MiMeDB: Showing metabocard for KDO-lipid IV(A) (MMDBc0031618)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:37 UTC

Update Date

2022-08-31 18:22:32 UTC

Metabolite ID

MMDBc0031618

Metabolite Identification

Common Name

KDO-lipid IV(A)

Description

KDO-lipid IV(a) is a part of lipopolysaccharide or LPS. Specifically it is lipid IVA glycosylated with a single 3-deoxy-D-manno-octulosonic acid (KDO) residue. KDO-lipid IV(a) is a saccharolipid. The most familiar saccharolipids are the acylated glucosamine precursors of the lipid A component of the lipopolysaccharides in Gram-negative bacteria. Typical lipid A molecules are disaccharides of glucosamine, which are derivatized with as many as seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in E. coli is Kdo2-Lipid A, a hexa-acylated disaccharide of glucosamine that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo) residues.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07101213442D          
 
110112  0  0  1  0            999 V2000
    9.9633   -8.0866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6735   -7.6768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2529   -7.6768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9633   -8.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6735   -6.8518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3838   -8.0866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2529   -6.8518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5318   -8.0866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3838   -6.4365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3838   -8.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0950   -4.7866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

 
  Mrv0541 07101213442D          
 
110112  0  0  1  0            999 V2000
    9.9633   -8.0866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6735   -7.6768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2529   -7.6768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9633   -8.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6735   -6.8518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3838   -8.0866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2529   -6.8518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.3838   -6.4365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5373   -8.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
MMDBc0031618

> <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@@]3(C[C@@H](O)[C@@H](O)[C@H](O3)[C@H](O)CO)C(O)=O)[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/C76H142N2O30P2/c1-5-9-13-17-21-25-29-33-37-41-53(80)45-61(86)77-65-71(104-63(88)47-55(82)43-39-35-31-27-23-19-15-11-7-3)68(91)59(102-74(65)108-110(97,98)99)51-100-73-66(78-62(87)46-54(81)42-38-34-30-26-22-18-14-10-6-2)72(105-64(89)48-56(83)44-40-36-32-28-24-20-16-12-8-4)70(107-109(94,95)96)60(103-73)52-101-76(75(92)93)49-57(84)67(90)69(106-76)58(85)50-79/h53-60,65-74,79-85,90-91H,5-52H2,1-4H3,(H,77,86)(H,78,87)(H,92,93)(H2,94,95,96)(H2,97,98,99)/t53-,54-,55-,56-,57-,58-,59-,60-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,76-/m1/s1

> <INCHI_KEY>
GPNCBCJEDRRCDW-ACUQGRCXSA-N

> <FORMULA>
C76H142N2O30P2

> <MOLECULAR_WEIGHT>
1625.8836

> <EXACT_MASS>
1624.912264238

> <JCHEM_ACCEPTOR_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
178.8106067211818

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonooxy)oxan-2-yl]methoxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
11.311730076000003

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.3011056187013832

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6048445031505265

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491373200891335

> <JCHEM_POLAR_SURFACE_AREA>
509.8400000000001

> <JCHEM_REFRACTIVITY>
400.8092

> <JCHEM_ROTATABLE_BOND_COUNT>
67

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(kdo)-lipid iva

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-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      15.906  -8.935   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.936 -21.255   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.600 -18.950   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      23.922 -13.555   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      25.258 -11.260   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      21.260 -19.715   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      23.932 -19.715   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      15.906  -7.395   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.580  -9.710   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.313  -9.496   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.600 -22.030   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      25.258 -14.330   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      22.586 -13.869   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      26.594 -12.025   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.260 -21.245   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.580  -6.630   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.244  -8.935   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      17.308 -10.852   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      18.588  -8.680   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      14.610 -23.570   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      26.594 -13.555   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      25.258 -15.870   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      27.919 -11.260   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      19.924 -22.020   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      13.244  -7.395   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.610  -5.182   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      12.040  -9.761   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      13.274 -24.335   0.000  0.00  0.00           C+0
HETATM   55  N   UNK     0      28.766 -14.330   0.000  0.00  0.00           N+0
HETATM   56  C   UNK     0      26.604 -16.635   0.000  0.00  0.00           C+0
HETATM   57  P   UNK     0      27.919  -9.720   0.000  0.00  0.00           P+0
HETATM   58  C   UNK     0      19.924 -23.570   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      11.877  -6.712   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      15.855  -4.407   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      13.101  -4.356   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      13.274 -25.875   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      30.102 -13.555   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      26.604 -18.175   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      27.766 -15.870   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      26.379  -9.710   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      27.909  -8.180   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      29.459  -9.720   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      18.598 -24.325   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      15.855  -2.846   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      11.938 -26.640   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      31.427 -14.330   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      30.092 -12.015   0.000  0.00  0.00           O+0
HETATM   74  C   UNK     0      27.930 -18.950   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      18.598 -25.865   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      11.938 -28.180   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      31.438 -15.870   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      27.930 -20.480   0.000  0.00  0.00           C+0
HETATM   79  O   UNK     0      29.256 -18.175   0.000  0.00  0.00           O+0
HETATM   80  C   UNK     0      17.272 -26.650   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      10.602 -28.945   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      32.764 -16.635   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      30.102 -16.635   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0      29.266 -21.245   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      17.272 -28.190   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      10.602 -30.485   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      32.753 -18.195   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      29.266 -22.785   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      15.946 -28.955   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0       9.266 -31.260   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      34.110 -18.991   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      30.592 -23.570   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      15.946 -30.495   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       9.266 -32.800   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      34.110 -20.551   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      30.602 -25.100   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      14.610 -31.270   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      35.456 -21.326   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      31.928 -25.865   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      35.446 -22.866   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      31.928 -27.394   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      36.782 -23.641   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      33.264 -28.170   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      36.772 -25.182   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      33.254 -29.710   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      38.108 -25.946   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0      34.590 -30.485   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0      38.098 -27.486   0.000  0.00  0.00           C+0
HETATM  109  C   UNK     0      34.590 -32.014   0.000  0.00  0.00           C+0
HETATM  110  C   UNK     0      39.423 -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   27                                                       
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   14                                                            
CONECT   24   15   28   29                                                  
CONECT   25   17   30   31                                                  
CONECT   26   18   32   33                                                  
CONECT   27   20   34   35   36                                             
CONECT   28   24   37                                                       
CONECT   29   24                                                            
CONECT   30   25   38   39                                                  
CONECT   31   25   40                                                       
CONECT   32   26   41                                                       
CONECT   33   26                                                            
CONECT   34   27   42                                                       
CONECT   35   27   43                                                       
CONECT   36   27   44   45                                                  
CONECT   37   28   46                                                       
CONECT   38   30   47   48                                                  
CONECT   39   30                                                            
CONECT   40   31   49   47                                                  
CONECT   41   32   50                                                       
CONECT   42   34   51   52                                                  
CONECT   43   35   53   51                                                  
CONECT   44   36                                                            
CONECT   45   36                                                            
CONECT   46   37   54                                                       
CONECT   47   38   55   40                                                  
CONECT   48   38   56                                                       
CONECT   49   40   57                                                       
CONECT   50   41   58                                                       
CONECT   51   42   59   43                                                  
CONECT   52   42   60   61                                                  
CONECT   53   43                                                            
CONECT   54   46   62                                                       
CONECT   55   47   63                                                       
CONECT   56   48   64   65                                                  
CONECT   57   49   66   67   68                                             
CONECT   58   50   69                                                       
CONECT   59   51                                                            
CONECT   60   52   70                                                       
CONECT   61   52                                                            
CONECT   62   54   71                                                       
CONECT   63   55   72   73                                                  
CONECT   64   56   74                                                       
CONECT   65   56                                                            
CONECT   66   57                                                            
CONECT   67   57                                                            
CONECT   68   57                                                            
CONECT   69   58   75                                                       
CONECT   70   60                                                            
CONECT   71   62   76                                                       
CONECT   72   63   77                                                       
CONECT   73   63                                                            
CONECT   74   64   78   79                                                  
CONECT   75   69   80                                                       
CONECT   76   71   81                                                       
CONECT   77   72   82   83                                                  
CONECT   78   74   84                                                       
CONECT   79   74                                                            
CONECT   80   75   85                                                       
CONECT   81   76   86                                                       
CONECT   82   77   87                                                       
CONECT   83   77                                                            
CONECT   84   78   88                                                       
CONECT   85   80   89                                                       
CONECT   86   81   90                                                       
CONECT   87   82   91                                                       
CONECT   88   84   92                                                       
CONECT   89   85   93                                                       
CONECT   90   86   94                                                       
CONECT   91   87   95                                                       
CONECT   92   88   96                                                       
CONECT   93   89   97                                                       
CONECT   94   90                                                            
CONECT   95   91   98                                                       
CONECT   96   92   99                                                       
CONECT   97   93                                                            
CONECT   98   95  100                                                       
CONECT   99   96  101                                                       
CONECT  100   98  102                                                       
CONECT  101   99  103                                                       
CONECT  102  100  104                                                       
CONECT  103  101  105                                                       
CONECT  104  102  106                                                       
CONECT  105  103  107                                                       
CONECT  106  104  108                                                       
CONECT  107  105  109                                                       
CONECT  108  106  110                                                       
CONECT  109  107                                                            
CONECT  110  108                                                            
MASTER        0    0    0    0    0    0    0    0  110    0  224    0
END

Synonyms

Value	Source
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate	ChEBI
3-Deoxy-D-manno-octulosonyl-lipid IV(a)	ChEBI
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphate	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphoric acid	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphoric acid	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphoric acid	Generator

Molecular Formula

C₇₆H₁₄₂N₂O₃₀P₂

Average Mass

1625.8836

Monoisotopic Mass

1624.912264238

IUPAC Name

(2R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-3-(phosphonooxy)oxan-2-yl]methoxy}oxane-2-carboxylic acid

Traditional Name

(kdo)-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@@]3(C[C@@H](O)[C@@H](O)[C@H](O3)[C@H](O)CO)C(O)=O)[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/C76H142N2O30P2/c1-5-9-13-17-21-25-29-33-37-41-53(80)45-61(86)77-65-71(104-63(88)47-55(82)43-39-35-31-27-23-19-15-11-7-3)68(91)59(102-74(65)108-110(97,98)99)51-100-73-66(78-62(87)46-54(81)42-38-34-30-26-22-18-14-10-6-2)72(105-64(89)48-56(83)44-40-36-32-28-24-20-16-12-8-4)70(107-109(94,95)96)60(103-73)52-101-76(75(92)93)49-57(84)67(90)69(106-76)58(85)50-79/h53-60,65-74,79-85,90-91H,5-52H2,1-4H3,(H,77,86)(H,78,87)(H,92,93)(H2,94,95,96)(H2,97,98,99)/t53-,54-,55-,56-,57-,58-,59-,60-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,76-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

lipid As (CHEBI:27439 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	3.72	ALOGPS
logP	11.31	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	0.6	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	26	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	509.84 Å²	ChemAxon
Rotatable Bond Count	67	ChemAxon
Refractivity	400.81 m³·mol⁻¹	ChemAxon
Polarizability	178.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0018189000-bab8c94d64d4d246a561	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-1519223000-af65ac0fd99c577268af	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bw9-2329251000-b437d8f531d53e26bafb	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05p2-9163224001-ccfaf88f2e0f5454f666	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-7fa42647ff5cc1e51040	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-3eb605d4860dc7fbec9c	2019-02-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007284	CMP-3-Deoxy-D-manno-octulosonate	Cytidine monophosphate	Not Available	3-deoxy-D-manno-octulosonic acid transferase	VMH	30371894

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	172	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	22	Pig ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	88	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	116	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

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
Human Feces	Detected but not Quantified									HMDB

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

C06024

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25203768

PDB ID

Not Available

ChEBI ID

27439

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for KDO-lipid IV(A) (MMDBc0031618)

MOL for #<Metabolite:0x00007fa4e909cc80>

3D MOL for #<Metabolite:0x00007fa4e909cc80>

3D SDF for #<Metabolite:0x00007fa4e909cc80>

3D-SDF for #<Metabolite:0x00007fa4e909cc80>

PDB for #<Metabolite:0x00007fa4e909cc80>

3D PDB for #<Metabolite:0x00007fa4e909cc80>

SMILES for #<Metabolite:0x00007fa4e909cc80>

INCHI for #<Metabolite:0x00007fa4e909cc80>

Structure for #<Metabolite:0x00007fa4e909cc80>

3D Structure for #<Metabolite:0x00007fa4e909cc80>