MiMeDB: Showing metabocard for 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate (MMDBc0031752)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:47:48 UTC

Update Date

2022-08-31 18:24:19 UTC

Metabolite ID

MMDBc0031752

Metabolite Identification

Common Name

2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate

Description

2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate is an intermediate in LPS synthesis. It is a substrate for the protein tetraacyldisaccharide 4'-kinase which catalyzes the reaction: ATP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6-)-2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl beta-phosphate = ADP + 2,3,2',3'-tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07191209052D          
 
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M  END

 
  Mrv0541 07191209052D          
 
 91 92  0  0  1  0            999 V2000
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   17.5519   -8.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9640  -17.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2731  -11.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3938  -13.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8270  -16.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9943  -11.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1041  -13.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9889  -12.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1041  -14.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7047  -12.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8197  -15.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6992  -13.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8144  -15.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4148  -13.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5302  -16.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4094  -14.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5302  -17.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1197  -15.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
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  2  6  1  6  0  0  0
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  5 10  1  0  0  0  0
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 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
 22 28  1  6  0  0  0
 23 29  1  0  0  0  0
 25 30  1  0  0  0  0
 25 31  1  6  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 29 34  1  0  0  0  0
 30 35  1  0  0  0  0
 30 36  1  1  0  0  0
 32 37  1  6  0  0  0
 33 38  1  0  0  0  0
 34 39  1  0  0  0  0
 35 40  1  6  0  0  0
 36 41  1  0  0  0  0
 37 42  1  0  0  0  0
 38 43  1  0  0  0  0
 39 44  1  0  0  0  0
 40 45  1  0  0  0  0
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 42 48  1  0  0  0  0
 42 49  1  0  0  0  0
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 43 51  1  0  0  0  0
 44 52  1  0  0  0  0
 45 53  1  0  0  0  0
 45 54  2  0  0  0  0
 46 55  1  0  0  0  0
 51 56  1  0  0  0  0
 52 57  1  0  0  0  0
 53 58  1  0  0  0  0
 55 59  1  0  0  0  0
 55 60  1  6  0  0  0
 56 61  1  0  0  0  0
 57 62  1  0  0  0  0
 58 63  1  0  0  0  0
 58 64  1  1  0  0  0
 59 65  1  0  0  0  0
 61 66  1  0  0  0  0
 62 67  1  0  0  0  0
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 66 70  1  0  0  0  0
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 70 74  1  0  0  0  0
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 80 82  1  0  0  0  0
 81 83  1  0  0  0  0
 82 84  1  0  0  0  0
 83 85  1  0  0  0  0
 84 86  1  0  0  0  0
 85 87  1  0  0  0  0
 86 88  1  0  0  0  0
 87 89  1  0  0  0  0
 88 90  1  0  0  0  0
 89 91  1  0  0  0  0
  7 10  1  0  0  0  0
 32 35  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031752

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C68H129N2O20P/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(88-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)55(49-71)86-67(61)85-50-56-64(81)66(89-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4)62(68(87-56)90-91(82,83)84)70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2/h51-56,61-68,71-75,80-81H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,82,83,84)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1

> <INCHI_KEY>
HLDJGHAAKRKPAV-QDORLFPLSA-N

> <FORMULA>
C68H129N2O20P

> <MOLECULAR_WEIGHT>
1325.727

> <EXACT_MASS>
1324.88763109

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
156.14757684125212

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}methyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
5.85

> <JCHEM_LOGP>
12.919159918333333

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.2356871807703245

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1734659893746509

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7987589285644994

> <JCHEM_POLAR_SURFACE_AREA>
346.85999999999996

> <JCHEM_REFRACTIVITY>
346.72880000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
60

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipid A-disaccharide-1-P

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-12         0                                  
HETATM    1  C   UNK     0      18.598 -15.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.924 -14.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.272 -14.330   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.598 -16.635   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      19.924 -12.790   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      21.250 -15.095   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      17.272 -12.790   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      15.926 -15.095   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      17.272 -17.410   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.598 -12.015   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      21.250 -12.015   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.250 -16.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.926 -12.015   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.272 -18.950   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.936 -16.635   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      22.586 -11.250   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.586 -17.410   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.924 -17.410   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      15.926 -10.475   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.936 -19.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.922 -12.025   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.596 -18.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.936 -21.255   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.600 -18.950   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.922 -13.555   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      25.258 -11.260   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      21.260 -19.715   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      23.932 -19.715   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.600 -22.030   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      25.258 -14.330   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      22.586 -13.869   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      26.594 -12.025   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.260 -21.245   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.610 -23.570   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      26.594 -13.555   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      25.258 -15.870   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      27.919 -11.260   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.924 -22.020   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.274 -24.335   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      28.766 -14.330   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      26.604 -16.635   0.000  0.00  0.00           C+0
HETATM   42  P   UNK     0      27.919  -9.720   0.000  0.00  0.00           P+0
HETATM   43  C   UNK     0      19.924 -23.570   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.274 -25.875   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      30.102 -13.555   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      26.604 -18.175   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      27.766 -15.870   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      26.379  -9.710   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      27.909  -8.180   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      29.459  -9.720   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      18.598 -24.325   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      11.938 -26.640   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      31.427 -14.330   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      30.092 -12.015   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      27.930 -18.950   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      18.598 -25.865   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      11.938 -28.180   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      31.438 -15.870   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      27.930 -20.480   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      29.256 -18.175   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      17.272 -26.650   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      10.602 -28.945   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      32.764 -16.635   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      30.102 -16.635   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      29.266 -21.245   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      17.272 -28.190   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      10.602 -30.485   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      32.753 -18.195   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      29.266 -22.785   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      15.946 -28.955   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       9.266 -31.260   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      34.110 -18.991   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      30.592 -23.570   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      15.946 -30.495   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0       9.266 -32.800   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      34.110 -20.551   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      30.602 -25.100   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      14.610 -31.270   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      35.456 -21.326   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      31.928 -25.865   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      35.446 -22.866   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      31.928 -27.394   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      36.782 -23.641   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      33.264 -28.170   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      36.772 -25.182   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      33.254 -29.710   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      38.108 -25.946   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      34.590 -30.485   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      38.098 -27.486   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      34.590 -32.014   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      39.424 -28.272   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13   10                                                  
CONECT    8    3                                                            
CONECT    9    4   14   15                                                  
CONECT   10    5    7                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17   18                                                  
CONECT   13    7   19                                                       
CONECT   14    9   20                                                       
CONECT   15    9                                                            
CONECT   16   11   21                                                       
CONECT   17   12   22                                                       
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14   23   24                                                  
CONECT   21   16   25   26                                                  
CONECT   22   17   27   28                                                  
CONECT   23   20   29                                                       
CONECT   24   20                                                            
CONECT   25   21   30   31                                                  
CONECT   26   21   32                                                       
CONECT   27   22   33                                                       
CONECT   28   22                                                            
CONECT   29   23   34                                                       
CONECT   30   25   35   36                                                  
CONECT   31   25                                                            
CONECT   32   26   37   35                                                  
CONECT   33   27   38                                                       
CONECT   34   29   39                                                       
CONECT   35   30   40   32                                                  
CONECT   36   30   41                                                       
CONECT   37   32   42                                                       
CONECT   38   33   43                                                       
CONECT   39   34   44                                                       
CONECT   40   35   45                                                       
CONECT   41   36   46   47                                                  
CONECT   42   37   48   49   50                                             
CONECT   43   38   51                                                       
CONECT   44   39   52                                                       
CONECT   45   40   53   54                                                  
CONECT   46   41   55                                                       
CONECT   47   41                                                            
CONECT   48   42                                                            
CONECT   49   42                                                            
CONECT   50   42                                                            
CONECT   51   43   56                                                       
CONECT   52   44   57                                                       
CONECT   53   45   58                                                       
CONECT   54   45                                                            
CONECT   55   46   59   60                                                  
CONECT   56   51   61                                                       
CONECT   57   52   62                                                       
CONECT   58   53   63   64                                                  
CONECT   59   55   65                                                       
CONECT   60   55                                                            
CONECT   61   56   66                                                       
CONECT   62   57   67                                                       
CONECT   63   58   68                                                       
CONECT   64   58                                                            
CONECT   65   59   69                                                       
CONECT   66   61   70                                                       
CONECT   67   62   71                                                       
CONECT   68   63   72                                                       
CONECT   69   65   73                                                       
CONECT   70   66   74                                                       
CONECT   71   67   75                                                       
CONECT   72   68   76                                                       
CONECT   73   69   77                                                       
CONECT   74   70   78                                                       
CONECT   75   71                                                            
CONECT   76   72   79                                                       
CONECT   77   73   80                                                       
CONECT   78   74                                                            
CONECT   79   76   81                                                       
CONECT   80   77   82                                                       
CONECT   81   79   83                                                       
CONECT   82   80   84                                                       
CONECT   83   81   85                                                       
CONECT   84   82   86                                                       
CONECT   85   83   87                                                       
CONECT   86   84   88                                                       
CONECT   87   85   89                                                       
CONECT   88   86   90                                                       
CONECT   89   87   91                                                       
CONECT   90   88                                                            
CONECT   91   89                                                            
MASTER        0    0    0    0    0    0    0    0   91    0  184    0
END

Synonyms

Value	Source
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate	ChEBI
2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl beta-phosphate	ChEBI
2,3-Bis-(beta-hydroxymyristoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(beta-hydroxymyristoyl)-D-glucosaminyl beta-phosphate	ChEBI
Lipid a disaccharide	ChEBI
Lipid a-disaccharide-1-p	ChEBI
Lipid a-disaccharide-1-phosphate	ChEBI
Tetraacyldisaccharide 1-phosphate	Kegg
[2-N,3-O-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl]-(1->6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphate]	Kegg
2,3-Bis[(3R)-3-hydroxytetradecanoyl]-beta-D-glucosaminyl-(1->6)-2,3-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate	Kegg
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphate	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphoric acid	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphoric acid	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphate	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphoric acid	Generator
2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl b-phosphate	Generator
2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl b-phosphoric acid	Generator
2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl beta-phosphoric acid	Generator
2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl β-phosphate	Generator
2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl β-phosphoric acid	Generator
2,3-Bis-(b-hydroxymyristoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(b-hydroxymyristoyl)-D-glucosaminyl b-phosphate	Generator
2,3-Bis-(b-hydroxymyristoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(b-hydroxymyristoyl)-D-glucosaminyl b-phosphoric acid	Generator
2,3-Bis-(beta-hydroxymyristoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(beta-hydroxymyristoyl)-D-glucosaminyl beta-phosphoric acid	Generator
2,3-Bis-(β-hydroxymyristoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(β-hydroxymyristoyl)-D-glucosaminyl β-phosphate	Generator
2,3-Bis-(β-hydroxymyristoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(β-hydroxymyristoyl)-D-glucosaminyl β-phosphoric acid	Generator
Lipid a-disaccharide-1-phosphoric acid	Generator
Tetraacyldisaccharide 1-phosphoric acid	Generator
[2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl]-(1->6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphate]	Generator
[2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl]-(1->6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphoric acid]	Generator
[2-N,3-O-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl]-(1->6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphoric acid]	Generator
[2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1->6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphate]	Generator
[2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1->6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphoric acid]	Generator
2,3-Bis[(3R)-3-hydroxytetradecanoyl]-b-D-glucosaminyl-(1->6)-2,3-bis[(3R)-3-hydroxytetradecanoyl]-a-D-glucosaminyl 1-phosphate	Generator
2,3-Bis[(3R)-3-hydroxytetradecanoyl]-b-D-glucosaminyl-(1->6)-2,3-bis[(3R)-3-hydroxytetradecanoyl]-a-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis[(3R)-3-hydroxytetradecanoyl]-beta-D-glucosaminyl-(1->6)-2,3-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis[(3R)-3-hydroxytetradecanoyl]-β-D-glucosaminyl-(1->6)-2,3-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosaminyl 1-phosphate	Generator
2,3-Bis[(3R)-3-hydroxytetradecanoyl]-β-D-glucosaminyl-(1->6)-2,3-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphate	Generator
2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate	Generator
2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate	ChEBI
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-a-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphate	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-a-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphoric acid	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphoric acid	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-α-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphate	Generator
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-α-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphoric acid	Generator

Molecular Formula

C₆₈H₁₂₉N₂O₂₀P

Average Mass

1325.727

Monoisotopic Mass

1324.88763109

IUPAC Name

{[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}methyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid

Traditional Name

lipid A-disaccharide-1-P

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC

InChI Identifier

InChI=1S/C68H129N2O20P/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(88-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)55(49-71)86-67(61)85-50-56-64(81)66(89-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4)62(68(87-56)90-91(82,83)84)70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2/h51-56,61-68,71-75,80-81H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,82,83,84)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1

InChI Key

HLDJGHAAKRKPAV-QDORLFPLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
Saccharolipid
Disaccharide phosphate
N-acyl-alpha-hexosamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Fatty acid ester
Monoalkyl phosphate
Alkyl phosphate
Dicarboxylic acid or derivatives
Fatty amide
Hydroxy acid
N-acyl-amine
Fatty acyl
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid ester
Carboxamide group
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

lipid As (CHEBI:18380 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.85	ALOGPS
logP	12.92	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	1.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	346.86 Å²	ChemAxon
Rotatable Bond Count	60	ChemAxon
Refractivity	346.73 m³·mol⁻¹	ChemAxon
Polarizability	156.15 Å³	ChemAxon
Number of Rings	2	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	splash10-0a5i-9077000000-fb97c94534c7d2e30470	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-9132001010-45398bc37124f083ab02	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05ai-9542100060-e4b149d832201050e4b5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9213012000-f08e8ce45347e7162adc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100001000-c18a6ea9cb3a8e40c69c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-72748762d9de8d450bf3	2015-09-15	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
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	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

C04932

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13831140

PDB ID

Not Available

ChEBI ID

18380

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate (MMDBc0031752)

MOL for #<Metabolite:0x00005634c28dd928>

3D MOL for #<Metabolite:0x00005634c28dd928>

3D SDF for #<Metabolite:0x00005634c28dd928>

3D-SDF for #<Metabolite:0x00005634c28dd928>

PDB for #<Metabolite:0x00005634c28dd928>

3D PDB for #<Metabolite:0x00005634c28dd928>

SMILES for #<Metabolite:0x00005634c28dd928>

INCHI for #<Metabolite:0x00005634c28dd928>

Structure for #<Metabolite:0x00005634c28dd928>

3D Structure for #<Metabolite:0x00005634c28dd928>