MiMeDB: Showing metabocard for (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoic acid (MMDBc0054764)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:34:05 UTC

Update Date

2022-08-12 20:09:04 UTC

Metabolite ID

MMDBc0054764

Metabolite Identification

Common Name

(17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoic acid

Description

(4Z,7Z,10Z,13Z,15E,17S,19Z)-17-hydroperoxydocosa-4,7,10,13,15,19-hexaenoate, also known as (17S)-hpdha(1-) or (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Based on a literature review very few articles have been published on (4Z,7Z,10Z,13Z,15E,17S,19Z)-17-hydroperoxydocosa-4,7,10,13,15,19-hexaenoate.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652306172221342D          

 39 38  0  0  1  0            999 V2000
   -3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5375   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 15  3  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 21 26  1  6  0  0  0
 26 25  1  0  0  0  0
 27  3  1  0  0  0  0
 28  5  1  0  0  0  0
 29  6  1  0  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 32 11  1  0  0  0  0
 33 12  1  0  0  0  0
 34 13  1  0  0  0  0
 35 14  1  0  0  0  0
 36 15  1  0  0  0  0
 37 16  1  0  0  0  0
 38 19  1  0  0  0  0
 21 39  1  6  0  0  0
M  CHG  1  24  -1
M  END

  Mrv1652306172221342D          

 39 38  0  0  1  0            999 V2000
   -3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5375   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 15  3  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 21 26  1  6  0  0  0
 26 25  1  0  0  0  0
 27  3  1  0  0  0  0
 28  5  1  0  0  0  0
 29  6  1  0  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 32 11  1  0  0  0  0
 33 12  1  0  0  0  0
 34 13  1  0  0  0  0
 35 14  1  0  0  0  0
 36 15  1  0  0  0  0
 37 16  1  0  0  0  0
 38 19  1  0  0  0  0
 21 39  1  6  0  0  0
M  CHG  1  24  -1
M  END
> <DATABASE_ID>
MMDBc0054764

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC)=C(/[H])C[C@]([H])(OO)C(\[H])=C(/[H])\C(\[H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-2-3-15-18-21(26-25)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(23)24/h3,5-8,11-16,19,21,25H,2,4,9-10,17-18,20H2,1H3,(H,23,24)/p-1/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+/t21-/m0/s1

> <INCHI_KEY>
BNHQALRBDJVUQB-YTQNUIGOSA-M

> <FORMULA>
C22H31O4

> <MOLECULAR_WEIGHT>
359.487

> <EXACT_MASS>
359.222783058

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.77087972109925

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z,7Z,10Z,13Z,15E,17S,19Z)-17-hydroperoxydocosa-4,7,10,13,15,19-hexaenoate

> <JCHEM_LOGP>
5.970989137999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.711074265112282

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885498349496062

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237376144824798

> <JCHEM_POLAR_SURFACE_AREA>
69.59

> <JCHEM_REFRACTIVITY>
125.092

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,7Z,10Z,13Z,15E,17S,19Z)-17-hydroperoxydocosa-4,7,10,13,15,19-hexaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850  -6.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.620  -8.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.160  -8.002   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.930  -6.668   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.470  -6.668   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.240  -8.002   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.240  -5.335   0.000  0.00  0.00           O-1
HETATM   25  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      -5.390  -4.001   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.470  -1.334   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.850  -1.334   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.930   1.334   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.310  -4.001   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.620   2.667   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.310  -6.668   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.540   2.667   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.850  -9.336   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.310  -4.001   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.770   1.334   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.540  -0.000   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   15   27                                                  
CONECT    4    5    6                                                       
CONECT    5    4    7   28                                                  
CONECT    6    4    8   29                                                  
CONECT    7    5    9   30                                                  
CONECT    8    6   10   31                                                  
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13   32                                                  
CONECT   12   10   14   33                                                  
CONECT   13   11   16   34                                                  
CONECT   14   12   17   35                                                  
CONECT   15    3   18   36                                                  
CONECT   16   13   19   37                                                  
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   21   38                                                  
CONECT   20   17   22                                                       
CONECT   21   18   19   26   39                                             
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   26                                                            
CONECT   26   21   25                                                       
CONECT   27    3                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   19                                                            
CONECT   39   21                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   76    0
END

Synonyms

Value	Source
(17S)-HPDHA(1-)	ChEBI
(17S)-HPDoHE(1-)	ChEBI
(17S)-Hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate	ChEBI
(4Z,7Z,10Z,13Z,15E,17S,19Z)-Hydroperoxydocosahexaenoate	ChEBI
(17S)-Hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoic acid	Generator
(4Z,7Z,10Z,13Z,15E,17S,19Z)-Hydroperoxydocosahexaenoic acid	Generator
(4Z,7Z,10Z,13Z,15E,17S,19Z)-17-Hydroperoxydocosa-4,7,10,13,15,19-hexaenoic acid	Generator

Molecular Formula

C₂₂H₃₁O₄

Average Mass

359.487

Monoisotopic Mass

359.222783058

IUPAC Name

(4Z,7Z,10Z,13Z,15E,17S,19Z)-17-hydroperoxydocosa-4,7,10,13,15,19-hexaenoate

Traditional Name

(4Z,7Z,10Z,13Z,15E,17S,19Z)-17-hydroperoxydocosa-4,7,10,13,15,19-hexaenoate

CAS Registry Number

Not Available

SMILES

[H]\C(CC)=C(/[H])C[C@]([H])(OO)C(\[H])=C(/[H])\C(\[H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCC([O-])=O

InChI Identifier

InChI=1S/C22H32O4/c1-2-3-15-18-21(26-25)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(23)24/h3,5-8,11-16,19,21,25H,2,4,9-10,17-18,20H2,1H3,(H,23,24)/p-1/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+/t21-/m0/s1

InChI Key

BNHQALRBDJVUQB-YTQNUIGOSA-M

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoic acid (MMDBc0054764)

MOL for #<Metabolite:0x00007fd5d4a17aa0>

3D MOL for #<Metabolite:0x00007fd5d4a17aa0>

3D SDF for #<Metabolite:0x00007fd5d4a17aa0>

3D-SDF for #<Metabolite:0x00007fd5d4a17aa0>

PDB for #<Metabolite:0x00007fd5d4a17aa0>

3D PDB for #<Metabolite:0x00007fd5d4a17aa0>

SMILES for #<Metabolite:0x00007fd5d4a17aa0>

INCHI for #<Metabolite:0x00007fd5d4a17aa0>

Structure for #<Metabolite:0x00007fd5d4a17aa0>

3D Structure for #<Metabolite:0x00007fd5d4a17aa0>