MiMeDB: Showing metabocard for 1-MLCL(0:0/12:0/15:0/25:0) (MMDBc0043537)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 12:18:35 UTC

Update Date

2022-09-01 00:05:44 UTC

Metabolite ID

MMDBc0043537

Metabolite Identification

Common Name

1-MLCL(0:0/12:0/15:0/25:0)

Description

1-MLCL(0:0/12:0/15:0/25:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/12:0/15:0/25:0) contains one chain of at the C1 position, one chain of dodecanoic acid at the C2 position, one chain of pentadecanoic acid at the C3 position, one chain of pentacosanoic acid 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 inter¬≠mediate 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

m227
  Mrv1572003191616482D          

 82 81  0  0  1  0            999 V2000
   28.9801   -8.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3984   -7.9046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   28.9258   -6.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4528   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3440   -5.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2253   -7.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5639   -7.5431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.6598   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6987   -5.2740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7374   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6210   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7762   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8926   -6.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4795   -6.1326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.8473   -4.8685    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.9759   -5.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8473   -3.5722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9410   -9.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9798   -9.8262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.0186   -9.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9022   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0574   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1458  -10.6705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7327  -10.7128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1285   -9.3528    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1285   -8.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7090  -10.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1782   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1782   -7.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4641   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7500   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0358   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3217   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6076   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8935   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1794   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4653   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7512   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0371   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3229   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3430   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3430   -8.6423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6288   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9147   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2006   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4865   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7723   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0582   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3441   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6300   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9159   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2018   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4877   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7735   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0594   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3453   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4314  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4314  -11.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7173  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0032  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2890  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5749  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8608  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1467  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4326  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7185  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0044  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2903  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5761  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8620  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1479  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4338  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7197  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0056  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2915  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5774  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1491  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4350  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7209  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0068  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  9  8  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  1  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 28  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
 19 18  1  0  0  0  0
 19 23  1  0  0  0  0
 19 24  1  1  0  0  0
 20 19  1  0  0  0  0
 21 18  1  0  0  0  0
 22 20  1  0  0  0  0
 22 41  1  0  0  0  0
 23 57  1  0  0  0  0
 25  4  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 21  1  0  0  0  0
 28 29  2  0  0  0  0
 28 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
 39 40  1  0  0  0  0
 41 42  2  0  0  0  0
 41 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  1  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
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 57 58  2  0  0  0  0
 57 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  1  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
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 72 73  1  0  0  0  0
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 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
M  END

m227
  Mrv1572003191616482D          

 82 81  0  0  1  0            999 V2000
   28.9801   -8.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3984   -7.9046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   28.9258   -6.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4528   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3440   -5.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2253   -7.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5639   -7.5431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.6598   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6987   -5.2740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7374   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6210   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7762   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8926   -6.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4795   -6.1326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.8473   -4.8685    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.9759   -5.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8473   -3.5722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9410   -9.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9798   -9.8262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.0186   -9.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9022   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0574   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1458  -10.6705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7327  -10.7128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1285   -9.3528    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1285   -8.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7090  -10.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1782   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1782   -7.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4641   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7500   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0358   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3217   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6076   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8935   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1794   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4653   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7512   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0371   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3229   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3430   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3430   -8.6423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6288   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9147   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2006   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4865   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7723   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0582   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3441   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6300   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9159   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2018   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4877   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7735   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0594   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3453   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4314  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4314  -11.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7173  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0032  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2890  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5749  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8608  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1467  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4326  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7185  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0044  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2903  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5761  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8620  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1479  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4338  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7197  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0056  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2915  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5774  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1491  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4350  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7209  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0068  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
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M  END
> <DATABASE_ID>
MMDBc0043537

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C61H120O16P2/c1-4-7-10-13-16-19-21-23-24-25-26-27-28-29-30-31-32-34-37-40-43-46-49-61(66)77-58(53-71-59(64)47-44-41-38-36-33-22-20-17-14-11-8-5-2)55-75-79(69,70)73-52-56(63)51-72-78(67,68)74-54-57(50-62)76-60(65)48-45-42-39-35-18-15-12-9-6-3/h56-58,62-63H,4-55H2,1-3H3,(H,67,68)(H,69,70)/t56-,57+,58+/m0/s1

> <INCHI_KEY>
BXMGEQYOSOTVEP-FOCARYSPSA-N

> <FORMULA>
C61H120O16P2

> <MOLECULAR_WEIGHT>
1171.563

> <EXACT_MASS>
1170.80516178

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
199

> <JCHEM_AVERAGE_POLARIZABILITY>
140.94973073112106

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(pentacosanoyloxy)-3-(pentadecanoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
8.50

> <JCHEM_LOGP>
18.570337819000002

> <ALOGPS_LOGS>
-6.95

> <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>
230.87999999999997

> <JCHEM_REFRACTIVITY>
314.9143

> <JCHEM_ROTATABLE_BOND_COUNT>
66

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-(pentacosanoyloxy)-3-(pentadecanoyloxy)propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: m227                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-16         0                                  
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HETATM    8  C   UNK     0      49.765  -8.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.971  -9.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.177  -8.809   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      51.559  -9.845   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      44.382  -9.845   0.000  0.00  0.00           O+0
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HETATM   19  C   UNK     0      44.762 -18.342   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      42.968 -17.306   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      48.351 -18.342   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      41.174 -18.342   0.000  0.00  0.00           O+0
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HETATM   24  H   UNK     0      46.168 -19.997   0.000  0.00  0.00           H+0
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HETATM   26  O   UNK     0      50.640 -15.919   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      49.857 -19.431   0.000  0.00  0.00           O+0
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HETATM   29  O   UNK     0      45.133 -13.578   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      43.800 -11.367   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      42.467 -12.139   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      41.134 -11.367   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      39.801 -12.139   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      38.468 -11.367   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      37.135 -12.139   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      35.802 -11.367   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      34.469 -12.139   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      33.136 -11.367   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      31.803 -12.139   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      30.469 -11.367   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      39.840 -17.572   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      39.840 -16.132   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      38.507 -18.343   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      37.174 -17.572   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      35.841 -18.343   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      34.508 -17.572   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      33.175 -18.343   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      31.842 -17.572   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      30.509 -18.343   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      29.176 -17.572   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      27.843 -18.343   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      26.510 -17.572   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      25.177 -18.343   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      23.844 -17.572   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      22.511 -18.343   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      21.178 -17.572   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      41.872 -20.688   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      41.872 -22.128   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      40.539 -19.917   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      39.206 -20.688   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      37.873 -19.917   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      36.540 -20.688   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      35.207 -19.917   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      33.874 -20.688   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      32.541 -19.917   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      31.208 -20.688   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      29.875 -19.917   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      28.542 -20.688   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      27.209 -19.917   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      25.876 -20.688   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      24.543 -19.917   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      23.210 -20.688   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      21.877 -19.917   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      20.544 -20.688   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      19.211 -19.917   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      17.878 -20.688   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      16.545 -19.917   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      15.212 -20.688   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      13.879 -19.917   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      12.546 -20.688   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      11.213 -19.917   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0       9.880 -20.688   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    6    7    3                                             
CONECT    3    2    5                                                       
CONECT    4    1   25                                                       
CONECT    5    3   15                                                       
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    9   11                                                       
CONECT    9    8   13   14   10                                             
CONECT   10    9   12                                                       
CONECT   11    8   15                                                       
CONECT   12   10                                                            
CONECT   13    9   28                                                       
CONECT   14    9                                                            
CONECT   15   16   17    5   11                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   19   21                                                       
CONECT   19   18   23   24   20                                             
CONECT   20   19   22                                                       
CONECT   21   18   25                                                       
CONECT   22   20   41                                                       
CONECT   23   19   57                                                       
CONECT   24   19                                                            
CONECT   25    4   26   27   21                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   13   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   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   40                                                       
CONECT   40   39                                                            
CONECT   41   22   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   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   56                                                       
CONECT   56   55                                                            
CONECT   57   23   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   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                                                            
MASTER        0    0    0    0    0    0    0    0   82    0  162    0
END

Synonyms

Not Available

Molecular Formula

C₆₁H₁₂₀O₁₆P₂

Average Mass

1171.563

Monoisotopic Mass

1170.80516178

IUPAC Name

[(2S)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(pentacosanoyloxy)-3-(pentadecanoyloxy)propoxy]phosphinic acid

Traditional Name

(2S)-3-{[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-(pentacosanoyloxy)-3-(pentadecanoyloxy)propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C61H120O16P2/c1-4-7-10-13-16-19-21-23-24-25-26-27-28-29-30-31-32-34-37-40-43-46-49-61(66)77-58(53-71-59(64)47-44-41-38-36-33-22-20-17-14-11-8-5-2)55-75-79(69,70)73-52-56(63)51-72-78(67,68)74-54-57(50-62)76-60(65)48-45-42-39-35-18-15-12-9-6-3/h56-58,62-63H,4-55H2,1-3H3,(H,67,68)(H,69,70)/t56-,57+,58+/m0/s1

InChI Key

BXMGEQYOSOTVEP-FOCARYSPSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00013 g/L	ALOGPS
logP	8.5	ALOGPS
logP	18.57	ChemAxon
logS	-7	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	314.91 m³·mol⁻¹	ChemAxon
Polarizability	140.95 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	splash10-0v59-0953112214-6dfafde3f804db14b505	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-100u-1955201313-72f2d3c3580a27f8442f	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-5793203120-a3746d52f18b2c4e303b	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00ry-0895000213-1ada18dd070fc10175c9	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-9484020101-777599f40ecef9428f3f	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9143000100-abf48aa9715e41de4928	2019-02-23	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	Human feces; Human saliva	Unknown

Exposure Sources

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 1-MLCL(0:0/12:0/15:0/25:0) (MMDBc0043537)

MOL for #<Metabolite:0x0000556b6adfc228>

3D MOL for #<Metabolite:0x0000556b6adfc228>

3D SDF for #<Metabolite:0x0000556b6adfc228>

3D-SDF for #<Metabolite:0x0000556b6adfc228>

PDB for #<Metabolite:0x0000556b6adfc228>

3D PDB for #<Metabolite:0x0000556b6adfc228>

SMILES for #<Metabolite:0x0000556b6adfc228>

INCHI for #<Metabolite:0x0000556b6adfc228>

Structure for #<Metabolite:0x0000556b6adfc228>

3D Structure for #<Metabolite:0x0000556b6adfc228>