MiMeDB: Showing metabocard for (heptosyl)2-Kdo2-lipid A (MMDBc0032140)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:04:00 UTC

Update Date

2022-08-31 18:30:49 UTC

Metabolite ID

MMDBc0032140

Metabolite Identification

Common Name

(heptosyl)2-Kdo2-lipid A

Description

(Heptosyl)2-Kdo2-lipid A is a component of lipopolysaccharide. Bacterial lipopolysaccharides (LPS) typically consist of a hydrophobic domain inserted into the outer membrane known as lipid A (or endotoxin), a phosphorylated "core" oligosaccharide and a distal polysaccharide (or O antigen). The core oligosaccharides are conceptually divided into two regions: inner core and outer core. The inner core is highly conserved, comprises three deoxy-D-manno-octulosonic acid (KDO) and L-glycero-D-manno-heptose (Hep) and is often phosphorylated. The inner core oligosaccharide plays a critical role in essential barrier function of the outer membrane. The outer core comprises a tri-hexose backbone modified with varying side-branch substitutions of hexose and acetamidohexose residues. The outer core provides an attachment site for O-antigen. The completed lipid A-KDO2 serves as the acceptor on which the core oligosaccharide chains are assembled by sequential glycosyl transfer from nucleotide sugar precursors. This process involves a co-ordinated complex of membrane-associated glycosyltransferases acting at the cytoplasmic face of the plasma membrane.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005141513372D          

179184  0  0  0  0            999 V2000
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  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
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166179  1  0  0  0  0
148163  2  0  0  0  0
151164  1  0  0  0  0
M  CHG  5  41  -1  71  -1  72  -1 146  -1 147  -1
M  END


  Mrv1533005141513372D          

179184  0  0  0  0            999 V2000
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    9.2305   -6.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6430  -10.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6430  -11.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6430  -14.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1999   -8.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7874   -9.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1999   -9.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7874  -10.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1999  -11.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7874  -11.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1999  -12.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 78140  1  0  0  0  0
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171172  1  0  0  0  0
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174175  1  0  0  0  0
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176177  1  0  0  0  0
149178  2  0  0  0  0
166179  1  0  0  0  0
148163  2  0  0  0  0
151164  1  0  0  0  0
M  CHG  5  41  -1  71  -1  72  -1 146  -1 147  -1
M  END
> <DATABASE_ID>
MMDBc0032140

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OCC2OC(OP([O-])([O-])=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)OC(COC2(CC(OC3(CC(O)C(O)C(O3)C(O)CO)C(C)=C)C(OC3OC(C(O)CO)C(O)C(OC4OC(C(O)CO)C(O)C(O)C4O)C3O)C(O2)C(O)CO)C([O-])=O)C1OP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C126H230N2O49P2/c1-9-15-21-27-33-39-40-46-52-58-64-70-99(143)164-87(68-62-56-50-44-37-31-25-19-13-5)74-101(145)168-118-103(128-97(141)73-86(67-61-55-49-43-36-30-24-18-12-4)163-98(142)69-63-57-51-45-38-32-26-20-14-6)120(161-81-94-105(147)117(167-100(144)72-85(134)66-60-54-48-42-35-29-23-17-11-3)102(121(165-94)177-179(158,159)160)127-96(140)71-84(133)65-59-53-47-41-34-28-22-16-10-2)166-95(116(118)176-178(155,156)157)82-162-126(124(153)154)76-93(173-125(83(7)8)75-88(135)104(146)113(174-125)91(138)79-131)115(114(175-126)92(139)80-132)171-123-110(152)119(109(151)112(170-123)90(137)78-130)172-122-108(150)106(148)107(149)111(169-122)89(136)77-129/h84-95,102-123,129-139,146-152H,7,9-82H2,1-6,8H3,(H,127,140)(H,128,141)(H,153,154)(H2,155,156,157)(H2,158,159,160)/p-5

> <INCHI_KEY>
DBFYJNVGWVVVGJ-UHFFFAOYSA-I

> <FORMULA>
C126H225N2O49P2

> <MOLECULAR_WEIGHT>
2614.101

> <EXACT_MASS>
2612.467863529

> <JCHEM_ACCEPTOR_COUNT>
43

> <JCHEM_ATOM_COUNT>
404

> <JCHEM_AVERAGE_POLARIZABILITY>
288.6146671028401

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
20

> <JCHEM_FORMAL_CHARGE>
-5

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(1,2-dihydroxyethyl)-4-{[6-(1,2-dihydroxyethyl)-4,5-dihydroxy-2-(prop-1-en-2-yl)oxan-2-yl]oxy}-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)oxane-2-carboxylate

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
17.392470255666662

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.300670571448559

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6048145891032921

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9545764666198275

> <JCHEM_POLAR_SURFACE_AREA>
814.0400000000004

> <JCHEM_REFRACTIVITY>
653.9053000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
106

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1,2-dihydroxyethyl)-4-{[6-(1,2-dihydroxyethyl)-4,5-dihydroxy-2-(prop-1-en-2-yl)oxan-2-yl]oxy}-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)oxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0      -7.043   4.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.948   3.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.322   2.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.790   1.968   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.885   3.214   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.511   4.621   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.669   6.189   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -9.201   6.350   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.764   7.435   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -7.391   8.841   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -9.480   3.697   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -8.227   0.883   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.164   0.561   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.353   3.053   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.927   2.779   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.301   1.372   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.231   1.211   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.136   2.457   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.510   3.864   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.022   4.025   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.648   5.432   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.206   0.126   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.415   5.110   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.789   6.517   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.947   4.949   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.852   6.195   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.857  -0.195   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.389  -0.356   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.389  -1.896   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.723  -2.666   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.056  -1.896   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.056  -0.356   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.723   0.414   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.723   1.954   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.389   2.724   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.056   2.724   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.390   1.954   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.055  -2.666   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.390  -2.666   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.056  -5.860   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.390  -4.206   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0       8.724  -1.896   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.012  -4.096   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -3.345  -4.866   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -3.345  -6.406   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.012  -7.176   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -0.678  -6.406   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -0.678  -4.866   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -3.379  -3.294   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -4.719  -3.291   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -2.940  -1.896   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -2.012  -8.716   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.656  -7.177   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -4.679  -7.177   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -6.013  -6.407   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -4.679  -8.717   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -6.013  -4.867   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       6.122  -8.029   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       7.479  -8.758   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       7.479 -10.298   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       8.813 -11.069   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      10.146 -10.298   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      10.146  -8.758   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       8.813  -7.988   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       6.145 -11.068   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       6.274 -14.648   0.000  0.00  0.00           O+0
HETATM   67  N   UNK     0      13.340 -12.163   0.000  0.00  0.00           N+0
HETATM   68  O   UNK     0      11.480  -7.989   0.000  0.00  0.00           O+0
HETATM   69  P   UNK     0       4.658 -11.467   0.000  0.00  0.00           P+0
HETATM   70  O   UNK     0       4.235  -9.911   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       3.059 -11.955   0.000  0.00  0.00           O-1
HETATM   72  O   UNK     0       5.347 -13.156   0.000  0.00  0.00           O-1
HETATM   73  C   UNK     0      13.352  -6.716   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      16.269  -7.765   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      16.589  -9.271   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      18.054  -9.747   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      19.199  -8.717   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      18.879  -7.210   0.000  0.00  0.00           C+0
HETATM   79  O   UNK     0      17.414  -6.734   0.000  0.00  0.00           O+0
HETATM   80  C   UNK     0       5.019 -15.641   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0       6.529 -17.102   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0       4.480 -18.422   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0       6.367 -19.891   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       4.254 -21.260   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       6.176 -22.689   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0       6.064 -25.622   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0       3.892 -26.594   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0       5.511 -28.363   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0       3.290 -28.993   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0       5.500 -30.701   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0       2.539 -31.086   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0       4.845 -32.814   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0       3.751 -23.917   0.000  0.00  0.00           C+0
HETATM   94  O   UNK     0       3.481 -15.565   0.000  0.00  0.00           O+0
HETATM   95  O   UNK     0       2.941 -18.353   0.000  0.00  0.00           O+0
HETATM   96  C   UNK     0       2.113 -19.651   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0       2.433 -21.157   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0       1.288 -22.187   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0       1.609 -23.694   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0       0.464 -24.724   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0       0.784 -26.231   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      -0.360 -27.261   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      -0.040 -28.767   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      -1.184 -29.798   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      -0.864 -31.304   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      -2.009 -32.335   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0      -1.688 -33.841   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0      -2.833 -34.872   0.000  0.00  0.00           C+0
HETATM  109  C   UNK     0      -2.513 -36.378   0.000  0.00  0.00           C+0
HETATM  110  O   UNK     0       0.597 -19.376   0.000  0.00  0.00           O+0
HETATM  111  C   UNK     0      12.027 -13.593   0.000  0.00  0.00           C+0
HETATM  112  C   UNK     0      12.797 -14.927   0.000  0.00  0.00           C+0
HETATM  113  C   UNK     0      12.027 -16.261   0.000  0.00  0.00           C+0
HETATM  114  C   UNK     0      12.797 -17.594   0.000  0.00  0.00           C+0
HETATM  115  C   UNK     0      12.027 -18.928   0.000  0.00  0.00           C+0
HETATM  116  C   UNK     0      12.797 -20.262   0.000  0.00  0.00           C+0
HETATM  117  C   UNK     0      12.027 -21.595   0.000  0.00  0.00           C+0
HETATM  118  C   UNK     0      12.797 -22.929   0.000  0.00  0.00           C+0
HETATM  119  C   UNK     0      12.027 -24.263   0.000  0.00  0.00           C+0
HETATM  120  C   UNK     0      12.797 -25.596   0.000  0.00  0.00           C+0
HETATM  121  C   UNK     0      12.027 -26.930   0.000  0.00  0.00           C+0
HETATM  122  C   UNK     0      12.797 -28.264   0.000  0.00  0.00           C+0
HETATM  123  C   UNK     0      12.170 -29.670   0.000  0.00  0.00           C+0
HETATM  124  C   UNK     0      13.577 -30.297   0.000  0.00  0.00           C+0
HETATM  125  O   UNK     0      10.496 -13.425   0.000  0.00  0.00           O+0
HETATM  126  O   UNK     0      10.487 -16.261   0.000  0.00  0.00           O+0
HETATM  127  C   UNK     0       9.717 -17.594   0.000  0.00  0.00           C+0
HETATM  128  C   UNK     0      10.487 -18.928   0.000  0.00  0.00           C+0
HETATM  129  C   UNK     0       9.717 -20.262   0.000  0.00  0.00           C+0
HETATM  130  C   UNK     0      10.487 -21.595   0.000  0.00  0.00           C+0
HETATM  131  C   UNK     0       9.717 -22.929   0.000  0.00  0.00           C+0
HETATM  132  C   UNK     0      10.487 -24.263   0.000  0.00  0.00           C+0
HETATM  133  C   UNK     0       9.717 -25.596   0.000  0.00  0.00           C+0
HETATM  134  C   UNK     0      10.487 -26.930   0.000  0.00  0.00           C+0
HETATM  135  C   UNK     0       9.717 -28.264   0.000  0.00  0.00           C+0
HETATM  136  C   UNK     0      10.487 -29.597   0.000  0.00  0.00           C+0
HETATM  137  O   UNK     0       8.177 -17.594   0.000  0.00  0.00           O+0
HETATM  138  C   UNK     0       9.860 -31.004   0.000  0.00  0.00           C+0
HETATM  139  C   UNK     0      10.630 -32.338   0.000  0.00  0.00           C+0
HETATM  140  O   UNK     0      20.023  -6.180   0.000  0.00  0.00           O+0
HETATM  141  O   UNK     0      15.445 -10.302   0.000  0.00  0.00           O+0
HETATM  142  O   UNK     0      18.375 -11.254   0.000  0.00  0.00           O+0
HETATM  143  N   UNK     0      22.618  -9.763   0.000  0.00  0.00           N+0
HETATM  144  P   UNK     0      19.703  -4.674   0.000  0.00  0.00           P+0
HETATM  145  O   UNK     0      17.831  -5.175   0.000  0.00  0.00           O+0
HETATM  146  O   UNK     0      19.219  -2.747   0.000  0.00  0.00           O-1
HETATM  147  O   UNK     0      21.493  -4.335   0.000  0.00  0.00           O-1
HETATM  148  C   UNK     0      17.230 -12.284   0.000  0.00  0.00           C+0
HETATM  149  C   UNK     0      21.553 -11.106   0.000  0.00  0.00           C+0
HETATM  150  C   UNK     0      18.000 -13.618   0.000  0.00  0.00           C+0
HETATM  151  C   UNK     0      17.230 -14.951   0.000  0.00  0.00           C+0
HETATM  152  C   UNK     0      18.000 -16.285   0.000  0.00  0.00           C+0
HETATM  153  C   UNK     0      17.230 -17.619   0.000  0.00  0.00           C+0
HETATM  154  C   UNK     0      18.000 -18.953   0.000  0.00  0.00           C+0
HETATM  155  C   UNK     0      17.230 -20.286   0.000  0.00  0.00           C+0
HETATM  156  C   UNK     0      18.000 -21.620   0.000  0.00  0.00           C+0
HETATM  157  C   UNK     0      17.230 -22.954   0.000  0.00  0.00           C+0
HETATM  158  C   UNK     0      18.000 -24.287   0.000  0.00  0.00           C+0
HETATM  159  C   UNK     0      17.230 -25.621   0.000  0.00  0.00           C+0
HETATM  160  C   UNK     0      18.000 -26.955   0.000  0.00  0.00           C+0
HETATM  161  C   UNK     0      17.230 -28.288   0.000  0.00  0.00           C+0
HETATM  162  C   UNK     0      18.000 -29.622   0.000  0.00  0.00           C+0
HETATM  163  O   UNK     0      15.709 -12.043   0.000  0.00  0.00           O+0
HETATM  164  O   UNK     0      15.690 -14.951   0.000  0.00  0.00           O+0
HETATM  165  C   UNK     0      22.960 -11.733   0.000  0.00  0.00           C+0
HETATM  166  C   UNK     0      21.627 -12.503   0.000  0.00  0.00           C+0
HETATM  167  C   UNK     0      23.034 -13.129   0.000  0.00  0.00           C+0
HETATM  168  C   UNK     0      22.003 -14.273   0.000  0.00  0.00           C+0
HETATM  169  C   UNK     0      22.773 -15.607   0.000  0.00  0.00           C+0
HETATM  170  C   UNK     0      22.003 -16.941   0.000  0.00  0.00           C+0
HETATM  171  C   UNK     0      22.773 -18.274   0.000  0.00  0.00           C+0
HETATM  172  C   UNK     0      22.003 -19.608   0.000  0.00  0.00           C+0
HETATM  173  C   UNK     0      22.773 -20.942   0.000  0.00  0.00           C+0
HETATM  174  C   UNK     0      22.003 -22.275   0.000  0.00  0.00           C+0
HETATM  175  C   UNK     0      22.773 -23.609   0.000  0.00  0.00           C+0
HETATM  176  C   UNK     0      21.743 -24.753   0.000  0.00  0.00           C+0
HETATM  177  C   UNK     0      22.887 -25.784   0.000  0.00  0.00           C+0
HETATM  178  O   UNK     0      20.058 -11.474   0.000  0.00  0.00           O+0
HETATM  179  O   UNK     0      20.089 -12.583   0.000  0.00  0.00           O+0
CONECT    1    2    7    6                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   14                                                  
CONECT    6    1    5                                                       
CONECT    7    1    9    8                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    2                                                            
CONECT   12    3                                                            
CONECT   13    4                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   17   15   22                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   20   23   18                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   16                                                            
CONECT   23   19   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   17   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   30   28   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   39   40                                             
CONECT   32   31   33                                                       
CONECT   33   28   34   32                                                  
CONECT   34   33   36   35                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38   29   43                                                       
CONECT   39   31   42   41                                                  
CONECT   40   31   58                                                       
CONECT   41   39                                                            
CONECT   42   39                                                            
CONECT   43   38   48   49   44                                             
CONECT   44   45   43                                                       
CONECT   45   46   54   44                                                  
CONECT   46   45   47   52                                                  
CONECT   47   46   48   53                                                  
CONECT   48   47   43                                                       
CONECT   49   43   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   46                                                            
CONECT   53   47                                                            
CONECT   54   45   55   56                                                  
CONECT   55   54   57                                                       
CONECT   56   54                                                            
CONECT   57   55                                                            
CONECT   58   40   59                                                       
CONECT   59   58   60   64                                                  
CONECT   60   61   59   65                                                  
CONECT   61   60   62   66                                                  
CONECT   62   61   63   67                                                  
CONECT   63   62   64   68                                                  
CONECT   64   63   59                                                       
CONECT   65   60   69                                                       
CONECT   66   61   80                                                       
CONECT   67   62  111                                                       
CONECT   68   63   73                                                       
CONECT   69   65   71   72   70                                             
CONECT   70   69                                                            
CONECT   71   69                                                            
CONECT   72   69                                                            
CONECT   73   68   74                                                       
CONECT   74   73   75   79                                                  
CONECT   75   76   74  141                                                  
CONECT   76   75   77  142                                                  
CONECT   77   76   78  143                                                  
CONECT   78   77   79  140                                                  
CONECT   79   78   74                                                       
CONECT   80   66   81   94                                                  
CONECT   81   82   80                                                       
CONECT   82   81   83   95                                                  
CONECT   83   82   84                                                       
CONECT   84   83   85                                                       
CONECT   85   84   93                                                       
CONECT   86   87   93                                                       
CONECT   87   86   88                                                       
CONECT   88   87   89                                                       
CONECT   89   88   90                                                       
CONECT   90   89   91                                                       
CONECT   91   90   92                                                       
CONECT   92   91                                                            
CONECT   93   85   86                                                       
CONECT   94   80                                                            
CONECT   95   82   96                                                       
CONECT   96   97  110   95                                                  
CONECT   97   96   98                                                       
CONECT   98   97   99                                                       
CONECT   99   98  100                                                       
CONECT  100   99  101                                                       
CONECT  101  100  102                                                       
CONECT  102  101  103                                                       
CONECT  103  102  104                                                       
CONECT  104  103  105                                                       
CONECT  105  104  106                                                       
CONECT  106  105  107                                                       
CONECT  107  106  108                                                       
CONECT  108  107  109                                                       
CONECT  109  108                                                            
CONECT  110   96                                                            
CONECT  111   67  112  125                                                  
CONECT  112  111  113                                                       
CONECT  113  112  114  126                                                  
CONECT  114  113  115                                                       
CONECT  115  114  116                                                       
CONECT  116  115  117                                                       
CONECT  117  116  118                                                       
CONECT  118  117  119                                                       
CONECT  119  118  120                                                       
CONECT  120  119  121                                                       
CONECT  121  120  122                                                       
CONECT  122  121  123                                                       
CONECT  123  122  124                                                       
CONECT  124  123                                                            
CONECT  125  111                                                            
CONECT  126  113  127                                                       
CONECT  127  126  128  137                                                  
CONECT  128  127  129                                                       
CONECT  129  128  130                                                       
CONECT  130  129  131                                                       
CONECT  131  130  132                                                       
CONECT  132  131  133                                                       
CONECT  133  132  134                                                       
CONECT  134  133  135                                                       
CONECT  135  134  136                                                       
CONECT  136  135  138                                                       
CONECT  137  127                                                            
CONECT  138  136  139                                                       
CONECT  139  138                                                            
CONECT  140   78  144                                                       
CONECT  141   75                                                            
CONECT  142   76  148                                                       
CONECT  143   77  149                                                       
CONECT  144  140  145  146  147                                             
CONECT  145  144                                                            
CONECT  146  144                                                            
CONECT  147  144                                                            
CONECT  148  142  150  163                                                  
CONECT  149  143  165  178                                                  
CONECT  150  148  151                                                       
CONECT  151  150  152  164                                                  
CONECT  152  151  153                                                       
CONECT  153  152  154                                                       
CONECT  154  153  155                                                       
CONECT  155  154  156                                                       
CONECT  156  155  157                                                       
CONECT  157  156  158                                                       
CONECT  158  157  159                                                       
CONECT  159  158  160                                                       
CONECT  160  159  161                                                       
CONECT  161  160  162                                                       
CONECT  162  161                                                            
CONECT  163  148                                                            
CONECT  164  151                                                            
CONECT  165  149  166                                                       
CONECT  166  165  167  179                                                  
CONECT  167  166  168                                                       
CONECT  168  167  169                                                       
CONECT  169  168  170                                                       
CONECT  170  169  171                                                       
CONECT  171  170  172                                                       
CONECT  172  171  173                                                       
CONECT  173  172  174                                                       
CONECT  174  173  175                                                       
CONECT  175  174  176                                                       
CONECT  176  175  177                                                       
CONECT  177  176                                                            
CONECT  178  149                                                            
CONECT  179  166                                                            
MASTER        0    0    0    0    0    0    0    0  179    0  368    0
END

Synonyms

Not Available

Molecular Formula

C₁₂₆H₂₂₅N₂O₄₉P₂

Average Mass

2614.101

Monoisotopic Mass

2612.467863529

IUPAC Name

6-(1,2-dihydroxyethyl)-4-{[6-(1,2-dihydroxyethyl)-4,5-dihydroxy-2-(prop-1-en-2-yl)oxan-2-yl]oxy}-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)oxane-2-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OCC2OC(OP([O-])([O-])=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)OC(COC2(CC(OC3(CC(O)C(O)C(O3)C(O)CO)C(C)=C)C(OC3OC(C(O)CO)C(O)C(OC4OC(C(O)CO)C(O)C(O)C4O)C3O)C(O2)C(O)CO)C([O-])=O)C1OP([O-])([O-])=O

InChI Identifier

InChI=1S/C126H230N2O49P2/c1-9-15-21-27-33-39-40-46-52-58-64-70-99(143)164-87(68-62-56-50-44-37-31-25-19-13-5)74-101(145)168-118-103(128-97(141)73-86(67-61-55-49-43-36-30-24-18-12-4)163-98(142)69-63-57-51-45-38-32-26-20-14-6)120(161-81-94-105(147)117(167-100(144)72-85(134)66-60-54-48-42-35-29-23-17-11-3)102(121(165-94)177-179(158,159)160)127-96(140)71-84(133)65-59-53-47-41-34-28-22-16-10-2)166-95(116(118)176-178(155,156)157)82-162-126(124(153)154)76-93(173-125(83(7)8)75-88(135)104(146)113(174-125)91(138)79-131)115(114(175-126)92(139)80-132)171-123-110(152)119(109(151)112(170-123)90(137)78-130)172-122-108(150)106(148)107(149)111(169-122)89(136)77-129/h84-95,102-123,129-139,146-152H,7,9-82H2,1-6,8H3,(H,127,140)(H,128,141)(H,153,154)(H2,155,156,157)(H2,158,159,160)/p-5

InChI Key

DBFYJNVGWVVVGJ-UHFFFAOYSA-I

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Oligosaccharide phosphate
Oligosaccharide
Saccharolipid
Pentacarboxylic acid or derivatives
Hexose phosphate
N-acyl-alpha-hexosamine
Fatty acyl glycoside
C-glucuronide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
C-glycosyl compound
Ketal
Monoalkyl phosphate
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Alkyl phosphate
Pyran
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Hydroxy acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.087 g/L	ALOGPS
logP	3.67	ALOGPS
logP	17.39	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	0.6	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	43	ChemAxon
Hydrogen Donor Count	20	ChemAxon
Polar Surface Area	814.04 Å²	ChemAxon
Rotatable Bond Count	106	ChemAxon
Refractivity	653.91 m³·mol⁻¹	ChemAxon
Polarizability	288.61 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018389	Heptosyl-KDO2-lipid A	Hydrogen Ion	ADP-heptose--LPS heptosyltransferase 2		PathBank	31602464
MMDBr0018390	(heptosyl)2-Kdo2-lipid A	Hydrogen Ion	Lipopolysaccharide core biosynthesis protein rfaG	Synthesis	PathBank	31602464

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for (heptosyl)2-Kdo2-lipid A (MMDBc0032140)

MOL for #<Metabolite:0x0000564af39f2d80>

3D MOL for #<Metabolite:0x0000564af39f2d80>

3D SDF for #<Metabolite:0x0000564af39f2d80>

3D-SDF for #<Metabolite:0x0000564af39f2d80>

PDB for #<Metabolite:0x0000564af39f2d80>

3D PDB for #<Metabolite:0x0000564af39f2d80>

SMILES for #<Metabolite:0x0000564af39f2d80>

INCHI for #<Metabolite:0x0000564af39f2d80>

Structure for #<Metabolite:0x0000564af39f2d80>

3D Structure for #<Metabolite:0x0000564af39f2d80>