0  0  0  0  0  0  0  0999 V2000
   -8.8997    1.4870    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5006    1.6957   -0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0169    0.3201   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6752    0.3679   -1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6470    0.9805   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5443    0.2031    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -0.3766    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -0.3317    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210   -1.7697    0.3111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6782   -2.5762    1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -2.3310    0.7514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4759   -1.3677    1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6349    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881    0.3201    1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -0.3288    2.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2660    0.7500    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -0.3530   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647   -0.4509   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478    0.5514    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    1.2715   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759    0.4790   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7459   -0.3616   -2.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6137   -0.1755   -2.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -1.3818   -2.6939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9076    0.5016    0.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6180    1.4813   -0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0527    2.3318    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8524    2.1268    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5942    2.3320   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0121   -0.3167    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7219   -0.0984   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    0.8839   -2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741   -0.6689   -1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9439    2.0313    0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304    1.1129   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    0.1428    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409   -0.9276    2.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148    0.0703    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187    0.3317   -0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1926   -2.1903   -0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599   -3.1776    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931   -1.2410    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -0.7237   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6171    1.2218    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3066   -1.0572    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.6471    0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6612    1.1485   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -1.1887   -0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -1.3697   -0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5416    1.2653    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105   -0.0256    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385    1.9195    0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6821    2.0535   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7391   -0.2052   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0010    1.2007   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2804   -2.3477   -2.7112 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  6
 11 41  1  6
 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-hydroxyeicosa-5,9,14-trienoic acid	ChEBI
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoate	Generator
11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoate	HMDB
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid	HMDB
Hexophilin a3	HMDB
HXA3 CPD	HMDB
8-EH-2	HMDB
Hepoxilin a	HMDB
(5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoate	HMDB
(5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoic acid	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoate	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acid	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoate	HMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acid	HMDB
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoate	HMDB
8-Hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoate	HMDB
8-Hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoic acid	HMDB
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoate	HMDB
Hepoxilin a3	MeSH

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

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

Traditional Name

HXA3 cpd

CAS Registry Number

85589-24-8

SMILES

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

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-CIQDQOFUSA-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:15631 )
epoxy fatty acid (CHEBI:15631 )
trienoic fatty acid (CHEBI:15631 )
hydroxy fatty acid (CHEBI:15631 )
Epoxyeicosatrienoic acids (LMFA03080012 )

Ontology

Not Available

Epidermis (HMDB: HMDB0004688)

Cell

Leukocyte (HMDB: HMDB0004688)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Membrane (HMDB: HMDB0004688)
Extracellular (HMDB: HMDB0004688)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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	0.0094 g/L	ALOGPS
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	38.57 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]+	189.533	31661259
DarkChem	[M-H]-	187.016	31661259
DeepCCS	[M+H]+	197.208	30932474
DeepCCS	[M-H]-	194.566	30932474
DeepCCS	[M-2H]-	229.142	30932474
DeepCCS	[M+Na]+	204.369	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hepoxilin A3	CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O	3932.1	Standard polar	33892256
Hepoxilin A3	CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O	2437.3	Standard non polar	33892256
Hepoxilin A3	CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O	2635.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hepoxilin A3,1TMS,isomer #1	CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C	2718.9	Semi standard non polar	33892256
Hepoxilin A3,1TMS,isomer #2	CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C	2635.3	Semi standard non polar	33892256
Hepoxilin A3,2TMS,isomer #1	CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2688.4	Semi standard non polar	33892256
Hepoxilin A3,1TBDMS,isomer #1	CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2962.0	Semi standard non polar	33892256
Hepoxilin A3,1TBDMS,isomer #2	CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2891.9	Semi standard non polar	33892256
Hepoxilin A3,2TBDMS,isomer #1	CCCCC/C=C\C[C@@H]1O[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	3167.0	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 - Hepoxilin A3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-02vi-8693000000-2485293cd435c17c3c1c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hepoxilin A3 GC-MS (2 TMS) - 70eV, Positive	splash10-00fs-9504200000-b478b5ac38b9ea248120	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hepoxilin A3 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hepoxilin A3 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 A3 10V, Positive-QTOF	splash10-014i-0119000000-f183a896d40b122d34a6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Positive-QTOF	splash10-0100-3912000000-8c6e6837752424382cf9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Positive-QTOF	splash10-05tf-9320000000-fd16a39bb680bae04d1e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 10V, Negative-QTOF	splash10-000i-0029000000-babbe7e5cbfec6729e52	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Negative-QTOF	splash10-014r-1849000000-46fca9cc7712fb3e7876	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Negative-QTOF	splash10-0a4l-9510000000-19c94ffaa2521c24fe09	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 10V, Positive-QTOF	splash10-0gb9-0119000000-2cd5dffbb345957a1712	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Positive-QTOF	splash10-0gb9-9447000000-9642f8a03a6be023dd7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Positive-QTOF	splash10-014l-9100000000-81bd5dcd190a81446961	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 10V, Negative-QTOF	splash10-000i-0009000000-9f5846a55564d3c61df3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Negative-QTOF	splash10-000i-1679000000-85590dd00f0e1fcb79da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Negative-QTOF	splash10-00kf-8941000000-b2f817f4c6f5d27eefd8	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Epidermis
Leukocyte

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000114 +/- 0.000087 uM	Adult (>18 years old)	Both	Normal	21359215	details

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

FDB023406

KNApSAcK ID

Not Available

Chemspider ID

4573947

KEGG Compound ID

C14808

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hepoxilin

METLIN ID

7070

PubChem Compound

5460414

PDB ID

Not Available

ChEBI ID

15631

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

Savidge TC, Newman PG, Pan WH, Weng MQ, Shi HN, McCormick BA, Quaroni A, Walker WA: Lipopolysaccharide-induced human enterocyte tolerance to cytokine-mediated interleukin-8 production may occur independently of TLR-4/MD-2 signaling. Pediatr Res. 2006 Jan;59(1):89-95. Epub 2005 Dec 2. [PubMed:16326999 ]
Sutherland M, Schewe T, Nigam S: Biological actions of the free acid of hepoxilin A3 on human neutrophils. Biochem Pharmacol. 2000 Feb 15;59(4):435-40. [PubMed:10644052 ]
Demin PM, Reynaud D, Pace-Asciak CR: Chemical synthesis and actions of 11,12-thiirano-hepoxilin A3. J Lipid Mediat Cell Signal. 1996 Jan;13(1):63-72. [PubMed:8998598 ]
Murphy RC, Zarini S: Glutathione adducts of oxyeicosanoids. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:471-82. [PubMed:12432937 ]
Mills L, Reynaud D, Pace-Asciak CR: Hepoxilin-evoked intracellular reorganization of calcium in human neutrophils: a confocal microscopy study. Exp Cell Res. 1997 Feb 1;230(2):337-41. [PubMed:9024792 ]
Pace-Asciak CR, Reynaud D, Laneuville O, Grinstein S, Nigam S: Hepoxilin A3 inhibits agonist-evoked rise in free intracellular calcium in human neutrophils. Adv Exp Med Biol. 1997;400A:375-80. [PubMed:9547579 ]
Mrsny RJ, Gewirtz AT, Siccardi D, Savidge T, Hurley BP, Madara JL, McCormick BA: Identification of hepoxilin A3 in inflammatory events: a required role in neutrophil migration across intestinal epithelia. Proc Natl Acad Sci U S A. 2004 May 11;101(19):7421-6. Epub 2004 May 3. [PubMed:15123795 ]
Nigam S, Patabhiraman S, Ciccoli R, Ishdorj G, Schwarz K, Petrucev B, Kuhn H, Haeggstrom JZ: The rat leukocyte-type 12-lipoxygenase exhibits an intrinsic hepoxilin A3 synthase activity. J Biol Chem. 2004 Jul 9;279(28):29023-30. Epub 2004 May 3. [PubMed:15123652 ]
Reynaud D, Demin PM, Sutherland M, Nigam S, Pace-Asciak CR: Hepoxilin signaling in intact human neutrophils: biphasic elevation of intracellular calcium by unesterified hepoxilin A3. FEBS Lett. 1999 Mar 12;446(2-3):236-8. [PubMed:10100848 ]
Yu Z, Schneider C, Boeglin WE, Marnett LJ, Brash AR: The lipoxygenase gene ALOXE3 implicated in skin differentiation encodes a hydroperoxide isomerase. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9162-7. Epub 2003 Jul 24. [PubMed:12881489 ]
Anton R, Puig L, Esgleyes T, de Moragas JM, Vila L: Occurrence of hepoxilins and trioxilins in psoriatic lesions. J Invest Dermatol. 1998 Apr;110(4):303-10. [PubMed:9540966 ]
Pace-Asciak CR, Reynaud D, Rounova O, Demin P, Pivnitsky KK: Hepoxilin A3 is metabolized into its omega-hydroxy metabolite by human neutrophils. Adv Exp Med Biol. 1999;469:535-8. [PubMed:10667379 ]
Dho S, Grinstein S, Corey EJ, Su WG, Pace-Asciak CR: Hepoxilin A3 induces changes in cytosolic calcium, intracellular pH and membrane potential in human neutrophils. Biochem J. 1990 Feb 15;266(1):63-8. [PubMed:2106877 ]
Hurley BP, Siccardi D, Mrsny RJ, McCormick BA: Polymorphonuclear cell transmigration induced by Pseudomonas aeruginosa requires the eicosanoid hepoxilin A3. J Immunol. 2004 Nov 1;173(9):5712-20. [PubMed:15494523 ]
Nigam S, Nodes S, Cichon G, Corey EJ, Pace-Asciak CR: Receptor-mediated action of hepoxilin A3 releases diacylglycerol and arachidonic acid from human neutrophils. Biochem Biophys Res Commun. 1990 Sep 28;171(3):944-8. [PubMed:2171511 ]
Reynaud D, Rounova O, Demin PM, Pivnitsky KK, Pace-Asciak CR: Hepoxilin A3 is oxidized by human neutrophils into its omega-hydroxy metabolite by an activity independent of LTB4 omega-hydroxylase. Biochim Biophys Acta. 1997 Oct 18;1348(3):287-98. [PubMed:9366245 ]
Pace-Asciak CR: Hepoxilins: a review on their cellular actions. Biochim Biophys Acta. 1994 Nov 17;1215(1-2):1-8. [PubMed:7947989 ]

Showing metabocard for Hepoxilin A3 (HMDB0004688)

MOL for HMDB0004688 (Hepoxilin A3)

3D MOL for HMDB0004688 (Hepoxilin A3)

3D SDF for HMDB0004688 (Hepoxilin A3)

3D-SDF for HMDB0004688 (Hepoxilin A3)

PDB for HMDB0004688 (Hepoxilin A3)

3D PDB for HMDB0004688 (Hepoxilin A3)

SMILES for HMDB0004688 (Hepoxilin A3)

INCHI for HMDB0004688 (Hepoxilin A3)

Structure for HMDB0004688 (Hepoxilin A3)

3D Structure for HMDB0004688 (Hepoxilin A3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra