MiMeDB: Showing metabocard for 1',3'-bis-[1-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol (MMDBc0055149)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:44:46 UTC

Update Date

2022-08-12 20:09:15 UTC

Metabolite ID

MMDBc0055149

Metabolite Identification

Common Name

1',3'-bis-[1-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol

Description

1,1'-dioleyl 2,2'-dilysocardiolipin(2-) belongs to the class of organic compounds known as 1'-(acyl-sn-glycero-3-phospho),3'-(acyl-sn-glycero-3-phospho)-sn-glycerols. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1-monoacylglyerol chain. Based on a literature review a significant number of articles have been published on 1,1'-dioleyl 2,2'-dilysocardiolipin(2-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221442D          

 68 67  0  0  1  0            999 V2000
   25.6697   -9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6697   -8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3841   -7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3841   -6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0986   -6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0986   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8131   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8131   -4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5275   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5275   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8131   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0986   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3841   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6697   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9552   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2407   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5262   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3828   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9539   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0960   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6684   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3815   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8118   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6684   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3815   -4.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8118   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1124   -2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   18.9374   -3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506   -2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.8256   -3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0973   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2394   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8105   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5249   -3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.2420   -4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -3.2704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.2420   -2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.6684   -3.6829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -3.6829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  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  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 34 32  1  0  0  0  0
 41 35  1  0  0  0  0
 41 37  1  0  0  0  0
 42 36  1  0  0  0  0
 42 38  1  0  0  0  0
 43 39  1  0  0  0  0
 43 40  1  0  0  0  0
 44 33  1  0  0  0  0
 45 34  1  0  0  0  0
 41 46  1  1  0  0  0
 42 47  1  6  0  0  0
 48 43  1  0  0  0  0
 49 44  2  0  0  0  0
 50 45  2  0  0  0  0
 55 35  1  0  0  0  0
 55 44  1  0  0  0  0
 56 36  1  0  0  0  0
 56 45  1  0  0  0  0
 57 37  1  0  0  0  0
 58 38  1  0  0  0  0
 59 39  1  0  0  0  0
 60 40  1  0  0  0  0
 61 51  1  0  0  0  0
 61 52  2  0  0  0  0
 61 57  1  0  0  0  0
 61 59  1  0  0  0  0
 62 53  1  0  0  0  0
 62 54  2  0  0  0  0
 62 58  1  0  0  0  0
 62 60  1  0  0  0  0
 63 17  1  0  0  0  0
 64 18  1  0  0  0  0
 65 19  1  0  0  0  0
 66 20  1  0  0  0  0
 41 67  1  1  0  0  0
 42 68  1  6  0  0  0
M  CHG  2  51  -1  53  -1
M  END


  Mrv1652306172221442D          

 68 67  0  0  1  0            999 V2000
   25.6697   -9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6697   -8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3841   -7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3841   -6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0986   -6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0986   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8131   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8131   -4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5275   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5275   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8131   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0986   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3841   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6697   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9552   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2407   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5262   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3828   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9539   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0960   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6684   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3815   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8118   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6684   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3815   -4.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8118   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1124   -2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   18.9374   -3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506   -2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.8256   -3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0973   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2394   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8105   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5249   -3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.2420   -4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -3.2704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.2420   -2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.6684   -3.6829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -3.6829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  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  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 34 32  1  0  0  0  0
 41 35  1  0  0  0  0
 41 37  1  0  0  0  0
 42 36  1  0  0  0  0
 42 38  1  0  0  0  0
 43 39  1  0  0  0  0
 43 40  1  0  0  0  0
 44 33  1  0  0  0  0
 45 34  1  0  0  0  0
 41 46  1  1  0  0  0
 42 47  1  6  0  0  0
 48 43  1  0  0  0  0
 49 44  2  0  0  0  0
 50 45  2  0  0  0  0
 55 35  1  0  0  0  0
 55 44  1  0  0  0  0
 56 36  1  0  0  0  0
 56 45  1  0  0  0  0
 57 37  1  0  0  0  0
 58 38  1  0  0  0  0
 59 39  1  0  0  0  0
 60 40  1  0  0  0  0
 61 51  1  0  0  0  0
 61 52  2  0  0  0  0
 61 57  1  0  0  0  0
 61 59  1  0  0  0  0
 62 53  1  0  0  0  0
 62 54  2  0  0  0  0
 62 58  1  0  0  0  0
 62 60  1  0  0  0  0
 63 17  1  0  0  0  0
 64 18  1  0  0  0  0
 65 19  1  0  0  0  0
 66 20  1  0  0  0  0
 41 67  1  1  0  0  0
 42 68  1  6  0  0  0
M  CHG  2  51  -1  53  -1
M  END
> <DATABASE_ID>
MMDBc0055149

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC(O)COP([O-])(=O)OC[C@]([H])(O)COC(=O)CCCCCCC\C([H])=C(\[H])CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C45H86O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-44(49)55-35-41(46)37-57-61(51,52)59-39-43(48)40-60-62(53,54)58-38-42(47)36-56-45(50)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,41-43,46-48H,3-16,21-40H2,1-2H3,(H,51,52)(H,53,54)/p-2/b19-17-,20-18-/t41-,42-/m1/s1

> <INCHI_KEY>
TZWVVHWEXQUYPT-YDAWRACYSA-L

> <FORMULA>
C45H84O15P2

> <MOLECULAR_WEIGHT>
927.101

> <EXACT_MASS>
926.529643161

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
146

> <JCHEM_AVERAGE_POLARIZABILITY>
106.50294340553003

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-hydroxy-3-[(2-hydroxy-3-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}propyl phosphono)oxy]propyl (9Z)-octadec-9-enoate

> <JCHEM_LOGP>
10.925440603333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.192087790784743

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5900210458942348

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4040033610194245

> <JCHEM_POLAR_SURFACE_AREA>
230.46999999999997

> <JCHEM_REFRACTIVITY>
241.31270000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
48

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3-[(2-hydroxy-3-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}propyl phosphono)oxy]propyl (9Z)-octadec-9-enoate

> <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      47.917 -16.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.238   3.905   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      47.917 -15.345   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.572   3.135   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      49.250 -14.575   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.572   1.595   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.250 -13.035   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.905   0.825   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      50.584 -12.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.905  -0.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.584 -10.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.239  -1.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.918  -9.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.239  -3.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.918  -8.415   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.573  -3.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      53.251  -7.645   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.573  -5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      53.251  -6.105   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.906  -6.105   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      51.918  -5.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      50.584  -6.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.574  -6.105   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      49.250  -5.335   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.907  -5.335   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      47.917  -6.105   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.241  -6.105   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      46.583  -5.335   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.575  -5.335   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      45.249  -6.105   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.908  -6.105   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      43.916  -5.335   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.242  -5.335   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      39.915  -6.105   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.243  -6.105   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      37.247  -6.105   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.910  -6.105   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      31.913  -6.105   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      29.245  -6.105   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      38.581  -5.335   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      22.577  -5.335   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      30.579  -6.875   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      42.582  -6.105   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.576  -6.105   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      38.581  -3.795   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      22.577  -3.795   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      30.579  -8.415   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      42.582  -7.645   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      18.576  -7.645   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      33.810  -4.771   0.000  0.00  0.00           O-1
HETATM   52  O   UNK     0      35.350  -7.438   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      27.348  -4.771   0.000  0.00  0.00           O-1
HETATM   54  O   UNK     0      25.808  -7.438   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      41.248  -5.335   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      19.909  -5.335   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      35.914  -5.335   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      25.244  -5.335   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      33.246  -6.875   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      27.912  -6.875   0.000  0.00  0.00           O+0
HETATM   61  P   UNK     0      34.580  -6.105   0.000  0.00  0.00           P+0
HETATM   62  P   UNK     0      26.578  -6.105   0.000  0.00  0.00           P+0
HETATM   63  H   UNK     0      54.585  -8.415   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.239  -6.105   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      54.585  -5.335   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0       7.906  -7.645   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      38.581  -6.875   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      22.577  -6.875   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19   63                                                  
CONECT   18   16   20   64                                                  
CONECT   19   17   21   65                                                  
CONECT   20   18   22   66                                                  
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27   31                                                       
CONECT   30   28   32                                                       
CONECT   31   29   33                                                       
CONECT   32   30   34                                                       
CONECT   33   31   44                                                       
CONECT   34   32   45                                                       
CONECT   35   41   55                                                       
CONECT   36   42   56                                                       
CONECT   37   41   57                                                       
CONECT   38   42   58                                                       
CONECT   39   43   59                                                       
CONECT   40   43   60                                                       
CONECT   41   35   37   46   67                                             
CONECT   42   36   38   47   68                                             
CONECT   43   39   40   48                                                  
CONECT   44   33   49   55                                                  
CONECT   45   34   50   56                                                  
CONECT   46   41                                                            
CONECT   47   42                                                            
CONECT   48   43                                                            
CONECT   49   44                                                            
CONECT   50   45                                                            
CONECT   51   61                                                            
CONECT   52   61                                                            
CONECT   53   62                                                            
CONECT   54   62                                                            
CONECT   55   35   44                                                       
CONECT   56   36   45                                                       
CONECT   57   37   61                                                       
CONECT   58   38   62                                                       
CONECT   59   39   61                                                       
CONECT   60   40   62                                                       
CONECT   61   51   52   57   59                                             
CONECT   62   53   54   58   60                                             
CONECT   63   17                                                            
CONECT   64   18                                                            
CONECT   65   19                                                            
CONECT   66   20                                                            
CONECT   67   41                                                            
CONECT   68   42                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  134    0
END

Synonyms

Value	Source
1',3'-Bis-[1-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol	ChEBI
1',3'-Bis[1-(9Z)-octadecenoyl-sn-glycero-3-phospho]glycerol(2-)	ChEBI
Dioleyl dilysocardiolipin(2-)	ChEBI

Molecular Formula

C₄₅H₈₄O₁₅P₂

Average Mass

927.101

Monoisotopic Mass

926.529643161

IUPAC Name

(2R)-2-hydroxy-3-[(2-hydroxy-3-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}propyl phosphono)oxy]propyl (9Z)-octadec-9-enoate

Traditional Name

(2R)-2-hydroxy-3-[(2-hydroxy-3-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}propyl phosphono)oxy]propyl (9Z)-octadec-9-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC(O)COP([O-])(=O)OC[C@]([H])(O)COC(=O)CCCCCCC\C([H])=C(\[H])CCCCCCCC

InChI Identifier

InChI=1S/C45H86O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-44(49)55-35-41(46)37-57-61(51,52)59-39-43(48)40-60-62(53,54)58-38-42(47)36-56-45(50)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,41-43,46-48H,3-16,21-40H2,1-2H3,(H,51,52)(H,53,54)/p-2/b19-17-,20-18-/t41-,42-/m1/s1

InChI Key

TZWVVHWEXQUYPT-YDAWRACYSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1'-(acyl-sn-glycero-3-phospho),3'-(acyl-sn-glycero-3-phospho)-sn-glycerols. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1-monoacylglyerol chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphoglycerols

Direct Parent

1'-(acyl-sn-glycero-3-phospho),3'-(acyl-sn-glycero-3-phospho)-sn-glycerols

Alternative Parents

Substituents

1'-(acyl-sn-glycero-3-phospho),3'-(acyl-sn-glycero-3-phospho)-sn-glycerol
Glycerophosphoglycerophosphate
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2,2'-dilysocardiolipin(2-) (CHEBI:77256 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	10.93	ChemAxon
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	230.47 Å²	ChemAxon
Rotatable Bond Count	48	ChemAxon
Refractivity	241.31 m³·mol⁻¹	ChemAxon
Polarizability	106.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30786254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86289198

PDB ID

Not Available

ChEBI ID

77256

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 1',3'-bis-[1-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol (MMDBc0055149)

MOL for #<Metabolite:0x00007fecf46ddcb8>

3D MOL for #<Metabolite:0x00007fecf46ddcb8>

3D SDF for #<Metabolite:0x00007fecf46ddcb8>

3D-SDF for #<Metabolite:0x00007fecf46ddcb8>

PDB for #<Metabolite:0x00007fecf46ddcb8>

3D PDB for #<Metabolite:0x00007fecf46ddcb8>

SMILES for #<Metabolite:0x00007fecf46ddcb8>

INCHI for #<Metabolite:0x00007fecf46ddcb8>

Structure for #<Metabolite:0x00007fecf46ddcb8>

3D Structure for #<Metabolite:0x00007fecf46ddcb8>