MiMeDB: Showing metabocard for MLCL(0:0/12:0/15:1(11Z)/27:1(9Z)) (MMDBc0056784)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-07-07 22:02:38 UTC

Update Date

2023-12-14 16:53:50 UTC

Metabolite ID

MMDBc0056784

Metabolite Identification

Common Name

MLCL(0:0/12:0/15:1(11Z)/27:1(9Z))

Description

MLCL(0:0/12:0/15:1(11Z)/27:1(9Z)) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. MLCL(0:0/12:0/15:1(11Z)/27:1(9Z)) contains no chain at the C1 position, one dodecanoyl chain at the C2 position, one 11Z-pentadecenoyl chain at the C3 position, one 9Z-heptacosanoyl chain at the C4 position. MLCL is present in eukaryotes as part of the metabolic cycle of mitochondrial lipids. Removal of one acyl chain from a cardiolipin results in generation of monolysocardiolipin (MLCL). MLCL has been used as an intermediate in the synthesis of spin-labeled CL to study the interaction of CL with mitochondrial enzymes. Because a role for MLCL has been suggested in apoptosis, this molecule has been used to study its interaction with various enzymes involved in lipid remodeling and apoptosis. There are two species of monolysocardiolipins, 1-MLCL which is missing a fatty acid in position R1 the and 2-MLCL which is missing a fatty acid in position R4.

Structure

MOL SDF PDB SMILES InChI

MLCL(0:0/12:0/15:1(11Z)/27:1(9Z))
  Mrv1652312121922182D          

 83 82  0  0  0  0            999 V2000
   28.9804   -8.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3986   -7.9047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.9260   -6.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4530   -9.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3442   -5.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6600   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6989   -5.2740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7376   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6212   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7764   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8928   -6.0904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4797   -6.1327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.8475   -4.8685    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.9761   -5.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8475   -3.5722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9412   -9.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9800   -9.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.0188   -9.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9024   -9.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0576   -9.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1460  -10.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7329  -10.7129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1287   -9.3529    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1287   -8.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7092  -10.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5641   -7.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1784   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1784   -7.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4643   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7502   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0360   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3219   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6078   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8937   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1796   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4654   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7513   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0372   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3231   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3431   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3431   -8.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6290   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9149   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2007   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4866   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7725   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0584   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3443   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6301   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9160   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2019   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3769   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6628   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9486   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2345   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4316  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4316  -11.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7175  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0034  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2892  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5751  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8610  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1469  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4328  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7186  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8936  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1795  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4654  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7513  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0371  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3230  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6089  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8948  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1807  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4665  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7524  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0383  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3242  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6101  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8959  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1818  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4677  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7536  -10.6699    0.0000 C   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
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
  7 11  1  6  0  0  0
  7 12  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  1  0  0  0  0
 17 21  1  6  0  0  0
 17 22  1  1  0  0  0
 23  4  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 23 19  1  0  0  0  0
  2 26  1  6  0  0  0
 11 27  1  0  0  0  0
 20 40  1  0  0  0  0
 21 56  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 56 57  2  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 74 75  1  0  0  0  0
 75 76  1  0  0  0  0
 76 77  1  0  0  0  0
 77 78  1  0  0  0  0
 78 79  1  0  0  0  0
 79 80  1  0  0  0  0
 80 81  1  0  0  0  0
 81 82  1  0  0  0  0
 82 83  1  0  0  0  0
M  END

MLCL(0:0/12:0/15:1(11Z)/27:1(9Z))
  Mrv1652312121922182D          

 83 82  0  0  0  0            999 V2000
   28.9804   -8.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3986   -7.9047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.9260   -6.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4530   -9.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3442   -5.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6600   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6989   -5.2740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7376   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6212   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7764   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8928   -6.0904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4797   -6.1327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.8475   -4.8685    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.9761   -5.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8475   -3.5722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9412   -9.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9800   -9.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.0188   -9.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9024   -9.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0576   -9.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1460  -10.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7329  -10.7129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1287   -9.3529    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1287   -8.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7092  -10.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5641   -7.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1784   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1784   -7.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4643   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7502   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0360   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3219   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6078   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8937   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1796   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4654   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7513   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0372   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3231   -6.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3431   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3431   -8.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6290   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9149   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2007   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4866   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7725   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0584   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3443   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6301   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9160   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2019   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3769   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6628   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9486   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2345   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4316  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4316  -11.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7175  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0034  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2892  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5751  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8610  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1469  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4328  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7186  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8936  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1795  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4654  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7513  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0371  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4677  -11.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7536  -10.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
MMDBc0056784

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CO)(COP(O)(=O)OC[C@@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCC)OC(=O)CCCCCCC\C=C/CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C63H120O16P2/c1-4-7-10-13-16-19-21-23-24-25-26-27-28-29-30-31-32-33-34-36-39-42-45-48-51-63(68)79-60(55-73-61(66)49-46-43-40-38-35-22-20-17-14-11-8-5-2)57-77-81(71,72)75-54-58(65)53-74-80(69,70)76-56-59(52-64)78-62(67)50-47-44-41-37-18-15-12-9-6-3/h11,14,32-33,58-60,64-65H,4-10,12-13,15-31,34-57H2,1-3H3,(H,69,70)(H,71,72)/b14-11-,33-32-/t58-,59-,60-/m1/s1

> <INCHI_KEY>
XQRJGACICHTVQX-YPMIUSCKSA-N

> <FORMULA>
C63H120O16P2

> <MOLECULAR_WEIGHT>
1195.585

> <EXACT_MASS>
1194.80516178

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
201

> <JCHEM_AVERAGE_POLARIZABILITY>
141.8069283734551

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-pentadec-11-enoyloxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
8.75

> <JCHEM_LOGP>
18.735631835666673

> <ALOGPS_LOGS>
-7.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1918066351379855

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5897398907203089

> <JCHEM_PKA_STRONGEST_BASIC>
-2.983758125665924

> <JCHEM_POLAR_SURFACE_AREA>
230.88

> <JCHEM_REFRACTIVITY>
326.34950000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
66

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-{[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-pentadec-11-enoyloxy]propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-DEC-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: MLCL(0:0/12:0/15:1(11Z)/27:1(9Z))                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-DEC-19         0                                  
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HETATM   42  C   UNK     0      38.507 -18.344   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      37.174 -17.572   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      35.841 -18.344   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      34.508 -17.572   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      33.175 -18.344   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      31.842 -17.572   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      30.509 -18.344   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      29.176 -17.572   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      27.843 -18.344   0.000  0.00  0.00           C+0
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HETATM   52  C   UNK     0      24.970 -17.572   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      23.637 -18.344   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      22.304 -17.572   0.000  0.00  0.00           C+0
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HETATM   57  O   UNK     0      41.872 -22.128   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      40.539 -19.917   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      39.206 -20.688   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      37.873 -19.917   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      36.540 -20.688   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      35.207 -19.917   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      33.874 -20.688   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      32.541 -19.917   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      31.208 -20.688   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      29.668 -20.688   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      28.335 -19.917   0.000  0.00  0.00           C+0
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HETATM   69  C   UNK     0      25.669 -19.917   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      24.336 -20.688   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      23.003 -19.917   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      21.670 -20.688   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      20.337 -19.917   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      19.004 -20.688   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      17.671 -19.917   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      16.338 -20.688   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      15.005 -19.917   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      13.672 -20.688   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      12.339 -19.917   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      11.006 -20.688   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0       9.673 -19.917   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0       8.340 -20.688   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0       7.007 -19.917   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    5                                                       
CONECT    4    1   23                                                       
CONECT    5    3   13                                                       
CONECT    6    7    9                                                       
CONECT    7    6    8   11   12                                             
CONECT    8    7   10                                                       
CONECT    9    6   13                                                       
CONECT   10    8                                                            
CONECT   11    7   27                                                       
CONECT   12    7                                                            
CONECT   13   14   15    5    9                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   17   19                                                       
CONECT   17   16   18   21   22                                             
CONECT   18   17   20                                                       
CONECT   19   16   23                                                       
CONECT   20   18   40                                                       
CONECT   21   17   56                                                       
CONECT   22   17                                                            
CONECT   23    4   24   25   19                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    2                                                            
CONECT   27   11   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   20   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54                                                            
CONECT   56   21   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77   79                                                       
CONECT   79   78   80                                                       
CONECT   80   79   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82                                                            
MASTER        0    0    0    0    0    0    0    0   83    0  164    0
END

Synonyms

Value	Source
[(2R)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-pentadec-11-enoyloxy]propoxy]phosphinate	Generator

Molecular Formula

C₆₃H₁₂₀O₁₆P₂

Average Mass

1195.585

Monoisotopic Mass

1194.80516178

IUPAC Name

[(2R)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-pentadec-11-enoyloxy]propoxy]phosphinic acid

Traditional Name

(2R)-3-{[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-pentadec-11-enoyloxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CO)(COP(O)(=O)OC[C@@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCC)OC(=O)CCCCCCC\C=C/CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCC

InChI Identifier

InChI=1S/C63H120O16P2/c1-4-7-10-13-16-19-21-23-24-25-26-27-28-29-30-31-32-33-34-36-39-42-45-48-51-63(68)79-60(55-73-61(66)49-46-43-40-38-35-22-20-17-14-11-8-5-2)57-77-81(71,72)75-54-58(65)53-74-80(69,70)76-56-59(52-64)78-62(67)50-47-44-41-37-18-15-12-9-6-3/h11,14,32-33,58-60,64-65H,4-10,12-13,15-31,34-57H2,1-3H3,(H,69,70)(H,71,72)/b14-11-,33-32-/t58-,59-,60-/m1/s1

InChI Key

XQRJGACICHTVQX-YPMIUSCKSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0001 g/L	ALOGPS
logP	8.75	ALOGPS
logP	18.74	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	230.88 Å²	ChemAxon
Rotatable Bond Count	66	ChemAxon
Refractivity	326.35 m³·mol⁻¹	ChemAxon
Polarizability	141.81 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	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for MLCL(0:0/12:0/15:1(11Z)/27:1(9Z)) (MMDBc0056784)

MOL for #<Metabolite:0x00007fecad5865a0>

3D MOL for #<Metabolite:0x00007fecad5865a0>

3D SDF for #<Metabolite:0x00007fecad5865a0>

3D-SDF for #<Metabolite:0x00007fecad5865a0>

PDB for #<Metabolite:0x00007fecad5865a0>

3D PDB for #<Metabolite:0x00007fecad5865a0>

SMILES for #<Metabolite:0x00007fecad5865a0>

INCHI for #<Metabolite:0x00007fecad5865a0>

Structure for #<Metabolite:0x00007fecad5865a0>

3D Structure for #<Metabolite:0x00007fecad5865a0>