MiMeDB: Showing metabocard for 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate (MMDBc0031554)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:38:58 UTC

Update Date

2022-08-31 18:21:43 UTC

Metabolite ID

MMDBc0031554

Metabolite Identification

Common Name

2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate

Description

2,3,2'3'-tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates. Lipid IV(A) is involved in KDO metabolism. The enzyme is a single polypeptide that catalyzes the transfer of two KDO residues to a tetraacyldisaccharide-1,4'-bisphosphate precursor of lipid A, designated lipid IVA (Belunis, C. (PMID 7499229 ) E. coli KdtA (EcKdtA) is a bifunctional enzyme that transfers two KDO units from two CMP-KDO molecules to lipid IV(A). (PMID 20394418 ) The analog, KDO-lipid IVA, functions as an acceptor, but is mannosylated at less than 1% the rate of KDO2-lipid IVA. (PMID 9446588 )

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07091216172D          
 
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M  END

 
  Mrv0541 07091216172D          
 
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    9.9633  -13.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8417   -8.5018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9624  -10.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6727   -9.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2529  -14.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799  -15.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519   -8.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1260   -8.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6781  -11.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2529  -15.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799  -16.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5465   -9.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5426  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   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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  3  7  1  0  0  0  0
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 57 62  1  0  0  0  0
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 59 64  1  6  0  0  0
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 61 66  1  0  0  0  0
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 65 70  1  0  0  0  0
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  7 10  1  0  0  0  0
 36 39  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031554

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C68H130N2O23P2/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(90-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)56(89-68(61)93-95(84,85)86)50-87-67-62(70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2)66(64(55(49-71)88-67)92-94(81,82)83)91-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4/h51-56,61-68,71-75,80H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,81,82,83)(H2,84,85,86)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1

> <INCHI_KEY>
KVJWZTLXIROHIL-QDORLFPLSA-N

> <FORMULA>
C68H130N2O23P2

> <MOLECULAR_WEIGHT>
1405.7069

> <EXACT_MASS>
1404.8539615

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
160.63517717400714

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
12.795593886999997

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.3114555792425238

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6083911295058413

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9820492382196475

> <JCHEM_POLAR_SURFACE_AREA>
393.39

> <JCHEM_REFRACTIVITY>
357.6017

> <JCHEM_ROTATABLE_BOND_COUNT>
62

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipid iva

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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  P   UNK     0      14.386 -15.085   0.000  0.00  0.00           P+0
HETATM   15  C   UNK     0      17.272 -18.950   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.936 -16.635   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.586 -11.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.586 -17.410   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      19.924 -17.410   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      15.926 -10.475   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.376 -13.555   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.846 -15.085   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      14.376 -16.625   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      15.936 -19.715   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.922 -12.025   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.596 -18.950   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.936 -21.255   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.600 -18.950   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      23.922 -13.555   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      25.258 -11.260   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      21.260 -19.715   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      23.932 -19.715   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.600 -22.030   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      25.258 -14.330   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      22.586 -13.869   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      26.594 -12.025   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.260 -21.245   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.610 -23.570   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      26.594 -13.555   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      25.258 -15.870   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      27.919 -11.260   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      19.924 -22.020   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.274 -24.335   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0      28.766 -14.330   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0      26.604 -16.635   0.000  0.00  0.00           C+0
HETATM   46  P   UNK     0      27.919  -9.720   0.000  0.00  0.00           P+0
HETATM   47  C   UNK     0      19.924 -23.570   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      13.274 -25.875   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      30.102 -13.555   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      26.604 -18.175   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      27.766 -15.870   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      26.379  -9.710   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      27.909  -8.180   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      29.459  -9.720   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      18.598 -24.325   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      11.938 -26.640   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      31.427 -14.330   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      30.092 -12.015   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      27.930 -18.950   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      18.598 -25.865   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      11.938 -28.180   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      31.438 -15.870   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      27.930 -20.480   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      29.256 -18.175   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      17.272 -26.650   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      10.602 -28.945   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      32.764 -16.635   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      30.102 -16.635   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      29.266 -21.245   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      17.272 -28.190   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      10.602 -30.485   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      32.753 -18.195   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      29.266 -22.785   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      15.946 -28.955   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0       9.266 -31.260   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      34.110 -18.991   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      30.592 -23.570   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      15.946 -30.495   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       9.266 -32.800   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      34.110 -20.551   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      30.602 -25.100   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      14.610 -31.270   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      35.456 -21.326   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      31.928 -25.865   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      35.446 -22.866   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      31.928 -27.394   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      36.782 -23.641   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      33.264 -28.170   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      36.772 -25.182   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      33.254 -29.710   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      38.108 -25.946   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      34.590 -30.485   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      38.098 -27.486   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      34.590 -32.014   0.000  0.00  0.00           C+0
HETATM   95  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   14                                                       
CONECT    9    4   15   16                                                  
CONECT   10    5    7                                                       
CONECT   11    5   17                                                       
CONECT   12    6   18   19                                                  
CONECT   13    7   20                                                       
CONECT   14    8   21   22   23                                             
CONECT   15    9   24                                                       
CONECT   16    9                                                            
CONECT   17   11   25                                                       
CONECT   18   12   26                                                       
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   14                                                            
CONECT   24   15   27   28                                                  
CONECT   25   17   29   30                                                  
CONECT   26   18   31   32                                                  
CONECT   27   24   33                                                       
CONECT   28   24                                                            
CONECT   29   25   34   35                                                  
CONECT   30   25   36                                                       
CONECT   31   26   37                                                       
CONECT   32   26                                                            
CONECT   33   27   38                                                       
CONECT   34   29   39   40                                                  
CONECT   35   29                                                            
CONECT   36   30   41   39                                                  
CONECT   37   31   42                                                       
CONECT   38   33   43                                                       
CONECT   39   34   44   36                                                  
CONECT   40   34   45                                                       
CONECT   41   36   46                                                       
CONECT   42   37   47                                                       
CONECT   43   38   48                                                       
CONECT   44   39   49                                                       
CONECT   45   40   50   51                                                  
CONECT   46   41   52   53   54                                             
CONECT   47   42   55                                                       
CONECT   48   43   56                                                       
CONECT   49   44   57   58                                                  
CONECT   50   45   59                                                       
CONECT   51   45                                                            
CONECT   52   46                                                            
CONECT   53   46                                                            
CONECT   54   46                                                            
CONECT   55   47   60                                                       
CONECT   56   48   61                                                       
CONECT   57   49   62                                                       
CONECT   58   49                                                            
CONECT   59   50   63   64                                                  
CONECT   60   55   65                                                       
CONECT   61   56   66                                                       
CONECT   62   57   67   68                                                  
CONECT   63   59   69                                                       
CONECT   64   59                                                            
CONECT   65   60   70                                                       
CONECT   66   61   71                                                       
CONECT   67   62   72                                                       
CONECT   68   62                                                            
CONECT   69   63   73                                                       
CONECT   70   65   74                                                       
CONECT   71   66   75                                                       
CONECT   72   67   76                                                       
CONECT   73   69   77                                                       
CONECT   74   70   78                                                       
CONECT   75   71   79                                                       
CONECT   76   72   80                                                       
CONECT   77   73   81                                                       
CONECT   78   74   82                                                       
CONECT   79   75                                                            
CONECT   80   76   83                                                       
CONECT   81   77   84                                                       
CONECT   82   78                                                            
CONECT   83   80   85                                                       
CONECT   84   81   86                                                       
CONECT   85   83   87                                                       
CONECT   86   84   88                                                       
CONECT   87   85   89                                                       
CONECT   88   86   90                                                       
CONECT   89   87   91                                                       
CONECT   90   88   92                                                       
CONECT   91   89   93                                                       
CONECT   92   90   94                                                       
CONECT   93   91   95                                                       
CONECT   94   92                                                            
CONECT   95   93                                                            
MASTER        0    0    0    0    0    0    0    0   95    0  192    0
END

Synonyms

Value	Source
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate	ChEBI
Lipid a disaccharide bisphosphate	ChEBI
Lipid IV(a)	ChEBI
Lipid iva	Kegg
2-Deoxy-2-{[(3R)-3-hydroxytetradecanoyl]amino}-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phospho-alpha-D-glucopyranose	Kegg
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphate	Generator
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphoric acid	Generator
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphoric acid	Generator
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate	Generator
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphoric acid	Generator
Lipid a disaccharide bisphosphoric acid	Generator
2-Deoxy-2-{[(3R)-3-hydroxytetradecanoyl]amino}-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phospho-b-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phospho-a-D-glucopyranose	Generator
2-Deoxy-2-{[(3R)-3-hydroxytetradecanoyl]amino}-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phospho-β-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phospho-α-D-glucopyranose	Generator
2,3,2'3'-Tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphate	Generator
2,3,2'3'-Tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphoric acid	Generator
2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphoric acid	Generator
2,3,2'3'-Tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate	Generator
2,3,2'3'-Tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphoric acid	Generator
Lipid a precursor, salmonella typhimurium	MeSH
Lipid a precursors, bacterial	MeSH
Lipid a precursor ia	MeSH
Lipid a precursors, salmonella	MeSH
Compound 406	MeSH
Lipid a precursors, pseudomonas	MeSH
Tetraacyl disaccharide 1,4'-bisphosphate	MeSH

Molecular Formula

C₆₈H₁₃₀N₂O₂₃P₂

Average Mass

1405.7069

Monoisotopic Mass

1404.8539615

IUPAC Name

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

Traditional Name

lipid iva

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C68H130N2O23P2/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(90-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)56(89-68(61)93-95(84,85)86)50-87-67-62(70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2)66(64(55(49-71)88-67)92-94(81,82)83)91-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4/h51-56,61-68,71-75,80H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,81,82,83)(H2,84,85,86)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1

InChI Key

KVJWZTLXIROHIL-QDORLFPLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol 3-phosphate(2-) (CHEBI:74565 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	5.33	ALOGPS
logP	12.8	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	0.61	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	393.39 Å²	ChemAxon
Rotatable Bond Count	62	ChemAxon
Refractivity	357.6 m³·mol⁻¹	ChemAxon
Polarizability	160.64 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	splash10-029i-0419000000-605cb82c32daa4726adf	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-2936001001-595c04a099b74200efec	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-8978100003-4a52c47bfac648279767	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-9542103200-839d5cc8476dc47e87c1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9231001100-98e03379715375a1ce15	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a0ecfeea3dcc8eea4685	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

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

C04919

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10329124

PDB ID

Not Available

ChEBI ID

29056

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Belunis CJ, Clementz T, Carty SM, Raetz CR: Inhibition of lipopolysaccharide biosynthesis and cell growth following inactivation of the kdtA gene in Escherichia coli. J Biol Chem. 1995 Nov 17;270(46):27646-52. doi: 10.1074/jbc.270.46.27646. [PubMed:7499229 ]
Kadrmas JL, Raetz CR: Enzymatic synthesis of lipopolysaccharide in Escherichia coli. Purification and properties of heptosyltransferase i. J Biol Chem. 1998 Jan 30;273(5):2799-807. doi: 10.1074/jbc.273.5.2799. [PubMed:9446588 ]
Chung HS, Raetz CR: Interchangeable domains in the Kdo transferases of Escherichia coli and Haemophilus influenzae. Biochemistry. 2010 May 18;49(19):4126-37. doi: 10.1021/bi100343e. [PubMed:20394418 ]

Showing metabocard for 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate (MMDBc0031554)

MOL for #<Metabolite:0x00007fdb14d11518>

3D MOL for #<Metabolite:0x00007fdb14d11518>

3D SDF for #<Metabolite:0x00007fdb14d11518>

3D-SDF for #<Metabolite:0x00007fdb14d11518>

PDB for #<Metabolite:0x00007fdb14d11518>

3D PDB for #<Metabolite:0x00007fdb14d11518>

SMILES for #<Metabolite:0x00007fdb14d11518>

INCHI for #<Metabolite:0x00007fdb14d11518>

Structure for #<Metabolite:0x00007fdb14d11518>

3D Structure for #<Metabolite:0x00007fdb14d11518>