NP-MRD: Showing NP-Card for Lipid A (NP0336511)

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Record Information

Version

2.0

Created at

2024-09-11 06:36:51 UTC

Updated at

2024-09-11 06:36:51 UTC

NP-MRD ID

NP0336511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lipid A

Description

Lipid A, also known as e. Coli lipid a or a, lipid, 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. Lipid A is an extremely weak basic (essentially neutral) compound (based on its pKa). Lipid A exists in all living organisms, ranging from bacteria to humans. Lipid A was first documented in 2002 (PMID: 11948150). Lipid A has been found in Escherichia, Pseudomonas, Salmonella and meningococcus (PMID: 11948150 ; PMID: 12045108 ) (PMID: 25867074) (PMID: 12045108).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212422D          

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M  END


  Mrv0541 02241212422D          

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M  END
> <DATABASE_ID>
NP0336511

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93-,94-/m1/s1

> <INCHI_KEY>
GZQKNULLWNGMCW-PWQABINMSA-N

> <FORMULA>
C94H178N2O25P2

> <MOLECULAR_WEIGHT>
1798.365

> <EXACT_MASS>
1797.21939228

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
213.02106443447633

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
6.80

> <JCHEM_LOGP>
23.970289701666672

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.3114555767729859

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6083911229044969

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9820492382196555

> <JCHEM_POLAR_SURFACE_AREA>
405.53000000000003

> <JCHEM_REFRACTIVITY>
477.1784999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
88

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipid A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      27.370 -40.458   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.370 -41.998   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.704 -42.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.704 -39.688   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      30.038 -40.458   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      30.038 -41.998   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.045 -42.757   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.057 -44.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.397 -45.057   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.724 -44.276   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.712 -42.736   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      35.372 -41.977   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      32.730 -45.078   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      32.705 -41.999   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      31.371 -42.769   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      26.037 -39.688   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      28.704 -38.148   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      30.038 -37.378   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      38.040 -41.955   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      38.015 -38.875   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      36.687 -39.656   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      38.027 -40.415   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      39.354 -39.634   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      38.065 -45.035   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0      39.379 -42.714   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      43.399 -44.992   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      40.732 -45.013   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      39.392 -44.254   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      46.066 -44.970   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      44.726 -44.211   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      48.733 -44.948   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      47.393 -44.189   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      52.728 -44.146   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      51.401 -44.927   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      50.061 -44.167   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      54.068 -44.905   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      55.395 -44.124   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      56.735 -44.883   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      42.059 -44.232   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      42.047 -42.693   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      36.762 -48.896   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      40.744 -46.554   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      38.077 -46.575   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      36.749 -47.356   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      43.411 -46.532   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      42.084 -47.313   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      46.079 -46.510   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      44.751 -47.291   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      50.086 -47.248   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      48.746 -46.489   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      47.418 -47.269   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      51.413 -46.467   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      52.753 -47.226   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      54.080 -46.445   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      39.417 -47.334   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      39.429 -48.874   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      35.410 -46.597   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      23.388 -48.939   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      19.368 -46.661   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      22.035 -46.639   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      23.375 -47.399   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      16.701 -46.683   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      18.041 -47.442   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      14.033 -46.705   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      15.373 -47.464   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      10.039 -47.507   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      11.366 -46.726   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      12.706 -47.485   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       8.699 -46.748   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      20.708 -47.420   0.000  0.00  0.00           C+0
HETATM   71  N   UNK     0      28.704 -44.308   0.000  0.00  0.00           N+0
HETATM   72  C   UNK     0      27.370 -45.078   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      27.370 -46.618   0.000  0.00  0.00           O+0
HETATM   74  C   UNK     0      26.036 -44.308   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      23.369 -44.307   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      20.702 -44.307   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      22.035 -45.077   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      18.035 -44.307   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      19.368 -45.077   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      14.033 -45.076   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      15.367 -44.307   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      16.701 -45.077   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      12.700 -44.306   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      11.366 -45.076   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      10.033 -44.306   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      24.703 -45.078   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      24.703 -46.618   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      26.037 -42.768   0.000  0.00  0.00           O+0
HETATM   89  C   UNK     0      24.703 -41.998   0.000  0.00  0.00           C+0
HETATM   90  O   UNK     0      24.703 -40.458   0.000  0.00  0.00           O+0
HETATM   91  C   UNK     0      23.369 -42.768   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      20.702 -42.768   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      18.035 -42.768   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      19.368 -41.998   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      15.367 -42.768   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      16.701 -41.998   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      11.366 -41.998   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      12.700 -42.768   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      14.033 -41.998   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      10.033 -42.769   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0       8.699 -41.998   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0       7.365 -42.769   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      22.036 -41.998   0.000  0.00  0.00           C+0
HETATM  104  O   UNK     0      22.036 -40.458   0.000  0.00  0.00           O+0
HETATM  105  O   UNK     0      20.683 -38.159   0.000  0.00  0.00           O+0
HETATM  106  C   UNK     0      16.701 -40.501   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0      19.368 -40.480   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0      20.696 -39.699   0.000  0.00  0.00           C+0
HETATM  109  C   UNK     0      14.034 -40.523   0.000  0.00  0.00           C+0
HETATM  110  C   UNK     0      15.361 -39.742   0.000  0.00  0.00           C+0
HETATM  111  C   UNK     0      11.367 -40.545   0.000  0.00  0.00           C+0
HETATM  112  C   UNK     0      12.694 -39.764   0.000  0.00  0.00           C+0
HETATM  113  C   UNK     0       7.359 -39.807   0.000  0.00  0.00           C+0
HETATM  114  C   UNK     0       8.699 -40.566   0.000  0.00  0.00           C+0
HETATM  115  C   UNK     0      10.026 -39.785   0.000  0.00  0.00           C+0
HETATM  116  C   UNK     0       6.032 -40.588   0.000  0.00  0.00           C+0
HETATM  117  C   UNK     0       4.692 -39.829   0.000  0.00  0.00           C+0
HETATM  118  C   UNK     0       3.365 -40.609   0.000  0.00  0.00           C+0
HETATM  119  C   UNK     0      18.028 -39.720   0.000  0.00  0.00           C+0
HETATM  120  O   UNK     0      26.024 -36.608   0.000  0.00  0.00           O+0
HETATM  121  O   UNK     0      27.371 -37.378   0.000  0.00  0.00           O+0
HETATM  122  P   UNK     0      26.037 -38.148   0.000  0.00  0.00           P+0
HETATM  123  O   UNK     0      24.703 -37.378   0.000  0.00  0.00           O+0
CONECT    1   16    2    4                                                  
CONECT    2    1   88    3                                                  
CONECT    3    2   71    6                                                  
CONECT    4    1   17    5                                                  
CONECT    5    4    6                                                       
CONECT    6    5    3   15                                                  
CONECT    7   14    8   12                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   57                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12   19                                                  
CONECT   12    7   11                                                       
CONECT   13    8                                                            
CONECT   14    7   15                                                       
CONECT   15    6   14                                                       
CONECT   16    1  122                                                       
CONECT   17    4   18                                                       
CONECT   18   17                                                            
CONECT   19   11   22                                                       
CONECT   20   22                                                            
CONECT   21   22                                                            
CONECT   22   19   20   21   23                                             
CONECT   23   22                                                            
CONECT   24   10   28                                                       
CONECT   25   28                                                            
CONECT   26   30   39                                                       
CONECT   27   39   28                                                       
CONECT   28   24   25   27                                                  
CONECT   29   32   30                                                       
CONECT   30   26   29                                                       
CONECT   31   32   35                                                       
CONECT   32   29   31                                                       
CONECT   33   36   34                                                       
CONECT   34   33   35                                                       
CONECT   35   31   34                                                       
CONECT   36   33   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   26   27   40                                                  
CONECT   40   39                                                            
CONECT   41   44                                                            
CONECT   42   46   55                                                       
CONECT   43   55   44                                                       
CONECT   44   41   43   57                                                  
CONECT   45   48   46                                                       
CONECT   46   42   45                                                       
CONECT   47   48   51                                                       
CONECT   48   45   47                                                       
CONECT   49   52   50                                                       
CONECT   50   49   51                                                       
CONECT   51   47   50                                                       
CONECT   52   49   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
CONECT   55   42   43   56                                                  
CONECT   56   55                                                            
CONECT   57    9   44                                                       
CONECT   58   61                                                            
CONECT   59   63   70                                                       
CONECT   60   70   61                                                       
CONECT   61   58   60   87                                                  
CONECT   62   65   63                                                       
CONECT   63   59   62                                                       
CONECT   64   65   68                                                       
CONECT   65   62   64                                                       
CONECT   66   69   67                                                       
CONECT   67   66   68                                                       
CONECT   68   64   67                                                       
CONECT   69   66                                                            
CONECT   70   59   60                                                       
CONECT   71    3   72                                                       
CONECT   72   71   73   74                                                  
CONECT   73   72                                                            
CONECT   74   72   86                                                       
CONECT   75   77   86                                                       
CONECT   76   79   77                                                       
CONECT   77   75   76                                                       
CONECT   78   79   82                                                       
CONECT   79   76   78                                                       
CONECT   80   83   81                                                       
CONECT   81   80   82                                                       
CONECT   82   78   81                                                       
CONECT   83   80   84                                                       
CONECT   84   83   85                                                       
CONECT   85   84                                                            
CONECT   86   74   75   87                                                  
CONECT   87   61   86                                                       
CONECT   88    2   89                                                       
CONECT   89   88   90   91                                                  
CONECT   90   89                                                            
CONECT   91   89  103                                                       
CONECT   92   94  103                                                       
CONECT   93   96   94                                                       
CONECT   94   92   93                                                       
CONECT   95   96   99                                                       
CONECT   96   93   95                                                       
CONECT   97  100   98                                                       
CONECT   98   97   99                                                       
CONECT   99   95   98                                                       
CONECT  100   97  101                                                       
CONECT  101  100  102                                                       
CONECT  102  101                                                            
CONECT  103   91   92  104                                                  
CONECT  104  103  108                                                       
CONECT  105  108                                                            
CONECT  106  110  119                                                       
CONECT  107  119  108                                                       
CONECT  108  104  105  107                                                  
CONECT  109  112  110                                                       
CONECT  110  106  109                                                       
CONECT  111  112  115                                                       
CONECT  112  109  111                                                       
CONECT  113  116  114                                                       
CONECT  114  113  115                                                       
CONECT  115  111  114                                                       
CONECT  116  113  117                                                       
CONECT  117  116  118                                                       
CONECT  118  117                                                            
CONECT  119  106  107                                                       
CONECT  120  122                                                            
CONECT  121  122                                                            
CONECT  122   16  120  121  123                                             
CONECT  123  122                                                            
MASTER        0    0    0    0    0    0    0    0  123    0  248    0
END

View in JSmol

Synonyms

Value	Source
E. coli lipid a	ChEBI
Diphosphoryl hexaacyl lipid a	HMDB
Synthetic e. coli lipid a	HMDB
a, Lipid	HMDB
Lipid a	MeSH

Chemical Formula

C₉₄H₁₇₈N₂O₂₅P₂

Average Mass

1798.3650 Da

Monoisotopic Mass

1797.21939 Da

IUPAC Name

{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid

Traditional Name

lipid A

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[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]1OP(O)(O)=O

InChI Identifier

InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93-,94-/m1/s1

InChI Key

GZQKNULLWNGMCW-PWQABINMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

laurate ester (CHEBI:47040 )
lipid As (CHEBI:47040 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.8	ALOGPS
logP	23.97	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	0.61	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	405.53 Å²	ChemAxon
Rotatable Bond Count	88	ChemAxon
Refractivity	477.18 m³·mol⁻¹	ChemAxon
Polarizability	213.02 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

External Links

HMDB ID

HMDB0013244

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029354

KNApSAcK ID

Not Available

Chemspider ID

8052983

KEGG Compound ID

C13908

BioCyc ID

CPD0-1283

BiGG ID

Not Available

Wikipedia Link

Lipid A

METLIN ID

Not Available

PubChem Compound

9877306

PDB ID

Not Available

ChEBI ID

134256

Good Scents ID

Not Available

References

General References

Murzyn K, Pasenkiewicz-Gierula M: Structural properties of the water/membrane interface of a bilayer built of the E. coli lipid A. J Phys Chem B. 2015 May 7;119(18):5846-56. doi: 10.1021/jp5119629. Epub 2015 Apr 28. [PubMed:25867074 ]
Tzeng YL, Datta A, Kolli VK, Carlson RW, Stephens DS: Endotoxin of Neisseria meningitidis composed only of intact lipid A: inactivation of the meningococcal 3-deoxy-D-manno-octulosonic acid transferase. J Bacteriol. 2002 May;184(9):2379-88. doi: 10.1128/JB.184.9.2379-2388.2002. [PubMed:11948150 ]
Raetz CR, Whitfield C: Lipopolysaccharide endotoxins. Annu Rev Biochem. 2002;71:635-700. doi: 10.1146/annurev.biochem.71.110601.135414. Epub 2001 Nov 9. [PubMed:12045108 ]

Showing NP-Card for Lipid A (NP0336511)

MOL for NP0336511 (Lipid A)

3D MOL for NP0336511 (Lipid A)

3D SDF for NP0336511 (Lipid A)

3D-SDF for NP0336511 (Lipid A)

PDB for NP0336511 (Lipid A)

3D PDB for NP0336511 (Lipid A)

SMILES for NP0336511 (Lipid A)

INCHI for NP0336511 (Lipid A)

Structure for NP0336511 (Lipid A)

3D Structure for NP0336511 (Lipid A)