MiMeDB: Showing metabocard for 2-MLCL(12:0/12:0/25:0/0:0) (MMDBc0043821)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 12:31:54 UTC

Update Date

2022-09-01 00:07:52 UTC

Metabolite ID

MMDBc0043821

Metabolite Identification

Common Name

2-MLCL(12:0/12:0/25:0/0:0)

Description

2-MLCL(12:0/12:0/25:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(12:0/12:0/25:0/0:0) contains two chains of dodecanoic acid at the C1 and C2 positions, one chain of pentacosanoic acid at the C3 position, one chain of 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

m189
  Mrv1572003191617422D          

 79 78  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
   23.0617   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0617   -4.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3476   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6335   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9194   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2053   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4912   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7770   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0629   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3488   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6347   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9205   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2064   -5.2747    0.0000 C   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
   10.6312   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9171   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2030   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4889   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7748   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0606   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3465   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2041   -9.4137    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
 12 28  1  0  0  0  0
 13 41  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 54  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
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 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  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
 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
M  END

m189
  Mrv1572003191617422D          

 79 78  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
   23.0617   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0617   -4.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3476   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6335   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9194   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2053   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4912   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7770   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0629   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3488   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6347   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9205   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2064   -5.2747    0.0000 C   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
   10.6312   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9171   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2030   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4889   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7748   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0606   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3465   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2041   -9.4137    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
 12 28  1  0  0  0  0
 13 41  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 54  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
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 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  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
 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
M  END
> <DATABASE_ID>
MMDBc0043821

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C58H114O16P2/c1-4-7-10-13-16-19-20-21-22-23-24-25-26-27-28-29-30-31-34-36-38-41-44-56(61)68-47-53(59)48-70-75(64,65)71-49-54(60)50-72-76(66,67)73-52-55(74-58(63)46-43-40-37-33-18-15-12-9-6-3)51-69-57(62)45-42-39-35-32-17-14-11-8-5-2/h53-55,59-60H,4-52H2,1-3H3,(H,64,65)(H,66,67)/t53-,54-,55-/m1/s1

> <INCHI_KEY>
NFFXBASJMBDGIS-AKNLOROWSA-N

> <FORMULA>
C58H114O16P2

> <MOLECULAR_WEIGHT>
1129.482

> <EXACT_MASS>
1128.758211587

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
190

> <JCHEM_AVERAGE_POLARIZABILITY>
133.82261397935724

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
8.31

> <JCHEM_LOGP>
17.236631824000003

> <ALOGPS_LOGS>
-6.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1919460976256198

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.589879306985992

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4040033610194245

> <JCHEM_POLAR_SURFACE_AREA>
230.87999999999997

> <JCHEM_REFRACTIVITY>
301.1113

> <JCHEM_ROTATABLE_BOND_COUNT>
63

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.79e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: m189                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-16         0                                  
HETATM    1  C   UNK     0      54.096 -16.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      53.010 -14.755   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      53.995 -12.932   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      53.112 -18.342   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      52.909 -11.168   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      54.554 -14.223   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      51.453 -14.080   0.000  0.00  0.00           H+0
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
HETATM   13  O   UNK     0      46.466 -11.369   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0      49.428 -11.448   0.000  0.00  0.00           H+0
HETATM   15  P   UNK     0      53.848  -9.088   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0      55.955  -9.688   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      53.848  -6.668   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      46.557 -17.306   0.000  0.00  0.00           C+0
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
HETATM   23  O   UNK     0      43.206 -19.918   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      46.168 -19.997   0.000  0.00  0.00           H+0
HETATM   25  P   UNK     0      50.640 -17.459   0.000  0.00  0.00           P+0
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
HETATM   28  C   UNK     0      43.049  -9.075   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      43.049  -7.635   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      41.716  -9.846   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      40.382  -9.075   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      39.049  -9.846   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      37.716  -9.075   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      36.384  -9.846   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      35.050  -9.075   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      33.717  -9.846   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      32.384  -9.075   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      31.051  -9.846   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      29.718  -9.075   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      28.385  -9.846   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      45.133 -12.139   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      45.133 -13.578   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      43.800 -11.367   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      42.467 -12.139   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      41.134 -11.367   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      39.801 -12.139   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      38.468 -11.367   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      37.135 -12.139   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      35.802 -11.367   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      34.469 -12.139   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      33.136 -11.367   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      31.803 -12.139   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      30.469 -11.367   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      39.840 -17.572   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      39.840 -16.132   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      38.507 -18.343   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      37.174 -17.572   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      35.841 -18.343   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      34.508 -17.572   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      33.175 -18.343   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      31.842 -17.572   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      30.509 -18.343   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      29.176 -17.572   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      27.843 -18.343   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      26.510 -17.572   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      25.177 -18.343   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      23.844 -17.572   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      22.511 -18.343   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      21.178 -17.572   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      19.845 -18.343   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      18.512 -17.572   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      17.179 -18.343   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      15.846 -17.572   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      14.513 -18.343   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      13.180 -17.572   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      11.847 -18.343   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      10.514 -17.572   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       9.181 -18.343   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       7.848 -17.572   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   28                                                       
CONECT   13    9   41                                                       
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   54                                                       
CONECT   23   19                                                            
CONECT   24   19                                                            
CONECT   25    4   26   27   21                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   12   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   13   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                                                            
CONECT   54   22   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   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                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  156    0
END

Synonyms

Value	Source
[(2R)-2,3-Bis(dodecanoyloxy)propoxy][(2R)-2-hydroxy-3-({hydroxy[(2R)-2-hydroxy-3-(pentacosanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinate	Generator

Molecular Formula

C₅₈H₁₁₄O₁₆P₂

Average Mass

1129.482

Monoisotopic Mass

1128.758211587

IUPAC Name

[(2R)-2,3-bis(dodecanoyloxy)propoxy][(2R)-2-hydroxy-3-({hydroxy[(2R)-2-hydroxy-3-(pentacosanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid

Traditional Name

(2R)-2,3-bis(dodecanoyloxy)propoxy((2R)-2-hydroxy-3-{[hydroxy((2R)-2-hydroxy-3-(pentacosanoyloxy)propoxy)phosphoryl]oxy}propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C58H114O16P2/c1-4-7-10-13-16-19-20-21-22-23-24-25-26-27-28-29-30-31-34-36-38-41-44-56(61)68-47-53(59)48-70-75(64,65)71-49-54(60)50-72-76(66,67)73-52-55(74-58(63)46-43-40-37-33-18-15-12-9-6-3)51-69-57(62)45-42-39-35-32-17-14-11-8-5-2/h53-55,59-60H,4-52H2,1-3H3,(H,64,65)(H,66,67)/t53-,54-,55-/m1/s1

InChI Key

NFFXBASJMBDGIS-AKNLOROWSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00018 g/L	ALOGPS
logP	8.31	ALOGPS
logP	17.24	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-3.4	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	63	ChemAxon
Refractivity	301.11 m³·mol⁻¹	ChemAxon
Polarizability	133.82 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	splash10-01ti-0913341205-85499b708a7f8d8b0971	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0410-1824594104-eed519dfdffd6ba8bc2e	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-5454981100-f04540b2316222b33cd3	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001j-0906021102-97bcdd4dc14b2994f126	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003s-6908031000-675eea2fbfc878314d5a	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005a-9222030000-d3af77adace124d560d1	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

Not Available

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

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

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

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PDB ID

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ChEBI ID

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Food Biomarker Ontology

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References

Synthesis Reference

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General References

Baile MG, Lu YW, Claypool SM: The topology and regulation of cardiolipin biosynthesis and remodeling in yeast. Chem Phys Lipids. 2014 Apr;179:25-31. doi: 10.1016/j.chemphyslip.2013.10.008. Epub 2013 Nov 1. [PubMed:24184646 ]

Showing metabocard for 2-MLCL(12:0/12:0/25:0/0:0) (MMDBc0043821)

MOL for #<Metabolite:0x00007fecae03ece0>

3D MOL for #<Metabolite:0x00007fecae03ece0>

3D SDF for #<Metabolite:0x00007fecae03ece0>

3D-SDF for #<Metabolite:0x00007fecae03ece0>

PDB for #<Metabolite:0x00007fecae03ece0>

3D PDB for #<Metabolite:0x00007fecae03ece0>

SMILES for #<Metabolite:0x00007fecae03ece0>

INCHI for #<Metabolite:0x00007fecae03ece0>

Structure for #<Metabolite:0x00007fecae03ece0>

3D Structure for #<Metabolite:0x00007fecae03ece0>